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- W2536617752 abstract "In the two-stage model of skin carcinogenesis, it is believed that initiators bind to DNA and that tumor promoters such as phorbol 12-tetradecanoate 13-acetate (TPA) bind noncovalently to membrane-associated high-affinity re- ceptors, probably protein kinase C. Two other types of potent tumor-promoting substances, aplysiatoxin and teleocidin, ap- pear to act also by binding to and activating protein kinase C, even though their chemical structures are quite different. Therefore, we have undertaken computer modeling of the spacial relationship of various functional groups In these three chemical classes of tumor promoters in an attempt to explain how these diverse structures bind to the same receptor mole- cule. We propose a stereochemical model in which the oxygens in TPA at C-3, C-4, Cr9, and C-20 (0-3, 0-4, 0-9, and 0-20) correspond to the 0-11, N413, N-1, and 0424 positions In teleocidin and the 0-27, 0-3, 0-11, and 0-30 oxygens in aplysiatoxin, respectively. In this model all distances with respect to overlap of the corresponding atoms are <1 A. In addition, all three types of molecules have their hydrophobic moieties oriented in a similar position. This model is further discussed with respect to other compounds showing various degrees of activity as tumor promoters, including mezerein, ingenol, and 4a-TPA. The model explains how chemically diverse structures can have similar biological activity as tumor promoters and provides a basis for designing both agonists and antagonists of tumor promoters." @default.
- W2536617752 created "2016-10-28" @default.
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- W2536617752 date "2016-01-01" @default.
- W2536617752 modified "2023-09-27" @default.
- W2536617752 title "Computer-assisted molecular modeling of tumor promoters: Rationale for the activity of phorbol esters, teleocidin B, and aplysiatoxin (carcinogenesis/tumor promotion/protein kinase C/mezerein/ingenol)" @default.
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