Intercalative and nonintercalative binding of large cationic porphyrin ligands to polynucleotides

Carvlin, Mark J.; Mark, E.H.; Fiel, Robert J.; Howard, J. C.

doi:10.1093/nar/11.17.6141

Cited by 113 publications

(76 citation statements)

References 34 publications

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“…The CD spectra presented in Figures 2(a) and (b) coincide with the above mentioned data [6,9,11,12,21,23]. The linear dependence of the negative band intensity at r < 0.05 and the linear dependence of positive band intensity on r in the range from 0.02 to 0.16 in case of TOEPyP4-DNA complex indicate the homogeneous binding modes, in particular intercalation between the GC base pairs and a moderate surface binding on DNA minor groove.…”

Section: Discussionsupporting

confidence: 83%

“…On the basis of some experimental data [6,[11][12][13][14]23], we propose the following explanation. TOEPyP4 that intercalates into the GC rich sites induces not only local damages, but also causes distortion of the standard B-form of DNA [6,23].…”

Section: Discussionmentioning

confidence: 99%

“…TOEPyP4 that intercalates into the GC rich sites induces not only local damages, but also causes distortion of the standard B-form of DNA [6,23]. As a result, the intercalation or selfstacking becomes possible into the AT sites, which were impossible for Zn-porphyrin in absence of TOEPy P4.…”

Section: Discussionmentioning

confidence: 99%

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CD and DSC Investigation of Individual and Complex Influence of Meso-Tetra(4-Oxiethylpyridil) Porphyrin (TOEPyP4) and Its Zn-Complex on DNA

Monaselidze¹,

Kiziria²,

Gorgoshidze³

et al. 2012

AJAC

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CD spectra of (DNA-TOEPyP4) + ZnTOEPyP4, (DNA-ZnTOEPyP4) + TOEPyP4, and DNA + (TOEPyP4-ZnTOEPyP4) complexes have been studied. It is shown that CD spectra of these triple complexes significantly differ from the DNA-TOEPyP4 and DNA-ZnTOEPyP4 double complex spectra, and they are not sum of these double complexes. Especially some strong differences in CD spectra of the triple and double complexes were observed when both porphyrins were added simultaneously into the DNA solution. In this case, ZnTOEPyP4 revealed a dominant influence on CD spectrum form. Zn-porphyrin also caused a strong intensity of positive band at 416 nm and a negative band at 437 nm when it was added into solution containing the DNA-TOEPyP4 complex. On the basis of obtained data, it was supposed that the observed significant changes in CD spectra of triple complexes were connected to an altered DNA conformation initiated by intercalation of porphyrin TOEPyP4 into GC-rich sites. The melting process analysis of the double complexes was carried out. The mechanisms of individual and joint influence of the porphyrins on DNA, and influence of binding modes on stability of these complexes are also discussed.

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Section: Discussionsupporting

confidence: 83%

Section: Discussionmentioning

confidence: 99%

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CD and DSC Investigation of Individual and Complex Influence of Meso-Tetra(4-Oxiethylpyridil) Porphyrin (TOEPyP4) and Its Zn-Complex on DNA

Monaselidze¹,

Kiziria²,

Gorgoshidze³

et al. 2012

AJAC

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“…[3][4][5] For the binding, three major modes have been proposed: intercalation, outside binding in the groove, and outside binding with self-stacking along the DNA surface. 6) These binding modes have been suggested using the physicochemical method of viscometry 7,8) and spectroscopic techniques such as UV-visible absorption, [6][7][8] circular dichroism (CD), [6][7][8][9] fluorescence, 10,11) and NMR spectroscopy. 12,13) For the photonuclease activity, cationic TMPyP is more efficient in strand scission of plasmid DNA than an anionic porphyrin like hematoporphyrin derivative (HPD).…”

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confidence: 99%

Solution Properties and Photonuclease Activity of Cationic Bis-porphyrins Linked with a Series of Aliphatic Diamines.

Yamakawa

Ishikawa

Uno

2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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The development of efficient photo-induced DNA cleavage agents has been of particular interest for biomedical applications such as cancer photodynamic therapy (PDT). Toward this objective, we synthesized a series of cationic bis-porphyrins with various lengths of diamino alkyl linkage, N,N-bis{4-[10,15,20-tris(1-methylpyridinium-4-yl)porphyrin-5-yl]benzoyl}oligomethylenediamine hexaiodide. They were expected to show more efficient photocleavage of DNA than unichromophore meso-tetrakis(4-N-methylpyridiniumyl)porphine (TMPyP), which is well known to cleave DNA effectively on illumination. The cationic bis-porphyrins were found to self-aggregate in aqueous solution, and the aggregation property was accounted for by the formation of an intermolecular dimer. Because conservative-type circular dichroism spectra of the bis-porphyrins were induced in the Soret region on binding to calf thymus DNA, we assigned their binding mode to outside self-stacking on the DNA surface. Their photonuclease activity using plasmid DNA decreased as the number of their linker hydrocarbons increased, and was well correlated with their tendency for dimerization. The inhibitory effect of azide anion, N 3 ؊ , and the enhancement effect of D 2 O suggest that singlet oxygen was probably involved in the photocleavage of DNA.Key words porphyrin; DNA; photocleavage; aggregation; singlet oxygen plex DNA, and photonuclease activity. We show that these cationic bis-porphyrins formed intermolecular dimers in aqueous solution, and bound to calf thymus DNA (CTDNA) with outside self-stacking. Their photocleavage efficiency of plasmid DNA diminished as the number of their linker hydrocarbons increased, and correlated with their tendency for dimerization. ExperimentalInstrumentation The 1 H-NMR spectra were recorded on a JEOL GX-400 or JNM-A-500 spectrometer. The MALDI-TOF (matrix-assisted laser desorption/ionization time-of-flight) mass spectra (MS) were measured on a Bruker REFLEX TM . The UV-visible absorption measurement was performed on a Beckman DU650 spectrophotometer. The CD spectra were recorded on a JASCO J-720 spectropolarimeter. Elemental analyses were performed at the Analytical Center, Kumamoto University. Materials and MethodsReagents for the synthesis of cationic bis-porphyrins were purchased from Tokyo Kasei Chemical Co. Thionyl chloride was distilled before use. Hexane, methylene chloride, and triethylamine were distilled in the presence of P 2 O 5 .24) 5-(4-methoxycarbonylphenyl)-10,15,20-tris(4-pyridyl)porphine (TPyPCOOCH 3 ) and 5-(4-carboxyphenyl)-10,15,20-tris(4-pyridyl)porphine (TPyPCOOH) were synthesized according to the previous method.25) CTDNA was purchased from Sigma Chemical Co., and the solution was quantitated spectrophotometrically using e 260 ϭ13200 M (base pairs) Ϫ1 · cm Ϫ1 . The tosylate salt of TMPyP was purchased from Dojin Chemical Co.General Procedure for the Synthesis of Non-charged Bis-porphyrins Linked with a Series of Aliphatic Diamines TPyPCOOH (250 mg, 0.378 mmol) was dissolved in 35 ml of thionyl chloride unde...

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“…It has been established that the DNA-binding-mode preference of cationic porphyrins (e.g. the external binding versus intercalation) can be modulated not only by changes in the coordinated metal, but also by altcration in their periphery (Carvlin et al, 1983;Pasternack et al, 1983). Phthalocyanines closely resemble porphyrins in many of their phy sico-chemical, photophysical and photosensitizing properties.…”

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confidence: 99%

Interactions of chloroaluminium‐tetramethyl‐tetrapyridino‐porphyrazine with DNA

Gantchev

Ali

Lier

1993

European Journal of Biochemistry

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The interaction of chloroaluminium-tetramethyl-tetrapyridinoporphyrazine (ClAlTMPyPa) with DNA was investigated by absorptiodemission and circular-dichroic spectroscopy. Formation of a DNA-porphyrazine complex was evidenced by quenching of the ClAlTMPyPa fluorescence, a hypochromic red shift of the absorption band in the visible part of the spectrum and induction of a characteristic CD band with high positive ellipticity. Scatchard analysis of the spectral changes in low ionic strength buffer suggested an association constant of 9.7 2 0 . 6 X 10' M-'. Quenching of the fluorescence of a DNA-ethidium complex by added ClAlTMPyPa was shown to result rrom direct DNA-dye interaction rather than the displacement of ethidium from DNA. Our data suggest that porphyrazine binds to the outside of the DNA helix, involving interactions which are not limited to electrostatic forces only. The computer assisted modelling of ClAlTMPyPa-DNA interactions showed that the energy-minimized intermolecular orientation involves face-on binding of the ligand, preferably on the minor DNA groove.The interaction of cationic meso-tetrapyridyl substituted porphyrins with polynucleotides has previously been studied to probe nucleic acid structure and dynamics (Pasternack and Gibbs, 1989; Raner ct al., 1989;Marzilli, 1990). It has been established that the DNA-binding-mode preference of cationic porphyrins (e.g. the external binding versus intercalation) can be modulated not only by changes in the coordinated metal, but also by altcration in their periphery (Carvlin et al., 1983;Pasternack et al., 1983). Phthalocyanines closely resemble porphyrins in many of their phy sico-chemical, photophysical and photosensitizing properties. Current interest in the biological activities of phthalocyanines relates to their potential use as tumor-localizing photosensitizers for the photodynamic therapy of cancer (Rosenthal, 1991 ; Paquette and van Lier, 1992). Among the new photosensitizers for photodynamic therapy and other photobiological applications (e.g. in photochemical DNA footprinting), phthalocyanine analogues, such as tetramethyl-metalloporphyrazincs, are promising candidates. Due to the size criterion and their histochemical staining behaviour, tetramethyl-porphyrazines are believcd to bind intrahelically to DNA (Scott, 1972). However, detailed analysis of the DNA-binding properties of cationic porphyrazines have not been reported. In the present study. we characterize the interactions of chloroaluminiumLctramcthyl-tetrapyridinoporphyrazine (Cl AlTMPyPa, Fig. 1 ) with natural, long-chain DNA using absorption, fluorescence and CD spectroscopy. The optical properties of the DNA-

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Intercalative and nonintercalative binding of large cationic porphyrin ligands to polynucleotides

Cited by 113 publications

References 34 publications

CD and DSC Investigation of Individual and Complex Influence of Meso-Tetra(4-Oxiethylpyridil) Porphyrin (TOEPyP4) and Its Zn-Complex on DNA

CD and DSC Investigation of Individual and Complex Influence of Meso-Tetra(4-Oxiethylpyridil) Porphyrin (TOEPyP4) and Its Zn-Complex on DNA

Solution Properties and Photonuclease Activity of Cationic Bis-porphyrins Linked with a Series of Aliphatic Diamines.

Interactions of chloroaluminium‐tetramethyl‐tetrapyridino‐porphyrazine with DNA

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