Novel iron complexes bearing N6-substituted adenosine derivatives: Synthesis, magnetic, 57Fe Mössbauer, DFT, and in vitro cytotoxicity studies

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8719-8728

  Trávníček, Zdeněk ^a   Mikulík, Jiří ^a   Čajan, Michal ^a   Zbořil, Radek ^a   Popa, Igor ^a  

^a PALACKÝ UNIVERSITY   (Czech Republic)

Author keywords

57Fe M ssbauer spectroscopy; Adenosine derivatives; Cytotoxicity; DFT calculations; Iron complexes

Indexed keywords

ADENOSINE DERIVATIVE; IRON 57; IRON COMPLEX; N6 (2 FLUOROBENZYL)ADENOSINE; N6 (2 TRIFLUOROMETHYLBENZYL)ADENOSINE; N6 (3 TRIFLUOROMETHYLBENZYL)ADENOSINE; N6 (4 CHLOROBENZYL)ADENOSINE; N6 (4 FLUOROBENZYL)ADENOSINE; N6 (4 TRIFLUOROMETHOXYBENZYL)ADENOSINE; N6 (4 TRIFLUOROMETHYLBENZYL)ADENOSINE; RIBOSE; UNCLASSIFIED DRUG; WATER;

ANALYTIC METHOD; ARTICLE; BREAST ADENOCARCINOMA; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL COMPOSITION; CHRONIC MYELOID LEUKEMIA; COMPLEX FORMATION; CONDUCTANCE; CONTROLLED STUDY; CRYSTAL; CYTOTOXICITY; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; FLAME PHOTOMETRY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INFRARED SPECTROSCOPY; MAGNETISM; MAGNETOCHEMICAL ANALYSIS; MASS SPECTROMETRY; MELANOMA; MOSSBAUER SPECTROSCOPY; OSTEOSARCOMA; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TEMPERATURE DEPENDENCE; THERMAL ANALYSIS;

ADENOSINE; ALGORITHMS; CELL LINE, TUMOR; HUMANS; INHIBITORY CONCENTRATION 50; IRON; MAGNETIC RESONANCE SPECTROSCOPY; MAGNETICS; ORGANOMETALLIC COMPOUNDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; SPECTROSCOPY, MOSSBAUER;

EID: 51549120114     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.082     Document Type: Article

References (27)

1. Skoog F., Hamzi H.G., Szweykowska A.M., Leonard N.J., Carraway K.L., Fujii T., Helgeson J.P., and Loeppky R.N. Phytochemistry 6 (1967) 1169
2. Raynaud F.I., Whittaker S.R., Fischer P.M., McClue S., Walton M.I., Barrie S.E., Garrett M.D., Rogers P., Clarke S.J., Kelland L.R., Valenti M., Brunton L., Eccles S., Lane D.P., and Workman P. Clin. Cancer Res. 11 (2005) 4875
3. Maloň M., Trávníček Z., Maryško M., Zbořil R., Mašláň M., Marek J., Doležal K., Rolčík J., Kryštof V., and Strnad M. Inorg. Chim. Acta 323 (2001) 119
4. Maloň M., Trávníček Z., Maryško M., Zbořil R., Mašláň M., Marek J., Doležal K., Holub J., Rolčík J., and Strnad M. Transition Met. Chem. 27 (2002) 580
5. Trávníček Z., Maloň M., Zatloukal M., Doležal K., Strnad M., and Marek J. J. Inorg. Biochem. 94 (2003) 307
6. Trávníček Z., Klanicová A., Popa I., and Rolčík J. J. Inorg. Biochem. 99 (2005) 776
7. Mikulski C.M., Cocco S., De Franco N., and Moore T. Inorg. Chim. Acta 106 (1985) 89
8. Mikulski C.M., Minutella R., De Franco N., and Karayannis N.M. Inorg. Chim. Acta 106 (1985) L33
9. Capparelli M.V., Goodgame D.M.L., Hayman P.B., Skapski A.C., and Hathway D.E. FEBS Lett. 1632 (1983) 241
10. Karayannis N.M., Cronin J.T., Mikulski C.M., Pytlewski L.L., and Labes M.M. J. Inorg. Nucl. Chem. 33 (1971) 4344
11. Mikulski C.M., Mattucci L., Weiss L., and Karayannis N.M. Inorg. Chim. Acta 107 (1985) 147
12. Mikulski C.M., Kurlan M.K., Bayne M., Gaul M., and Karayannis N.M. Inorg. Chim. Acta 123 (1986) 27
13. Karayannis N.M., Mikulski C.M., Speca A.N., and Cronin J.T. Inorg. Nucl. Chem. Lett. 17 (1981) 261
14. Mikulski C.M., Fleming J., Fleming D., and Karayannis N.M. Inorg. Chem. 11 (1972) 2330
15. Allen F.A. Acta Crystallogr., Sect. B: Struct. Sci. 58 (2002) 380
16. Capparelli M.V., Goodgame D.M.L., Hayman P.B., and Skapski A.C. Inorg. Chim. Acta 125 (1986) L47
17. Schmale H.W., Gyr E., and Dubler E. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 56 (2000) 957
18. Boča R., Baran P., Dlháň L., Šima J., Wiesinger G., Renz F., El-Ayaan U., and Linert W. Polyhedron 16 (1997) 47
19. Kahn O. Molecular Magnetism (1993), Wiley-VCH, New York
20. Geary W.J. Coord. Chem. Rev. 7 (1971) 81
21. Doležal, K.; Popa, I.; Zatloukal, M.; Lenobel, R.; Hradecká, D.; Vojtěšek, B.; Uldrijan, S.; Mlejnek, P.; Werbrouck, S.; Strnad, M. European Patent Office, FR. (WO2004058791), 2004.
22. Pouchert, C.J. The Aldrich Library if Infrared Spectra (Edition III); Aldrich Chemical: 1001 W. St. Paul. Ave., Milwukee, Wisconsin, 53233, 1981.
23. Fujita T., and Sakaguchi T. Chem. Pharm. Bull. 25 (1977) 2419
24. Nakamoto K. Infrared and Raman spectra of Inorganic and Coordination Compounds (1997), Wiley, New York
25. Sreekanth A., and Prathapachandra Kurup M.R. Polyhedron 23 (2004) 969
26. 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.; Gonzalez, C.; and Pople, J.A.; Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford CT, 2004.
27. Trávníček Z., Szüčová L., and Popa I. J. Inorg. Biochem. 101 (2007) 477