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Titolo:
Synthesis and tumor-promoting activities of 12-epi-phorbol-12, 13-dibutyrate
Autore:
Irie, K; Nakahara, A; Ikawa, Y; Tanaka, M; Nakagawa, Y; Nakamura, Y; Ohigashi, H; Wender, PA;
Indirizzi:
Kyoto Univ, Grad Sch Agr, Div Appl Life Sci, Kyoto 6068502, Japan Kyoto Univ Kyoto Japan 6068502 , Div Appl Life Sci, Kyoto 6068502, Japan Stanford Univ, Dept Chem, Stanford, CA 94305 USA Stanford Univ Stanford CA USA 94305 iv, Dept Chem, Stanford, CA 94305 USA
Titolo Testata:
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY
fascicolo: 11, volume: 64, anno: 2000,
pagine: 2429 - 2436
SICI:
0916-8451(200011)64:11<2429:SATAO1>2.0.ZU;2-V
Fonte:
ISI
Lingua:
ENG
Soggetto:
PROTEIN-KINASE-C; PHORBOL ESTER-BINDING; EPSTEIN-BARR VIRUS; INDUCTION; DOMAINS; DERIVATIVES; ISOZYMES; SEQUENCE; ANALOGS; OXIDASE;
Keywords:
12-epi-phorbol-12,13-dibutyrate; Epstein-Barr virus; phorbol ester; protein kinase C; tumor promoter;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Agriculture,Biology & Environmental Sciences
Life Sciences
Citazioni:
33
Recensione:
Indirizzi per estratti:
Indirizzo: Irie, K Kyoto Univ, Grad Sch Agr, Div Appl Life Sci, Kyoto 6068502, Japan Kyoto Univ Kyoto Japan 6068502 pl Life Sci, Kyoto 6068502, Japan
Citazione:
K. Irie et al., "Synthesis and tumor-promoting activities of 12-epi-phorbol-12, 13-dibutyrate", BIOS BIOT B, 64(11), 2000, pp. 2429-2436

Abstract

12-Epi-phorbol-12,13-dibutyrate (1), the C12-epimer of the most frequentlyused phorbol ester probe, phorbol-12,13-dibutyrate (PDBu), has been synthesized from phorbol in 9 steps in order to investigate the structural requirements for tumor-promoting activity. Compound 1 showed about 100-fold weaker in vitro biological activities related to in vivo tumor promotion, Epstein-Barr virus early antigen (EBV-EA)-inducing ability, superoxide (O-2(-)) generation-inducing ability, and binding to the protein kinase C (PKC) regulatory domain surrogate peptides. The results indicated that the beta -stereochemistry at position 12 of the phorbol skeleton is important for optimal activity. Binding selectivity to each PKC C1 domain of 1 was almost equal to that of PDBu.

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Documento generato il 08/04/20 alle ore 12:16:21