Literature DB >> 22560586

The macrocycle of leinamycin imparts hydrolytic stability to the thiol-sensing 1,2-dithiolan-3-one 1-oxide unit of the natural product.

Santhosh Sivaramakrishnan1, Leonid Breydo, Daekyu Sun, Kent S Gates.   

Abstract

Reaction of cellular thiols with the 1,2-dithiolan-3-one 1-oxide moiety of leinamycin triggers the generation of DNA-damaging reactive intermediates. Studies with small, synthetic analogues of leinamycin reveal that the macrocyclic portion of the natural product imparts remarkable hydrolytic stability to the 1,2-dithiolan-3-one 1-oxide heterocycle without substantially compromising its thiol-sensing property.
Copyright © 2012 Elsevier Ltd. All rights reserved.

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Year:  2012        PMID： 22560586      PMCID： PMC3376404          DOI： 10.1016/j.bmcl.2012.04.003

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


  40 in total

Review 1.  Mechanisms of DNA damage by leinamycin.

Authors:  K S Gates
Journal:  Chem Res Toxicol       Date:  2000-10       Impact factor: 3.739

Review 2.  Mechanisms of in situ activation for DNA-targeting antitumor agents.

Authors:  Scott E Wolkenberg; Dale L Boger
Journal:  Chem Rev       Date:  2002-07       Impact factor: 60.622

3.  A fluorimetric assay for the spontaneous release of an N7-alkylguanine residue from duplex DNA.

Authors:  Ekaterina Shipova; Kent S Gates
Journal:  Bioorg Med Chem Lett       Date:  2005-04-15       Impact factor: 2.823

4.  On the mechanism of toxicity of illudins: the role of glutathione.

Authors:  T C McMorris; M J Kelner; W Wang; S Moon; R Taetle
Journal:  Chem Res Toxicol       Date:  1990 Nov-Dec       Impact factor: 3.739

5.  Attractive through-space S-O interaction in the DNA-cleaving antitumor antibiotic leinamycin.

Authors:  S Wu; A Greer
Journal:  J Org Chem       Date:  2000-08-11       Impact factor: 4.354

6.  DNA strand scission by the novel antitumor antibiotic leinamycin.

Authors:  M Hara; Y Saitoh; H Nakano
Journal:  Biochemistry       Date:  1990-06-19       Impact factor: 3.162

7.  Entering the leinamycin rearrangement via 2-(trimethylsilyl)ethyl sulfoxides.

Authors:  Kripa Keerthi; Kent S Gates
Journal:  Org Biomol Chem       Date:  2007-04-13       Impact factor: 3.876

Review 8.  Making and working with hydrogen sulfide: The chemistry and generation of hydrogen sulfide in vitro and its measurement in vivo: a review.

Authors:  Martin N Hughes; Miguel N Centelles; Kevin P Moore
Journal:  Free Radic Biol Med       Date:  2009-09-19       Impact factor: 7.376

9.  Cellular response and molecular mechanism of antitumor activity by leinamycin in MiaPaCa human pancreatic cancer cells.

Authors:  Stephen Bassett; Rheanna Urrabaz; Daekyu Sun
Journal:  Anticancer Drugs       Date:  2004-08       Impact factor: 2.248

10.  Two (E,E)- and (Z,E)-thiazol-5-ylpenta-2,4-dienones.

Authors:  Leonid Breydo; Charles L Barnes; Kent S Gates
Journal:  Acta Crystallogr C       Date:  2002-07-12       Impact factor: 1.172
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  2 in total

1.  Synthesis and evaluation of 8,4'-dideshydroxy-leinamycin revealing new insights into the structure-activity relationship of the anticancer natural product leinamycin.

Authors:  Tao Liu; Ming Ma; Hui-Ming Ge; Chunying Yang; John Cleveland; Ben Shen
Journal:  Bioorg Med Chem Lett       Date:  2015-05-30       Impact factor: 2.823

2.  Leinamycin E1 acting as an anticancer prodrug activated by reactive oxygen species.

Authors:  Sheng-Xiong Huang; Bong-Sik Yun; Ming Ma; Hirak S Basu; Dawn R Church; Gudrun Ingenhorst; Yong Huang; Dong Yang; Jeremy R Lohman; Gong-Li Tang; Jianhua Ju; Tao Liu; George Wilding; Ben Shen
Journal:  Proc Natl Acad Sci U S A       Date:  2015-06-08       Impact factor: 11.205
  2 in total

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