Aggregation of meso-tetra-(p-sulphonatophenyl)porphine and its cu(II) and zn(II) complexes in aqueous solution

Corsini, A.; Herrmann, Otto

doi:10.1016/0039-9140(86)80084-4

Cited by 50 publications

(13 citation statements)

References 15 publications

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“…This relationship may indicate that axial ligands have undesirable steric interactions with the biological target. Some TPPS4 derivatives stack significantly in solution (9,32,35). To determine whether the monomeric form of the porphyrin was important for the activity, the selfstacking of these derivatives was evaluated by measuring the optical spectrum of each of the metallo-TPPS4 derivatives as a function of added NaCl.…”

Section: Resultsmentioning

confidence: 99%

Inactivation of Human Immunodeficiency Virus Type 1 by Porphyrins

Vzorov¹,

Dixon

Trommel

et al. 2002

Antimicrob Agents Chemother

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We have evaluated the anti-human immunodeficiency virus (HIV) activity of a series of natural and synthetic porphyrins to identify compounds that could potentially be used as microbicides to provide a defense against infection by sexually transmitted virus. For assays we used an epithelial HeLa-CD4 cell line with an integrated long terminal repeat-␤-galactosidase gene. For structure-activity analysis, we divided the porphyrins tested into three classes: (i) natural porphyrins, (ii) metallo-tetraphenylporphyrin tetrasulfonate (metallo-TPPS4) derivatives, and (iii) sulfonated tetra-arylporphyrin derivatives. None of the natural porphyrins studied reduced infection by more than 80% at a concentration of 5 g/ml in these assays. Some metal chelates of TPPS4 were more active, and a number of sulfonated tetra-aryl derivatives showed significantly higher activity. Some of the most active compounds were the sulfonated tetranaphthyl porphyrin (TNapPS), sulfonated tetra-anthracenyl porphyrin (TAnthPS), and sulfonated 2,6-difluoro-meso-tetraphenylporphine [TPP(2,6-F2)S] and its copper chelate [TPP(2,6-F2)S,Cu], which reduced infection by 99, 96, 94, and 96%, respectively. Our observations indicate that at least some of these compounds are virucidal, i.e., that they render the virus noninfectious. The active compounds were found to inhibit binding of the HIV type 1 gp120 to CD4 and also to completely inhibit the ability of Env proteins expressed from recombinant vectors to induce cell fusion with receptor-bearing target cells. These results support the conclusion that modified porphyrins exhibit substantial activity against HIV and that their target is the HIV Env protein.

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Section: Resultsmentioning

confidence: 99%

Inactivation of Human Immunodeficiency Virus Type 1 by Porphyrins

Vzorov¹,

Dixon

Trommel

et al. 2002

Antimicrob Agents Chemother

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“…The assignment of the phenyl proton resonance has been made on the basis of literature data, which report for TPPS in DMSO (the authors do not indicate if TPPS was the free ligand or the salt) a reversal of the normal spectral position of the proton signals, with the ortho-protons appearing at lower field than the meta, 36 as a consequence of the very limited extent of monomer aggregation in this solvent, even at concentrations as high as 0.044 mol dm Ϫ 3 . Each diorganotin(IV) unit should bind two monodentate sulfonato groups of two different ligand molecules, achieving hexacoordination by binding two solvent molecules.…”

Section: H Nmr and 13 C Nmr Spectramentioning

confidence: 99%

Organometallic complexes with biological molecules. IX. Diorgano- and triorgano‐tin(IV)[meso‐tetra (4-sulfonatophenyl)porphinate] derivatives: solid‐state and solution‐phase structural aspects and in vivo effects

Pellerito¹,

Fiore²,

Giuliani³

et al. 1997

Appl. Organometal. Chem.

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“…Hence triplet desactivation could occur through the dimeric material for example. as stated by Corsini and Herrmann (1986) ?P + PP + PP + P This would prevent the porphyrin photoionization.…”

Section: Porphyrins In the Absence Of Any Substratementioning

confidence: 81%

Photo‐cidnp Evidence for Charge‐transfer Interaction Between Synthetic Water‐soluble Porphyrins and Guanine*

Nouën

Marko

Vermeersch

et al. 1989

Photochem & Photobiology

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Photoreactions of aqueous solutions of synthetic water‐soluble porphyrins were studied by the 1H and 13C CIDNP technique. Strong polarizations, which were very sensitive to the presence of added acid, were observed on the cationic porphyrins (TMePyPH2‐TAPPH2) when irradiated through continuous UV‐visible light. They resulted from the reverse electron transfer between the semi‐oxidized and the semi‐reduced species of the derivative. When the experiments were carried out in the presence of nucleobases, guanine (and its derivatives) was the only residue that was polarized. This is thoroughly interpreted in terms of a reversible electron transfer reaction leading to guanine photooxidation by the porphyrin excited triplet state. It was shown to be drastically pH‐dependent and was correlated to the redox potential of the porphyrin. It was not affected by the incident wavelength. The reaction proceeded through the intermediate formation of the correlated radical‐ion pair: porphyrin radical anion‐guanine radical cation. This study suggested that a Type I (free radical) reaction could be one of the primary processes in DNA photosensitization by porphyrins.

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Aggregation of meso-tetra-(p-sulphonatophenyl)porphine and its cu(II) and zn(II) complexes in aqueous solution

Cited by 50 publications

References 15 publications

Inactivation of Human Immunodeficiency Virus Type 1 by Porphyrins

Inactivation of Human Immunodeficiency Virus Type 1 by Porphyrins

Organometallic complexes with biological molecules. IX. Diorgano- and triorgano‐tin(IV)[meso‐tetra (4-sulfonatophenyl)porphinate] derivatives: solid‐state and solution‐phase structural aspects and in vivo effects

Photo‐cidnp Evidence for Charge‐transfer Interaction Between Synthetic Water‐soluble Porphyrins and Guanine*

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