Literature DB >> 12901927

Establishment of substituent effects in the DNA binding subunit of CBI analogues of the duocarmycins and CC-1065.

Jay P Parrish1, David B Kastrinsky, Frederic Stauffer, Michael P Hedrick, Inkyu Hwang, Dale L Boger.   

Abstract

An extensive series of CBI analogues of the duocarmycins and CC-1065 exploring substituent effects within the first indole DNA binding subunit is detailed. In general, substitution at the indole C5 position led to cytotoxic potency enhancements that can be >/=1000-fold providing simplified analogues containing a single DNA binding subunit that are more potent (IC(50)=2-3 pM) than CBI-TMI, duocarmycin SA, or CC-1065.

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Year:  2003        PMID： 12901927     DOI： 10.1016/s0968-0896(03)00194-9

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  11 in total

1.  Systematic exploration of the structural features of yatakemycin impacting DNA alkylation and biological activity.

Authors:  Mark S Tichenor; Karen S MacMillan; John D Trzupek; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2007-08-11       Impact factor: 15.419

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

Authors:  Mika Uematsu; Daniel M Brody; Dale L Boger
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

3.  Synthesis and evaluation of a series of C5'-substituted duocarmycin SA analogs.

Authors:  William M Robertson; David B Kastrinsky; Inkyu Hwang; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2010-03-25       Impact factor: 2.823

4.  Efficacious cyclic N-acyl O-amino phenol duocarmycin prodrugs.

Authors:  Amanda L Wolfe; Katharine K Duncan; Nikhil K Parelkar; Douglas Brown; George A Vielhauer; Dale L Boger
Journal:  J Med Chem       Date:  2013-05-10       Impact factor: 7.446

5.  A novel, unusually efficacious duocarmycin carbamate prodrug that releases no residual byproduct.

Authors:  Amanda L Wolfe; Katharine K Duncan; Nikhil K Parelkar; Scott J Weir; George A Vielhauer; Dale L Boger
Journal:  J Med Chem       Date:  2012-06-12       Impact factor: 7.446

6.  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

Review 7.  Fundamental relationships between structure, reactivity, and biological activity for the duocarmycins and CC-1065.

Authors:  Karen S MacMillan; Dale L Boger
Journal:  J Med Chem       Date:  2009-10-08       Impact factor: 7.446

8.  Determination of the biological activity and structure activity relationships of drugs based on the highly cytotoxic duocarmycins and CC-1065.

Authors:  Lutz F Tietze; Birgit Krewer; J Marian von Hof; Holm Frauendorf; Ingrid Schuberth
Journal:  Toxins (Basel)       Date:  2009-12-02       Impact factor: 4.546

9.  The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry-Biology Interface.

Authors:  Dale L Boger
Journal:  J Org Chem       Date:  2017-10-13       Impact factor: 4.354

10.  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
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