Porphyrins in complex with DNA: Modes of interaction and oxidation reactions

Pratviel, Geneviève

doi:10.1016/j.ccr.2015.07.003

Cited by 68 publications

(54 citation statements)

References 194 publications

(268 reference statements)

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“…Hexagonal packing of DNA and RNA was observed for DNA and RNA complexes with Cetyltrimethyl Ammonium Bromide (CTBA) and for Dimethyldioctadecyl Ammonium Bromide (DDAB) complexes is observed lamellar structure. Variations in the internal spacing and degree of long-range ordering are dependent on both surfactant type and concentrations of added salt [19][20][21][22][23][24][25][26][27][28][29]. When we increased the amount of salt into our complexes, we observed that the d spacing (d=2Π/r) are increased.…”

mentioning

confidence: 68%

A Thermodynamic Study on Hydration and Dehydration of DNA and RNA −Amphiphile Complexes

Heidari¹

2016

J Bioengineer & Biomedical Sci

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confidence: 68%

A Thermodynamic Study on Hydration and Dehydration of DNA and RNA −Amphiphile Complexes

Heidari¹

2016

J Bioengineer & Biomedical Sci

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“…and the extinction coefficient for the porphyrin in the fully bound form, respectively. The results clearly signal that among the three sets of porphyrins (4−6), the binding affinity of 3-/4-N-methylpyridyl derivatives are higher compared to 2-N-methylpyridyl derivatives presumably due to the more effective electrostatic interaction between the positively charged porphyrin and the phosphate moiety of nucleotide in the former than the later 43. obtained are higher than the reported non-fluorinated cationic pyridinium porphyrins 41 which discloses that the pentafluorophenyl groups play an essential role to control DNA interaction abilities.…”

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confidence: 85%

Synthesis, structure, electrochemical, DNA interaction and antimicrobial studies of fluorinated trans-dicationic pyridinium porphyrins

2016

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A series of trans-pyridyl porphyrins, 5,15-di(pentafluorophenyl)-10,20-bis(2ꞌ/3ꞌ/4ꞌ-pyridyl)porphyrin (1−3), trans-dicationic pyridinium porphyrins, 5,15-di(pentafluorophenyl)-10,20-bis(2ꞌ/3ꞌ/4ꞌ-Nmethylpyridyl)porphyrins (4−6) and their copper(II) and zinc(II) derivatives were synthesized. These compounds were characterized using various spectroscopic methods, electrochemical and single crystal X-ray crystallographic studies. The trans-dicationic porphyrin derivatives exhibit red shifted absorption spectra over the simple pyridyl porphyrins. The reduction potentials of trans-pyridyl porphyrins are more positive than those of MTPPs. Crystal structure of 3c is forming networks of molecules through Zn-N coordination displaying large number of channels. The intermolecular interactions involving fluorine contributes considerably to the crystal packing in all the structures which was further confirmed by computational Hirshfeld surface analysis. The dicationic porphyrins were further explored for its DNA interaction abilities and antimicrobial activities. The UV-visible and fluorescence spectroscopic titrations indicate that the porphyrins bind with the calf thymus DNA by outside groove binding mode with or without self-stacking. The intrinsic binding constants K b of these dicationic porphyrins to DNA was found to be in the range of 10 5 −10 6 M −1 . The results reveal that among the three sets of porphyrins (4−6), the 3-/4-pyridyl derivatives display higher DNA binding activities compared to the 2-pyridyl analogues.The photocleavage experiments disclose that the porphyrins employ 1 O 2 -mediated mechanism in cleaving DNA and the freebase and zinc(II) derivatives show better photoinduced cleavage ability compared to its copper(II) analogues. The dicationic porphyrins also show significant antimicrobial activities than those of non-fluorinated analogues.Trans-dicationic pyridinium porphyrins: Synthesis, structure, electrochemical, DNA interaction and antimicrobial studies of fluorinated trans-pyridyl and trans-dicationic pyridinium porphyrins are reported and the studies indicate that they are superior artificial nucleases than its non-fluorinated analogues; bind with the calf thymus DNA by outside groove binding mode with or without self-stacking, also show significant antimicrobial activities than those of nonfluorinated analogues.

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“…The interaction of porphyrins with biomolecules (DNA, proteins) is the aim of a number of drug design studies . In this context, organometallic complexes are a very important class of compounds that interact with DNA .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopic/electrochemical characterization and DNA interaction study of novel ferrocenyl‐substituted porphyrins

Auras

Meller

Silva

et al. 2018

Applied Organom Chemis

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We report the synthesis and characterization of two new mesoferrocenylporphyrins, with the ferrocenyl unit attached at the para position of a C 6 F 4 group by a C-N bond with -NH(CH 2 ) 2 NH-(2a) and -NH(CH 2 ) 4 NH-(2b) spacers. Compounds 2a and 2b were characterized through elemental analyses, electrospray ionization high-resolution mass spectrometry, 1 H NMR, UV-visible and fluorescence spectroscopies, electrochemistry and spectroelectrochemistry. The free base porphyrin 2 was included for comparison purposes. The binding ability of 2 and the porphyrin derivatives 2a and 2b with calf thymus DNA was determined using UV-visible and fluorescence spectroscopies. The results suggest that the interaction of these systems most probably occurs through π-stacking by non-classical modes involving the partial insertion of the C 6 F 5 ring between adjacent base pairs on DNA and possible hydrogen interaction with the aliphatic -NH(CH 2 ) n NH-(n = 2 or 4) groups with calf thymus DNA. Moreover, we also demonstrate that porphyrins generate singlet oxygen species and show good photostability after irradiation.

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Porphyrins in complex with DNA: Modes of interaction and oxidation reactions

Cited by 68 publications

References 194 publications

A Thermodynamic Study on Hydration and Dehydration of DNA and RNA −Amphiphile Complexes

A Thermodynamic Study on Hydration and Dehydration of DNA and RNA −Amphiphile Complexes

Synthesis, structure, electrochemical, DNA interaction and antimicrobial studies of fluorinated trans-dicationic pyridinium porphyrins

Synthesis, spectroscopic/electrochemical characterization and DNA interaction study of novel ferrocenyl‐substituted porphyrins

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