The amide hydrogen of (-)-indolactam-V and benzolactam-V8's plays a critical role in protein kinase C binding and tumor-promoting activities.

Y Nakagawa, K Irie, Y Nakamura, H Ohigashi

Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Japan.

Bioorganic & medicinal chemistry letters 2001 Mar 12

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To investigate the role of the amide hydrogen of (-)-indolactam-V (1) and benzolactam-V8's on protein kinase C (PKC) binding and tumor promotion, 8-decylbenzolactone-V8 (6), a new lactone analogue of 8-decylbenzolactam-V8 (4), was synthesized from 2-nitrophenylpyruvic acid (7) in 11 steps. The PKC binding ability and tumor-promoting activities in vitro of 6 were much lower than those of 1 and 4, suggesting that the amide hydrogen of 1 and benzolactam-V8's plays a critical role in tumor promotion. However, it is noteworthy that 6 showed significant selectivity in the PKC isozyme surrogate binding.

Citation

Y Nakagawa, K Irie, Y Nakamura, H Ohigashi. The amide hydrogen of (-)-indolactam-V and benzolactam-V8's plays a critical role in protein kinase C binding and tumor-promoting activities. Bioorganic & medicinal chemistry letters. 2001 Mar 12;11(5):723-8