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Frontiers of Chemistry in China

ISSN 1673-3495

ISSN 1673-3614(Online)

CN 11-5726/O6

Front. Chem. China    2008, Vol. 3 Issue (4) : 406-412    https://doi.org/10.1007/s11458-008-0073-5
Interaction of water-soluble bridged porphyrin with DNA
WANG Kai, ZHANG Zhi, GUO Qianni, BAO Xiaoping, LI Zaoying
College of Chemistry and Molecular Sciences, Wuhan University;
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Abstract A water-soluble porphyrin dimer (Por Dimer) containing eight positive charges, bridged by 4,4′-dicarboxy-2,2′-bipyridine, has been synthesized. With Meso-tetrakis(N-methyl-pyridium-4-yl)porphyrin (H2TMPyP) as the reference compound, the water-soluble porphyrin dimer was investigated for its interaction with DNA by absorption, fluorescence, and circular dichroism (CD) spectroscopy. The apparent affinity binding constant (Kapp = 1.2 × 106) of Por Dimer binding to CT DNA was measured by a competition method with ethidium bromide (EB) (that of H2TMPyP was 6.9 × 106). The cleavage ability of Por Dimer to pBR322 plasmid DNA was studied by gel electrophoresis. The results suggest that the binding modes of Por Dimer were complex and involve both intercalation and outside binding.
Issue Date: 05 December 2008
 Cite this article:   
ZHANG Zhi,WANG Kai,LI Zaoying, et al. Interaction of water-soluble bridged porphyrin with DNA[J]. Front. Chem. China, 2008, 3(4): 406-412.
 URL:  
https://academic.hep.com.cn/fcc/EN/10.1007/s11458-008-0073-5
https://academic.hep.com.cn/fcc/EN/Y2008/V3/I4/406
1 Uno H, Masumoto A, Ono N . Hexagonal columnar porphyrin assembly by unique trimericcomplexation of a porphyrin dimer with-stacking: remarkable thermalbehavior in a solid. J Am Chem Soc, 2003, 125: 12082–12083.
doi:10.1021/ja036203f
2 Kubo Y, Ishii Y, Yoshizawa T, Tokita S . Effective cation-assistedchirality induction using a dibenzo-diaza-30-crown-10 with bis-(zinc(II)porphyrin) units. Chem Commun, 2004, 1394–1395
3 Cheng F, Drain C M, Grohmann K . Porphyrins linked directly to the 5, 5′ positionsof 2, 2′-bipyridine: a new supramolecular building block andswitch. Inorg Chem, 2003, 42: 2075–2083.
doi:10.1021/ic025985v
4 Qin Y, Bakker E . Eliminationof dimer formation in in III porphyrin-based anion-selective membranesby covalent attachment of the ionophore. Anal Chem, 2004, 76: 4379–4386.
doi:10.1021/ac049577f
5 Blake I M, Krivokapic A, Katterle M, Anderson H L . Anderson, fusion and planarization of a quinoidal porphyrin dimer. Chem Commun, 2002, 1662–1663
6 Hajjaj F, Yoon Z S, Yoon M C, Park J, Satake A, Kim D H, Kobuke Y . Assemblies of supramolecularporphyrin dimers in pentagonal and hexagonal arrays exhibiting light-harvestingantenna function. J Am Chem Soc, 2006, 128: 4612–4623.
doi:10.1021/ja0583214
7 Ema T, Nemugaki S, Tsuboi S, Utaka M . Synthesis andCD spectrum of chiral porphyrin dimer. Tetrahedron Lett, 1995, 36: 5905–5908
8 Gust D, Moore T A, Moore A L . Mimicking bacterial photosynthesis. Pure & Appl Chem, 1998, 70: 2189–2200.
doi:10.1351/pac199870112189
9 Wanger R W, Lindsey J S, Seth J, Palaniappan V, Bocian D F . Molecular optoelectronicgates. J Am Chem Soc, 1996, 118: 3996–3997.
doi:10.1021/ja9602657
10 Brandon E J, Kollmar C, Miller J S . Orbital overlap and antiferromagnetic coupling in substitutedtetraphenylporphinatomanganate (iii) tetracyanoethenide based magnets.The Importance of σ-dz2-pz Overlap. J Am Chem Soc, 1998, 120: 1822.
doi: 10.1021/ja973452t
11 Anderson H L, Martin S J, Bradly D C . Synthesis and third-order nonlinear optical propertiesof a conjugated porphyrin polymer. AngewChem Int Ed Engl, 1994, 33: 655–657.
doi:10.1002/anie.199406551
12 MacDonald I J, Dougherty T J . Basic principles of photodynamictherapy. J Porphyrins Phthalocyanines, 2001, 5: 105–129.
doi:10.1002/jpp.328
13 Zupán K, Herényi L, Tóth K, Egyeki M, Csı´k G . Binding of cationic porphyrinto isolated DNA and nucleoprotein complex: quantitative analysis ofbinding forms under various experimental conditions. Biochemistry, 2005, 44: 15000–15006.
doi:10.1021/bi0510227
14 Mettath S, Munson B R, Pandey R K . DNA interaction and photocleavage properties of porphyrinscontaining cationic substituents at the peripheral position. Bioconjugate Chem, 1999, 10: 94–102.
doi:10.1021/bc9800872
15 Pratviel G, Pitie M, Bernadou J, Meunier B . Furfuralals indikator einer DNA-spaltung durch hydroxylierung des C5′-kohlenstoffatomsvon desoxyribose. Angew Chem Int Ed Engl, 1991, 6: 718–720
16 Bejune S A, Shelton A H, Mcmillin D R . New dicationic porphyrin ligands suited for intercalationinto b-form DNA. Inorg Chem, 2003, 42: 8465–8475.
doi:10.1021/ic035092i
17 Sari M A, Battioni J P, Dupre∘ D, Mansuy D, Le Pecq J B . Interaction of cationic porphyrins withDNA: importance of the number and position of the charges and minimumstructural requirements for intercalation. Biochemistry, 1990, 29: 4205–4215.
doi:10.1021/bi00469a025
18 Ohyama T, Mita H, Yamamoto Y . Binding of 5,10,15,20-tetrakis (nmethylpyridinium -4-yl)-21H,23H-porphyrinto an AT-rich region of a duplex DNA. BiophysChem, 2005, 113: 53–59.
doi:10.1016/j.bpc.2004.07.039
19 Kima J O, Leea Y A, Jina B, Parka T, Songb R, Kim S K . Binding mode of cationic monomer and dimer porphyrin with nativeand synthetic polynucleotides studied by polarized light spectroscopy. Biophys Chem, 2004, 111: 63–71.
doi:10.1016/j.bpc.2004.04.004
20 Clauss S L, Pastel M J . Stable porfimer sodium compositionsand methods for their manufacture. EuropePatent. 0568323B1, 1997
21 Genady A R, Gabel D . Synthesis of triazole-andpyridine-bridged porphyrin-chlorin and porphyrin dimers. Tetrahedron Lett, 2003, 44: 2915–2917.
doi:10.1016/S0040-4039(03)00468-4
22 Li D, Casas C, Etemad-Moghadam G, Meunier B . Synthesisof water-soluble, cationic functionalized metalloporphyrins havinga cytotoxic activity. New J Chem, 1990, 14: 421–431
23 Ishikawa Y, Yamakawa N, Uno T . Potent DNA photocleavage by zinc(ii) complexes of cationicbis-porphyrins linked with aliphatic diamine. Bioorg Med Chem, 2002, 10: 1953–1960.
doi:10.1016/S0968-0896(02)00003-2
24 Kochevar I E, Redmond R W . Photosensitized productionof singlet oxygen. Methods Enzymol, 2000, 319: 20–28.
doi:10.1016/S0076-6879(00)19004-4
25 Jain R K, Sarracino D A, Richert C . A Tetraphenylporphyrin-peptide hybrid with high affinityfor single-stranded DNA. Chem Commun, 1998, 3: 423–424.
doi:10.1039/a707803j
26 Uno T, Hamasaki K, Tanigawa M, Shimabayashi S . Shimabayashi,Binding of meso- tetrakis(n-methylpyridinium-4-yl)porphyrin to doublehelical RNA and DNA RNA hybrids. InorgChem, 1997, 36: 1676–1683.
doi:10.1021/ic960824a
27 Fiel R J, Howard J C, Mark E H, Datta-Gupta N . Interactionof DNA with a porphyrin ligand: evidence for intercalation. Nucleic Acids Res, 1979, 6: 3093–3118.
doi:10.1093/nar/6.9.3093
28 Dougherty G J, Pilbrow R, Skorobogaty A, Smith T D . Electronspin resonance spectroscopic and spectrophotometric investigationof the binding of tetracationic porphyrins and porphyrazines withcalf thymus DNA. J Chem Soc, Faraday Trans, 1985, 2(81): 1739–1759
29 Kelly J M, Murphy M J, Mcconnell D J, Ohuigin C . Acomparative study of the interaction of 5,10,15,20-tetrakis (n-methylpyridinium-4-yl)porphyrinand its zinc complex with dna using fluorescence spectroscopy andtopoisomerization. Nucleic Acids Res, 1985, 13: 167–184.
doi:10.1093/nar/13.1.167
30 Gandini S C M, Borissevitch I E, Perussi J R, Imasato H, Tabak M . Aggregation of meso-tetrakis(4-n-methyl-pyridiniumyl)porphyrin in its free base, fe(iii) and mn(iii) forms due to the interactionwith DNA in aqueous solutions: optical absorption, fluorescence andlight scattering studies. J Lumin, 1998, 78: 53–61.
doi:10.1016/S0022-2313(97)00278-0
31 Carvlin M J, Mark E, Fiel R J . Intercalative and nonintercalative binding of large cationicporphyrin ligands to polynucleotides. NucleicAcids Res, 1983, 11, 6141–6154.
doi:10.1093/nar/11.17.6141
32 Pasternack R F, Giannetto A, Pagano P, Gibbs E J . Self-assemblyof porphyrins on nucleic acids and polypeptides. J Am Chem Soc, 1991, 113: 7799–7800.
doi:10.1021/ja00020a072
33 Carvlin M J, Fiel R J . Intercalative and nonintercalativebinding of largecationic porphyrin ligands to calf thymus DNA. Nucleic Acids Res, 1983, 11: 6121–6139.
doi:10.1093/nar/11.17.6121
34 Chen X D, Liu M H . Induced chirality of binaryaggregates of oppositely charged water-soluble porphyrins on DNA matrix. J Inorg Biochem, 2003, 94: 106–113.
doi:10.1016/S0162-0134(02)00645-1
35 Pasternack R F, Gibbs E J, Villafranca J . Interactions of porphyrins with nucleic acids. Biochemistry, 1983, 22: 2406–2414.
doi:10.1021/bi00279a016
36 Tian J N, Liu J Q, Xie J P, Yao X J, Hua Z D, Chen X G . Binding of wogonin to human serum albumin: a common binding siteof wogonin in subdomain IIA. J PhotochemPhotobio B: Biol, 2004, 74: 39–45.
doi:10.1016/j.jphotobiol.2004.01.001
37 Zhong W Y, Yu J S, Liang Y O . Chlorobenzylidine-herring sperm DNA interaction: bindingmode and thermodynamic studies. SpectrochimActa Part A, 2003, 59: 1281–1288.
doi:10.1016/S1386-1425(02)00301-3
38 LePecq J B, Paoletti C . A fluorescent complex betweenethidium bromide and nucleic acids, physical-chemical characterization. J Mol Bio, 1967, 27: 87–106.
doi:10.1016/0022-2836(67)90353-1
39 Li Y J, Li X F, Li Y L, Liu H B, Wang S, Gan H Y, Li J B, Wang N, He X R, Zhu D B . Controlled self-assembly bbehavior ofan amphiphilic bisporphyrinbipyridinium-palladium complex: from multibilayervesicles to hollow ccapsules. Angew ChemInt Ed, 2006, 45: 3639–3643.
doi:10.1002/anie.200600554
40 Tomohiro Y, Satake A, Kobuke Y . Synthesis of bipyridylene-bridged bisporphyrin by nickel-mmediatedcoupling reaction: on-off control of cofacial porphyrin unit by reversiblecomplexation. J Org Chem, 2001, 66: 8442–8446.
doi:10.1021/jo015852b
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