A class of novel AA-Trp-Trp-OBzl: Synthesis, in vitro anti-proliferation, in vivo anti-tumor action, and intercalation mechanism

MedChemComm

Volumn 2, Issue 2, 2011, Pages 126-131

  Liu, Liu ^a   Wei, Lei ^a   Yang, Yifan ^a   Zhao, Ming ^a   Zhang, Xiaoyi ^a   Zheng, Meiqing ^a   Wang, Yuji ^a   Peng, Shiqi ^a  

^a CAPITAL MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BETA CARBOLINE 3 CARBONYLTRYPTOPHAN BENZYL ESTER DERIVATIVE; CYTARABINE; DNA; N TRYPTOPHANYL BETA CARBOLINE 3 CARBOXYLIC ACID BENZYL ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ACUTE TOXICITY; ANALYTICAL PARAMETERS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN HEPG2; CELL STRAIN K 562; CHEMICAL MODIFICATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG EFFICACY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IMMUNE RESPONSE; IN VITRO STUDY; IN VIVO STUDY; INTERCALATION COMPLEX; LD 50; LIVER CARCINOMA; MELANOMA CELL; MOLECULAR DOCKING; MOUSE; NONHUMAN; PHARMACOPHORE; PRIORITY JOURNAL; REACTION ANALYSIS; RING OPENING; SARCOMA 180; SINGLE DRUG DOSE; SOLID TUMOR; SPLEEN INDEX; TOXICITY TESTING; WEIGHT GAIN;

MUS;

EID: 79952527130     PISSN: 20402503     EISSN: 20402511     Source Type: Journal    
DOI: 10.1039/c0md00208a     Document Type: Article

References (20)

1. G. Momekov A. Bakalova M. Karavanova Novel approaches towards development of non-classical platinum-based antineoplastic agents: Design of platinum complexes characterized by an alternative DNA-binding pattern and/or tumor-targeted cytotoxicity Curr. Med. Chem. 2005 12 2177 2191 (Pubitemid 41179706)
2. A. Bolognese G. Correale M. Manfra A. Lavecchia O. Mazzoni E. Novellino P. La Colla G. Sanna R. Loddo Antitumor agents 3. Design, synthesis, and biological evaluation of new pyridoisoquinolindion and dihydrothienoquinolin- dione derivatives with potent cytotoxic activity J. Med. Chem. 2004 47 849 858 (Pubitemid 38176788)
3. M. A. Lynch O. Duval A. Sukhanova J. Devy S. P. Mackay R. D. Waigh I. Nabiev Synthesis, biological activity and comparative analysis of DNA binding affinities and human DNA topoisomerase I inhibitory activities of novel 12-alkoxy-benzo[c]phenanthridinium salts Bioorg. Med. Chem. Lett. 2001 11 2643 2646 (Pubitemid 32823374)
4. R. Cao W. Peng H. Chen Y. Ma X. Liu X. Hou H. Guan A. Xu DNA binding properties of 9-substituted harmine derivatives Biochem. Biophys. Res. Commun. 2005 338 1557 1563 (Pubitemid 41608427)
5. M. Laronze M. Boisbrun S. Leonce B. Pfeiffer P. Renard O. Lozach L. Meijer A. Lansiaux C. Bailly J. Sapi J. Y. Laronze Synthesis and anticancer activity of new pyrrolocarbazoles and pyrrolo-beta-carbolines Bioorg. Med. Chem. 2005 13 2263 2283 (Pubitemid 40261144)
6. A. M. Sobhani S. A. Ebrahimi M. J. Mahmoudian An in vitro evaluation of human DNA topoisomerase I inhibition by Peganum harmala L. seeds extract and its beta-carboline alkaloids Pharm Pharm Sci 2002 5 19 23 (Pubitemid 34463347)
7. M. Zhao L. Bi W. Wang C. Wang M. Baudy-Floc J. Ju S. Peng Synthesis and cytotoxic activities of beta-carboline amino acid ester conjugates Bioorg. Med. Chem. 2006 14 6998 7010 (Pubitemid 44307639)
8. J. H. Wu M. Zhao K. D. Qian K. H. Lee S. M. Natschke S. Q. Peng Novel N-(3-carboxyl-9-benzyl-beta-carboline-1-yl)ethylamino acids: Synthesis, anti- tumor evaluation, intercalating determination, 3D QSAR analysis and docking investigation Eur. J. Med. Chem. 2009 44 4153 4161
9. J. H. Wu C. Y. Li M. Zhao W. J. Wang Y. J. Wang S. Q. Peng A class of novel carboline intercalators: Their synthesis, in vitro anti-proliferation, in vivo anti- tumor action and 3D QSAR analysis Bioorg. Med. Chem. 2010 18 6220 6229
10. A. M. Sobhani S. R. Amini J. D. A. Tyndall E. Azizi M. Daneshtalab A. Khalaj A theory of mode of action of azolylalkylquinolines as DNA binding agents using automated flexible ligand docking J Mol Graphics Model 2006 25 459 469
11. A. Marco C. Loza-MejíaRafael L. R. Alfonso Molecular modeling of tricyclic compounds with anilino substituents and their intercalation complexes with DNA sequences J. Mol. Graphics Modell. 2009 27 900 907
12. C. M. A. Alves S. Naik P. J. G. Coutinho Novel long alkyl side chain benzo[a]phenoxazinium chlorides: synthesis, photophysical behaviour and DNA interaction Tetrahedron 2009 65 10441 10452
13. C. M. Venkatachalam X. Jiang T. Oldfield M. Waldman LigandFit: a novel method for the shape-directed rapid docking of ligands to protein active sites J. Mol. Graphics Modell. 2003 21 289 307 (Pubitemid 35441326)
14. A. M. Sobhani S. R. Amini J. D. A. Tyndall E. Azizi M. Daneshtalab A. Khalaj A theory of mode of action of azolylalkylquinolines as DNA binding agents using automated flexible ligand docking J. Mol. Graphics Modell. 2006 25 459 469 (Pubitemid 44667585)
15. Z. Rezaei H. Firouzabadi N. Iranpoor A. Ghaderi M. R. Jafari A. A. Jafari H. R. Zare Design and one-pot synthesis of α-aminophosphonates and bis(α- aminophosphonates) by iron(III) chloride and cytotoxic activity Eur. J. Med. Chem. 2009 44 4266 4275
16. N. Li Y. Ma C. Yang L. P. Guo X. R. Yang Interaction of anticancer drug mitoxantrone with DNA analyzed by electrochemical and spectroscopic methods Biophys. Chem. 2005 116 199 205 (Pubitemid 40962447)
17. U. Varadarajan C. Alfonso U. N. Balachandran Copper(II) complexes of N4 tetradentate ligands with flexible alkyl spacers: Crystal structure, DNA binding and cleavage studies Polyhedron 2007 26 3008 3016
18. P. U. Maheswari M. Palaniandavar DNA binding and cleavage properties of certain tetrammine ruthenium(II) complexes of modified 1,10-phenanthrolines- effect of hydrogen-bonding on DNA-binding affinity J. Inorg. Biochem. 2004 98 219 230 (Pubitemid 38087955)
19. T. S. Pitchumony H. S. Evans M. Palaniandavar Synthesis, structure and DNA interaction of cobalt(III) bis-complexes of 1,3-bis(2-pyridylimino) isoindoline and 1,4,7-triazacyclononane J. Inorg. Biochem. 2005 99 2110 2118 (Pubitemid 41562853)
20. F. Arjmand M. Aziz Synthesis and characterization of dinuclear macrocyclic cobalt(II), copper(II) and zinc(II) complexes derived from 2,2,2′,2′-S, S[bis(bis- N, N-2-thiobenzimidazolyloxalato-1,2-ethane) ]: DNA binding and cleavage studies Eur. J. Med. Chem. 2009 44 834 844