Novel 6,12-disubstituted chrysene as potent anticancer agent: Synthesis, in vitro and in vivo study

European Journal of Medicinal Chemistry

Volumn 45, Issue 10, 2010, Pages 4687-4691

  Banik, Bimal K ^a   Becker, Frederick F ^b  

^a UNIVERSITY OF TEXAS PAN AMERICAN   (United States)

^b UNIVERSITY OF TEXAS   (United States)

Author keywords

Anticancer agents; In vitro assay; In vivo test; Substituted chrysenes

Indexed keywords

ANTINEOPLASTIC AGENT; CHRYSENE DERIVATIVE; CISPLATIN; N,N (6,12 CHRYSENYL) BIS[4 (1 PIPERIDINYL)BUTANE] 1,4 DIAMINE; N,N (6,12 CHRYSENYL) BIS[4 (1 PIPERIDINYL)BUTANE] 1,4 DICARBOXIAMIDE; N,N (6,12 CHRYSENYL) BIS[4 (4N METHYLPIPERAZINYL)BUTANE] 1,4 DIAMINE; N,N (6,12 CHRYSENYL) BIS[4 (4N METHYLPIPERAZINYL)BUTANE] 1,4 DICARBOXIMIDE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL STRAIN HL 60; CONTROLLED STUDY; CYTOTOXICITY; DRUG MECHANISM; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; LYMPHOMA; MOUSE; NONHUMAN; OVARY CANCER; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; CHRYSENES; FEMALE; HUMANS; MICE; OVARIAN NEOPLASMS;

EID: 77956190830     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2010.07.033     Document Type: Article

References (34)

1. R.G. Harvey Polycyclic Aromatic Hydrocarbons 1997 Wiley-VCH
2. J.E. Rice, and Z.W. Cai An intramolecular arene-triflate coupling reaction for the regiospecific synthesis of substituted benzofluoranthenes J. Med. Chem. 58 1993 1415 1424
3. K.W. Bair, C.W. Andrews, R.L. Tuttle, V.C. Knick, M. Cory, and D.D. McKee 2-(Arylmethyl)amino-2methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding J. Med. Chem. 34 1991 1983 1990
4. K.W. Bair, R.I. Tuttle, V.C. Knick, M. Cory, and D.D. McKee (1-Pyrenylmethyl)amino alcohols, a new class of antitumor DNA intercalators. Discovery and initial amine side chain structure-activity studies J. Med. Chem. 33 1990 2385 2393
5. V.K. Malviya, P.Y. Liu, D.S. Alberts, E.A. Surwit, J.B. Craig, and E.V. Hanningan Evaluation of amonafide in cervical cancer phase II Am. J. Clin. Oncol. 15 1992 41 44
6. R. Rosell, J. Carles, A. Abad, N. Ribelles, A. Barnadas, A. Benavides, and M. Martin Phase I study of mitonafide in 120 h continuous infusion in non small cell lung cancer Invest. New Drugs 10 1992 171 175
7. S.M. Sami, R.T. Dorr, D.S. Alberts, and W.A. Remers 2-Substituted 1,2-dihydro-3H-dibenz[de, h]isoquinoline-1,3-diones. A new class of anti-tumor agent J. Med. Chem. 36 1993 765 770
8. S.M. Sami, R.T. Dorr, A.M. Solyion, D.S. Alberts, and W.A. Remers Amino-substituted2-[2′-(dimethylamino)ethyl]-1,2-dihydro-3H-dibenz[de, h]isoquinoline-1,3-diones. Synthesis, anti-tumor activity and quantitative structure-activity relationship J. Med. Chem. 38 1995 983 993
9. T. Fukushima, Y. Kawai, T. Nakayama, T. Yamaguchi, A. Yoshida, Y. Urasaki, S. Imamura, K. Kamiya, H. Tsutani, T. Ueda, and T. Nakamura Superior cytotoxic potency of mitoxantrone in interaction with DNA: comparison with that of daunorubicin Oncol. Res. 8 1996 95 100
10. W.A. Denny, G.W. Rewcastle, and B.C. Ganguley Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of minimal DNA-intercalating agents which may not act via topoisomerase II J. Med. Chem. 33 1990 814 819
11. P. Cherubim, L.W. Deady, M. Dorkos, N.H. Qazi, B.C. Baguley, and W.A. Denny Synthesis and biological evaluation of phenanthrene-derived carboxamides as cytotoxic agents Anti-Cancer Drug Des. 8 1993 429 438
12. H.H. Lee, B.D. Palmer, M. Boyd, B.C. Baguley, and W.A. Denny Potential antitumor agents 64 synthesis and antitumor evaluation of dibenzo[1,4]dioxin-1- carboxamides: a new class of weakly binding DNA-intercalating agents J. Med. Chem. 35 1992 258 266
13. M. Agbandje, T.C. Jenkins, R. McKenna, A.P. Reszka, and S. Neidle Anthrecene-9,10-diones as potential anticancer agents. Synthesis, DNA-binding, and biological studies on a series of 2,6-disubstituted derivatives J. Med. Chem. 35 1992 1418
14. S. Venitt, C. Crofton-Sleigh, M. Agbandje, T.C. Jenkins, and S. Neidle Anthracene-9,10-diones as potential anticancer agents: bacterial mutation studies of amido-substituted derivatives reveal an unexpected lack of mutagenicity J. Med. Chem. 41 1998 3748 3752
15. R.B. Perni, M.P. Wentland, J.I. Huang, R.G. Powles, S. Aldous, K.M. Klinbeil, A.D. Peverley, R.G. Robinson, T.H. Corbett, J.L. Jones, K.C. Mattes, J.B. Rake, and S.A. Coughlin Synthesis and antitumor activity of 4-aminomethylthioxanthenone and 5-aminomethylbenzothiopyranoindazole derivatives J. Med. Chem. 41 1998 3645 3654
16. P.J. Perry, S.M. Gowan, A.P. Reszka, P. Polucci, T.C. Jenkins, L.R. Kelland, and S. Neidle 1,4 and 2,6-Disubstituted amidoanthracene-9,10-dione derivatives as inhibitors of human telomerase J. Med. Chem. 41 1998 3253 3260
17. S.E. Wright, L.H. Hines, and J.C. White Effects of the lipophilic anticancer drug teniposide (VM-26) on membrane transport Chem.-Biol. Interact. 1 1990 31 48
18. T.R. Tritton Cell surface action of adriamycin Pharmacol. Ther. 49 1991 293 309
19. G.V. Born, and G.M. Housely Effects of modification of the membranes of intact erythrocytes on the anti-haemolytic action of chlorpromazine Br. J. Pharmcol. 79 1983 481 487
20. Y.H. Chen, and W.H. Huestis Role of membrane lipid distribution in chlorpromazine-induced shape change of human erythrocytes Biochim. Biophys. Acta 1323 1997 299 309
21. N. Motohashi, T. Kurihara, K. Satoh, H. Sakagami, I. Mucsi, R. Pusztai, M. Szabo, and J. Molnar Antitumor activity of benzo[a]phenothiazines Anticancer Res. 19 1999 1837 1842
22. F.F. Becker, and B.K. Banik Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of some chrysene derivatives Bioorg. Med. Chem. Lett. 8 1998 2877 2880
23. B.K. Banik, and F.F. Becker Synthesis, electrophilic substitution and structure-activity relationship studies of polycyclic aromatic compounds for the development of anticancer agents Curr. Med. Chem. 8 2001 1513 1533
24. B.K. Banik, and F.F. Becker Polycylic aromatic compounds as anticancer agents: structure-activity relationships of new chrysene and pyrene derivatives Bioorg. Med. Chem. 9 2001 593
25. F.F. Becker, C. Mukhopadhyay, L. Hackfeld, I. Banik, and B.K. Banik Polycyclic aromatic compounds as anticancer agents: synthesis and biological evaluation of dibenzofluorene derivatives Bioorg. Med. Chem. 8 2000 2693 2699
26. I. Banik, F.F. Becker, and B.K. Banik Stereoselective synthesis of β-lactams with polyaromatic imines: entry to new and novel anticancer agents J. Med. Chem. 46 2003 12 15
27. S. Samajdar, F.F. Becker, and B.K. Banik Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate Tetrahedron Lett. 41 2000 8017 8020
28. B.K. Banik, C. Mukhopadhyay, M.S. Venkatraman, and F.F. Becker A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine Tetrahedron Lett. 39 1998 7343 7346
29. M.K. Basu, F.F. Becker, and B.K. Banik Ultrasound-promoted highly efficient reduction of aromatic nitro compounds to the aromatic amines by samarium/ammonium chloride Tetrahedron Lett. 41 2000 6551 6554
30. B.K. Banik, M. Suhendra, I. Banik, and F.F. Becker Indium/ammonium chloride mediated selective reduction of aromatic nitro compounds: practical synthesis of 6-aminochrysene Synth. Commun. 30 2000 3745 3754
31. B.K. Banik, I. Banik, and F.F. Becker Indium/ammonium chloride-induced selective reduction of aromatic nitro compounds Org. Synth. 81 2004 188
32. B.K. Banik, O. Zegrocka, I. Banik, L. Hackfeld, and F.F. Becker Samarium-induced iodine-catalyzed reduction of imines: synthesis of amine derivatives Tetrahedron Lett. 40 1999 6731 6734
33. A. Ghatak, F.F. Becker, and B.K. Banik Samarium induced alkyl halide mediated reductive coupling of ketones Tetrahedron Lett. 41 2000 3793 3796
34. K.R. Piwowar-Landis, D. Chen, Q.C. Cui, V. Minic, F.F. Becker, B.K. Banik, and Q.P.V Apoptotic-inducing activity of novel polycyclic aromatic compounds in human leukemic cells Int. J. Mol. Med. 17 2006 931 935