Novel trans-dichloridoplatinum(II) complexes with 3- and 4-acetylpyridine: Synthesis, characterization, DFT calculations and cytotoxicity

European Journal of Medicinal Chemistry

Volumn 44, Issue 5, 2009, Pages 1921-1925

  Rakić, Gordana M ^a   Grgurić Šipka, Sanja ^a   Kaluderović, Goran N ^b   Gómez Ruiz, Santiago ^c   Bjelogrlić, Snežana K ^d   Radulović, Siniša S ^d   Tešić, Živoslav Lj ^a  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

^c UNIVERSIDAD REY JUAN CARLOS   (Spain)

^d INSTITUTE FOR ONCOLOGY AND RADIOLOGY OF SERBIA   (Serbia)

Author keywords

Antitumoral activity; DFT; Platinum(II); X ray

Indexed keywords

3 ACETYLPYRIDINE; 4 ACETYLPYRIDINE; CISPLATIN; PLATINUM DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ARTICLE; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; DENSITY FUNCTIONAL THEORY; DRUG EXPOSURE; DRUG SYNTHESIS; FEMALE; GEOMETRY; HELA CELL; HUMAN; HUMAN CELL; INFRARED RADIATION; ISOMER; MELANOMA B16; MOUSE; NONHUMAN; OSTEOSARCOMA CELL; PROTON NUCLEAR MAGNETIC RESONANCE; UTERINE CERVIX CANCER; X RAY DIFFRACTION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MOLECULAR STRUCTURE; PLATINUM COMPOUNDS; PYRIDINES; SPECTRUM ANALYSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 62749093668     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.11.004     Document Type: Article

References (43)

1. Wang D., and Lippard S.J. Nat. Rev. Drug Discov. 4 (2005) 307-320
2. Kelland L. Nat. Rev. Cancer 7 (2007) 573-584
3. Natile G., and Coluccia M. Coord. Chem. Rev. 216-217 (2001) 383-410
4. Farrell N., and Kelland L.R. In: Farrell N.P. (Ed). Platinum-Based Drugs in Cancer Therapy (2000), Humana Press, Totowa 321-338
5. Mijatović S., Maksimović-Ivanić D., Radović J., Miljković D., Kalud{combining short stroke overlay}erović G.N., Sabo T.J., and Trajković V. Cell. Mol. Life Sci. 62 (2005) 1275-1282
6. Mellor H.R., Snelling S., Hall M.D., Modok S., Jaffar M., Hambley T.W., and Callaghan R. Biochem. Pharmacol. 70 (2005) 1137-1146
7. Hall M.D., and Hambley T.W. Coord. Chem. Rev. 1-2 (2002) 49-67
8. Kalud{combining short stroke overlay}erović G.N., Schmidt H., Paschke R., Kalinowski B., Dietrich A., Mueller T., and Steinborn D. J. Inorg. Biochem. 101 (2007) 543-549
9. Grgurić-Šipka S., Kowol C.R., Valiahdi S.-M., Eichinger R., Jakupec M.A., Roller A., Alexander, Shova S., Arion V.B., and Keppler B.K. Eur. J. Inorg. Chem. (2007) 2870-2878
10. Jakupec M.A., Galanski M., Arion V.B., Hartinger C.G., and Keppler B.K. Dalton Trans. (2008) 183-194
11. Kelter G., Sweeney N., Strohfeldt K., Fiebig H.-H., and Tacke M. Anti-Cancer Drugs 16 (2005) 1091-1098
12. Gómez-Ruiz S., Kalud{combining short stroke overlay}erović G.N., Prashar S., Polo-Cerón D., Fajardo M., Žižak Z., Sabo T.J., and Juranić Z.D. J. Inorg. Biochem. 102 (2008) 1558-1570
13. Gómez-Ruiz S., Kalud{combining short stroke overlay}erović G.N., Prashar S., Hey-Hawkins E., Erić A., Žižak Z., and Juranić Z. J. Inorg. Biochem. 102 (2008) 2087-2096
14. O'Dwyer P.J., Stevenson J.P., and Johnson S.W. Drugs 59 (2000) 19-27
15. Cvitkovic E., and Bekradda M. Semin. Oncol. 26 (1999) 647-662
16. Graham J., Muhsin M., and Kirkpatrick P. Nat. Rev. Drug Discov. 3 (2004) 11-12
17. Comess K.M., Costello C.E., and Lippard S.J. Biochemistry 29 (1990) 2102-2110
18. Farrell N., Ha T.T.B., Souchard J.P., Wimmer F.L., Cross S., and Johnson N.P. J. Med. Soc. 32 (1989) 2240-2241
19. Leng M., Locker D., Giraud-Panis M.J., Schwart A., Initini F.P., Natile G., Pisano C., Boccarelli A., Giordano D., and Coluccia M. Mol. Pharmacol. 58 (2000) 1525-1535
20. Connors T.A., Cleare M.J., and Harrap K.R. Cancer Treat. Rep. 63 (1979) 1499-1502
21. Radulović S., Tešić Z., and Manić S. Curr. Med. Chem. 9 (2002) 1611-1618
22. Manić S., Tešić Z., Juranić Z., Radulović S., Vrvić M., Potkonjak B., and Ilić Z. J. Exp. Clin. Cancer Res. 21 (2002) 519-526
23. Manić S., Tešić Z., Juranić Z., and Radulović S. J. BUON 6 (2001) 279-284
24. Lazic M.J., And{combining short stroke overlay}elković K.K., Sladić D.M., Tešić Z.L., and Radulović S.S. J. Exp. Clin. Cancer Res. 24 (2005) 63-68
25. Farrell N., Kelland L.R., Roberts J.D., and Van Beusichem M. Cancer Res. 52 (1992) 5065-5072
26. Kalinowska-Lis U., Ochocki J., and Matlawska-Wasowska K. Coord. Chem. Rev. 252 (2008) 1328-1345
27. Arandjelović S., Tešić Z., and Radulović S. Med. Chem. Rev. - Online 2 (2005) 415-422
28. Wheate N.J., and Collins J.G. Coord. Chem. Rev. 241 (2003) 133-145
29. Servidei T., Ferlini C., Riccardi A., Meco D., Scambia G., Segni G., Manzotti C., and Riccardi R. Eur. J. Cancer 37 (2001) 930-938
30. Tessier C., and Rochon F.D. Inorg. Chim. Acta 295 (1999) 25-38
31. Keller R.N., Moeller T., and Quagliano J.V. Inorg. Synth. 2 (1963) 247-250
32. SCALE3 ABSPACK: Empirical absorption correction, CrysAlis - Software package, Oxford Diffraction Ltd., 2006.
33. G.M. Sheldrick, SHELXS-97, Program for Crystal Structure Solution, Göttingen, 1997.
34. G.M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, Göttingen, 1997.
35. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., and Gonzalez C. GAUSSIAN 03, Revision C.02 (2004), Gaussian, J.A. Pople, Inc., Wallingford, CT
36. Becke A.D. J. Chem. Phys. 98 (1993) 5648-5652
37. Lee C., Yang W., and Parr R.G. Phys. Rev. B 37 (1988) 785-789
38. Vosko S.H., Wilk L., and Nusair M. Can. J. Phys. 58 (1980) 1200-1211
39. Stephens P.J., Devlin F.J., Chabalowski C.F., and Frisch M.J. J. Phys. Chem. 98 (1994) 11623-11627
40. Dunning Jr. T.H., and Hay P.J. Modern Theoretical Chemistry. third ed. vol. 3 (1976), Plenum, New York 1-28
41. Andrae D., Häußermann U., Dolg M., Stoll H., and Preuß H. Theor. Chem. Acc. 77 (1990) 123-141
42. Cossi M., Scalmani G., Rega N., and Barone V. J. Chem. Phys. 117 (2002) 43-54
43. Skehan P., Storeng R., Scudiero D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., and Boyd M.R. J. Natl. Cancer Inst. 82 (1990) 1107-1112