Literature DB >> 15203171

Design, synthesis, and evaluation of estradiol-linked genotoxicants as anti-cancer agents.

U Sharma1, J C Marquis, A Nicole Dinaut, S M Hillier, B Fedeles, P T Rye, J M Essigmann, R G Croy.   

Abstract

A series of bifunctional compounds was prepared consisting of 17beta estradiol linked to a DNA damaging N,N-bis-(2-chloroethyl)aniline. The objective of our studies was to determine the characteristics of the linker that permitted both reaction with DNA and binding of the resultant covalent adducts to the estrogen receptor. Linker characteristics were pivotal determinants underlying the ability of the compounds to kill selectively breast cancer cells that express the estrogen receptor.

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Year:  2004        PMID: 15203171      PMCID: PMC4096836          DOI: 10.1016/j.bmcl.2004.04.064

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  9 in total

1.  Design, synthesis, and structure-activity relationships of novel non-imidazole histamine H(3) receptor antagonists.

Authors:  I D Linney; I M Buck; E A Harper; S B Kalindjian; M J Pether; N P Shankley; G F Watt; P T Wright
Journal:  J Med Chem       Date:  2000-06-15       Impact factor: 7.446

Review 2.  DNA and its associated processes as targets for cancer therapy.

Authors:  Laurence H Hurley
Journal:  Nat Rev Cancer       Date:  2002-03       Impact factor: 60.716

3.  Inhibition of DNA repair as a means of increasing the antitumor activity of DNA reactive agents.

Authors: 
Journal:  Adv Drug Deliv Rev       Date:  1997-07-07       Impact factor: 15.470

Review 4.  DNA repair mechanisms associated with cellular resistance to antitumor drugs: potential novel targets.

Authors:  J M Barret; B T Hill
Journal:  Anticancer Drugs       Date:  1998-02       Impact factor: 2.248

Review 5.  Role of organic cation transporters in drug absorption and elimination.

Authors:  L Zhang; C M Brett; K M Giacomini
Journal:  Annu Rev Pharmacol Toxicol       Date:  1998       Impact factor: 13.820

6.  Structural insights into the mode of action of a pure antiestrogen.

Authors:  A C Pike; A M Brzozowski; J Walton; R E Hubbard; A G Thorsell; Y L Li; J A Gustafsson; M Carlquist
Journal:  Structure       Date:  2001-02-07       Impact factor: 5.006

7.  Targeting of tumor cells and DNA by a chlorambucil-spermidine conjugate.

Authors:  J L Holley; A Mather; R T Wheelhouse; P M Cullis; J A Hartley; J P Bingham; G M Cohen
Journal:  Cancer Res       Date:  1992-08-01       Impact factor: 12.701

8.  Synthesis and biological activity of DNA damaging agents that form decoy binding sites for the estrogen receptor.

Authors:  S M Rink; K J Yarema; M S Solomon; L A Paige; B M Tadayoni-Rebek; J M Essigmann; R G Croy
Journal:  Proc Natl Acad Sci U S A       Date:  1996-12-24       Impact factor: 11.205

9.  A rationally designed genotoxin that selectively destroys estrogen receptor-positive breast cancer cells.

Authors:  Kaushik Mitra; John C Marquis; Shawn M Hillier; Peter T Rye; Beatriz Zayas; Annie S Lee; John M Essigmann; Robert G Croy
Journal:  J Am Chem Soc       Date:  2002-03-06       Impact factor: 15.419

  9 in total
  9 in total

1.  Design, synthesis, and initial biological evaluation of a steroidal anti-estrogen-doxorubicin bioconjugate for targeting estrogen receptor-positive breast cancer cells.

Authors:  Kinh-Luan Dao; Rupa R Sawant; J Adam Hendricks; Victoria Ronga; Vladimir P Torchilin; Robert N Hanson
Journal:  Bioconjug Chem       Date:  2012-04-04       Impact factor: 4.774

2.  Synthesis and evaluation of 11β-(4-substituted phenyl) estradiol analogs: transition from estrogen receptor agonists to antagonists.

Authors:  Robert N Hanson; Edward Hua; J Adam Hendricks; David Labaree; Richard B Hochberg
Journal:  Bioorg Med Chem       Date:  2012-05-07       Impact factor: 3.641

3.  Selective estrogen receptor modulator delivery of quinone warheads to DNA triggering apoptosis in breast cancer cells.

Authors:  Kuan-Wei Peng; Huali Wang; Zhihui Qin; Gihani T Wijewickrama; Meiling Lu; Zhican Wang; Judy L Bolton; Gregory R J Thatcher
Journal:  ACS Chem Biol       Date:  2009-12-18       Impact factor: 5.100

4.  Convergent synthesis of a steroidal antiestrogen-mitomycin C hybrid using "click" chemistry.

Authors:  Robert N Hanson; Edward Hua; David Labaree; Richard B Hochberg; Kyle Proffitt; John M Essigmann; Robert G Croy
Journal:  Org Biomol Chem       Date:  2012-09-25       Impact factor: 3.876

Review 5.  Design and Applications of Bifunctional Small Molecules: Why Two Heads Are Better Than One.

Authors:  Timothy W Corson; Nicholas Aberle; Craig M Crews
Journal:  ACS Chem Biol       Date:  2008-11-21       Impact factor: 5.100

6.  Estrogen Receptor {alpha} Enhances the Rate of Oxidative DNA Damage by Targeting an Equine Estrogen Catechol Metabolite to the Nucleus.

Authors:  Zhican Wang; Gihani T Wijewickrama; Kuan-Wei Peng; Birgit M Dietz; Long Yuan; Richard B van Breemen; Judy L Bolton; Gregory R J Thatcher
Journal:  J Biol Chem       Date:  2009-01-21       Impact factor: 5.157

Review 7.  Potential mechanisms of estrogen quinone carcinogenesis.

Authors:  Judy L Bolton; Gregory R J Thatcher
Journal:  Chem Res Toxicol       Date:  2007-12-04       Impact factor: 3.739

Review 8.  Drug conjugates-an emerging approach to treat breast cancer.

Authors:  Mahmud Hasan; Rehana K Leak; Robert E Stratford; Darius P Zlotos; Paula A Witt-Enderby
Journal:  Pharmacol Res Perspect       Date:  2018-07-05

Review 9.  Targeting the androgen receptor with steroid conjugates.

Authors:  Paul M Levine; Michael J Garabedian; Kent Kirshenbaum
Journal:  J Med Chem       Date:  2014-07-08       Impact factor: 7.446

  9 in total

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