Literature DB >> 18479747

Lethality to leukemia cell lines of DNA interstrand cross-links generated by Cloretazine derived alkylating species.

Philip G Penketh1, Raymond P Baumann, Kimiko Ishiguro, Krishnamurthy Shyam, Helen A Seow, Alan C Sartorelli.   

Abstract

Cloretazine [1,2-bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(methylamino)carbonyl]hydrazine; VNP40101M; 101M] is a relatively new prodrug with activity in elderly acute myelogenous leukemia (AML) patients. Its therapeutic action is due largely to the production of 1-(3-cytosinyl),2-(1-guanyl)ethane cross-links (G-C ethane cross-links) in DNA. The numbers of cross-links produced in three experimental leukemia lines (L1210, U937 and HL-60) were fewer than 10 per genome at their respective LC50 concentrations. Only 1 in approximately 20,000 90CE molecules produces a cross-link in the AGT (O6-alkylguanine-DNA alkyltransferase) negative L1210 and U937 cell lines and 1 in 400,000 in the AGT positive HL-60 cell line.

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Year:  2008        PMID: 18479747      PMCID: PMC2888535          DOI: 10.1016/j.leukres.2008.03.005

Source DB:  PubMed          Journal:  Leuk Res        ISSN: 0145-2126            Impact factor:   3.156


  32 in total

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3.  Initial sequencing and comparative analysis of the mouse genome.

Authors:  Robert H Waterston; Kerstin Lindblad-Toh; Ewan Birney; Jane Rogers; Josep F Abril; Pankaj Agarwal; Richa Agarwala; Rachel Ainscough; Marina Alexandersson; Peter An; Stylianos E Antonarakis; John Attwood; Robert Baertsch; Jonathon Bailey; Karen Barlow; Stephan Beck; Eric Berry; Bruce Birren; Toby Bloom; Peer Bork; Marc Botcherby; Nicolas Bray; Michael R Brent; Daniel G Brown; Stephen D Brown; Carol Bult; John Burton; Jonathan Butler; Robert D Campbell; Piero Carninci; Simon Cawley; Francesca Chiaromonte; Asif T Chinwalla; Deanna M Church; Michele Clamp; Christopher Clee; Francis S Collins; Lisa L Cook; Richard R Copley; Alan Coulson; Olivier Couronne; James Cuff; Val Curwen; Tim Cutts; Mark Daly; Robert David; Joy Davies; Kimberly D Delehaunty; Justin Deri; Emmanouil T Dermitzakis; Colin Dewey; Nicholas J Dickens; Mark Diekhans; Sheila Dodge; Inna Dubchak; Diane M Dunn; Sean R Eddy; Laura Elnitski; Richard D Emes; Pallavi Eswara; Eduardo Eyras; Adam Felsenfeld; Ginger A Fewell; Paul Flicek; Karen Foley; Wayne N Frankel; Lucinda A Fulton; Robert S Fulton; Terrence S Furey; Diane Gage; Richard A Gibbs; Gustavo Glusman; Sante Gnerre; Nick Goldman; Leo Goodstadt; Darren Grafham; Tina A Graves; Eric D Green; Simon Gregory; Roderic Guigó; Mark Guyer; Ross C Hardison; David Haussler; Yoshihide Hayashizaki; LaDeana W Hillier; Angela Hinrichs; Wratko Hlavina; Timothy Holzer; Fan Hsu; Axin Hua; Tim Hubbard; Adrienne Hunt; Ian Jackson; David B Jaffe; L Steven Johnson; Matthew Jones; Thomas A Jones; Ann Joy; Michael Kamal; Elinor K Karlsson; Donna Karolchik; Arkadiusz Kasprzyk; Jun Kawai; Evan Keibler; Cristyn Kells; W James Kent; Andrew Kirby; Diana L Kolbe; Ian Korf; Raju S Kucherlapati; Edward J Kulbokas; David Kulp; Tom Landers; J P Leger; Steven Leonard; Ivica Letunic; Rosie Levine; Jia Li; Ming Li; Christine Lloyd; Susan Lucas; Bin Ma; Donna R Maglott; Elaine R Mardis; Lucy Matthews; Evan Mauceli; John H Mayer; Megan McCarthy; W Richard McCombie; Stuart McLaren; Kirsten McLay; John D McPherson; Jim Meldrim; Beverley Meredith; Jill P Mesirov; Webb Miller; Tracie L Miner; Emmanuel Mongin; Kate T Montgomery; Michael Morgan; Richard Mott; James C Mullikin; Donna M Muzny; William E Nash; Joanne O Nelson; Michael N Nhan; Robert Nicol; Zemin Ning; Chad Nusbaum; Michael J O'Connor; Yasushi Okazaki; Karen Oliver; Emma Overton-Larty; Lior Pachter; Genís Parra; Kymberlie H Pepin; Jane Peterson; Pavel Pevzner; Robert Plumb; Craig S Pohl; Alex Poliakov; Tracy C Ponce; Chris P Ponting; Simon Potter; Michael Quail; Alexandre Reymond; Bruce A Roe; Krishna M Roskin; Edward M Rubin; Alistair G Rust; Ralph Santos; Victor Sapojnikov; Brian Schultz; Jörg Schultz; Matthias S Schwartz; Scott Schwartz; Carol Scott; Steven Seaman; Steve Searle; Ted Sharpe; Andrew Sheridan; Ratna Shownkeen; Sarah Sims; Jonathan B Singer; Guy Slater; Arian Smit; Douglas R Smith; Brian Spencer; Arne Stabenau; Nicole Stange-Thomann; Charles Sugnet; Mikita Suyama; Glenn Tesler; Johanna Thompson; David Torrents; Evanne Trevaskis; John Tromp; Catherine Ucla; Abel Ureta-Vidal; Jade P Vinson; Andrew C Von Niederhausern; Claire M Wade; Melanie Wall; Ryan J Weber; Robert B Weiss; Michael C Wendl; Anthony P West; Kris Wetterstrand; Raymond Wheeler; Simon Whelan; Jamey Wierzbowski; David Willey; Sophie Williams; Richard K Wilson; Eitan Winter; Kim C Worley; Dudley Wyman; Shan Yang; Shiaw-Pyng Yang; Evgeny M Zdobnov; Michael C Zody; Eric S Lander
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Review 4.  The anatomy of viral DNA molecules.

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Journal:  Annu Rev Biochem       Date:  1967       Impact factor: 23.643

5.  Interstrand cross-linking of DNA by difunctional alkylating agents.

Authors:  P D Lawley; P Brookes
Journal:  J Mol Biol       Date:  1967-04-14       Impact factor: 5.469

Review 6.  Clinical relevance of MGMT in the treatment of cancer.

Authors:  Stanton L Gerson
Journal:  J Clin Oncol       Date:  2002-05-01       Impact factor: 44.544

7.  Temozolomide: the effect of once- and twice-a-day dosing on tumor tissue levels of the DNA repair protein O(6)-alkylguanine-DNA-alkyltransferase.

Authors:  T P Spiro; L Liu; S Majka; J Haaga; J K Willson; S L Gerson
Journal:  Clin Cancer Res       Date:  2001-08       Impact factor: 12.531

8.  Comparison of DNA lesions produced by tumor-inhibitory 1,2-bis(sulfonyl)hydrazines and chloroethylnitrosoureas.

Authors:  P G Penketh; K Shyam; A C Sartorelli
Journal:  Biochem Pharmacol       Date:  2000-02-01       Impact factor: 5.858

9.  1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(methylamino)carbonyl]hydrazine (VNP40101M): II. Role of O6-alkylguanine-DNA alkyltransferase in cytotoxicity.

Authors:  R P Baumann; K Shyam; P G Penketh; J S Remack; T P Brent; A C Sartorelli
Journal:  Cancer Chemother Pharmacol       Date:  2003-12-17       Impact factor: 3.333

10.  1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[(methylamino)carbonyl]hydrazine (VNP40101M): I. Direct inhibition of O6-alkylguanine-DNA alkyltransferase (AGT) by electrophilic species generated by decomposition.

Authors:  P G Penketh; K Shyam; R P Baumann; J S Remack; T P Brent; A C Sartorelli
Journal:  Cancer Chemother Pharmacol       Date:  2003-12-24       Impact factor: 3.333

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  13 in total

1.  4-nitrobenzyloxycarbonyl derivatives of O(6)-benzylguanine as hypoxia-activated prodrug inhibitors of O(6)-alkylguanine-DNA alkyltransferase (AGT), which produces resistance to agents targeting the O-6 position of DNA guanine.

Authors:  Rui Zhu; Mao-Chin Liu; Mei-Zhen Luo; Philip G Penketh; Raymond P Baumann; Krishnamurthy Shyam; Alan C Sartorelli
Journal:  J Med Chem       Date:  2011-10-17       Impact factor: 7.446

2.  pH-dependent general base catalyzed activation rather than isocyanate liberation may explain the superior anticancer efficacy of laromustine compared to related 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)hydrazine prodrugs.

Authors:  Philip G Penketh; Richard A Finch; Rachel Sauro; Raymond P Baumann; Elena S Ratner; Krishnamurthy Shyam
Journal:  Chem Biol Drug Des       Date:  2017-07-17       Impact factor: 2.817

3.  Preclinical evaluation of Laromustine for use in combination with radiation therapy in the treatment of solid tumors.

Authors:  Sara Rockwell; Yanfeng Liu; Helen A Seow; Kimiko Ishiguro; Raymond P Baumann; Philip G Penketh; Krishnamurthy Shyam; Oluwatoyin M Akintujoye; Peter M Glazer; Alan C Sartorelli
Journal:  Int J Radiat Biol       Date:  2011-12-20       Impact factor: 2.694

4.  1,2-Bis(methylsulfonyl)-1-(2-chloroethyl)-2-[[1-(4-nitrophenyl)ethoxy]carbonyl]hydrazine (KS119): a cytotoxic prodrug with two stable conformations differing in biological and physical properties.

Authors:  Philip G Penketh; Raymond P Baumann; Krishnamurthy Shyam; Hugh S Williamson; Kimiko Ishiguro; Rui Zhu; Emma S E Eriksson; Leif A Eriksson; Alan C Sartorelli
Journal:  Chem Biol Drug Des       Date:  2011-09-06       Impact factor: 2.817

5.  KS900: A hypoxia-directed, reductively activated methylating antitumor prodrug that selectively ablates O(6)-alkylguanine-DNA alkyltransferase in neoplastic cells.

Authors:  Raymond P Baumann; Kimiko Ishiguro; Philip G Penketh; Krishnamurthy Shyam; Rui Zhu; Alan C Sartorelli
Journal:  Biochem Pharmacol       Date:  2011-03-17       Impact factor: 5.858

6.  Reductive activation of the prodrug 1,2-bis(methylsulfonyl)-1-(2-chloroethyl)-2-[[1-(4-nitrophenyl)ethoxy]carbonyl]hydrazine (KS119) selectively occurs in oxygen-deficient cells and overcomes O(6)-alkylguanine-DNA alkyltransferase mediated KS119 tumor cell resistance.

Authors:  Raymond P Baumann; Philip G Penketh; Kimiko Ishiguro; Krishnamurthy Shyam; Yong L Zhu; Alan C Sartorelli
Journal:  Biochem Pharmacol       Date:  2009-12-11       Impact factor: 5.858

7.  Chloroethylating and methylating dual function antineoplastic agents display superior cytotoxicity against repair proficient tumor cells.

Authors:  Rui Zhu; Raymond P Baumann; Eric Patridge; Philip G Penketh; Krishnamurthy Shyam; Kimiko Ishiguro; Alan C Sartorelli
Journal:  Bioorg Med Chem Lett       Date:  2013-01-11       Impact factor: 2.823

8.  Thioredoxin reductase is inhibited by the carbamoylating activity of the anticancer sulfonylhydrazine drug laromustine.

Authors:  Kevin P Rice; Edmund J Klinkerch; Scott A Gerber; Tyler R Schleicher; Tara J Kraus; Christopher M Buros
Journal:  Mol Cell Biochem       Date:  2012-08-05       Impact factor: 3.396

9.  Inhibition of human DNA polymerase beta activity by the anticancer prodrug Cloretazine.

Authors:  Abbie M Frederick; Marguerite L Davis; Kevin P Rice
Journal:  Biochem Biophys Res Commun       Date:  2008-11-21       Impact factor: 3.575

10.  Influence of phosphate and phosphoesters on the decomposition pathway of 1,2-bis(methylsulfonyl)-1-(2-chloroethyhydrazine (90CE), the active anticancer moiety generated by Laromustine, KS119, and KS119W.

Authors:  Philip G Penketh; Krishnamurthy Shyam; Rui Zhu; Raymond P Baumann; Kimiko Ishiguro; Alan C Sartorelli
Journal:  Chem Res Toxicol       Date:  2014-03-24       Impact factor: 3.739

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