Cationic porphyrin-DNA interactions: Importance of the number and position of the charges

Sari, Marie-Agnès; Battioni, Jean-Paul; Dupré, Denis J.; Mansuy, Daniel; Pecq, J.‐B. Le

doi:10.1016/0006-2952(88)90483-2

Cited by 13 publications

(12 citation statements)

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“…Due to the success of porphyrins as photosensitizers, studies aimed at understanding the molecular interactions between porphyrins and DNA are of current interest. The interactions between free base and metalloderivatives of various mesosubstituted cationic porphyrins and various oligomers has been elucidated using UV−vis absorption, fluorescence, circular dichroism, and resonance Raman spectroscopies. − Intercalative binding of free base T4MPyP (Figure ) and its planar metalloderivatives is preferred at GC-rich sequences and is characterized by a large bathochromic shift (>15 nm) in the Soret absorption band and an induced negative circular dichroism in the Soret region of T4MPyP. In addition, these interactions bring about a decrease in fluorescence intensity.…”

Section: Introductionmentioning

confidence: 99%

Singlet Excited State Dynamics of Tetrakis(4-N-methylpyridyl)porphine Associated with DNA Nucleotides

et al. 1997

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The singlet excited state behavior of tetrakis(4-N-methylpyridyl)porphine (T4MPyP) in the presence of the four mononucleotides of DNA in aqueous solution has been examined. Addition of the nucleotides of adenine, thymine, or cytosine to a solution containing T4MPyP results in an increase in the fluorescence intensity of the porphyrin, while addition of guanine substantially quenches the intensity. Optical absorption measurements demonstrate noncovalent interactions of the nucleotides with the porphyrin, resulting in bathochromic shifts in the Soret region. Binding constants for the base:porphyrin complexes were determined from steady-state absorption data to be 1743 ± 68, 385 ± 15, 2433 ± 150, and 198 ± 7 M-1 for dAMP, dTMP, dGMP, and dCMP, respectively. The T4MPyP singlet state lifetime increases from 5.29 to 11.3, 10.3, and 7.8 ns in the presence of dAMP, dTMP, and dCMP, respectively. In the case of dGMP, the lifetime data was best fit to a Lorentzian distribution centered at 0.69 ns and a discrete component at 3 ns. The quenching was modeled using an excited state reaction mechanism coupled with ground state complexation. The quenching is attributed to electron transfer between guanine (the most reducing of the bases) and T4MPyP (i.e., reductive quenching of the porphyrin singlet state).

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Section: Introductionmentioning

confidence: 99%

Singlet Excited State Dynamics of Tetrakis(4-N-methylpyridyl)porphine Associated with DNA Nucleotides

et al. 1997

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“…The advantages and drawbacks of PDT are extensively reviewed. [10][11][12][13] Although the binding mode is still controversial, [14][15][16][17][18][19] the ability of 5,10,15,20-tetrakis(4′-N-methypyridinium)porphyrin to strongly bind DNA has been known for over 20 years, but negatively charged tetrabenzoate porphyrins do not bind strongly. Similarly, the mechanism of action of these compounds is also under debate, but it probably arises from the formation of singlet oxygen and subsequent damage to lipids, proteins, and nucleic acids, as well as hypoxia.…”

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confidence: 99%

“…[20][21][22][23][24][25] The assays chosen herein (DNA binding and cleavage, and water-octanol partition coefficient) are currently standards used to identify potential new PDT agents. [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] Therefore, a directed porphyrin library is made in order to bind or cross the cell membrane (which generally contain negatively charged lipids), to be reasonably soluble under physiological conditions, and to bind nucleic acids. Thus, the members of the libraries should be amphipathic with some positive charge.…”

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confidence: 99%

“…As an indicator of bioactivity, [10][11][12][13][14][15][16][19][20][21][22][23][24][25] the eight novel porphyrins thus found were incubated with a supercoiled plasmid DNA (ϕ-X174) for 2-12 h in the dark at room temperature and then irradiated for up to 90 min at 35 °C with continuous 50 foot-candles white light with a 450 nm cutoff filter that eliminates blue light. To test for sequence specificity of the resultant single strand nicks (and amplify the signal), some samples were treated with S1 nuclease.…”

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confidence: 99%

“…These observed spectral changes are consistent with those observed for most other porphyrin-DNA complexes. [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25] Together with the photocleavage experiments, the evidence that this small cadre of porphyrins (~0.5% of the parent library) bind to DNA is unequivocal. 31 Since the mechanism, the mode of binding, and the localization of PDT agents is under intense investigation, libraries such as these may aid in the determination of what factors direct porphyrins to certain cellular structures and tissues.…”

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confidence: 99%

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Combinatorial Synthesis and Modification of Functional Porphyrin Libraries: Identification of New, Amphipathic Motifs for Biomolecule Binding

et al. 1999

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In the past few years there has been an explosive growth in the development of chemically diverse libraries of molecules. Combinatorial libraries have proven to be a powerful method to examine structure-function relationships, and the synthesis and screening of small molecule libraries is emerging as an important strategy for drug discovery. 1 Several strategies have been employed to create and characterize these linear-and core-structured combinatorial libraries including: (i) solid phase and solution phase synthesis and (ii) grid, deconvolution, and tagging methods to identify compounds. 1 We describe herein the synthesis and characterization of directed combinatorial libraries of mesotetraphenylporphyrin (H 2 TPP) derivatives 3 -core-structured libraries-where the largest contains 1540 compounds (including isomers) (Figure 1). The derivitization of entire libraries to make them amphipathic (Figure 1) and the iterative selection of winning compounds by DNA binding are described. As a demonstration of the methodology, we find the dipositively charged porphyrins bearing at least one hydroxyl group to be the most efficacious in the photoinitiated cleavage of plasmid DNA.Both naturally occurring and synthetic porphyrins have long been known to exist in a large variety of isomers. For example, there are 60 possible isomers for protoporphyrin due to the four methyl, two vinyl, and two propionate groups on the eight pyrrole positions, and there are 420 possible isomers of the heme a prosthetic group in cytochrome a. 4 Similarly, we and others have exploited the six possible compounds and isomers when two different arylaldehydes are employed in the synthesis of meso-substituted porphyrins [5][6][7] and libraries of chemically inert, lipophilic, alkyl-substituted H 2 TPPs have been made. 8,9 The Photo *

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Non-Covalent Interactions of Porphyrinoids with Duplex DNA

D’Urso

Fragalà

Purrello

2013

Topics in Heterocyclic Chemistry

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Cationic porphyrin-DNA interactions: Importance of the number and position of the charges

Cited by 13 publications

References 3 publications

Singlet Excited State Dynamics of Tetrakis(4-N-methylpyridyl)porphine Associated with DNA Nucleotides

Singlet Excited State Dynamics of Tetrakis(4-N-methylpyridyl)porphine Associated with DNA Nucleotides

Combinatorial Synthesis and Modification of Functional Porphyrin Libraries: Identification of New, Amphipathic Motifs for Biomolecule Binding

Non-Covalent Interactions of Porphyrinoids with Duplex DNA

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