Abstract
The DNA-binding behaviors of the fluorescein–porphyrinatozinc(II) complex Zn(Fl-PPTPP) (Fl-PPTPP = 5-(4-fluoresceinpropyloxy)phenyl-10,15,20-triphenylporphyrin) and fluorescein–porphyrinatocopper(II) complex Cu(Fl-PPTPP) with calf thymus DNA (CT-DNA) were investigated by UV–Vis absorption titrations, fluorescence spectra, viscosity measurements, thermal denaturation and circular dichroism. The results suggest that both complexes interact with CT-DNA by intercalation. In addition, their photocleavage reactions with pBR322 supercoiled plasmid DNA were investigated. Both complexes exhibit significant DNA cleavage activity, and singlet oxygen may play an important role in these reactions.
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Waskitoaji W, Hyakutake T, Kato J, Watanabe M, Nishide H (2009) Chem Lett 38:1164–1165
Shieh MJ, Peng CL, Lou PJ, Chiu CH, Tsai TY, Hsu CY, Yeh CY, Lai PS (2008) J Control Release 7:200–206
Poon CT, Zhao S, Wong WK, Kwong DWJ (2010) Tetrahedron Lett 51:664–668
Yedukondalu M, Ravikanth M (2011) Coord Chem Rev 255:547–573
Fiel RJ (1989) Porphyrin–nucleic acid interactions: a review. J Biomol Struct Dyn 6:1259–1273
Ishikawa Y, Yamakawa N, Uno T (2002) Bioorg Med Chem 10:1953–1960
D’Urso A, Mammana A, Balaz M, Holmes AE, Berova N, Lauceri R, Purrello R (2009) J Am Chem Soc 131:2046–2047
Li ZP, Xing YH, Zhang YH, Zhou GH et al (2009) J Coord Chem 62(4):564–576
Efthimiadou EK, Katsaros N, Karaliota A, Psomas G (2007) Bioorg Med Chem Lett 17:1238–1243
Benítez J, Guggeri L, Tomaz I, Pessoa JC, Moreno V, Lorenzo J (2009) J Inorg Biochem 103:1386–1390
Nejo AA, Kolawole GA, Opoku AR, Wolowska J, O’Brien P (2009) Inorg Chem Acta 362:3993–3998
McCrate A, Carlone M, Nielsen M, Swavey S (2010) Inorg Chem Commun 13:537–539
Vaz Serra V, Zamarrón A, Faustino MAF, Iglesias-de la Cruz MC, Blázquez A, Rodrigues JMM (2010) Bioorg Med Chem 18:6170–6178
Kelly TM, Tossi AB, McConnell DJ, Strekas TC (1985) Nucleic Acids Res 13:6017
Sternberg ED, Dolphin D, Bruckner C (1998) Tetrahedron 54:4151–4202
Oda K, Ogura S, Okura I (2000) J Photochem Photobiol B 59:20–25
Mező G, Herényi L, Habdas J, Majer Z, Kurdziel BM, Tóthf K, Csík G (2011) Biophys Chem 155:36–44
Mettath S, Munson BR, Pandey RK (1999) Bioconjug Chem 10:94–102
Yan XB, Weng M, Zhang MH, Shen T (1998) Dyes Pigm 36(3):259–272
Lu JZ, Tan XC, Huang JW, Dong CH (2005) Trans Met Chem 30:643–649
Lu JZ, Du YF, Wu B, Huang JW, Jiang J (2010) Trans Met Chem 35:451–456
Lu JZ, Huang JW, Fan LF, Liu J, Chen XL, Ji LN (2004) Inorg Chem Commun 7(9):1030–1033
Zhao P, Xu LC, Huang JW, Fu B, Yu HC, Ji LN (2008) Bioorg Chem 36:278–287
Lu JZ, Du YF, Guo HW (2011) J Coord Chem 64(7):1229–1239
Du YF, Lu JZ, Guo HW, Jiang J (2010) Trans Met Chem 35:859–864
Daryono HT, Shunsuke M, Takehiro A, Naoki Y, Hidenari I (2001) J Inorg Biochem 85:219–228
Pasternack RF, Gibbs EJ, Villafrancas JJ (1983) Biochemistry 22:2406–2414
Řeha D, Kabeláček M, Ryjáček F, Šponer J, Šponer JE, Elstner M, Suhai S, Hobza P (2002) J Am Chem Soc 124:3366–3376
Feng R, Konishi YS (1993) J Am Soc Mass Spectrom 4:638–642
Li T, Huang JW, Ma L, Ji LN (2003) Trans Met Chem 28:288–291
Chen B, Qin W, Wang P, Tian T, Ma HJ, Cao XP, Wu XJ, Zhou X, Zhang XL, Liu F, Zheng F, Li X (2003) Bioorg Med Chem Lett 13:3731–3733
Al-Azemi TF, Vinodh M (2011) Tetrahedron 67:2585–2590
Mehta G, Muthusamy S, Maiya BG, Arounaguiri S (1997) Tetrahedron Lett 38:7125–7129
Angelov D, Beylot B, Spassky A (2005) Biophys J 88:2766–2770
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We gratefully acknowledge the financial support for this work by Guangdong Pharmaceutical University (No. 43540119) and the National Natural Science Foundation of P. R. China (No. 81102753 &21101033).
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Lu, J., Pan, W., He, R. et al. DNA-binding and photocleavage studies of metallofluorescein–porphyrin complexes of zinc(II) and copper(II). Transition Met Chem 37, 497–503 (2012). https://doi.org/10.1007/s11243-012-9615-2
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DOI: https://doi.org/10.1007/s11243-012-9615-2