Literature DB >> 24900418

Strategy for Imidazotetrazine Prodrugs with Anticancer Activity Independent of MGMT and MMR.

Elrashied A E Garelnabi1, Dimitrios Pletsas1, Li Li1, Konstantinos Kiakos2, Nazira Karodia1, John A Hartley2, Roger M Phillips1, Richard T Wheelhouse1.   

Abstract

The imidazotetrazine ring is an acid-stable precursor and prodrug of highly reactive alkyl diazonium ions. We have shown that this reactivity can be managed productively in an aqueous system for the generation of aziridinium ions with 96% efficiency. The new compounds are potent DNA alkylators and have antitumor activity independent of the O6-methylguanine-DNA methyltransferase and DNA mismatch repair constraints that limit the use of Temozolomide.

Entities:  

Keywords:  13C NMR; DNA; Imidazotetrazine; Temozolomide; aziridinium; cancer

Year:  2012        PMID： 24900418      PMCID： PMC4025673          DOI： 10.1021/ml300132t

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  9 in total

Review 1.  Temozolomide: a review of its discovery, chemical properties, pre-clinical development and clinical trials.

Authors:  E S Newlands; M F Stevens; S R Wedge; R T Wheelhouse; C Brock
Journal:  Cancer Treat Rev       Date:  1997-01       Impact factor: 12.111

2.  Phase I clinical trial of mitozolomide.

Authors:  E S Newlands; G Blackledge; J A Slack; C Goddard; C J Brindley; L Holden; M F Stevens
Journal:  Cancer Treat Rep       Date:  1985 Jul-Aug

3.  Synthesis and biological activity of 5-{4-[2-(methyl-p-substituted phenylamino)ethoxy]benzyl}thiazolidine-2,4-diones.

Authors:  Hyo Jin Gim; BoMi Kang; Raok Jeon
Journal:  Arch Pharm Res       Date:  2007-09       Impact factor: 4.946

4.  Antitumor imidazotetrazines. 1. Synthesis and chemistry of 8-carbamoyl-3-(2-chloroethyl)imidazo[5,1-d]-1,2,3,5-tetrazin-4(3 H)-one , a novel broad-spectrum antitumor agent.

Authors:  M F Stevens; J A Hickman; R Stone; N W Gibson; G U Baig; E Lunt; C G Newton
Journal:  J Med Chem       Date:  1984-02       Impact factor: 7.446

5.  NMR and molecular modeling investigation of the mechanism of activation of the antitumor drug temozolomide and its interaction with DNA.

Authors:  B J Denny; R T Wheelhouse; M F Stevens; L L Tsang; J A Slack
Journal:  Biochemistry       Date:  1994-08-09       Impact factor: 3.162

6.  Antitumor activity and pharmacokinetics in mice of 8-carbamoyl-3-methyl-imidazo[5,1-d]-1,2,3,5-tetrazin-4(3H)-one (CCRG 81045; M & B 39831), a novel drug with potential as an alternative to dacarbazine.

Authors:  M F Stevens; J A Hickman; S P Langdon; D Chubb; L Vickers; R Stone; G Baig; C Goddard; N W Gibson; J A Slack
Journal:  Cancer Res       Date:  1987-11-15       Impact factor: 12.701

7.  Antitumor imidazotetrazines. 32. Synthesis of novel imidazotetrazinones and related bicyclic heterocycles to probe the mode of action of the antitumor drug temozolomide.

Authors:  A S Clark; B Deans; M F Stevens; M J Tisdale; R T Wheelhouse; B J Denny; J A Hartley
Journal:  J Med Chem       Date:  1995-04-28       Impact factor: 7.446

8.  Dual repair modulation reverses Temozolomide resistance in vitro.

Authors:  Vincent A Barvaux; Malcolm Ranson; Robert Brown; R Stanley McElhinney; T Brian H McMurry; Geoffrey P Margison
Journal:  Mol Cancer Ther       Date:  2004-02       Impact factor: 6.261

9.  Polar, functionalized guanine-O6 derivatives resistant to repair by O6-alkylguanine-DNA alkyltransferase: implications for the design of DNA-modifying drugs.

Authors:  Dimitrios Pletsas; Richard T Wheelhouse; Vassiliki Pletsa; Anna Nicolaou; Terence C Jenkins; Michael C Bibby; Soterios A Kyrtopoulos
Journal:  Eur J Med Chem       Date:  2006-02-03       Impact factor: 6.514
  9 in total
  4 in total

1.  Evaluation of novel imidazotetrazine analogues designed to overcome temozolomide resistance and glioblastoma regrowth.

Authors:  Yulian P Ramirez; Ann C Mladek; Roger M Phillips; Mikko Gynther; Jarkko Rautio; Alonzo H Ross; Richard T Wheelhouse; Jann N Sakaria
Journal:  Mol Cancer Ther       Date:  2014-10-28       Impact factor: 6.261

2.  Synthesis and quantitative structure-activity relationship of imidazotetrazine prodrugs with activity independent of O6-methylguanine-DNA-methyltransferase, DNA mismatch repair, and p53.

Authors:  Dimitrios Pletsas; Elrashied A E Garelnabi; Li Li; Roger M Phillips; Richard T Wheelhouse
Journal:  J Med Chem       Date:  2013-08-16       Impact factor: 7.446

3.  Glioblastoma multiforme therapy and mechanisms of resistance.

Authors:  Yulian P Ramirez; Jessica L Weatherbee; Richard T Wheelhouse; Alonzo H Ross
Journal:  Pharmaceuticals (Basel)       Date:  2013-11-25

4.  The medicinal chemistry of imidazotetrazine prodrugs.

Authors:  Catherine L Moody; Richard T Wheelhouse
Journal:  Pharmaceuticals (Basel)       Date:  2014-07-10
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.