Biopolym. Cell. 2002; 18(4):287-296.
Структура та функції біополімерів
Аналіз взаємодії антибіотика мітоксантрону з ДНК у присутності
кофеїну у водному розчині за даними 1Н-ЯМР спектроскопії
1Веселков О. Н., 1Висоцький С. О., 1Євстигнєєв М. П., 2Веселков Д. О., 1Димант Л. Н., 1Болотін П. О., 2Девіс Д. Б.
- Севастопольський національний технічний университет
вул. Університетська, 33, Севастополь, Україна, 99053 - Беркбек колледж Лондонского университета
Малет-стрит, Лондон WC1E 7НХ, Великобритания
Abstract
Методом одно- і двовимірної 1Н-ЯМР спектроскопії (500 МГц) вивчено зв'язування протипухлинного антибіотика мітоксантрону, або новантрону (NOV), з ДНК у присутності
кофеїну (CAF) у водному розчині. Комплексоутворення молекул проналізовано з урахуванням термодинамічних параметрів реакцій само- і гетероасоціації NOV і CAF та взаємодії
лігандів з дезокситетрануклеотидом 5'-d(TpCpGpA) за однакових експериментальних умов. Зроблено висновок про сиквенс-специфічність зв'язування NOV з піримідин-пуриновими послідовностями досліджуваного олігонуклеотиду. Показано, що зниження ефективності NOV, інтеркалюючого в ДНК при додаванні до розчину CAF, у значній мірі пов'язано з блокуванням молекулами
Повний текст: (PDF, російською)
References
[1]
Cotter FE. Therapeutic milestones. Novantrone (mitozantrone). Br J Clin Pract. 1988;42(5):207-9.
[2]
Drewinko B, Yang LY, Barlogie B, Trujillo JM. Comparative cytotoxicity of bisantrene, mitoxantrone, ametantrone, dihydroxyanthracenedione, dihydroxyanthracenedione diacetate, and doxorubicin on human cells in vitro. Cancer Res. 1983;43(6):2648-53.
[3]
Feofanov A, Sharonov S, Kudelina I, Fleury F, Nabiev I. Localization and molecular interactions of mitoxantrone within living K562 cells as probed by confocal spectral imaging analysis. Biophys J. 1997;73(6):3317-27.
[4]
Kapuscinski J, Darzynkiewicz Z. Relationship between the pharmacological activity of antitumor drugs Ametantrone and mitoxantrone (Novatrone) and their ability to condense nucleic acids. Proc Natl Acad Sci U S A. 1986;83(17):6302-6.
[5]
Smith PJ, Morgan SA, Fox ME, Watson JV. Mitoxantrone-DNA binding and the induction of topoisomerase II associated DNA damage in multi-drug resistant small cell lung cancer cells. Biochem Pharmacol. 1990;40(9):2069-78.
[6]
Kapuscinski J, Darzynkiewicz Z. Interactions of antitumor agents Ametantrone and Mitoxantrone (Novatrone) with double-stranded DNA. Biochem Pharmacol. 1985;34(24):4203-13.
[7]
Bailly C, Routier S, Bernier JL, Waring MJ. DNA recognition by two mitoxantrone analogues: influence of the hydroxyl groups. FEBS Lett. 1996;379(3):269-72.
[8]
Kapuscinski J, Darzynkiewicz Z, Traganos F, Melamed MR. Interactions of a new antitumor agent, 1,4-dihydroxy-5,8-bis[[2-[(2-hydroxyethyl)amino]-ethyl]amino]-9,10-anthracenedion e, with nucleic acids. Biochem Pharmacol. 1981;30(3):231-40.
[9]
Chen KX, Gresh N, Pullman B. A theoretical investigation on the sequence selective binding of mitoxantrone to double-stranded tetranucleotides. Nucleic Acids Res. 1986;14(9):3799-812.
[10]
Lown JW, Morgan AR, Yen SF, Wang YH, Wilson WD. Characteristics of the binding of the anticancer agents mitoxantrone and ametantrone and related structures to deoxyribonucleic acids. Biochemistry. 1985;24(15):4028-35.
[11]
Davies DB, Veselkov AN. Structural and thermodynamical analysis of molecular complexation by 1H NMR spectroscopy: Intercalation of ethidium bromide with the isomeric deoxytetranucleoside triphosphates 5'-d(GpCpGpC) and 5'-d(CpGpCpG) in aqueous solution. Journal of the Chemical Society - Faraday Transactions, 1996; 92 (19):3545-3557.
[12]
Mashkovskiy MD. Drugs. M.: Meditsina, 1985. 2: 107.
[13]
Beetham KL, Tolmach LJ. The sction of caffeine on X-irradiated HeLa cells: V. Identity of the sector of cells that expresses potentially lethal damage in G 1 and G 2. Radiat Res. 1982;91(1):199-211.
[14]
Selby CP, Sancar A. Molecular mechanisms of DNA repair inhibition by caffeine. Proc Natl Acad Sci U S A. 1990;87(9):3522-5.
[15]
Witte W, B?hme H. The action of caffeine on the survival of proteus mirabilis and its virulent phage VIr after UV-irradiation and treatment with nitrogen mustard. Mutat Res. 1972;16(2):133-9.
[16]
Fritzsche H, Petri I, Sch?tz H, Weller K, Sedmera P, Lang H. On the interaction of caffeine with nucleic acids. III. 1H NMR studies of caffeine--5'-adenosine monophosphate and caffeine-poly(riboadenylate) interactions. Biophys Chem. 1980;11(1):109-19.
[17]
Kimura H, Aoyama T. Decrease in sensitivity to ethidium bromide by caffeine, dimethylsulfoxide or 3-aminobenzamide due to reduced permeability. J Pharmacobiodyn. 1989;12(10):589-95.
[18]
Ross WE, Zwelling LA, Kohn KW. Relationship between cytotoxicity and DNA strand breakage produced by adriamycin and other intercalating agents. Int J Radiat Oncol Biol Phys. 1979;5(8):1221-4.
[19]
Ganapathi R, Grabowski D, Schmidt H, Yen A, Iliakis G. Modulation of adriamycin and N-trifluoroacetyladriamycin-14-valerate induced effects on cell cycle traverse and cytotoxicity in P388 mouse leukemia cells by caffeine and the calmodulin inhibitor trifluoperazine. Cancer Res. 1986;46(11):5553-7.
[20]
Iliakis G, Nusse M, Ganapathi R, Egner J, Yen A. Differential reduction by caffeine of adriamycin induced cell killing and cell cycle delays in Chinese hamster V79 cells. Int J Radiat Oncol Biol Phys. 1986;12(11):1987-95.
[21]
Traganos F, Kapuscinski J, Darzynkiewicz Z. Caffeine modulates the effects of DNA-intercalating drugs in vitro: a flow cytometric and spectrophotometric analysis of caffeine interaction with novantrone, doxorubicin, ellipticine, and the doxorubicin analogue AD198. Cancer Res. 1991;51(14):3682-9.
[22]
Larsen RW, Jasuja R, Hetzler RK, Muraoka PT, Andrada VG, Jameson DM. Spectroscopic and molecular modeling studies of caffeine complexes with DNA intercalators. Biophys J. 1996;70(1):443-52.
[23]
Kapuscinski J, Kimmel M. Thermodynamical model of mixed aggregation of intercalators with caffeine in aqueous solution. Biophys Chem. 1993;46(2):153-63.
[24]
Davies DB, Veselkov DA, Veselkov AN. Structure and thermodynamics of the hetero-association of aromatic molecules in aqueous solution determined by NMR spectroscopy. Mol Phys. 1999;97(3):439-51.
[25]
Davies DB, Veselkov DA, Kodintsev VV, Evstigneev MP, Veselkov AN. 1 H NMR investigation of the hetero-association of aromatic molecules in aqueous solution: factors involved in the stabilization of complexes of daunomycin and acridine drugs . Mol Phys. 2000;98(23):1961–71.
[26]
Davies DB, Veselkov DA, Evstigneev MP, Veselkov AN. Self-association of the antitumour agent novatrone (mitoxantrone) and its hetero-association with caffeine. Journal of the Chemical Society, Perkin Transactions 2. 2001;(1):61–7.
[27]
Lilley TH, Linsdell H, Maestre A. Association of caffeine in water and in aqueous solutions of sucrose. Faraday Trans. 1992;88(19):2865-70.
[28]
Veselkov AN, Djimant LN, Kodinzec VV, Lisutin VA, Parkes H, Davies D. 1H-NMR investigation of deoxytetranucleoside triphosphates D(TpGpCpA) self-association in aqueous solution. Biofizika. 1995; 40(2):283-92.
[29]
Davies DB, Karawajew L, Veselkov AN. 1H-NMR structural analysis of ethidium bromide complexation with self-complementary deoxytetranucleotides 5'-d(ApCpGpT), 5'-d(ApGpCpT), and 5'-d(TpGpCpA) in aqueous solution. Biopolymers. 1996;38(6):745-57.
[30]
Davies DB, Eaton RJ, Baranovsky SF, Veselkov AN. NMR investigation of the complexation of daunomycin with deoxytetranucleotides of different base sequence in aqueous solution. J Biomol Struct Dyn. 2000;17(5):887-901.
[31]
Eaton RJ, Baranovski? DA, Veselkov DA, Osetrov SG, Bolotin PA, Dymant LN, Pakhomov VI, Davis DV, Veselkov AN. [Study of the complex formation of daunomycin with deoxytetranucleotides with bases of differing sequence in an aqueous solution by 1H-NMR spectroscopy]. Biofizika. 2000;45(4):586-99.
[32]
Eaton RJ, Veselkov DA, Baranovskiy SF, Osetrov CG, Dymant LN, Devis DB, Veselkov AN. Investigation of self-assembly of molecules anthracycline antibiotic in an aqueous solution by 1H NMR. Khimicheskaya fizika. 2000; 19(2):98-104.
[33]
Davies DB, Djimant LN, Veselkov AN. 1H NMR investigation of self-association of aromatic drug molecules in aqueous solution. Structural and thermodynamical analysis. Faraday Trans. 1996;92(3):383-90.
[34]
Davies DB, Djimant LN, Veselkov AN. 1H NMR thermodynamical analysis of the interactions of proflavine with self-complementary deoxytetranucleotides of different base sequence. Nucleosides Nucleotides.1994;13(1-3):657-71.
[35]
McGhee JD, von Hippel PH. Theoretical aspects of DNA-protein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. J Mol Biol. 1974;86(2):469-89.
[36]
Pullman B. Molecular mechanism of specificity in DNA-antitumor drug interactions. Adv Drug Res. 1989. 18: 1-112.
[37]
Davies DB, Djimant LN, Baranovsky SF, Veselkov AN. 1H-NMR determination of the thermodynamics of drug complexation with single-stranded and double-stranded oligonucleotides in solution: ethidium bromide complexation with the deoxytetranucleotides 5'-d(ApCpGpT), 5'-d(ApGpCpT), and 5'-d(TpGpCpA). Biopolymers. 1997;42(3):285-95.
[38]
Chaires JB. Thermodynamics of the daunomycin-DNA interaction: ionic strength dependence of the enthalpy and entropy. Biopolymers. 1985;24(2):403-19.
[39]
Delbarre A, Roques BP, Le Pecq JB, Lallemand JY, Nguyen-Dat-Xuong. PMR studies of the self-association of DNA intercalating ellipticine derivatives in aqueous solution. Biophys Chem. 1976;4(3):275-9.
[40]
Ross PD, Subramanian S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry. 1981;20(11):3096-102.
[41]
Marky LA, Blumenfeld KS, Breslauer KJ. Calorimetric and spectroscopic investigation of drug-DNA interactions. I. The binding of netropsin to poly d(AT). Nucleic Acids Res. 1983;11(9):2857-70.
[42]
Sturtevant JM. Heat capacity and entropy changes in processes involving proteins. Proc Natl Acad Sci U S A. 1977;74(6):2236-40.
[43]
Reinert KE. Anthracycline-binding induced DNA stiffening, bending and elongation; stereochemical implications from viscometric investigations. Nucleic Acids Res. 1983;11(10):3411-30.
[44]
Veselkov DA, Davies DB, Djimant LN, Veselkov AN. Molecular basis of the protective action of caffeine on the complexation of intercalating ligands with DNA. Biopolym Cell. 2000; 16(6):468-81.
[45]
Davies DB, Veselkov DA, Djimant LN, Veselkov AN. Hetero-association of caffeine and aromatic drugs and their competitive binding with a DNA oligomer. Eur Biophys J. 2001;30(5):354-66.
