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Articles

Comparative study of the interaction of meso-tetrakis (N-para-trimethyl-anilium) porphyrin (TMAP) in its free base and Fe derivative form with oligo(dA.dT)15 and oligo(dG.dC)15

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Pages 1598-1611 | Received 18 Jun 2013, Accepted 05 Sep 2014, Published online: 02 Oct 2014

References

  • Ajloo, D., Hajipour, S., Saboury, A. A., & Zakavi, S. (2011). Effect of cationic and anionic porphyrins on the structure and activity of adenosine deaminase. Bulletin of the Korean Chemical Society, 32, 3411.10.5012/bkcs.2011.32.9.3411
  • Araki, K., Silva, C. A., Toma, H. E., Catalani, L. H., Medeiros, M. H., & Di Mascio, P. (2000). Zinc tetraruthenated porphyrin binding and photoinduced oxidation of calf-thymus DNA. Journal of Inorganic Biochemistry, 78, 269–273.10.1016/S0162-0134(00)00053-2
  • Balaz, M., Holmes, A. E., Benedetti, M., Proni, G., & Berova, N. (2005). Porphyrin substituted phosphoramidites: New building blocks for porphyrin-oligonucleotide syntheses. Bioorganic & Medicinal Chemistry, 13, 2413–2421.
  • Bathaie, S. Z., Bolhasani, A., Hoshyar, R., Ranjbar, B., Sabouni, F., & Moosavi-Movahedi, A. A. (2007). Interaction of saffron carotenoids as anticancer compounds with ctDNA, Oligo (dG. dC) 15, and Oligo (dA. dT) 15. DNA and Cell Biology, 26, 533–540.10.1089/dna.2007.0598
  • Bathaie, S. Z., Moosavi-Movahedi, A. A., & Saboury, A. A. (1999). Energetic and binding properties of DNA upon interaction with dodecyl trimethylammonium bromide. Nucleic Acids Research, 27, 1001–1005.10.1093/nar/27.4.1001
  • Bathaie, S. Z., Nikfarjam, L., Rahmanpour, R., & Moosavi-Movahedi, A. A. (2010). Spectroscopic studies of the interaction of aspirin and its important metabolite; salicylate ion; with DNA; A.T and G.C rich sequences. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 77, 1077–1083.10.1016/j.saa.2010.08.078
  • Bathaie, S. Z., Sedghgoo, F., Jafarnejad, A., Farzami, B., & Khayatian, M. (2008). Spectroscopic studies of STZ-induced methylated-DNA in both in vivo and in vitro Conditions. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 71, 803–808.10.1016/j.saa.2008.02.002
  • Ben-Hur, E., & Horowitz, B. (1995). Advances in photochemical approaches for blood sterilization. Photochemistry and Photobiology, 62, 383–388.10.1111/php.1995.62.issue-3
  • Bennett, M., Krah, A., Wien, F., Garman, E., Mckenna, R., Sanderson, M., & Neidle, S. (2000). A DNA-porphyrin minor-groove complex at atomic resolution: The structural consequences of porphyrin ruffling. Proceedings of the National Academy of Sciences, 97, 9476–9481.10.1073/pnas.160271897
  • Bonnett, R. (1995). Photosensitizers of the porphyrin and phthalocyanine series for photodynamic therapy. Chemical Society Reviews, 24, 19–33.
  • Chen, C., Cohen, J. S., Myers, C. E., & Sohn, M. (1984). Paramagnetic metalloporphyrins as potential contrast agents in NMR imaging. FEBS Letters, 168, 70–74.10.1016/0014-5793(84)80208-2
  • Chen, X., & Liu, M. (2003). Induced chirality of binary aggregates of oppositely charged water-soluble porphyrins on DNA matrix. Journal of Inorganic Biochemistry, 94, 106–113.10.1016/S0162-0134(02)00645-1
  • del, C. B. A. M. (1993). Porphyrins, porphyrias, cancer and photodynamic therapy - a model for carcinogenesis. Photochemistry and Photobiology, 20, 5–22.
  • Gandini, S. C. M., Borissevitch, I. E., Perussi, J. R., Imasato, H., & Tabak, M. (1998). Aggregation of meso-tetrakis (4-N-methyl-pyridiniumyl) porphyrin in its free base, Fe (III) and Mn (III) forms due to the interaction with DNA in aqueous solutions: Optical absorption, fluorescence and light scattering studies. Journal of Luminescence, 78, 53–61.10.1016/S0022-2313(97)00278-0
  • Gandini, S. C., Yushmanov, V. E., Perussi, J. R., Tabak, M., & Borissevitch, I. E. (1999). Binding of the Mn (III) complex of meso-tetrakis (4-N-methyl-pyridimumyl) porphyrin to DNA. Effect of ionic strength. Journal of Inorganic Biochemistry, 73, 35–40.10.1016/S0162-0134(98)10088-0
  • Ghadamgahi, M., Ajloo, D., & Moalem, M. (2012). Kinetic studies on the self-aggregation of a non ionic porphyrin in the presence and absence of ionic liquid by molecular dynamics simulation. Journal of Porphyrins and Phthalocyanines, 16, 1082–1093.10.1142/S1088424612500915
  • Ghadamgahi, M., & Ajloo, D. (2011). Calculation and prediction of rate and equilibrium constants for aggregation of porphyrin by molecular dynamics, docking and QSPR methods. Journal of Porphyrins and Phthalocyanines, 15, 240–256.10.1142/S1088424611003215
  • Ghaderi, M., Bathaie, S. Z., Saboury, A. A., Sharghi, H., & Tangestaninejad, S. (2007). Interaction of an Fe derivative of TMAP (Fe (TMAP) OAc) with DNA in comparison with free-base TMAP. International Journal of Biological Macromolecules, 41, 173–179.10.1016/j.ijbiomac.2007.01.014
  • Hambright, P., Fawwaz, R., Valk, P., McRae, J., & Bearden, A. J. (1975). The distribution of various water soluble radioactive metalloporphyrins in tumor bearing mice. Bioinorganic Chemistry, 5, 87–92.10.1016/S0006-3061(00)80224-0
  • Hoshyar, R., Bathaie, S. Z., & Ashrafi, M. (2008). Interaction of safranal and picrocrocin with ctDNA and their preferential mechanisms of binding to GC-and AT-rich oligonucleotides. DNA and Cell Biology, 27, 665–673.10.1089/dna.2008.0791
  • Hoshyar, R., Bathaie, S. Z., Kyani, A., & Mousavi, M. F. (2012). Is there any interaction between telomeric DNA structures, G-quadruplex and I-motif, with saffron active metabolites? Nucleosides, Nucleotides & Nucleic Acids, 31, 801–812.
  • Jia, T., Jiang, Z. X., Wang, K., & Li, Z. Y. (2006). Binding and photocleavage of cationic porphyrin-phenylpiperazine hybrids to DNA. Biophysical Chemistry, 119, 295–302.10.1016/j.bpc.2005.09.025
  • Kang, J., Wu, H., Lu, X., Wang, Y., & Zhou, L. (2005). Study on the interaction of new water-soluble porphyrin with DNA. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 61, 2041–2047.10.1016/j.saa.2004.08.009
  • Kim, J. O., Lee, Y. A., Jin, B., Park, T., Song, R., & Kim, S. K. (2004). Binding mode of cationic monomer and dimer porphyrin with native and synthetic polynucleotides studied by polarized light spectroscopy. Biophysical Chemistry, 111, 63–71.10.1016/j.bpc.2004.04.004
  • Kuroda, R., & Tanaka, H. (1994). DNA-porphyrin interactions probed by induced CD spectroscopy. Journal of the Chemical Society, Chemical Communications, 13, 1575–1576.
  • Lee, S., Jeon, S. H., Kim, B. J., Han, S. W., Jang, H. G., & Kim, S. K. (2001). Classification of CD and absorption spectra in the Soret band of H(2)TMPyP bound to various synthetic polynucleotides. Biophysical Chemistry, 92, 35–45.10.1016/S0301-4622(01)00181-8
  • Li, L., Song, G. W., & Fang, G. (2006). Determination of bovine serum albumin by a resonance light-scattering technique with the mixed-complex La(Phth)(phen)3+. Journal of Pharmaceutical and Biomedical Analysis, 40, 1198–1201.
  • Marzilli, L. G. (1990). Medical aspects of DNA-porphyrin interactions. New Journal of Chemistry, 14, 409–420.
  • Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry, 19, 1639–1662.10.1002/(ISSN)1096-987X
  • Mukundan, N. E., Petho, G., Dixon, D. W., & Marzilli, L. G. (1995). DNA-tentacle porphyrin interactions: AT over GC selectivity exhibited by an outside binding self-stacking porphyrin. Inorganic Chemistry, 34, 3677–3687.10.1021/ic00118a015
  • Novy, J., & Urbanova, M. (2007). Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG-dC)10 and (dA-dT)10. Biopolymers, 85, 349–358.10.1002/(ISSN)1097-0282
  • Nyarko, E., Hanada, N., Habib, A., & Tabata, M. (2004). Fluorescence and phosphorescence spectra of Au(III), Pt(II) and Pd(II) porphyrins with DNA at room temperature. Inorganica Chimica Acta, 357, 739–745.10.1016/j.ica.2003.08.023
  • Park, T., Kim, J. M., Han, S. W., Lee, D. J., & Kim, S. K. (2005). Dispersion of meso-tetrakis(N-methylpyridinium-4-yl)porphyrin on [d(A-T)n]2 oligonucleotides. Biochimica et Biophysica Acta (BBA) – General Subjects, 1726, 287–292.10.1016/j.bbagen.2005.08.002
  • Pasternack, R. F., Brigandi, R. A., Abrams, M. J., Williams, A. P., & Gibbs, J. (1990). Interactions of porphyrins and metalloporphyrins with single-stranded poly(dA). Inorganic Chemistry, 29, 4483–4486.10.1021/ic00347a030
  • Pasternack, R. F., Bustamante, C., Collings, P. J., Giannetto, A., & Gibbs, E. J. (1993). Porphyrin assemblies on DNA as studied by a resonance light-scattering technique. Journal of the American Chemical Society, 115, 5393–5399.10.1021/ja00066a006
  • Pasternack, R. F., & Collings, P. J. (1995). Resonance light scattering: A new technique for studying chromophore aggregation. Science, 269, 935–939.10.1126/science.7638615
  • Pasternack, R. F., Goldsmith, J. I., Szep, S., & Gibbs, E. J. (1998). A spectroscopic and thermodynamic study of porphyrin/DNA supramolecular assemblies. Biophysical Journal, 75, 1024–1031.10.1016/S0006-3495(98)77591-5
  • Patronas, N. J., Cohen, J. S., Knop, R. H., Dwyer, A. J., Colcher, D., Lundy, J., … Myers, C. E. (1986). Metalloporphyrin contrast agents for magnetic resonance imaging of human tumors in mice. Cancer Treatment Reports, 70, 391–395.
  • Sehlstedt, U., Kim, S. K., Carter, P., Goodisman, J., Vollano, J. F., Norden, B., & Dabrowiak, J. C. (1994). Interaction of cationic porphyrins with DNA. Biochemistry, 33, 417–426.10.1021/bi00168a005
  • Strickland, J. A., Marzilli, L. G., & Wilson, W. D. (1990). Binding of meso-tetrakis (n-methylpyridiniumyl)porphyrin isomers to DNA: Quantitative comparison of the influence of charge distribution and copper(II) derivatization. Biopolymers, 29, 1307–1323.10.1002/(ISSN)1097-0282
  • Tjahjono, D. H., Mima, S., Akutsu, T., Yoshioka, N., & Inoue, H. (2001). Interaction of metallopyrazoliumylporphyrins with calf thymus DNA. Journal of Inorganic Biochemistry, 85, 219–228.10.1016/S0162-0134(01)00186-6
  • Ward, B., Skorobogaty, A., & Dabrowiak, J. C. (1986). DNA binding specificity of a series of cationic metalloporphyrin complexes. Biochemistry, 25, 7827–7833.10.1021/bi00372a007
  • Wei, C., Jia, G., Yuan, J., Feng, Z., & Li, C. (2006). A spectroscopic study on the interactions of porphyrin with G-quadruplex DNAs. Biochemistry, 45, 6681–6691.10.1021/bi052356z
  • Yousef Elahi, M., Bathaie, S. Z., Kazemi, S. H., & Mousavi, M. F. (2011). DNA immobilization on a polypyrrole nanofiber modified electrode and its interaction with salicylic acid/aspirin. Analytical Biochemistry, 411, 176–184.10.1016/j.ab.2011.01.006
  • Yun, B. H., Jeon, S. H., Cho, T. S., Yi, S. Y., Sehlstedt, U., & Kim, S. K. (1998). Binding mode of porphyrins to poly [d (AT)2] and poly [d (GC)2]. Biophysical Chemistry, 70, 1–10.10.1016/S0301-4622(97)00031-8
  • Zanelli, G. D., & Kaelin, A. C. (1981). Synthetic porphyrins as tumour-localizing agents. The British Journal of Radiology, 54, 403–407.10.1259/0007-1285-

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