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24:
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backbone is of ether or ester type. Therefore, many studies exploited this sensitivity to explore coexisting lipid domains in dual-wavelength ratio measurements, to detect non-bilayer lipid phases, to map membrane structure changes. However, Prodan presence itself is found to change the structure of
610:
453:). Usually it is concentrated at the surface of the membrane, with some degree of penetration. Excited-state relaxation of prodan is sensitive to whether the linkage between phospholipid hydrocarbon tails and the
496:). Contrariwise, excited-state reduction potential is +1.6 V in the acetonitrile and +0.6 V in water (vs. NHE). Photostability of Prodan and Laurdan in low-polaritry environments is limited due to undergoing an
684:
468:
excitation techniques have been successfully applied. Fluorescence wavelength is highly sensitive to the polarity of the environment. For example, the emission wavelength shifts from 380 nm in
105:
706:
PospĂšil, Petr; Luxem, Katja E.; Ener, Maraia; SĂ˝kora, Jan; Kocábová, Jana; Gray, Harry B.; VlÄŤek, Jr., AntonĂn; Hof, Martin (28 August 2014).
272:
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In proteins, Prodan and Badan are quenched by non-covalent bonding with tryptophan and the oxidation of it by excited Prodan/Badan.
422:
Prodan was proposed as a membrane dye by Weber and Farris in 1979. Since then, multiple derivatives have been introduced, such as
500:
in the excited state, with subsequent reactions with triplet oxygen (this also diminishes its quantum yield, which is 0.95 in
708:"Fluorescence Quenching of (Dimethylamino)naphthalene Dyes Badan and Prodan by Tryptophan in Cytochromes P450 and Micelles"
415:
derivative) used as a membrane probe with environment-sensitive coloration, as well as a non-covalently bonding probe for
759:"Bright and photostable push-pull pyrene dye visualizes lipid order variation between plasma and intracellular membranes"
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Suhaj, Adam; Le Marois, Alix; Williamson, David J.; Suhling, Klaus; Lorenz, Christian D.; Owen, Dylan M. (31 May 2018).
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Niko, Yosuke; Didier, Pascal; Mely, Yves; Konishi, Gen-ichi; Klymchenko, Andrey S. (11 January 2016).
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The
Molecular Probes™ Handbook: A Guide to Fluorescent Probes and Labeling Technologies
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InChI=1S/C15H17NO/c1-4-15(17)13-6-5-12-10-14(16(2)3)8-7-11(12)9-13/h5-10H,4H2,1-3H3
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and consequently high sensibility to the polarity of its environment (solvent or
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Absorption of Prodan lies in the UV range (361 nm in methanol), but
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and a quasi-reversible one at —0.88 in aqueous buffer (pH 7.3) (vs.
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Except where otherwise noted, data are given for materials in their
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692:(11 ed.). Thermo Fisher Scientific. 2010. pp. 579–584.
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627:"PRODAN differentially influences its local environment"
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522:"Prodan (6-Propionyl-2-Dimethylaminonaphthalene)"
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488:shows a reversible reduction peak at —1.85 V in
181:
550:. National Center for Biotechnology Information
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449:, including the physical state of surrounding
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611:Safety Data Sheet. Sigma-Aldrich Co., 2018
575:"N,N-Dimethyl-6-propionyl-2-naphthylamine"
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341:137 °C (279 °F; 410 K)
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632:Physical Chemistry Chemical Physics
441:, Prodan has a large excited-state
280:CCC(=O)C1=CC2=C(C=C1)C=C(C=C2)N(C)C
172:
13:
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713:Journal of Physical Chemistry B
504:but only 0.03 in cyclohexane).
389:(at 25 °C , 100 kPa).
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366:May cause skin/eye irritation
353:Occupational safety and health
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1:
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430:) and thiol-reactive Badan (
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434:derivative) and Acrylodan.
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524:. Thermo Fisher Scientific
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827:Dimethylamino compounds
426:Laurdan (derivative of
474:N,N-dimethylformamide
498:intersystem crossing
37:Preferred IUPAC name
720:(34): 10085–10091.
639:(23): 16060–16066.
331: g·mol
118:Beilstein Reference
18:
764:Scientific Reports
645:10.1039/C8CP00543E
486:Cyclic voltammetry
480:to 520 nm in
476:to 498 nm in
472:to 450 nm in
393:Infobox references
16:
778:10.1038/srep18870
726:10.1021/jp504625d
401:Chemical compound
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372:Safety data sheet
215:CompTox Dashboard
106:Interactive image
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41:1-propan-1-one
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822:Naphthalenes
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656:. Retrieved
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583:. Retrieved
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552:. Retrieved
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490:acetonitrile
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362:Main hazards
351:
65:Identifiers
48:Other names
470:cyclohexane
458:membranes.
428:lauric acid
413:naphthalene
409:fluorescent
356:(OHS/OSH):
289:Properties
138:CHEBI:51909
811:Categories
658:22 October
585:22 October
554:22 October
528:22 October
508:References
466:two-photon
424:lypophilic
324:Molar mass
203:3KRL7R0ZB7
149:ChemSpider
93:3D model (
82:70504-01-7
72:CAS Number
771:: 18870.
797:26750324
744:25079965
653:29850681
544:"Prodan"
478:methanol
455:glycerol
437:Being a
417:proteins
346:Hazards
123:2723587
788:4707542
735:4148165
548:PubChem
502:ethanol
411:dye (a
329:227.307
170:PubChem
17:Prodan
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785:
742:
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405:Prodan
374:(SDS)
273:SMILES
183:107729
53:Prodan
31:Names
690:(PDF)
579:Merck
482:water
407:is a
251:InChI
158:96896
129:ChEBI
95:JSmol
793:PMID
740:PMID
660:2019
649:PMID
587:2019
556:2019
530:2019
194:UNII
783:PMC
773:doi
730:PMC
722:doi
718:118
641:doi
494:NHE
378:SDS
220:EPA
173:CID
813::
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698:^
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317:O
314:N
308:H
302:C
222:)
218:(
97:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
