Literature DB >> 7774022

Duocarmycins, potent antitumor antibiotics produced by Streptomyces sp. structures and chemistry.

T Yasuzawa1, K Muroi, M Ichimura, I Takahashi, T Ogawa, K Takahashi, H Sano, Y Saitoh.   

Abstract

Seven novel potent antitumor antibiotics, duocarmycins A (1), C1 (2), C2 (3), D (4), B1 (5), B2 (6) and SA (7), were isolated from three independently collected Streptomyces sp. The complete structures, including absolute stereochemistry, were determined by spectral and chemical studies of those duocarmycins and several derivatives. Duocarmycins A (1) and SA (7) possess a 1,2,7,7a-tetrahydrocycloprop[1,2-c]indol-4-one subunit, a common pharmacophore with that of CC-1065 (10) found from Streptomyces zelensis.

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Year:  1995        PMID: 7774022     DOI: 10.1248/cpb.43.378

Source DB:  PubMed          Journal:  Chem Pharm Bull (Tokyo)        ISSN: 0009-2363            Impact factor:   1.645


  8 in total

1.  Synthesis and Preliminary Evaluation of Duocarmycin Analogues Incorporating the 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[2,3-e]indol-4-one (CNI) and 1,2,11,11a-Tetrahydrocyclopropa[c]naphtho[1,2-e]indol-4-one (iso-CNI) Alkylation Subunits.

Authors:  Carla M Gauss; Akiyuki Hamasaki; Jay P Parrish; Karen S Macmillan; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  Tetrahedron       Date:  2009-08-15       Impact factor: 2.457

2.  A unique class of duocarmycin and CC-1065 analogues subject to reductive activation.

Authors:  Wei Jin; John D Trzupek; Thomas J Rayl; Melinda A Broward; George A Vielhauer; Scott J Weir; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2007-11-17       Impact factor: 15.419

3.  Evaluation of a reductively activated duocarmycin prodrug against murine and human solid cancers.

Authors:  George A Vielhauer; Megan Swink; Nikhil K Parelkar; James P Lajiness; Amanda L Wolfe; Dale Boger
Journal:  Cancer Biol Ther       Date:  2013-06       Impact factor: 4.742

4.  Use of KW-2189, a DNA minor groove-binding agent, in patients with hepatocellular carcinoma: a north central cancer treatment group (NCCTG) phase II clinical trial.

Authors:  Steven R Alberts; Vera J Suman; Henry C Pitot; John K Camoriano; Joseph Rubin
Journal:  J Gastrointest Cancer       Date:  2007

5.  Structural necessity of indole C5-O-substitution of seco-duocarmycin analogs for their cytotoxic activity.

Authors:  Taeyoung Choi; Eunsook Ma
Journal:  Molecules       Date:  2010-11-08       Impact factor: 4.411

6.  Synthesis and biological evaluation of a novel pentagastrin-toxin conjugate designed for a targeted prodrug mono-therapy of cancer.

Authors:  Lutz F Tietze; Olaf Panknin; Birgit Krewer; Felix Major; Ingrid Schuberth
Journal:  Int J Mol Sci       Date:  2008-05-20       Impact factor: 6.208

7.  Cyclization of free radicals at the C-7 position of ethyl indole-2-carboxylate derivatives: an entry to a new class of Duocarmycin Analogues.

Authors:  Naim H Al-Said; Khaled Q Shawakfeh; Wasim N Abdullah
Journal:  Molecules       Date:  2005-12-31       Impact factor: 4.411

8.  A radical S-adenosyl-L-methionine enzyme and a methyltransferase catalyze cyclopropane formation in natural product biosynthesis.

Authors:  Wen-Bing Jin; Sheng Wu; Xiao-Hong Jian; Hua Yuan; Gong-Li Tang
Journal:  Nat Commun       Date:  2018-07-17       Impact factor: 14.919

  8 in total

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