Interactions of porphyrins with nucleotides and nucleic acids

Pasternack, Robert F.; Antebi, Adam; Ehrlich, Bruce; Sidney, David; Gibbs, Esther J.; Bassner, Sherri L.; Depoy, Lesile M.

doi:10.1016/0304-5102(84)80011-5

Cited by 30 publications

(27 citation statements)

References 13 publications

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“…The negative couplet is typical of an external interaction on the phosphate backbone accompanied by selfstacking of porphyrin molecules 9 and a positive band at 415(þ) suggests that interaction with an external groove took place as well. 8,39 In the UV spectral region, the absorption band of the complex at the 10/1 molar ratio did not change its magnitude or shape compared with (dA-dT) 10 alone, and the corresponding ECD spectrum decreased in magnitude slightly, which could be caused by the weak destacking of the nitrogen bases because of the interaction with the porphyrin. The positive couplet suggests that the right-handed helix of the nucleotide was retained.…”

mentioning

confidence: 93%

“…Binding in the external groove is characterized by a small red shift ( 8 nm) and small hypochromicity ( 10%) or even hyperchromicity of the Soret maximum and by positively-induced CD signal. 7,8 External binding to the phosphate backbone accompanied by the self-stacking of porphyrins is characterized by an exciton conservative CD signal with both negative and positive bands of the same magnitude. 9 Both UV and Soret regions were used in the ECD studies of bound porphyrin-oligonucleotide conjugates.…”

Section: Introductionmentioning

confidence: 99%

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Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG‐dC)₁₀and (dA‐dT)₁₀

Nový

Urbanová

2006

Biopolymers

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The interactions of two different porphyrins, without axial ligands-5,10,15,20-tetrakis(1-methylpyridinium-4-yl)porphyrin-Cu(II) tetrachloride (Cu(II)TMPyP) and with bulky meso substituents-5,10,15,20-tetrakis(N,N,N-trimethylanilinium-4-yl)porphyrin tetrachloride (TMAP), with (dG-dC)10 and (dA-dT)10 were studied by combination of vibrational circular dichroism (VCD) and electronic circular dichroism (ECD) spectroscopy at different [oligonucleotide]/[porphyrin] ratios, where [oligonucleotide] and [porphyrin] are the concentrations of oligonucleotide per base-pair and porphyrin, respectively. The combination of VCD and ECD spectroscopy enables us to identify the types of interactions, and to specify the sites of interactions: The intercalative binding mode of Cu(II)TMPyP with (dG-dC)(10), which has been well described, was characterized by a new VCD "marker" and it was shown that the interaction of Cu(II)TMPyP with (dA-dT)10 via external binding to the phosphate backbone and major groove binding caused transition from the B to the non-B conformer. TMAP interacted with the major groove of (dG-dC)10, was semi-intercalated into (dA-dT)10, and caused significant variation in the structure of both oligonucleotides at the higher concentration of porphyrin. The spectroscopic techniques used in this study revealed that porphyrin binding with AT sequences caused substantial variation of the DNA structure. It was shown that VCD spectroscopy is an effective tool for the conformational studies of nucleic acid-porphyrin complexes in solution.

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confidence: 93%

Section: Introductionmentioning

confidence: 99%

Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG‐dC)₁₀and (dA‐dT)₁₀

Nový

Urbanová

2006

Biopolymers

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“…There is a large body of information available in the literature on the complexation of water-soluble, substituted, and cationic porphyrins and metalloporphyrins with nucleic acids in solution (1)(2)(3)(4)(5)(6)(7)(8)(9)(10). These studies indicate that tetrakis(4-Nmethylpyridy1)porphine [H2TMpyP] and its zinc derivative display different affinities for GC and AT rich regions of DNA.…”

Section: Introductionmentioning

confidence: 99%

Relative cross section and time-resolved fluorescence of porphyrin–DNA complexes

Liu¹,

Koningstein²,

Yevdokimov³

1991

Can. J. Chem.

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“…Aside (10,11,12), have shown that the metal complexes of meso-tetra-(N-methyl-4-pyridyl) porphine, H2T4MPyP cannot only bind to DNA but that the mode of binding (both outside binding and intercalation have been observed) and base preferences exhibited by the compounds are strongly influenced by the nature of the bound metal ion and porphyrin structure. DNase I footprinting studies involving the porphyrins and a 139-base pair restriction fragment of pBR-322 DNA revealed that Mn+3, Fe+3, Co+3 and Zn+2-T4MPyP bind in the minor groove of AT rich sequences of DNA while Cu+2 and Ni+2--T4MPyP bind to both AT and GC sites (13).…”

Section: Introductionmentioning

confidence: 99%

Cationic porphyrins as probes of DNA structure

1986

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The DNA binding specificity of a group of cationic manganese porphyrin complexes has been examined using DNase I footprinting methodology and by observing the sites of porphyrin-induced DNA strand scission in the presence of potassium superoxide.The compounds, which possess systematic changes in total charge, its distribution on the periphery on the macrocycle and ligand shape, bind in the minor groove of AT rich regions of DNA. While changes in total charge and charge arrangement do not significantly influence specificity, a shape change which blocks close ligand contact with the minor groove relaxes the original AT specificity causing the compound to cleave at both AT and GC sites. The observed changes in binding sequence specificity were interpreted in terms of electrostatic and steric factors associated with both the compounds and DNA.

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Interactions of porphyrins with nucleotides and nucleic acids

Cited by 30 publications

References 13 publications

Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG‐dC)₁₀and (dA‐dT)₁₀

Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG‐dC)₁₀and (dA‐dT)₁₀

Relative cross section and time-resolved fluorescence of porphyrin–DNA complexes

Cationic porphyrins as probes of DNA structure

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Interactions of porphyrins with nucleotides and nucleic acids

Cited by 30 publications

References 13 publications

Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG‐dC)10and (dA‐dT)10

Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG‐dC)10and (dA‐dT)10

Relative cross section and time-resolved fluorescence of porphyrin–DNA complexes

Cationic porphyrins as probes of DNA structure

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Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG‐dC)₁₀and (dA‐dT)₁₀

Vibrational and electronic circular dichroism study of the interactions of cationic porphyrins with (dG‐dC)₁₀and (dA‐dT)₁₀