The role of carboxymethyl substituents in the interaction of tetracationic porphyrins with DNA

European Biophysics Journal

Volumn 41, Issue 9, 2012, Pages 723-732

  Kovaleva, Oxana A ^a,b   Tsvetkov, Vladimir B ^c,d   Shchyolkina, Anna K ^a   Borisova, Olga F ^a   Ol'shevskaya, Valentina A ^e   Makarenkov, Anton V ^e   Semeikin, Alexander S ^f   Shtil, Alexander A ^g   Kaluzhny, Dmitry N ^a  

^a ENGELHARDT INSTITUTE OF MOLECULAR BIOLOGY   (Russian Federation)

^b MOSCOW INSTITUTE OF PHYSICS AND TECHNOLOGY   (Russian Federation)

^c INSTITUTE OF BIOMEDICAL CHEMISTRY   (Russian Federation)

^d TOPCHIEV INSTITUTE OF PETROCHEMICAL SYNTHESIS   (Russian Federation)

^e A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^f IVANOVO STATE UNIVERSITY OF CHEMISTRY AND TECHNOLOGY   (Russian Federation)

^g N N BLOKHIN RUSSIAN CANCER RESEARCH CENTER   (Russian Federation)

Author keywords

Absorption; Affinity; DNA; Fluorescence; Molecular docking; Porphyrins

Indexed keywords

CALF THYMUS DNA; DNA; PORPHYRIN; PYRIDINIUM DERIVATIVE;

ARTICLE; CHEMISTRY; MOLECULAR DOCKING; SYNTHESIS;

DNA; MOLECULAR DOCKING SIMULATION; PORPHYRINS; PYRIDINIUM COMPOUNDS;

EID: 84866548005     PISSN: 01757571     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00249-012-0848-y     Document Type: Article

References (32)

1. Berezin M, Berezina N, Semeikin A, V'yugin A (2007) Thermochemistry of solution of some quaternized derivatives of tetra(4-pyridyl)porphine in water Russ J Gen Chem 77(11):1955-1958 doi:10.1134/S1070363207110199
2. Biron E, Voyer N (2005) Synthesis of cationic porphyrin modified amino acids Chem Commun (Camb) (37):4652-4654 doi: 10.1039/b508380j
3. Borisova O, Golova Y, Gottikh B, Zibrov A, Il'icheva I, Lysov Y, Mamayeva O, Chernov B, Chernyi A, Shchyolkina A (1991) Parallel double stranded helices and the tertiary structure of nucleic acids J Biomol Struct Dynam 8(6):1187-1210
4. Borissova OF, Potapov AP, Surovaya AN, Trubitsyn SN, Volkenstein MV (1972) The dependence of fluorescence quantum yield of the tRNA-acriflavine complexes on the conformational changes in tRNA FEBS Lett 27(1):167-170
5. Chirvony VS, Galievsky VA, Kruk NN, Dzhagarov BM, Turpin P-Y (1997) Photophysics of cationic 5, 10, 15, 20-tetrakis-(4-Nmethylpyridyl) porphyrin bound to DNA, [poly(dA-dT)]2 and [poly(dG-dC)]2: on a possible charge transfer process between guanine and porphyrin in its excited singlet state J Photochem Photobiol B 40(2):154-162 doi:10.1016/s1011-1344(97)00043-2
6. Ding L, Balzarini J, Schols D, Meunier B, de Clercq E (1992) Anti-human immunodeficiency virus effects of cationic metalloporphyrin-ellipticine complexes Biochem Pharmacol 44(8): 1675-1679 doi: 10.1016/0006-2952(92)90486-3
7. Dutikova IuV, Borisova OF, Shchelkina AK, Lin J, Huang S, Shtil AA, Kaliuzhnyi DN (2010) 5, 10, 15, 20-Tetra-(N-methyl-3-pyridyl)porphyrin destabilizes the anti-arallel telomeric quadruplex d(TTAGGG)4 Mol Biol (Mosk) 44(5):929-937
8. Ford KG, Neidle S (1995) Perturbations in DNA structure upon interaction with porphyrins revealed by chemical probes, DNA footprinting and molecular modelling Bioorg Med Chem 3(6):671-677 doi:10.1016/0968-0896(95)00052-i
9. Frau S, Bernadou J, Meunier B (1997) Nuclease activity and binding characteristics of a cationic "manganese porphyrin-bis(benzimidazole) dye (Hoechst 33258)" conjugate Bioconjug Chem 8(2):222-231 doi:10.1021/ bc970007e
10. Garcia G, Sarrazy V, Sol V, Le Morvan C, Granet R, Alves S, Krausz P (2009) DNA photocleavage by porphyrin-olyamine conjugates Bioorg Med Chem17(2):767-776 doi:10.1016/j.bmc.2008.11.047
11. Gasteiger J, Marsili M (1978) A new model for calculating atomic charges in molecules Tetrahedron Lett 19(34):3181-3184 doi: 10.1016/s0040-4039(01)94977- 9
12. Haeubl M, Reith LM, Gruber B, Karner U, Muller N, Knor G, Schoefberger W (2009) DNA interactions and photocatalytic strand cleavage by artificial nucleases based on water-soluble gold(III) porphyrins J Biol Inorg Chem 14(7):1037-1052 doi: 10.1007/s00775-009-0547-z
13. Hui XW, Gresh N, Pullman B (1990) Modelling of the binding specificity in the interactions of cationic porphyrins with DNA Nucleic Acids Res 18(5):1109-1114
14. Jain A, Rajeswari MR (2002) Preferential binding of quinolones to DNA with alternating G, C/A, T sequences: a spectroscopic study J Biomol Struct Dyn 20(2):291-299
15. Jasuja R, Jameson DM, Nishijo CK, Larsen RW (1997) Singlet excited state dynamics of tetrakis(4-N-methylpyridyl)porphine associated with DNA nucleotides J Phys Chem B 101(8): 1444-1450 doi:10.1021/jp962684w
16. Kim JO, Lee YA, Yun BH, Han SW, Kwag ST, Kim SK (2004) Binding of meso-tetrakis(N-methylpyridinium-4-yl)porphyrin to AT oligomers: effect of chain length and the location of the porphyrin stacking Biophys J 86(2):1012-1017 doi:10.1016/s0006-3495(04)74176-4
17. Luo Y, Chang CK, Kessel D (1996) Rapid initiation of apoptosis by photodynamic therapy Photochem Photobiol 63(4):528-534
18. Magde D, Wong R, Seybold PG (2002) Fluorescence quantum yields and their relation to lifetimes of rhodamine 6G and fluorescein in nine solvents: improved absolute standards for quantum yields Photochem Photobiol 75(4):327-334
19. McGhee JD, von Hippel PH (1974) Theoretical aspects of DNAprotein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice J Mol Biol 86(2):469-489 doi: 10.1016/0022-2836(74)90031-X
20. Mezo G, Herenyi L, Habdas J, Majer Z, Mysliwa-Kurdziel B, Toth K, Csik G (2011) Syntheses and DNA binding of new cationic porphyrin-tetrapeptide conjugates Biophys Chem 155(1):36-44 doi:10.1016/j.bpc.2011.02.007
21. Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ (2009) AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility J Comput Chem 30(16):2785-2791 doi:10.1002/jcc.21256
22. Pasternack RF (2003) Circular dichroism and the interactions of water soluble porphyrins with DNA Chirality 15(4):329-332 doi: 10.1002/chir.10206
23. Pedretti A, Villa L, Vistoli G (2004) VEGA -an open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming J Comput Aided Mol Des 18(3):167-173 doi:10.1023/B:JCAM.0000035186. 90683.f2
24. Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE (2004) Chimera a visualization system for exploratory research and analysis J Comput Chem 25(13): 1605-1612 doi:10.1002/jcc.20084
25. Powell MJD (1977) Restart procedures for the conjugate gradient method Math Progr 12(1):241-254 doi:10.1007/bf01593790
26. Sari MA, Battioni JP, Dupre D, Mansuy D, Le Pecq JB (1990) Interaction of cationic porphyrins with DNA: importance of the number and position of the charges and minimum structural requirements for intercalation Biochemistry 29(17):4205-4215
27. Shieh YA, Yang SJ, Wei MF, Shieh MJ (2010) Aptamer-based tumortargeted drug delivery for photodynamic therapy ACS Nano 4(3):1433-1442 doi:10.1021/nn901374b
28. Steenkeste K, Tfibel F, Perree-Fauvet M, Briandet R, Fontaine-Aupart MP (2010) Tracking the photosensitizing antibacterial activity of mono(acridyl)bis(arginyl)porphyrin (MABAP) by time-resolved spectroscopy J Phys Chem A 114(9):3334-3339 doi:10.1021/jp910387a
29. Stewart JJP (2007) Semiempirical molecular orbital methods In: Reviews in computational chemistry Wiley, New York, pp 45-81 doi:10.1002/9780470125786.ch2
30. Strickland JA, Marzilli LG, Gay KM, Wilson WD (1988) Porphyrin and metalloporphyrin binding to DNA polymers: rate and equilibrium binding studies Biochemistry 27(24):8870-8878 doi:10.1021/bi00424a027
31. Tada-Oikawa S, Hirayama J, Hirakawa K, Kawanishi S (2009) DNA damage and apoptosis induced by photosensitization of 5,10,15,20-tetrakis (N-methyl-4-yridyl)-21H,23H-orphyrin via singlet oxygen generation Photochem Photobiol 85(6) doi: 10.1111/j.1751-1097.2009.00600.x
32. Tjahjono DH, Mima S, Akutsu T, Yoshioka N, Inoue H (2001) Interaction of metallopyrazoliumylporphyrins with calf thymus DNA J Inorg Biochem 85(2-3):219-228 doi:10.1016/S0162-0134(01)00186-6