Literature DB >> 18515101

Effect of linkage geometry on biological activity in thiourea- and guanidine-substituted acridines and platinum-acridines.

Zhidong Ma1, Gilda Saluta, Gregory L Kucera, Ulrich Bierbach.   

Abstract

Novel thiourea- and guanidine-modified acridine-4-carboxamides (4, 7) and a corresponding platinum-intercalator conjugate (4') have been synthesized and evaluated as cytotoxic agents in human promyelocytic leukemia, HL-60, and a non-small cell lung cancer, NCI-H460. Modification of thiourea sulfur in derivative 4 with a DNA platinating moiety, giving 4', resulted in a pronounced cytotoxic enhancement, and the conjugate proved to be the most active of the newly synthesized compounds in NCI-H460 cells. Conjugate 4' represents a new chemotype with potential applications in the treatment of chemoresistant tumors.

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Year:  2008        PMID： 18515101      PMCID： PMC2474763          DOI： 10.1016/j.bmcl.2008.05.043

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


  21 in total

1.  DNA adducts of 9-anilinoacridine mustards: characterization by NMR.

Authors:  J Y Fan; S J Ohms; M Boyd; W A Denny
Journal:  Chem Res Toxicol       Date:  1999-12       Impact factor: 3.739

2.  Unusual intercalation of acridin-9-ylthiourea into the 5'-GA/TC DNA base step from the minor groove: implications for the covalent DNA adduct profile of a novel platinum-intercalator conjugate.

Authors:  Hemanta Baruah; Ulrich Bierbach
Journal:  Nucleic Acids Res       Date:  2003-07-15       Impact factor: 16.971

Review 3.  Acridine derivatives as chemotherapeutic agents.

Authors:  William A Denny
Journal:  Curr Med Chem       Date:  2002-09       Impact factor: 4.530

Review 4.  Crystal structures of acridines complexed with nucleic acids.

Authors:  Adrienne Adams
Journal:  Curr Med Chem       Date:  2002-09       Impact factor: 4.530

5.  Metal-intercalator-mediated self-association and one-dimensional aggregation in the structure of the excised major DNA adduct of a platinum-acridine agent.

Authors:  Hemanta Baruah; Cynthia S Day; Marcus W Wright; Ulrich Bierbach
Journal:  J Am Chem Soc       Date:  2004-04-14       Impact factor: 15.419

6.  Potential antitumor agents. 42. Structure-activity relationships for acridine-substituted dimethyl phosphoramidate derivatives of 9-anilinoacridine.

Authors:  G W Rewcastle; G J Atwell; B C Baguley; W A Denny
Journal:  J Med Chem       Date:  1984-08       Impact factor: 7.446

7.  Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions.

Authors:  Zhidong Ma; Cynthia S Day; Ulrich Bierbach
Journal:  J Org Chem       Date:  2007-06-07       Impact factor: 4.354

8.  Structure-activity relationships in platinum-acridinylthiourea conjugates: effect of the thiourea nonleaving group on drug stability, nucleobase affinity, and in vitro cytotoxicity.

Authors:  Margaret C Ackley; Colin G Barry; Amanda M Mounce; Michael C Farmer; Beth-Erin Springer; Cynthia S Day; Marcus W Wright; Susan J Berners-Price; Suzanne M Hess; Ulrich Bierbach
Journal:  J Biol Inorg Chem       Date:  2004-04-06       Impact factor: 3.358

9.  Phase II study of XR 5000 (DACA), an inhibitor of topoisomerase I and II, administered as a 120-h infusion in patients with non-small cell lung cancer.

Authors:  C Dittrich; B Coudert; L Paz-Ares; F Caponigro; M Salzberg; T Gamucci; X Paoletti; C Hermans; D Lacombe; P Fumoleau
Journal:  Eur J Cancer       Date:  2003-02       Impact factor: 9.162

10.  Unprecedented monofunctional metalation of adenine nucleobase in guanine- and thymine-containing dinucleotide sequences by a cytotoxic platinum-acridine hybrid agent.

Authors:  Colin G Barry; Hemanta Baruah; Ulrich Bierbach
Journal:  J Am Chem Soc       Date:  2003-08-13       Impact factor: 15.419
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  5 in total

1.  Non-traditional platinum compounds for improved accumulation, oral bioavailability, and tumor targeting.

Authors:  Katherine S Lovejoy; Stephen J Lippard
Journal:  Dalton Trans       Date:  2009-10-01       Impact factor: 4.390

2.  Comparative chemogenomics to examine the mechanism of action of dna-targeted platinum-acridine anticancer agents.

Authors:  Kahlin Cheung-Ong; Kyung Tae Song; Zhidong Ma; Daniel Shabtai; Anna Y Lee; David Gallo; Lawrence E Heisler; Grant W Brown; Ulrich Bierbach; Guri Giaever; Corey Nislow
Journal:  ACS Chem Biol       Date:  2012-09-05       Impact factor: 5.100

Review 3.  The Next Generation of Platinum Drugs: Targeted Pt(II) Agents, Nanoparticle Delivery, and Pt(IV) Prodrugs.

Authors:  Timothy C Johnstone; Kogularamanan Suntharalingam; Stephen J Lippard
Journal:  Chem Rev       Date:  2016-02-11       Impact factor: 60.622

4.  (Z)-2-Phenyl-3-pivaloyl-1,1-dipropyl-guanidine.

Authors:  Muhammad Said; Ghulam Murtaza; Eva Freisinger; Saeed Anwar; Abdur Rauf
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-08-08

5.  Acylated mono-, bis- and tris- cinchona-based amines containing ferrocene or organic residues: synthesis, structure and in vitro antitumor activity on selected human cancer cell lines.

Authors:  Benedek Imre Károlyi; Szilvia Bösze; Erika Orbán; Pál Sohár; László Drahos; Emese Gál; Antal Csámpai
Journal:  Molecules       Date:  2012-02-24       Impact factor: 4.411
  5 in total

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