Non-Covalent Interactions of Porphyrinoids with Duplex DNA

D’Urso, Alessandro; Fragalà, Maria Elena; Purrello, Roberto

doi:10.1007/7081_2013_113

Cited by 12 publications

(7 citation statements)

References 163 publications

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“…The noncovalent interaction of achiral porphyrins with nucleic acids is still a hot topic, extensively studied. 1 In fact, porphyrins can act as chiroptical probes and meanwhile to act as photosensitizers in the presence of oxygen. It has been demonstrated that a photosensitizer needs to be bound to DNA to produce photodynamic damage 2 and the efficiency of this process depend on the type of interaction of the photosensitizer.…”

Section: Introductionmentioning

confidence: 99%

“…Synthetic porphyrinoids represent a useful tool to understand the complex reactions performed by these macrocycles in biological systems. 1,5 Therefore, the synthetic effort is focused on making water-soluble porphyrins also biocompatible. However, due to the great tendency of porphyrins to aggregate, it is difficult to use them in media with increasing hydrophilicity.…”

Section: Introductionmentioning

confidence: 99%

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Interactions of mono spermine porphyrin derivative with DNAs

et al. 2020

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In this work, we have characterized the interactions of monospermine porphyrin derivative with calf thymus DNA (ct‐DNA) and poly (dG‐dC)2 in both B and Z conformation. By several spectroscopic techniques (UV–vis, electronic circular dichroism and resonance light scattering), the binding modes of monospermine porphyrin derivative with different DNA sequences have been elucidated. In the presence of ct‐DNA, the porphyrin binds along the external double helix as well as in the presence of B conformation of poly (dG‐dC)2. Whilst when the Z form of the poly (dG‐dC)2 is induced, a slight intercalation of the porphyrin between the basis has been detected.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Interactions of mono spermine porphyrin derivative with DNAs

et al. 2020

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“…They are part of an important family of fluorophores, which have been widely used for photosensitization and optical recording materials [2,3,10]. Porphyrins are well known to form chiral aggregate in the presence of DNA and act as the stabilizer for the secondary structure of nucleic acid [11][12][13][14][15]. 5, 10, 15, 20-Tetrakis (1-methylpyridinium-4-yl) porphyrin p-toluene sulfonate (TMPyP) is one of the water soluble cationic porphyrins.…”

Section: Introductionmentioning

confidence: 99%

Chiral stacking of cyanine or porphyrin as cationic fluorescent dyes in the presence of anionic polysaccharide of hyaluronic acid

et al. 2020

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Cyanine dye or porphyrin are part of an important family of fluorophores, which have been widely used for photosensitization and optical recording materials. We compared herein the aggregation behaviors of two types of cationic dyes of cyanine or porphyrin in the presence of hyaluronic acid, which contains D-glucuronic acid as anionic helical polysaccharide. UV-Vis absorption and photoluminescence spectra of those aqueous solutions revealed that fluorescent dyes of cyanine form Hand J-aggregates in the presence of hyaluronic acid. In particular, photoluminescent quenching through the Hand J-aggregates was observed in the mixture of anionic hyaluronic acid and the cationic cyanine dyes. On the contrary, increment of the intensities of the emission was confirmed in the mixture of porphyrin-hyaluronic acid through the effective interaction between the cationic porphyrin and anionic hyaluronic acid, which was confirmed by remarkable split-Cotton effects of induced circular dichroism in the visible region, though the UV-Vis spectra of porphyrin with hyaluronic acid did not show any sign of aggregation of porphyrin itself. Further addition of hyaluronic acid resulted in the decrease of the extent of the induced circular dichroism, though photoluminescent intensity was kept without quenching. It was also confirmed that the light scattering could be detected only when the remarkable split-Cotton effects were observed. Therefore, cationic porphyrin and anionic hyaluronic acid form complex and the complex might assemble to show the light scattering, though the single molecule of porphyrin was surrounded by polysaccharides and isolated without dye-aggregation.

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“…Porphyrins are one of the earliest classes of DNA ligands. Their interactions with GQ DNA were first studied in 1998 [ 33 ], and with dsDNA as far back as 1979 [ 34 ], and are still of great interest [ 35 ]. Porphyrins are aromatic, planar, and the size of their macrocycle (~10 Å) matches that of a G-tetrad (~11 Å), leading to an efficient π-π stacking.…”

Section: Introductionmentioning

confidence: 99%

Interactions Between Spermine-Derivatized Tentacle Porphyrins and The Human Telomeric DNA G-Quadruplex

Sabharwal

Chen

Lee

et al. 2018

IJMS

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G-rich DNA sequences have the potential to fold into non-canonical G-Quadruplex (GQ) structures implicated in aging and human diseases, notably cancers. Because stabilization of GQs at telomeres and oncogene promoters may prevent cancer, there is an interest in developing small molecules that selectively target GQs. Herein, we investigate the interactions of meso-tetrakis-(4-carboxysperminephenyl)porphyrin (TCPPSpm4) and its Zn(II) derivative (ZnTCPPSpm4) with human telomeric DNA (Tel22) via UV-Vis, circular dichroism (CD), and fluorescence spectroscopies, resonance light scattering (RLS), and fluorescence resonance energy transfer (FRET) assays. UV-Vis titrations reveal binding constants of 4.7 × 106 and 1.4 × 107 M−1 and binding stoichiometry of 2–4:1 and 10–12:1 for TCPPSpm4 and ZnTCPPSpm4, respectively. High stoichiometry is supported by the Job plot data, CD titrations, and RLS data. FRET melting indicates that TCPPSpm4 stabilizes Tel22 by 36 ± 2 °C at 7.5 eq., and that ZnTCPPSpm4 stabilizes Tel22 by 33 ± 2 °C at ~20 eq.; at least 8 eq. of ZnTCPPSpm4 are required to achieve significant stabilization of Tel22, in agreement with its high binding stoichiometry. FRET competition studies show that both porphyrins are mildly selective for human telomeric GQ vs duplex DNA. Spectroscopic studies, combined, point to end-stacking and porphyrin self-association as major binding modes. This work advances our understanding of ligand interactions with GQ DNA.

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Non-Covalent Interactions of Porphyrinoids with Duplex DNA

Cited by 12 publications

References 163 publications

Interactions of mono spermine porphyrin derivative with DNAs

Interactions of mono spermine porphyrin derivative with DNAs

Chiral stacking of cyanine or porphyrin as cationic fluorescent dyes in the presence of anionic polysaccharide of hyaluronic acid

Interactions Between Spermine-Derivatized Tentacle Porphyrins and The Human Telomeric DNA G-Quadruplex

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