Literature DB >> 3346875

Stereoelectronic factors influencing the biological activity and DNA interaction of synthetic antitumor agents modeled on CC-1065.

M A Warpehoski1, I Gebhard, R C Kelly, W C Krueger, L H Li, J P McGovren, M D Prairie, N Wicnienski, W Wierenga.   

Abstract

The synthesis, physicochemical properties, and biological activities of a series of novel spiro cyclopropyl compounds, modeled on the potent antitumor antibiotic CC-1065 (1), are described. Many of these synthetic analogues are significantly more effective than 1 against murine tumors. In particular, compound 27 exhibits high activity and potency. Structure-activity analysis supports a molecular mechanism for biological action involving hydrophobic interaction of the drug with DNA and acid-catalyzed alkylation of DNA.

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Year:  1988        PMID： 3346875     DOI： 10.1021/jm00398a017

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  14 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.  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

3.  In vitro evaluation of a novel chemotherapeutic agent, Adozelesin, in gynecologic-cancer cell lines.

Authors:  H N Nguyen; B U Sevin; H Averette; J Perras; R Hightower; R Ramos; D Donato; M Penalver
Journal:  Cancer Chemother Pharmacol       Date:  1992       Impact factor: 3.333

4.  Phase I trial of Adozelesin using the treatment schedule of daily x5 every 3 weeks.

Authors:  B J Foster; P M LoRusso; E Poplin; M Zalupski; M Valdivieso; A Wozniak; L Flaherty; D A Kasunic; R H Earhart; L H Baker
Journal:  Invest New Drugs       Date:  1996       Impact factor: 3.850

5.  Synthesis and evaluation of a thio analogue of duocarmycin SA.

Authors:  Karen S MacMillan; James P Lajiness; Carlota Lopez Cara; Romeo Romagnoli; William M Robertson; Inkyu Hwang; Pier Giovanni Baraldi; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2009-10-17       Impact factor: 2.823

6.  Therapeutic efficacy of the cyclopropylpyrroloindole, carzelesin, against xenografts derived from adult and childhood solid tumors.

Authors:  P J Houghton; P J Cheshire; J D Hallman; J A Houghton
Journal:  Cancer Chemother Pharmacol       Date:  1995       Impact factor: 3.333

7.  Adozelesin, a selected lead among cyclopropylpyrroloindole analogs of the DNA-binding antibiotic, CC-1065.

Authors:  L H Li; R C Kelly; M A Warpehoski; J P McGovren; I Gebhard; T F DeKoning
Journal:  Invest New Drugs       Date:  1991-05       Impact factor: 3.850

8.  Rational design, synthesis, and evaluation of key analogues of CC-1065 and the duocarmycins.

Authors:  Mark S Tichenor; Karen S MacMillan; James S Stover; Scott E Wolkenberg; Maria G Pavani; Lorenzo Zanella; Abdel N Zaid; Gianpiero Spalluto; Thomas J Rayl; Inkyu Hwang; Pier Giovanni Baraldi; Dale L Boger
Journal:  J Am Chem Soc       Date:  2007-10-19       Impact factor: 15.419

9.  Rapid and efficient hybridization-triggered crosslinking within a DNA duplex by an oligodeoxyribonucleotide bearing a conjugated cyclopropapyrroloindole.

Authors:  E A Lukhtanov; M A Podyminogin; I V Kutyavin; R B Meyer; H B Gamper
Journal:  Nucleic Acids Res       Date:  1996-02-15       Impact factor: 16.971

Review 10.  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
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