Literature DB >> 26069351

A five-membered lactone prodrug of CBI-based analogs of the duocarmycins.

Mika Uematsu1, Daniel M Brody1, Dale L Boger1.   

Abstract

The preparation, characterization and examination of the CBI-based 5-membered lactone 5 capable of serving as a prodrug or protein (antibody) conjugation reagent are disclosed along with its incorporation into the corresponding CC-1065 and duocarmycin analog 6, and the establishment of their properties.

Entities:  

Keywords:  CBI; CC-1065; duocarmycin; prodrug

Year:  2015        PMID： 26069351      PMCID： PMC4459655          DOI： 10.1016/j.tetlet.2014.11.038

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  50 in total

1.  CC-1065 and the Duocarmycins: Synthetic Studies.

Authors:  Dale L. Boger; Christopher W. Boyce; Robert M. Garbaccio; Joel A. Goldberg
Journal:  Chem Rev       Date:  1997-05-08       Impact factor: 60.622

2.  Duocarmycin SA, a new antitumor antibiotic from Streptomyces sp.

Authors:  M Ichimura; T Ogawa; K Takahashi; E Kobayashi; I Kawamoto; T Yasuzawa; I Takahashi; H Nakano
Journal:  J Antibiot (Tokyo)       Date:  1990-08       Impact factor: 2.649

3.  Synthesis and antitumor activity of CBI-bearing ester and carbamate prodrugs of CC-1065 analogue.

Authors:  Yuqiang Wang; Lianfa Li; Zhiming Tian; Wei Jiang; James W Larrick
Journal:  Bioorg Med Chem       Date:  2006-12-01       Impact factor: 3.641

4.  Molecular basis for sequence-specific DNA alkylation by CC-1065.

Authors:  L H Hurley; C S Lee; J P McGovren; M A Warpehoski; M A Mitchell; R C Kelly; P A Aristoff
Journal:  Biochemistry       Date:  1988-05-17       Impact factor: 3.162

5.  CC-1065 (NSC 298223), a potent new antitumor agent improved production and isolation, characterization and antitumor activity.

Authors:  D G Martin; C Biles; S A Gerpheide; L J Hanka; W C Krueger; J P McGovren; S A Mizsak; G L Neil; J C Stewart; J Visser
Journal:  J Antibiot (Tokyo)       Date:  1981-09       Impact factor: 2.649

6.  A strategy for tumor-selective chemotherapy by enzymatic liberation of seco-duocarmycin SA-derivatives from nontoxic prodrugs.

Authors:  L F Tietze; M Lieb; T Herzig; F Haunert; I Schuberth
Journal:  Bioorg Med Chem       Date:  2001-07       Impact factor: 3.641

7.  Characteristics of antitumor activity of KW-2189, a novel water-soluble derivative of duocarmycin, against murine and human tumors.

Authors:  E Kobayashi; A Okamoto; M Asada; M Okabe; S Nagamura; A Asai; H Saito; K Gomi; T Hirata
Journal:  Cancer Res       Date:  1994-05-01       Impact factor: 12.701

8.  Synthesis and antitumor activity of duocarmycin derivatives.

Authors:  S Nagamura; Y Kanda; E Kobayashi; K Gomi; H Saito
Journal:  Chem Pharm Bull (Tokyo)       Date:  1995-09       Impact factor: 1.645

Review 9.  CC-1065 and the duocarmycins: unraveling the keys to a new class of naturally derived DNA alkylating agents.

Authors:  D L Boger; D S Johnson
Journal:  Proc Natl Acad Sci U S A       Date:  1995-04-25       Impact factor: 11.205

10.  Total synthesis and evaluation of iso-duocarmycin SA and iso-yatakemycin.

Authors:  Karen S MacMillan; Trinh Nguyen; Trihn Nguyen; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-01-28       Impact factor: 15.419
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