Alcian blue stain - Knowledge

1067:~0.7 x1.1 nm) makes its diffusion very slow in less permeable parts of the tissue and thus prevent it from staining highly negative yet compact structures such as chromatin and nissl substance. However prolonged staining (few days at 25 °C) or DNA denaturing conditions may allow Alcian blue to also stain the nucleus. The isolation of the positive charge from the aromatic electron cloud by the intervening methylene bridges makes the localized positive charged regions "hard" ions in contrast to soft ions where the charge is delocalized over the whole aromatic pi cloud. When these hard cations encounter the hard anions e.g. in form of sulfate they form salts without regard for the precise chemical nature of the anion. The resulting salts are highly stable but can be slowly exchanged with high concentration of salts. Washing with water or alkali treatment after staining causes base catalyzed hydrolysis and removal of the pendant positively charged side chains and the resulting compound is 1084:

and other impurities and by various extraction methods up to 80% pure extracts can be made. Actually the dye does not necessary contain all 4 substituents but might contain 2 or 3 of them and have various geometric isomers. But anyhow the manufacture of 8GX by ICI had stopped by Mid-1970s because of environmental hazards and very small lots were available that were received from alternate sources. Only recently Alcian Blue has been re manufactured in bulk using safer procedures but the newer product does not have the suffix X (or S) since the manufacture process (and the exact product composition) is somewhat different.

941:

claimed an average of about three side chains per molecule, but analyses by Prof Scotts lab suggested between three and four. Most of them are at the 2(3) positions, as in the formula and sometimes a cartoon representation uses the methylene bridge criss crossing across the bond between these two positions to indicate that it could bind either of these two positions. A large number of isomers, differing in the positions of the cationic groups, are possible. Alcian blue 7GX carries fewer isothiouronium groups than 8GX. Similarly 5GX and 2GX may have even fewer side groups but it was not rigorously proven.

543: 209: 134: 393: 91: 630: 31: 360: 612:"Alcian blue is highly selective for the tissue substances (given the proper solution pH), and forms insoluble complexes that withstand harsh subsequent treatment (like PAS) without destaining. That is what makes this dye so important. Do any other dyes have this attribute? Yes, two others to be exact, out of thousands listed in the Colour Index and Conn's Biological Stains." These two are ' 835:. In aqueous solution Alcian blues continue to be metachromatic at molar concentrations one hundredth those at which toluidine blue is mainly orthochromatic. Only a very small shoulder of the absorption curve at 670–680 nm represent the monomeric dye, which is usually the minority and becomes even lesser minority (<10M) in presence of salts. However, when the solvent is 995:, but NaCl, KCl, LiBr are potential alternatives) can be used where the smaller (faster diffusing) salt cation competes with alcian blue to bind to the anionic sites. Target material specific critical electrolyte concentration (CEC) is supposed to selectively identify sulphated, carboxylated and phosphated structures for example as the targets. 1093:

blue is a skin sensitiser and corrosive (partly due to the acidic pH needed to maintain it unhydrolyzed in solution) and harmful by skin absorption. Most vendor MSDS (Material safety datasheet) mention that effect of ingestion not known or target organ not known. However some do mention that potential target organs are teeth and kidneys.

839:—a non-protic solvent of moderately high dielectric constant, Alcian blue does not aggregate and a big monomeric absorption peak can be well visualized. A similar spectral shift to the longer monomeric peak is also observed when solvents like ethanol (or ethanol water mixture) is used as a vehicle or when nonionic detergents like 232:

InChI=1S/C56H68N16S4.4ClH.Cu/c1-65(2)53(66(3)4)73-29-33-17-21-37-41(25-33)49-58-45(37)57-46-38-22-18-35(31-75-55(69(9)10)70(11)12)27-43(38)51(59-46)64-52-44-28-36(32-76-56(71(13)14)72(15)16)20-24-40(44)48(63-52)62-50-42-26-34(19-23-39(42)47(60-49)61-50)30-74-54(67(5)6)68(7)8;;;;;/h17-28H,29-32H2,1-16H3;4*1H;/q+2;;;;;+2/p-4

250:

InChI=1/C56H68N16S4.4ClH.Cu/c1-65(2)53(66(3)4)73-29-33-17-21-37-41(25-33)49-58-45(37)57-46-38-22-18-35(31-75-55(69(9)10)70(11)12)27-43(38)51(59-46)64-52-44-28-36(32-76-56(71(13)14)72(15)16)20-24-40(44)48(63-52)62-50-42-26-34(19-23-39(42)47(60-49)61-50)30-74-54(67(5)6)68(7)8;;;;;/h17-28H,29-32H2,1-16H3;4*1H;/q+2;;;;;+2/p-4

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but not the chromatin and nissel substance, the mechanism of which had been a mystery for a long time and various theories were proposed. Though the presumed basis of the staining is its positive charge attracted to negative structures (e.g. acidic sugars), bulkiness (width 2.5–3 nm, compared to

1092:

Alcian blue is an eye and respiratory tract irritant. Solid Alcian blue is a combustible powder and should never be handled close to heat or a naked flame. Heating Alcian blue produces toxic fumes of nitrogen compounds. It can react violently if mixed with oxidising materials. The solution of Alcian

599:

Prof J. E. Scott worked to decipher the chemistry of Alcian blue, which was known only to the Industry but kept as a tight trade secret. After spending 3 man-years of effort in 1972 he published the structure of Alcian blue and was able to get ICI to confirm it in 1973, incidentally in the same time

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Alcian blue carrying a large aromatic surface that can participate in Van der Waal's interaction as well as multiple localized charges. Thus it can be coated onto surfaces and significantly modify surface property and charge. Some cells in culture grow better on surfaces coated with positive charge

940:

side chains imparting its bulkiness and positive charges. In order to qualify as an alcian blue family member there has to be at least 2 side chains and the mixtures often have 3 chains in average to qualify as 8G. Four tetramethylisothiouronium groups per molecule are shown in the picture. ICI had

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The historic Alcian Blue varied so much batch to batch that only the 8GX (e.g. not even the 8GS) batch produced by ICI was later decided to be the biologically useful ones. Commercially available batches usually contained about 49% of the actual dye and rest used to be Sulfate, boric acid, dextrin

1057:

are generally basophilic because they have a very high density of negative charge due to the sugar phosphate backbone. However, in contrast to other basic i.e. cationic dyes, Alcian blue usually (given the right pH and salt concentrations, and normal temperature and duration in minutes, not hours)

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gives a recommended shelf life of 6 months. An Alcian blue solution with a precipitate should be discarded and replaced, not filtered and used. Some dyes sold as Alcian blue 8G are unstable in solutions at pH 5.6 and above; they precipitate in less than 24 hours. Batches of Alcian blue that do not

948:

aromatic nucleus has a large conjugated system with a CBN (Conjugated bond number) of 48. However it is the charges on the isothiouronium side groups that still keeps it water-soluble. These side groups can carry bulkier alkyl or aryl substituents rather than the 8x2 methyl groups as in the image

1101:

This stain was originally discovered by ICI in the 1940s as a member of the competitive dye industry for the purpose of industrial dying. It was used for some time for staining textiles, leather products and inks. ICI sold thousands of tons of alcian blue and filed multiple patents regarding its

595:

dyestuffs department under N. H. Haddock and C. Wood in the early 1940s and patented in 1947, originally as a textile dye. In 1950 it was used by Steedman as a selective dye for mucins. While the popularity of Alcian blue expanded exponentially, the difficulty involved in its production due to

607:

had to stop, there have now been environmentally safe alternative industrial manufacturing of this dye that is supposed to work as well as 8GX but is called 8G since it is made differently. In attempt to answer what was the importance of discovering an alternative method of manufacturing this

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The etymology of the name is not certain, and whether to capitalize it is an editorial style choice. Two major scientific and medical dictionaries use the lowercase styling, but there is also worthy support for the capitalized styling (discussed below). According to Elsevier's dictionary of

242:

InChI=1/C56H68N16S4.4ClH.Cu/c1-65(2)53(66(3)4)73-29-33- 17-21-37-41(25-33)49-58-45(37)57-46-38-22-18-35(31-75-55 (69(9)10)70(11)12)27-43(38)51(59-46)64-52-44-28-36(32-76- -56(71(13)14)72(15)16)20-24-40(44)48(63-52)62-50-42-26- 34(19-23-39(42)47(60-49)61-50)30-74-54(67(5)6)68(7)8;;;;;/h17-

768:

The solid Alcian blue is obtained as greenish-black (or sometimes dark bluish violet) crystals with metallic sheen. The aqueous solution is bright greenish-blue. Though the compound alcian blue itself is unstable (see stability below) the staining it produces is stable and light fast .

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of very large size, too large to be even dialysed. Thus even at a fairly high dilution, it has an absorption maximum at ~600–615 nm, which is actually not the absorption maximum of a dye monomer but that of the multimer. Since the absorbed light is of yellow orange spectrum, the

690:

However Prof. J. E. Scott who had cracked the chemistry of Alcian blue himself and later received confirmation from the manufacturer (ICI) wrote that Alcian was a trademark that ICI preferred to be spelt starting with a capital "A", and he presumes it came from the

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or Alcian blue. Alcian blue coated surfaces hold onto the negatively charge glycocalyx so tight that it can even be used to cover a layer of cells and then float it up to peel off the roof ("unroofing") to study the cytoplasmic side of the plasma membrane.

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and other similar dyes, this property that it does not change color either by change in concentration or by combination with substrates, makes it very suitable for microspectrophotometry. The apparent lack of metachromasia is not because it is truly

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form stable solutions cannot be used in Scott's "critical electrolyte concentration" methods for histochemical characterization of different glycosaminoglycans, which require solutions at pH 5.7-5.8 with variable concentrations of MgCl

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manufacturing process to keep its chemistry a tight secret. However ICI had had trouble with the dye's solubility under textile dyeing conditions, and various process changes in manufacturing were made during the 1950s and 1960s.

1015:: Alcian blue 8G differs from most other dyes in that it can deteriorate even in the solid state, changing to an insoluble pigment. Acidic solutions of Alcian blue 8G are often stable for some years. Churukian's lab manual 887:

It is water-soluble. When each of the pair of substituents on the pendant group nitrogens are toluyl, the solubility in water at 20 °C is about 9.5% w/w; and similarly a few other solubilities are: 6.0% in absolute

1071:, which forms a blue water-insoluble dye precipitate. The precipitates are so robust that they withstand harsh conditions like PAS or other counterstaining and also dehydration and embedding treatments (in contrast 585:, attempts were made to reversibly modify it so that it would be carried into fabric in a solution and then easily precipitated (ingrained) into an unleachable but finely well dispersed deposit (hence the name " 596:

environmentally hazardous intermediate steps made its availability difficult and ICI stopped producing it by 1973. Many of the alternate sources sold similar looking color products with unreliable staining.

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especially for light microscopy in paraffin embedded sections and in semithin resin sections. The tissue parts that specifically stain by this dye become blue to bluish-green after staining and are called

952:

The metals in the Phthallocyanine nucleus and substituted groups directly attached to the aromatic nucleus determine colors of the members of the metal phthallocyanine family e.g. Alcian Blue and the

539:

In addition to its wide use as a stain, Alcian blue has also been used in other diverse applications e.g. gelling agent for lubricating fluids, modifiers for electrodes, charged coating agents etc.

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Alcian Blue has a relatively high solubility in salt solutions and stains slower than other dyes. By changing pH or ambient salt concentrations characteristic staining patterns can be obtained.

897: 1075:

is partially extracted away during dehydration). This unleachability is the chemical basis of the ingrain dyeing for which AB (Ingrain blue 1) was originally designed by the dye industry.

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given. These groups split off from the macrocyclic ring during the washing at the end of staining or by rather mild conditions (e.g. pH above 5.6) or during spontaneous degradation.

1027: 535:"Probably no other dyestuff has been applied to such wide variety of problems in biology and medicine. On the other hand, no other dyestuff had such a chequered history as AB." 524:

but from 1970's, partly due to lack of availability of Alcian and partly due to length and tediousness of the procedure, alternative methods had to be developed e.g.

525: 274:

CN(C)C(=(C)C)SCC1=CC2=C(C=C1)C3=NC4=NC(=NC5=C6C=C(C=CC6=C(5)N=C7C8=C(C=CC(=C8)CSC(=(C)C)N(C)C)C(=N7)N=C23)CSC(=(C)C)N(C)C)C9=C4C=CC(=C9)CSC(=(C)C)N(C)C.....

1810:

Churukian CJ, Frank M, Horobin RW (2000). "Alcian blue pyridine variant – a superior alternative to alcian blue 8GX: staining performance and stability".

1581: 373: 1128:

Alcian blue has been used as an adhesive to help stick glycol methacrylate sections to glass slides (which have negatively charged silicate groups).

1004: 1362: 1344: 717:

data from various sources e.g. works by another dye expert Prof. R. W. Horobin—one of the two chief editors of the 10th edition of the 75-year-old

1142: 752: 684: 617: 900:(Log P) of −9.7, suggesting it is rather water-soluble (lipid-soluble if Log P > 0, and good lipid stains generally have a Log P > 7). 740: 802: 266: 1559: 2416: 896:

and 3.25% ethylene glycol, whereas it is practically insoluble in xylene. In relative/partitioning terms, Alcian Blue 8G has a log

1715:

Schenk, Eric (January 1981). "Notes on Technic: Note from the Biological Stain Commission a Newly Certified Dye—Alcian Blue 8GX".

1978:

Archimbaud E.; Islam A.; Preisler H. D. (1986). "Alcian blue method for attaching glycol methacrylate sections to glass slides".

1880: 1687: 2493: 1154:

Alcian Blue has been used as a gelling agent for lubricating fluids likely due to the stacking properties of this macrocylic

368: 1949: 1599:

Horobin, R. W.; Goldstein, D. J. (1 September 1972). "Impurities and staining characteristics of Alcian Blue samples".

1035: 1752:"Simultaneous differential staining by a cationic carbocyanine dye of nucleic acids, proteins and conjugated proteins" 2023: 1667: 1257: 971:

At pH 1.0 it stains only sulfated polysaccharides and at pH 2.5 also stains carboxyl group containing sugars such as

223: 908:

is not, because, within a few hours all of suspended Alcian blue precipitates if isopropanol is tried as a vehicle.

2117: 380: 520:. Biochemists had used it to assay acid polysaccharides in urine since the 1960s for diagnosis of diseases like 45:

Alcian blue 8GX, Ingrain blue 1, C.I. 74240, "chloromethylated copper phthalocyanine-thiourea reaction products"

2219: 1499: 924:

It is a tetravalent basic (cationic) dye with a copper (Cu, coordination 4 of 6, orbital configuration d with

2552: 1792: 1016: 531:

John E. Scott, the first person outside the dye industry to crack the chemical secret of this dye, comments:

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Scott, J. E. (1 December 1973). "Alcian dyes: I.C.I. cease manufacture and release details of composition".

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A staining method where at a fixed pH of about 5.5, different critical salt concentration (classically MgCl

604: 592: 445: 166: 129: 2448: 2352: 1012: 722: 187: 513: 2478: 868: 739:

ring nor any of the colors of the Kingfisher, but in common with Alcian blue, has hydrolyzable charged

498: 1358: 1340: 714: 1043: 204: 2562: 2498: 2361: 743:

side-chains and similar stability of the final stained product. On the other hand, there are other

1517: 464:, sialylated glycocalyx of cells etc. For many of these targets it is one of the most widely used 2286: 2567: 2521: 1177: 1172: 957: 933: 925: 859:

of 120,000 i.e. Alcian blue is detectable at half the molar concentration of popular dyes like

566: 554: 509: 1567: 1544: 2453: 2390: 2356: 2328: 1221: 1120:

In addition to its use as a dye or stain Alcian blue also finds other material science uses.

521: 111: 2042: 620:, which are again both equally unavailable and also lack the brilliant contrast of the blue. 2371: 2110: 819: 794: 702: 634: 175: 67: 1377: 983:, which would also stain albeit relatively weakly by their half sulfate esters at pH 1.0. 706: 645: 396:

Micromass cultures of C3H-10T1/2 cells at varied oxygen tensions stained with Alcian blue.

8: 2146: 1068: 953: 828: 473: 57: 1046:) is more stable than the original alcian blue dyes and may be just as good as a stain. 542: 448:

product) has been historically the most common and the most reliable member. It is used

208: 133: 2488: 2079: 2054: 1835: 1624: 1432: 1303: 856: 836: 469: 461: 17: 2557: 2505: 2340: 2214: 2084: 2019: 1995: 1931: 1926: 1909: 1827: 1773: 1732: 1663: 1616: 1493: 1424: 1389: 1307: 1253: 1206: 1059: 709:". Prof. Scott also states that Alcian green was merely a mixture of Alcian blue and 453: 2095: 1839: 1436: 916:

The sample compound with Merck index number 218 has a melting point of 148 °C.

904:

is an acceptable substitute for ethanol as a potential vehicle for Alcian blue, but

155: 2468: 2366: 2074: 2066: 1987: 1921: 1819: 1763: 1724: 1628: 1608: 1455: 1416: 1299: 406: 289: 2348: 2103: 2013: 1657: 1642: 1247: 1182: 980: 893: 748: 591:"). From this attempt, Alcian blue (Ingrain blue 1) was first synthesized by the 1855:"Spectral studies of toluidine blue O in the presence of sodium dodecyl sulfate" 657:

in Alcian blue might have been coined by contraction (and slight alteration) of

2376: 2304: 2295: 2269: 1226: 1189: 1167: 1072: 1064: 945: 937: 929: 872: 864: 860: 852: 807: 798: 782: 778: 744: 736: 659: 578: 351: 243:-28H,29-32H2,1-16H3;4*1H;/q+2;;;;;+2/p-4/fC56H68N16S4.4 Cl.Cu/h;4*1h;/qm;4*-1;m 1991: 1823: 1728: 2546: 2463: 2438: 2406: 2290: 2281: 2265: 2189: 1935: 1659:

Handbook of Biological Dyes and Stains: Synthesis and Industrial Applications

1194: 1138: 876: 728: 710: 613: 608:

compound, a company (Anatech Ltd, USA) that remanufactured Alcian blue says:

574: 122: 1854: 2483: 2443: 2426: 2421: 2201: 1831: 1393: 1211: 1054: 840: 790: 517: 494: 2088: 1999: 1777: 1736: 1620: 1428: 1311: 644:

was converted to this bird and caused the calmness of the seas during the

2531: 2473: 2458: 2321: 2164: 2138: 2055:"The quantitative measurement of Alcian Blue-glycosaminoglycan complexes" 976: 972: 905: 692: 582: 581:

in 1907. Attracted by the brilliance, stability and insolubility of this

550: 490: 392: 2047: 476:. Use of alcian blue has historically been a popular staining method in 2526: 2381: 2316: 2260: 2242: 1612: 1420: 1031: 502: 332: 102: 2070: 508:

methods. Alcian blue can be used to quantitate acidic glycans both in

2237: 2184: 2174: 1768: 1751: 810:

but because "it is already fully metachromatic" in aqueous solution.

664: 629: 624: 477: 457: 1910:"Dyes and other colorants in microtechnique and biomedical research" 350:

Except where otherwise noted, data are given for materials in their

2299: 2274: 2252: 2179: 2169: 2126: 1977: 1513: 1290:

Scott John E (1996). "Alcian blue. Now you see it, now you don't".

1155: 901: 505: 465: 449: 432:) is any member of a family of polyvalent basic dyes, of which the 1881:"How Do Dyes Impart Color to Different Components of the Tissues?" 90: 2431: 2411: 2229: 1040: 889: 823: 786: 732: 641: 444:, formerly called Alcian blue 8GX from the name of a batch of an 142: 570: 2156: 1890:(2 ed.). Carpinteria, California: Dako. pp. 159–166 1697:(2 ed.). Carpinteria, California: Dako. pp. 159–166 1216: 855:

one of the most highly colored chromophores yet known with a

813: 755:, which have not acquired "Alcian" as a part of their names. 486: 80: 30: 1852: 192: 2134: 1853:

Jebaramya, J; Ilanchelian, M; Prabahar, S (December 2009).

1688:""Special Stains" - Influence of Dye Chemistry on Staining" 1523: 832: 827:

transmitted/reflected light is perceived by our eye as the

818:

In aqueous solution large numbers of Alcian blue molecules

421: 701:", which has a "romantic and poetic associations with the 512:

quantitation in solution or for staining glycoproteins in

418: 1519:

Dorland's Illustrated Medical Dictionary [online]

412: 1486:

McGraw-Hill Dictionary of Scientific and Technical Terms

1950:"Lifeline Cell Technology MSDS: 1.0% Alcian Blue Stain" 1285: 1283: 1281: 1049: 713:

and not a single compound, which is also supported by

2125: 1809: 687:, which is a tetraphenyl-phthalocyanine with copper. 424: 1115: 663:.". Oxford online dictionary mentions that it was a 415: 1278: 409: 2015:Introduction to Electron Microscopy for Biologists 1030:(Alcian Blue-tetrakis(methylpyridinium) chloride, 986: 772: 1862:Digest Journal of Nanomaterials and Biostructures 2544: 1886:. In Kumar, George L.; Kiernan, John A. (eds.). 1693:. In Kumar, George L.; Kiernan, John A. (eds.). 1598: 1110: 960:and sulfonated copper phthalocyanine are green. 154: 1149: 846: 683:This hypothesis is consistent with the name of 66: 1793:"Re: [Histonet] Dry Stains Shelf Life" 1681: 1679: 1375: 1105: 603:After the interim crisis since the 1970s when 493:"). Alcian blue staining can be combined with 2111: 1750:Green, Marie R.; Pastewka, Jullia V. (1974). 1749: 600:that ICI also had just stopped producing it. 1506: 1289: 1756:Journal of Histochemistry and Cytochemistry 1676: 1078: 1007:—one of the editors of the 10th edition of 2118: 2104: 2052: 1477: 814:Absorption maximum affected by aggregation 207: 132: 110: 2078: 1925: 1767: 1566:. Oxford University Press. Archived from 1450: 1448: 1446: 1252:. Springer Science & Business Media. 966: 640:whose name comes from a Greek myth where 460:and other body structures, some types of 174: 1378:"Alcian blue 8GS: a new stain for mucin" 843:are used, that make exogenous micelles. 628: 625:Etymology and capitalization of "Alcian" 577:derivatives had led to the discovery of 541: 391: 1907: 1878: 1685: 1546:Elsevier's dictionary of chemoetymology 1488:(5th ed.). Headword "alcian blue". 1096: 867:and the analogous Schiff bases used in 203: 2545: 2417:Jaswant Singh–Bhattacharji (JSB) stain 1714: 1655: 1643:"Stainsfile - Compare phthalocyanines" 1483: 1443: 1239: 1009:Conn's Biological Stains" 10th ed 2002 797:aggregates, Alcian blue is apparently 758: 123: 2099: 1406: 1245: 235:Key: KDXHLJMVLXJXCW-UHFFFAOYSA-J 1512: 2018:. Academic Press. 22 October 2008. 1790: 1050:Explanation of staining selectivity 956:itself are blue, but brominated or 898:octanol-water Partition coefficient 793:due to switching from monomeric to 253:Key: KDXHLJMVLXJXCW-XBHQNQODAQ 145: 13: 2494:Grocott's methenamine silver stain 1304:10.1111/j.1600-0722.1996.tb00038.x 1087: 679:(ine) with a phonetic respelling". 671:"1940s: Alcian perhaps from (phth) 14: 2579: 2127:Microbial and histological stains 2036: 1292:European Journal of Oral Sciences 1116:Uses other than as a dye or stain 958:chlorinated copper phthalocyanine 777:Unlike tricyclic thiazines (e.g. 1927:10.1111/j.1478-4408.2006.00009.x 1275:March 1989 vol. 35 no. 3 374–379 1131: 911: 405: 358: 316: 307: 301: 29: 2006: 1971: 1942: 1901: 1872: 1846: 1803: 1784: 1743: 1708: 1649: 1635: 1592: 1574: 1552: 1537: 1249:Stains and Cytochemical Methods 1028:pyridine variant of alcian blue 987:Electrolyte controlled staining 773:Paradoxic lack of Metachromasia 719:Conn's Biological Stains Manual 452:acidic polysaccharides such as 354:(at 25 °C , 100 kPa). 1656:Sabnis, R. W. (7 April 2010). 1400: 1369: 1351: 1333: 1318: 1266: 1246:Hayat, M. A. (31 March 1993). 322: 313: 295: 1: 1549:. Amsterdam: Elsevier. p. 11. 1232: 1111:Drug interference in staining 936:) with three or four pendent 882: 831:of slightly greenish blue or 2053:Whiteman P (February 1973). 1888:Special Stains and H & E 1879:Horobin, Richard W. (2010). 1695:Special Stains and H & E 1686:Horobin, Richard W. (2010). 1456:"Three Dyes, Three Dilemmas" 1202:Imperial Chemical Industries 1150:Gelling or lubricating agent 998: 919: 847:Molar extinction coefficient 569:found to coat the inside of 7: 1908:Kiernan, J A (2006-02-01). 1161: 1123: 1106:Uses in biological staining 1013:Biological Stain Commission 1011:published on behalf of the 723:Biological Stain Commission 721:published on behalf of the 10: 2584: 2220:Periodic acid–Schiff stain 1957:Lifeline Cell Technologies 1582:"Alcian green, 37370-50-6" 1522:, Elsevier, archived from 1498:: CS1 maint: postscript ( 1465:. Anatech Ltd. Autumn 2001 560: 15: 2514: 2399: 2339: 2251: 2228: 2200: 2155: 2133: 2028:– via Google Books. 1992:10.3109/10520298609110719 1824:10.3109/10520290009066493 1729:10.3109/10520298109067298 1672:– via Google Books. 1662:. John Wiley & Sons. 1601:The Histochemical Journal 1564:Oxford English Dictionary 1543:Alexander Senning. 2007. 1262:– via Google Books. 1058:preferably stains acidic 715:thin layer chromatography 348: 282: 262: 219: 50: 42: 37: 28: 2362:Light Green SF yellowish 2353:Masson's trichrome stain 2312:Auramine–rhodamine stain 1484:Parker, SP, ed. (1994), 1079:Manufacturing and purity 863:, tryarylmethanes (e.g. 763: 573:vessels used to process 1376:Steedman H. F. (1950). 979:intensify the stain of 526:Dimethyl methylene blue 510:microspectrophotometric 2479:Schaeffer–Fulton stain 2449:Gömöri trichrome stain 1178:Phthalocyanine Green G 1173:Phthalocyanine Blue BN 967:pH controlled staining 649: 557: 528:(DMB or DMMB) method. 397: 2454:Luxol fast blue stain 2329:Auramine phenol stain 1914:Coloration Technology 1570:on February 26, 2018. 1222:Intestinal metaplasia 954:copper phthalocyanine 851:Alcians blue carries 632: 545: 522:mucopolysaccharidosis 395: 2553:Carbohydrate methods 2499:Warthin–Starry stain 2372:Phosphomolybdic acid 1329:: 59–60. March 1948. 1097:Uses in Dye Industry 653:chemoetymology, the 2515:Tissue stainability 2287:Ziehl–Neelsen stain 2147:Perls Prussian blue 2043:Histological Stains 1797:www.histosearch.com 1069:Phthalocyanine Blue 829:complementary color 759:Physical properties 667:and also specifies 555:Barrett's esophagus 514:polyacrylamide gels 474:electron microscopy 462:mucopolysaccharides 344: g·mol 25: 2489:Bielschowsky stain 2391:Van Gieson's stain 2357:Lillie's trichrome 1613:10.1007/BF01012530 1421:10.1007/BF00274974 1382:Q. J. Microsc. Sci 1327:The I.C.I. Journal 1273:Clinical Chemistry 1060:glycosaminoglycans 650: 558: 454:glycosaminoglycans 398: 381:Infobox references 24:Alcian blue stain 23: 18:Alcian Blue (band) 16:For the band, see 2540: 2539: 2341:Connective tissue 2071:10.1042/bj1310343 1959:. 15 January 2008 1812:Biotech Histochem 1791:Kiernan, John A. 1207:Glycosaminoglycan 801:. In common with 789:etc.), which are 735:having neither a 549:highlighting the 547:Alcian blue stain 389:Chemical compound 387: 386: 188:CompTox Dashboard 92:Interactive image 2575: 2367:Biebrich scarlet 2120: 2113: 2106: 2097: 2096: 2092: 2082: 2030: 2029: 2010: 2004: 2003: 1980:Stain Technology 1975: 1969: 1968: 1966: 1964: 1954: 1946: 1940: 1939: 1929: 1905: 1899: 1898: 1896: 1895: 1885: 1876: 1870: 1869: 1859: 1850: 1844: 1843: 1807: 1801: 1800: 1788: 1782: 1781: 1771: 1769:10.1177/22.8.774 1747: 1741: 1740: 1717:Stain Technology 1712: 1706: 1705: 1703: 1702: 1692: 1683: 1674: 1673: 1653: 1647: 1646: 1639: 1633: 1632: 1596: 1590: 1589: 1578: 1572: 1571: 1556: 1550: 1541: 1535: 1534: 1532: 1531: 1510: 1504: 1503: 1497: 1489: 1481: 1475: 1474: 1472: 1470: 1460: 1452: 1441: 1440: 1404: 1398: 1397: 1373: 1367: 1366: 1365: 1361: 1355: 1349: 1348: 1347: 1343: 1337: 1331: 1330: 1322: 1316: 1315: 1287: 1276: 1270: 1264: 1263: 1243: 1038: 981:hyaluronic acids 857:molar extinction 495:H&E staining 485:(comparable to " 431: 430: 427: 426: 423: 420: 417: 414: 411: 371: 365: 362: 361: 343: 341: 324: 318: 315: 309: 303: 297: 290:Chemical formula 212: 211: 196: 194: 178: 158: 147: 136: 125: 114: 94: 70: 33: 26: 22: 2583: 2582: 2578: 2577: 2576: 2574: 2573: 2572: 2563:Phthalocyanines 2543: 2542: 2541: 2536: 2510: 2395: 2349:trichrome stain 2335: 2247: 2224: 2196: 2151: 2129: 2124: 2039: 2034: 2033: 2026: 2012: 2011: 2007: 1976: 1972: 1962: 1960: 1952: 1948: 1947: 1943: 1906: 1902: 1893: 1891: 1883: 1877: 1873: 1857: 1851: 1847: 1808: 1804: 1789: 1785: 1748: 1744: 1713: 1709: 1700: 1698: 1690: 1684: 1677: 1670: 1654: 1650: 1641: 1640: 1636: 1597: 1593: 1586:www.chemnet.com 1580: 1579: 1575: 1558: 1557: 1553: 1542: 1538: 1529: 1527: 1511: 1507: 1491: 1490: 1482: 1478: 1468: 1466: 1458: 1454: 1453: 1444: 1405: 1401: 1374: 1370: 1363: 1357: 1356: 1352: 1345: 1339: 1338: 1334: 1325:"Alcian Blue". 1324: 1323: 1319: 1288: 1279: 1271: 1267: 1260: 1244: 1240: 1235: 1183:Luxol fast blue 1164: 1152: 1134: 1126: 1118: 1113: 1108: 1099: 1090: 1088:Material safety 1081: 1052: 1034: 1022: 1005:John A. Kiernan 1001: 994: 989: 969: 922: 914: 885: 849: 816: 775: 766: 761: 749:Luxol fast blue 703:kingfisher bird 627: 563: 483:"Alcianophilic" 408: 404: 390: 383: 378: 377: 376: ?) 367: 363: 359: 355: 339: 337: 327: 321: 312: 306: 300: 292: 278: 275: 270: 269: 258: 255: 254: 251: 245: 244: 237: 236: 233: 227: 226: 215: 197: 190: 181: 161: 148: 117: 97: 84: 73: 60: 46: 21: 12: 11: 5: 2581: 2571: 2570: 2565: 2560: 2555: 2538: 2537: 2535: 2534: 2529: 2524: 2518: 2516: 2512: 2511: 2509: 2508: 2506:Wright's stain 2503: 2502: 2501: 2496: 2491: 2481: 2476: 2471: 2466: 2461: 2456: 2451: 2446: 2441: 2436: 2435: 2434: 2429: 2419: 2414: 2409: 2403: 2401: 2397: 2396: 2394: 2393: 2387: 2386: 2385: 2384: 2379: 2377:Fast Green FCF 2374: 2369: 2364: 2345: 2343: 2337: 2336: 2334: 2333: 2332: 2331: 2326: 2325: 2324: 2319: 2309: 2308: 2307: 2305:Methylene blue 2302: 2296:Carbol fuchsin 2279: 2278: 2277: 2272: 2270:Gentian violet 2257: 2255: 2249: 2248: 2246: 2245: 2240: 2234: 2232: 2226: 2225: 2223: 2222: 2217: 2212: 2206: 2204: 2198: 2197: 2195: 2194: 2193: 2192: 2187: 2182: 2177: 2172: 2161: 2159: 2153: 2152: 2150: 2149: 2143: 2141: 2131: 2130: 2123: 2122: 2115: 2108: 2100: 2094: 2093: 2050: 2045: 2038: 2037:External links 2035: 2032: 2031: 2024: 2005: 1986:(2): 121–123. 1970: 1941: 1900: 1871: 1845: 1802: 1783: 1762:(8): 774–781. 1742: 1723:(2): 129–131. 1707: 1675: 1668: 1648: 1634: 1607:(5): 391–399. 1591: 1573: 1551: 1536: 1505: 1476: 1442: 1415:(4): 379–380. 1399: 1388:(4): 477–479. 1368: 1350: 1332: 1317: 1277: 1265: 1258: 1237: 1236: 1234: 1231: 1230: 1229: 1227:Diaphonization 1224: 1219: 1214: 1209: 1204: 1199: 1198: 1197: 1190:Isothiouronium 1187: 1186: 1185: 1180: 1175: 1168:Phthalocyanine 1163: 1160: 1151: 1148: 1133: 1130: 1125: 1122: 1117: 1114: 1112: 1109: 1107: 1104: 1098: 1095: 1089: 1086: 1080: 1077: 1073:toluidine blue 1065:toluidine blue 1051: 1048: 1020: 1000: 997: 992: 988: 985: 968: 965: 946:phthalocyanine 938:isothiouronium 930:phthalocyanine 921: 918: 913: 910: 884: 881: 873:Crystal violet 865:pararosaniline 861:toluidine blue 853:Phthalocyanine 848: 845: 815: 812: 808:orthochromatic 799:orthochromatic 783:methylene blue 779:toluidine blue 774: 771: 765: 762: 760: 757: 745:phthalocyanine 737:phthalocyanine 681: 680: 660:phthalocyanine 626: 623: 622: 621: 588:ingrain dyeing 579:Phthalocyanine 562: 559: 537: 536: 468:dyes for both 438:Ingrain blue 1 434:Alcian blue 8G 388: 385: 384: 379: 357: 356: 352:standard state 349: 346: 345: 335: 329: 328: 325: 319: 310: 304: 298: 293: 288: 285: 284: 280: 279: 277: 276: 273: 265: 264: 263: 260: 259: 257: 256: 252: 249: 248: 246: 241: 240: 238: 234: 231: 230: 222: 221: 220: 217: 216: 214: 213: 205:DTXSID60388977 200: 198: 186: 183: 182: 180: 179: 171: 169: 163: 162: 160: 159: 151: 149: 141: 138: 137: 127: 119: 118: 116: 115: 107: 105: 99: 98: 96: 95: 87: 85: 78: 75: 74: 72: 71: 63: 61: 56: 53: 52: 48: 47: 44: 40: 39: 35: 34: 9: 6: 4: 3: 2: 2580: 2569: 2568:Staining dyes 2566: 2564: 2561: 2559: 2556: 2554: 2551: 2550: 2548: 2533: 2530: 2528: 2525: 2523: 2520: 2519: 2517: 2513: 2507: 2504: 2500: 2497: 2495: 2492: 2490: 2487: 2486: 2485: 2482: 2480: 2477: 2475: 2472: 2470: 2469:Movat's stain 2467: 2465: 2464:Moeller stain 2462: 2460: 2457: 2455: 2452: 2450: 2447: 2445: 2442: 2440: 2439:Janus Green B 2437: 2433: 2430: 2428: 2425: 2424: 2423: 2422:H&E stain 2420: 2418: 2415: 2413: 2410: 2408: 2407:Cresyl violet 2405: 2404: 2402: 2398: 2392: 2389: 2388: 2383: 2380: 2378: 2375: 2373: 2370: 2368: 2365: 2363: 2360: 2359: 2358: 2354: 2350: 2347: 2346: 2344: 2342: 2338: 2330: 2327: 2323: 2320: 2318: 2315: 2314: 2313: 2310: 2306: 2303: 2301: 2297: 2294: 2293: 2292: 2291:Kinyoun stain 2288: 2285: 2284: 2283: 2280: 2276: 2273: 2271: 2267: 2266:Methyl violet 2264: 2263: 2262: 2259: 2258: 2256: 2254: 2250: 2244: 2241: 2239: 2236: 2235: 2233: 2231: 2227: 2221: 2218: 2216: 2213: 2211: 2208: 2207: 2205: 2203: 2202:Carbohydrates 2199: 2191: 2190:Sudan Black B 2188: 2186: 2183: 2181: 2178: 2176: 2173: 2171: 2168: 2167: 2166: 2163: 2162: 2160: 2158: 2154: 2148: 2145: 2144: 2142: 2140: 2136: 2132: 2128: 2121: 2116: 2114: 2109: 2107: 2102: 2101: 2098: 2090: 2086: 2081: 2076: 2072: 2068: 2065:(2): 343–50. 2064: 2060: 2056: 2051: 2049: 2046: 2044: 2041: 2040: 2027: 2025:9780080888163 2021: 2017: 2016: 2009: 2001: 1997: 1993: 1989: 1985: 1981: 1974: 1958: 1951: 1945: 1937: 1933: 1928: 1923: 1919: 1915: 1911: 1904: 1889: 1882: 1875: 1867: 1863: 1856: 1849: 1841: 1837: 1833: 1829: 1825: 1821: 1818:(3): 147–50. 1817: 1813: 1806: 1798: 1794: 1787: 1779: 1775: 1770: 1765: 1761: 1757: 1753: 1746: 1738: 1734: 1730: 1726: 1722: 1718: 1711: 1696: 1689: 1682: 1680: 1671: 1669:9780470586235 1665: 1661: 1660: 1652: 1644: 1638: 1630: 1626: 1622: 1618: 1614: 1610: 1606: 1602: 1595: 1587: 1583: 1577: 1569: 1565: 1561: 1560:"Alcian blue" 1555: 1548: 1547: 1540: 1526:on 2014-01-11 1525: 1521: 1520: 1515: 1509: 1501: 1495: 1487: 1480: 1464: 1463:The Innovator 1457: 1451: 1449: 1447: 1438: 1434: 1430: 1426: 1422: 1418: 1414: 1410: 1403: 1395: 1391: 1387: 1383: 1379: 1372: 1360: 1354: 1342: 1336: 1328: 1321: 1313: 1309: 1305: 1301: 1297: 1293: 1286: 1284: 1282: 1274: 1269: 1261: 1259:9780306442940 1255: 1251: 1250: 1242: 1238: 1228: 1225: 1223: 1220: 1218: 1215: 1213: 1210: 1208: 1205: 1203: 1200: 1196: 1195:Alcian Yellow 1193: 1192: 1191: 1188: 1184: 1181: 1179: 1176: 1174: 1171: 1170: 1169: 1166: 1165: 1159: 1157: 1147: 1144: 1143:polyornithine 1140: 1139:poly-L-lysine 1132:Coating agent 1129: 1121: 1103: 1094: 1085: 1076: 1074: 1070: 1066: 1061: 1056: 1055:Nucleic acids 1047: 1045: 1042: 1039:, CB6503730, 1037: 1033: 1029: 1024: 1017: 1014: 1010: 1006: 1003:According to 996: 984: 982: 978: 974: 964: 961: 959: 955: 950: 947: 942: 939: 935: 931: 927: 917: 912:Melting point 909: 907: 903: 899: 895: 891: 880: 878: 874: 870: 866: 862: 858: 854: 844: 842: 838: 834: 830: 825: 821: 811: 809: 804: 800: 796: 792: 791:metachromatic 788: 784: 780: 770: 756: 754: 750: 747:dyes such as 746: 742: 738: 734: 730: 729:Alcian yellow 726: 724: 720: 716: 712: 711:Alcian yellow 708: 704: 700: 699: 694: 688: 686: 678: 674: 670: 669: 668: 666: 662: 661: 656: 647: 643: 639: 637: 631: 619: 615: 614:Alcian yellow 611: 610: 609: 606: 601: 597: 594: 590: 589: 584: 580: 576: 575:phthalic acid 572: 568: 567:Monstral blue 556: 552: 548: 544: 540: 534: 533: 532: 529: 527: 523: 519: 518:western blots 515: 511: 507: 504: 500: 496: 492: 488: 484: 479: 475: 471: 467: 463: 459: 455: 451: 447: 443: 439: 436:(also called 435: 429: 402: 394: 382: 375: 370: 353: 347: 336: 334: 331: 330: 294: 291: 287: 286: 281: 272: 271: 268: 261: 247: 239: 229: 228: 225: 218: 210: 206: 202: 201: 199: 189: 185: 184: 177: 173: 172: 170: 168: 165: 164: 157: 153: 152: 150: 144: 140: 139: 135: 131: 128: 126: 124:ECHA InfoCard 121: 120: 113: 109: 108: 106: 104: 101: 100: 93: 89: 88: 86: 82: 77: 76: 69: 65: 64: 62: 59: 55: 54: 49: 41: 36: 32: 27: 19: 2532:Chromophobic 2484:Silver stain 2444:Giemsa stain 2427:Haematoxylin 2209: 2062: 2058: 2014: 2008: 1983: 1979: 1973: 1961:. Retrieved 1956: 1944: 1917: 1913: 1903: 1892:. Retrieved 1887: 1874: 1865: 1861: 1848: 1815: 1811: 1805: 1796: 1786: 1759: 1755: 1745: 1720: 1716: 1710: 1699:. Retrieved 1694: 1658: 1651: 1637: 1604: 1600: 1594: 1585: 1576: 1568:the original 1563: 1554: 1545: 1539: 1528:, retrieved 1524:the original 1518: 1508: 1485: 1479: 1467:. Retrieved 1462: 1412: 1408: 1402: 1385: 1381: 1371: 1353: 1335: 1326: 1320: 1295: 1291: 1272: 1268: 1248: 1241: 1212:Proteoglycan 1153: 1135: 1127: 1119: 1100: 1091: 1082: 1053: 1025: 1008: 1002: 990: 977:uronic acids 973:sialic acids 970: 962: 951: 943: 928:distortion) 923: 915: 886: 850: 841:Triton X-100 822:together as 817: 776: 767: 753:Durazol blue 727: 718: 697: 696: 689: 685:Alcian green 682: 676: 672: 658: 654: 651: 646:Halcyon Days 635: 618:basic red 18 602: 598: 587: 586: 564: 551:goblet cells 546: 538: 530: 499:PAS staining 491:sudanophilic 487:eosinophilic 482: 441: 437: 433: 400: 399: 51:Identifiers 43:Other names 2522:Acidophilic 2474:Neutral red 2459:Methyl blue 2322:Rhodamine B 2215:Mucicarmine 2210:Alcian blue 2165:Sudan stain 2139:hemosiderin 2048:Stains File 1963:25 February 1920:(1): 1–21. 1469:25 February 1409:Histochemie 1036:123439-83-8 926:Jahn–Teller 906:isopropanol 741:thiouronium 693:old English 638:Kingfishers 633:One of the 583:chromophore 401:Alcian blue 283:Properties 130:100.046.990 2547:Categories 2527:Basophilic 2382:Sirius Red 2317:Auramine O 2261:Gram stain 2243:Thioflavin 2059:Biochem. J 1894:2018-02-26 1868:: 789–797. 1701:2018-02-26 1530:2014-05-14 1298:(1): 2–9. 1233:References 1158:compound. 894:Cellosolve 892:, 6.0% in 883:Solubility 877:Gram stain 803:Astra blue 503:van Gieson 458:cartilages 442:C.I. 74240 333:Molar mass 176:P4448TJR7J 103:ChemSpider 79:3D model ( 68:33864-99-2 58:CAS Number 2282:Acid-fast 2238:Congo red 2185:Oil Red O 2175:Sudan III 1936:1478-4408 1359:GB 587636 1341:GB 586340 999:Stability 932:nucleus ( 920:Chemistry 869:PAS stain 707:calm seas 665:trademark 478:histology 2558:Staining 2300:Fuchsine 2275:Safranin 2253:Bacteria 2180:Sudan IV 2170:Sudan II 1840:39534882 1832:10950177 1514:Elsevier 1494:citation 1437:35634762 1394:24540170 1162:See also 1156:aromatic 1124:Adhesive 1044:24860335 902:Methanol 824:micelles 506:staining 466:cationic 450:to stain 2432:Eosin Y 2412:Cyanine 2230:Amyloid 2089:4269149 2080:1177474 2000:3520961 1778:4137192 1737:6166095 1629:8999433 1621:4119152 1429:4780463 1312:8653492 1041:PubChem 890:ethanol 879:) etc. 795:stacked 787:azure A 733:azo dye 698:halcyon 642:Alcyone 636:Halcyon 561:History 374:what is 372: ( 156:3084579 143:PubChem 112:2341620 2157:Lipids 2087: 2077: 2022: 1998: 1934: 1838: 1830: 1776: 1735: 1666: 1627: 1619: 1435: 1427: 1392: 1364: 1346: 1310: 1256: 731:is an 695:word " 655:Alcian 616:' and 571:copper 516:or on 489:" or " 440:, and 369:verify 366: 267:SMILES 38:Names 2400:Other 1953:(PDF) 1884:(PDF) 1858:(PDF) 1836:S2CID 1691:(PDF) 1625:S2CID 1459:(PDF) 1433:S2CID 1217:Mucin 1137:like 820:stack 764:Color 677:cyan' 470:light 224:InChI 81:JSmol 2135:Iron 2085:PMID 2020:ISBN 1996:PMID 1965:2018 1932:ISSN 1828:PMID 1774:PMID 1733:PMID 1664:ISBN 1617:PMID 1500:link 1471:2018 1425:PMID 1390:PMID 1308:PMID 1254:ISBN 1026:The 975:and 944:The 934:CuPc 837:DMSO 833:cyan 785:and 751:and 705:and 565:The 501:and 472:and 167:UNII 2075:PMC 2067:doi 2063:131 1988:doi 1922:doi 1918:122 1820:doi 1764:doi 1725:doi 1609:doi 1417:doi 1300:doi 1296:104 1141:or 1032:CAS 875:in 675:(o) 605:ICI 593:ICI 553:of 456:in 446:ICI 342:.86 340:298 193:EPA 146:CID 2549:: 2351:: 2083:. 2073:. 2061:. 2057:. 1994:. 1984:61 1982:. 1955:. 1930:. 1916:. 1912:. 1864:. 1860:. 1834:. 1826:. 1816:75 1814:. 1795:. 1772:. 1760:22 1758:. 1754:. 1731:. 1721:56 1719:. 1678:^ 1623:. 1615:. 1603:. 1584:. 1562:. 1516:, 1496:}} 1492:{{ 1461:. 1445:^ 1431:. 1423:. 1413:37 1411:. 1386:91 1384:. 1380:. 1306:. 1294:. 1280:^ 1023:. 871:, 781:, 725:. 673:al 497:, 320:16 314:Cu 308:Cl 305:68 299:56 2355:/ 2298:/ 2289:/ 2268:/ 2137:/ 2119:e 2112:t 2105:v 2091:. 2069:: 2002:. 1990:: 1967:. 1938:. 1924:: 1897:. 1866:4 1842:. 1822:: 1799:. 1780:. 1766:: 1739:. 1727:: 1704:. 1645:. 1631:. 1611:: 1605:4 1588:. 1533:. 1502:) 1473:. 1439:. 1419:: 1396:. 1314:. 1302:: 1021:2 993:2 648:. 428:/ 425:n 422:ə 419:ʃ 416:l 413:æ 410:ˈ 407:/ 403:( 364:Y 338:1 326:4 323:S 317:N 311:4 302:H 296:C 195:) 191:( 83:) 20:.

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