Complexation of biologically active aromatic compounds with DNA in the presence of theophylline

Journal of Biological Physics

Volumn 35, Issue 2, 2009, Pages 115-126

  Hernandez Santiago, A A ^a   Andrejuk, D D ^b   Cervantes Tavera, A M ^a   Davies, D B ^c   Evstigneev, M P ^b  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^b SEVASTOPOL STATE UNIVERSITY   (Russian Federation)

^c UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Caffeine; Competitive binding; Hetero association; Interceptor mechanism; Protector mechanism; Theophylline

Indexed keywords

AROMATIC COMPOUND; BROMIDE; DAUNORUBICIN; ETHIDIUM; LIGAND; MITOXANTRONE; NORFLOXACIN; OLIGONUCLEOTIDE; PROFLAVINE; THEOPHYLLINE;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; DRUG DETERMINATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 64749095031     PISSN: 00920606     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10867-008-9124-x     Document Type: Article

References (31)

1. A. Lelo J.O. Miners R. Robson D. Birkett 1986 Assessment of caffeine exposure: caffeine content of beverages, caffeine intake and plasma concentration of methylxanthines Clin. Pharmacol. Ther. 39 54 59
2. Baron, J.J., Roberts, H.: Caffeine. Springer, Berlin (1981)
3. P. Dews H.C. Grice A. Neims J. Wilson R. Wurtman 1984 Report of fourth international caffeine workshop Food Chem. Toxicol. 22 163 169 doi:10.1016/0278-6915(84)90098-X
4. S.M. D'Ambrosio 1994 Evaluation of the genotoxicity data on caffeine Regul. Toxicol. Pharmacol. 19 243 281 doi:10.1006/rtph.1994.1023
5. J. Sawynok 1995 Pharmacological rationale for the clinical use of caffeine Drugs 49 37 50
6. F. Traganos J. Kapuscinski Z. Darzynkiewicz 1991 Caffeine modulates the effects of DNA-intercalating drugs in vitro: a flow cytometric and spectrophotometric analysis of caffeine interaction with novatrone, doxorubicin, ellipticine, and the doxorubicin analague AD198 Cancer Res. 51 3682 3689
7. J. Piosik M. Zdunek J. Kapuscinski 2002 The modulation by xanthines of the DNA-damaging effect of polycyclic aromatic agents. Part II. The stacking complexes of caffeine with doxorubicin and mitoxantrone Biochem. Pharmacol. 63 635 646 doi:10.1016/S0006-2952(01)00903-0
8. J. Piosik K. Ulanowska A. Gwizdek-Wisniewska A. Czyz J. Kapuscinski G. Wegrzyn 2003 Alleviation of mutagenic effects of polycyclic aromatic agents (quinacrine mustard, ICR-191 and ICR-170) by caffeine and pentoxifylline Mutat. Res. 530 47 57 doi:10.1016/S0027-5107(03)00136-2
9. K. Ulanowska J. Piosik A. Gwizdek-Wisniewska G. Wegrzyn 2005 Formation of stacking complexes between caffeine (1,2,3-trimethylxanthine) and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine may attenuate biological effects of this neurotoxin Bioorg. Chem. 33 402 413 doi:10.1016/j.bioorg.2005.07.004
10. D.B. Davies D.A. Veselkov L.N. Djimant A.N. Veselkov 2001 Hetero-association of caffeine and aromatic drugs and their competitive binding with a DNA oligomer Eur. Biophys. J. 30 354 366 doi:10.1007/s002490100150
11. M.P. Evstigneev V.V. Khomich D.B. Davies 2006 Complexation of anthracycline drugs with DNA in the presence of caffeine Eur. Biophys. J. 36 1 11 doi:10.1007/s00249-006-0071-9
12. M.P. Evstigneev A.O. Lantushenko V.P. Evstigneev Y.V. Mykhina D.B. Davies 2008 Quantitation of the molecular mechanisms of biological synergism in a mixture of DNA-acting aromatic drugs Biophys. Chem. 132 148 158 doi:10.1016/j.bpc.2007.11.001
13. R.W. Larsen R. Jasuja R. Hetzler P.T. Muraoka V.G. Andrada D.M. Jameson 1996 Spectroscopic and molecular modelling studies of caffeine complexes with DNA intercalators Biophys. J. 70 443 452
14. M.B. Lyles I.L. Cameron H.R. Rawls 2001 Structural basis for the binding affinity of xanthines with the DNA intercalator acridine orange J. Med. Chem. 44 4650 4660 doi:10.1021/jm9904708
15. D.B. Davies D.A. Veselkov M.P. Evstigneev A.N. Veselkov 2001 Self-association of the antitumour agent novatrone (mitoxantrone) and its hetero-association with caffeine J. Chem. Soc. Perkin Trans. 2 61 67 doi:10.1039/b007042o
16. 1H NMR spectroscopy Russ. J. Bioorg. Chem. 31 453 459 doi:10.1007/s11171-005-0062-0
17. M.P. Evstigneev K.A. Rybakova D.B. Davies 2006 Complexation of norfloxacin with DNA in the presence of caffeine Biophys. Chem. 121 84 95 doi:10.1016/j.bpc.2005.12.003
18. N.I. Nakano S.J. Igarashi 1970 Molecular interactions of pyrimidines, purines, and some other heteroaromatic compounds in aqueous media Biochemistry 9 577 583 doi:10.1021/bi00805a019
19. 1H NMR chemical shift measurements Magn. Reson. Chem. 23 375 378 doi:10.1002/mrc.1260230518
20. 1H NMR chemical shift measurements Magn. Reson. Chem. 27 249 252 doi:10.1002/mrc. 1260270311
21. 1H NMR chemical shift study Magn. Reson. Chem. 27 592 598 doi:10.1002/mrc.1260270613
22. Goodman, A.G., Rall, T.W., Nies, A.S.: The pharmacological basis of therapeutics, pp. 618-637. Pergamon, NY (1990)
23. W.J.A. Wijnands T.B. Vree 1991 The clinical importance of the interaction between (fluoro)quinolones and the methylxanthines theophylline and caffeine J. Drug Ther. Res. 16 15 17
24. I.M. Johnson S.G. Bhuvan Kumar R. Malathi 2003 De-intercalation of ethidium bromide and acridine orange by xanthine derivatives and their modulatory effect on anticancer agents J. Biomol. Struct. Dyn. 20 677 685
25. A.N. Veselkov M.P. Evstigneev D.A. Veselkov D.B. Davies 2001 A generalized NMR-derived statistical-thermodynamical model of hetero-association of aromatic molecules in aqueous solution J. Chem. Phys. 115 2252 2266 doi:10.1063/1.1359767
26. 1H NMR investigation of self-association of aromatic drug molecules in aqueous solution. Structural and thermodynamical analysis J. Chem. Soc., Faraday Trans. 92 383 390 doi:10.1039/ft9969200383
27. A.L. Thakkar L.G. Tensmeyer W.L. Wilham 1971 NMR evidence for self-association of theophylline in aqueous solution J. Pharm. Sci. 60 1267 1268 doi:10.1002/jps.2600600841
28. D.B. Davies R.J. Eaton S.F. Baranovsky A.N. Veselkov 2000 NMR investigation of the complexation of daunomycin with deoxytetranucleotides of different base sequence in aqueous solution J. Biomol. Struct. Dyn. 17 887 901
29. I.M. Johnson S.G. Bhuvan Kumar R. Malathi 2003 RNA binding efficacy of theophylline, theobromine and caffeine J. Biomol. Struct. Dyn. 20 687 692
30. G.R. Zimmermann R.D. Jenison C.L. Wick J.-P. Simorre A. Pardi 1997 Interlocking structural motifs mediate molecular discrimination by a theophylline-binding RNA Nat. Struct. Biol. 4 644 649 doi:10.1038/nsb0897-644
31. M.B. Lyles I.L. Cameron 2002 Caffeine and other xanthines as cytochemical blockers and removers of heterocyclic DNA intercalators from chromatin Cell Biol. Int. 26 145 154 doi:10.1006/cbir.2001.0810