Knowledge

12-O-Tetradecanoylphorbol-13-acetate

Source 📝

39: 356: 239: 482: 149: 156: 628:
reactivation in PEL cell cultures via stimulation of the mitogen-activated protein kinase (MAPK)/extracellular signal-regulated kinase (ERK) pathway. The pathway involves the activation of the early-immediate viral protein RTA that contributes to the activation of the lytic cycle.
799:"A Comparison of Reactive Oxygen Species Generation by Rat Peritoneal Macrophages and Mast Cells Using the Highly Sensitive Real-Time Chemiluminescent Probe Pholasin: Inhibition of Antigen-Induced Mast Cell Degranulation by Macrophage-Derived Hydrogen Peroxide" 990:
Schaar, Dale; Goodell, Lauri; Aisner, Joseph; Cui, Xiao Xing; Han, Zheng Tao; Chang, Richard; Martin, John; Grospe, Stephanie; Dudek, Liesel; Riley, Joan; Manago, Jacqueline; Lin, Yong; Rubin, Eric H.; Conney, Allan; Strair, Roger K. (June 2006).
379:
InChI=1S/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1
389:
InChI=1/C36H56O8/c1-7-8-9-10-11-12-13-14-15-16-17-18-29(39)43-32-24(3)35(42)27(30-33(5,6)36(30,32)44-25(4)38)20-26(22-37)21-34(41)28(35)19-23(2)31(34)40/h19-20,24,27-28,30,32,37,41-42H,7-18,21-22H2,1-6H3/t24-,27+,28-,30-,32-,34-,35-,36-/m1/s1
610:
testing. Cells must be divided in a cytogenic test to view the chromosomes. TPA is used to stimulate division of B-cells during cytogenetic diagnosis of B-cell cancers such as
945:
Cohen, Adina; Brodie, Chaya; Sarid, Ronit (April 2006). "An essential role of ERK signalling in TPA-induced reactivation of Kaposi's sarcoma-associated herpesvirus".
924: 17: 495: 742: 621:
to stimulate T-cell activation, proliferation, and cytokine production, and is used in protocols for intracellular staining of these cytokines.
490: 405: 625: 707:
Blumberg (1988). "Protein kinase C as the receptor for the phorbol ester tumor promoters: sixth Rhoads memorial award lecture".
257: 993:"A phase I clinical trial of 12- O-tetradecanoylphorbol-13-acetate for patients with relapsed/refractory malignancies" 559:(PKC). The effects of TPA on PKC result from its similarity to one of the natural activators of classic PKC isoforms, 370: 853:"Megakaryocytic Differentiation of K562 Cells Induced by PMA Reduced the Activity of Respiratory Chain Complex IV" 502: 670: 663:"Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters" 611: 313: 234: 334: 196: 1049: 806: 709: 959: 1053: 351: 88:)-4a,7b-Dihydroxy-3-(hydroxymethyl)-1,1,6,8-tetramethyl-5-oxo-1,1a,1b,4,4a,5,7a,7b,8,9-decahydro-9a 38: 1122: 1107: 571: 1117: 1112: 954: 992: 914:. 3rd ed. Barch, Margaret J., Knutsen, Turid., Spurbeck, Jack L., eds. 1997. Lippincott-Raven. 1102: 866: 751: 322: 216: 125: 51: 8: 1097: 582:
in mouse macrophages. Thus, TPA/PMA has been routinely used as an inducer for endogenous
550: 115: 870: 755: 355: 238: 176: 1028: 889: 852: 833: 798: 774: 737: 684: 1074: 1020: 1012: 972: 894: 825: 779: 718: 689: 1032: 837: 1004: 964: 884: 874: 815: 769: 759: 679: 556: 433: 662: 578:
was identified as the major reactive oxygen species induced by TPA/PMA but not by
302: 879: 820: 546: 1060: 641: 633: 564: 473: 1008: 1091: 1016: 917: 227: 1024: 976: 898: 829: 607: 418:
CCCCCCCCCCCCCC(=O)O2C(C)1(O)C4/C=C(/C)C(=O)4(O)CC(\CO)=C/132(OC(C)=O)C3(C)C
968: 783: 722: 693: 764: 560: 637: 594: 590: 583: 575: 461: 247: 207: 636:
plant, a shrub found in Southeast Asia, exposure to which provokes a
618: 579: 413:
CCCCCCCCCCCCCC(=O)O1(2((C=C(C3(2C=C(C3=O)C)O)CO)41(C4(C)C)OC(=O)C)O)C
472:
Except where otherwise noted, data are given for materials in their
857: 277: 602:
TPA has a specific use in cancer diagnostics as a B-cell specific
155: 148: 603: 542: 289: 597: 553: 187: 167: 138: 92:-cyclopropabenzoazulene-9,9a-diyl 9a-acetate 9-tetradecanoate 339: 738:"Phorbol Diester Receptor Copurifies with Protein Kinase C" 268: 989: 549:
often employed in biomedical research to activate the
256: 1089: 944: 301: 743:Proceedings of the National Academy of Sciences 124: 925:"Flow Cytometry Intracellular Staining Guide" 354: 237: 215: 1052:at the U.S. National Library of Medicine 958: 888: 878: 819: 773: 763: 683: 321: 706: 660: 617:TPA is also commonly used together with 796: 350: 14: 1090: 912:The AGT cytogenetics laboratory manual 735: 228: 850: 382:Key: PHEDXBVPIONUQT-RGYGYFBISA-N 195: 175: 997:Cancer Chemotherapy and Pharmacology 101:TPA, PMA, Phorbol myristate acetate, 18:12-O-tetradecanoylphorbol-13-acetate 640:-like rash. It underwent a phase 1 392:Key: PHEDXBVPIONUQT-RGYGYFBIBK 292: 276: 24: 25: 1134: 1043: 32:-Tetradecanoylphorbol-13-acetate 519:-Tetradecanoylphorbol-13-acetate 480: 445: 37: 947:The Journal of General Virology 671:Journal of Biological Chemistry 589:TPA is also being studied as a 535:phorbol 12-myristate 13-acetate 476:(at 25 °C , 100 kPa). 983: 938: 905: 844: 790: 729: 700: 654: 451: 439: 13: 1: 685:10.1016/S0021-9258(18)34459-4 647: 531:tetradecanoyl phorbol acetate 103:Tetradecanoylphorbol acetate. 1050:Tetradecanoylphorbol+Acetate 880:10.1371/journal.pone.0096246 821:10.4049/jimmunol.169.10.5866 612:chronic lymphocytic leukemia 527:tetradecanoylphorbol acetate 7: 632:TPA was first found in the 10: 1139: 525:), also commonly known as 466:616.83 g/mol 1075:"Phase 1 Clinical Trials" 1009:10.1007/s00280-005-0125-1 807:The Journal of Immunology 470: 426: 401: 366: 108: 98: 50: 45: 36: 1054:Medical Subject Headings 1061:"NCI Dictionary Entry" 969:10.1099/vir.0.81619-0 765:10.1073/pnas.80.1.36 593:in the treatment of 52:Preferred IUPAC name 871:2014PLoSO...996246H 756:1983PNAS...80...36N 551:signal transduction 33: 927:. eBioscience, Inc 541:) is a diester of 503:Infobox references 27: 953:(Pt 4): 795–802. 814:(10): 5866–5873. 678:(13): 7847–7851. 661:Castagna (1982). 545:. It is a potent 511:Chemical compound 509: 508: 335:CompTox Dashboard 157:Interactive image 150:Interactive image 16:(Redirected from 1130: 1084: 1082: 1081: 1070: 1068: 1067: 1037: 1036: 987: 981: 980: 962: 942: 936: 935: 933: 932: 921: 915: 909: 903: 902: 892: 882: 848: 842: 841: 823: 803: 797:Swindle (2002). 794: 788: 787: 777: 767: 733: 727: 726: 704: 698: 697: 687: 667: 658: 557:protein kinase C 493: 487: 484: 483: 453: 447: 441: 434:Chemical formula 359: 358: 343: 341: 325: 305: 294: 280: 260: 241: 230: 219: 199: 179: 159: 152: 128: 41: 34: 26: 21: 1138: 1137: 1133: 1132: 1131: 1129: 1128: 1127: 1088: 1087: 1079: 1077: 1073: 1065: 1063: 1059: 1046: 1041: 1040: 988: 984: 960:10.1.1.321.5484 943: 939: 930: 928: 923: 922: 918: 910: 906: 849: 845: 801: 795: 791: 736:Niedel (1983). 734: 730: 710:Cancer Research 705: 701: 665: 659: 655: 650: 512: 505: 500: 499: 498:  ?) 489: 485: 481: 477: 456: 450: 444: 436: 422: 419: 414: 409: 408: 397: 394: 393: 390: 384: 383: 380: 374: 373: 362: 344: 337: 328: 308: 295: 283: 263: 250: 222: 202: 182: 162: 142: 131: 118: 104: 102: 94: 93: 23: 22: 15: 12: 11: 5: 1136: 1126: 1125: 1123:Phorbol esters 1120: 1115: 1110: 1108:Acetate esters 1105: 1100: 1086: 1085: 1071: 1057: 1045: 1044:External links 1042: 1039: 1038: 1003:(6): 789–795. 982: 937: 916: 904: 851:Huang (2014). 843: 789: 728: 699: 652: 651: 649: 646: 642:clinical trial 565:small molecule 561:diacylglycerol 547:tumor promoter 510: 507: 506: 501: 479: 478: 474:standard state 471: 468: 467: 464: 458: 457: 454: 448: 442: 437: 432: 429: 428: 424: 423: 421: 420: 417: 415: 412: 404: 403: 402: 399: 398: 396: 395: 391: 388: 387: 385: 381: 378: 377: 369: 368: 367: 364: 363: 361: 360: 347: 345: 333: 330: 329: 327: 326: 318: 316: 310: 309: 307: 306: 298: 296: 288: 285: 284: 282: 281: 273: 271: 265: 264: 262: 261: 253: 251: 246: 243: 242: 232: 224: 223: 221: 220: 212: 210: 204: 203: 201: 200: 192: 190: 184: 183: 181: 180: 172: 170: 164: 163: 161: 160: 153: 145: 143: 136: 133: 132: 130: 129: 121: 119: 114: 111: 110: 106: 105: 100: 96: 95: 55: 54: 48: 47: 43: 42: 9: 6: 4: 3: 2: 1135: 1124: 1121: 1119: 1118:Cyclopentenes 1116: 1114: 1113:Cyclopropanes 1111: 1109: 1106: 1104: 1101: 1099: 1096: 1095: 1093: 1076: 1072: 1062: 1058: 1055: 1051: 1048: 1047: 1034: 1030: 1026: 1022: 1018: 1014: 1010: 1006: 1002: 998: 994: 986: 978: 974: 970: 966: 961: 956: 952: 948: 941: 926: 920: 913: 908: 900: 896: 891: 886: 881: 876: 872: 868: 865:(5): e96246. 864: 860: 859: 854: 847: 839: 835: 831: 827: 822: 817: 813: 809: 808: 800: 793: 785: 781: 776: 771: 766: 761: 757: 753: 749: 745: 744: 739: 732: 724: 720: 716: 712: 711: 703: 695: 691: 686: 681: 677: 673: 672: 664: 657: 653: 645: 643: 639: 635: 630: 627: 622: 620: 615: 613: 609: 605: 600: 599: 596: 592: 587: 585: 581: 577: 573: 568: 566: 562: 558: 555: 552: 548: 544: 540: 536: 532: 528: 524: 520: 518: 504: 497: 492: 475: 469: 465: 463: 460: 459: 438: 435: 431: 430: 425: 416: 411: 410: 407: 400: 386: 376: 375: 372: 365: 357: 353: 352:DTXSID5023798 349: 348: 346: 336: 332: 331: 324: 320: 319: 317: 315: 312: 311: 304: 300: 299: 297: 291: 287: 286: 279: 275: 274: 272: 270: 267: 266: 259: 255: 254: 252: 249: 245: 244: 240: 236: 233: 231: 229:ECHA InfoCard 226: 225: 218: 214: 213: 211: 209: 206: 205: 198: 194: 193: 191: 189: 186: 185: 178: 174: 173: 171: 169: 166: 165: 158: 154: 151: 147: 146: 144: 140: 135: 134: 127: 123: 122: 120: 117: 113: 112: 107: 97: 91: 87: 83: 79: 75: 71: 67: 63: 59: 53: 49: 44: 40: 35: 31: 19: 1078:. Retrieved 1064:. Retrieved 1000: 996: 985: 950: 946: 940: 929:. Retrieved 919: 911: 907: 862: 856: 846: 811: 805: 792: 750:(1): 36–40. 747: 741: 731: 714: 708: 702: 675: 669: 656: 631: 624:TPA induces 623: 616: 601: 588: 586:production. 569: 538: 534: 530: 526: 522: 516: 514: 513: 197:ChEMBL279115 109:Identifiers 99:Other names 89: 85: 81: 77: 73: 69: 65: 61: 57: 29: 1103:Carcinogens 608:cytogenetic 595:hematologic 563:. TPA is a 427:Properties 235:100.109.485 177:CHEBI:37537 1098:Diterpenes 1092:Categories 1080:2005-07-02 1066:2005-07-02 931:2011-09-25 717:(1): 1–8. 648:References 638:poison ivy 584:superoxide 576:superoxide 462:Molar mass 323:NI40JAQ945 248:IUPHAR/BPS 208:ChemSpider 137:3D model ( 126:16561-29-8 116:CAS Number 1017:1432-0843 955:CiteSeerX 619:ionomycin 580:ionomycin 574:biology, 1033:33377618 1025:16231182 977:16528027 899:24817082 858:PLoS ONE 838:21433304 830:12421969 890:4015910 867:Bibcode 784:6296873 752:Bibcode 723:3275491 694:7085651 604:mitogen 543:phorbol 496:what is 494: ( 290:PubChem 1056:(MeSH) 1031:  1023:  1015:  975:  957:  897:  887:  836:  828:  782:  775:393304 772:  721:  692:  634:Croton 598:cancer 567:drug. 554:enzyme 533:, and 491:verify 488:  406:SMILES 278:C05151 188:ChEMBL 46:Names 1029:S2CID 834:S2CID 802:(PDF) 666:(PDF) 371:InChI 303:27924 217:25977 168:ChEBI 139:JSmol 1021:PMID 1013:ISSN 973:PMID 895:PMID 826:PMID 780:PMID 719:PMID 690:PMID 626:KSHV 591:drug 314:UNII 269:KEGG 258:2341 1005:doi 965:doi 885:PMC 875:doi 816:doi 812:169 770:PMC 760:doi 680:doi 676:257 606:in 572:ROS 570:In 539:PMA 523:TPA 515:12- 340:EPA 293:CID 84:,9a 72:,7b 68:,7a 64:,4a 60:,1b 56:(1a 28:12- 1094:: 1027:. 1019:. 1011:. 1001:57 999:. 995:. 971:. 963:. 951:87 949:. 893:. 883:. 873:. 861:. 855:. 832:. 824:. 810:. 804:. 778:. 768:. 758:. 748:80 746:. 740:. 715:48 713:. 688:. 674:. 668:. 644:. 614:. 529:, 449:56 443:36 80:,9 76:,8 1083:. 1069:. 1035:. 1007:: 979:. 967:: 934:. 901:. 877:: 869:: 863:9 840:. 818:: 786:. 762:: 754:: 725:. 696:. 682:: 537:( 521:( 517:O 486:N 455:8 452:O 446:H 440:C 342:) 338:( 141:) 90:H 86:S 82:R 78:R 74:S 70:S 66:R 62:S 58:R 30:O 20:)

Index

12-O-tetradecanoylphorbol-13-acetate
TPA
Preferred IUPAC name
CAS Number
16561-29-8
JSmol
Interactive image
Interactive image
ChEBI
CHEBI:37537
ChEMBL
ChEMBL279115
ChemSpider
25977
ECHA InfoCard
100.109.485
Edit this at Wikidata
IUPHAR/BPS
2341
KEGG
C05151
PubChem
27924
UNII
NI40JAQ945
CompTox Dashboard
DTXSID5023798
Edit this at Wikidata
InChI
SMILES

Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.