Dimerization of tetracationic porphyrins: ionic strength dependence

Dixon, Dabney W.; Steullet, Vera

doi:10.1016/s0162-0134(97)10005-8

Cited by 56 publications

(31 citation statements)

References 74 publications

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“…The estimated values of the dimerization constants are presented in Table 1. The range of the dimerization constants is the same to that known from the literature for water solution [35,36]. Values of the dimerization constants from Table 1 are insignificantly decreasing along with the time of monolith samples drying.…”

Section: Discussionsupporting

confidence: 57%

Spectroscopic characterization of water-soluble cationic porphyrins in sol–gel silica matrices and coatings

Dargiewicz¹,

Makarska²,

Radzki³

2002

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Silica aeorogels doped with different concentrations of water-soluble cationic porphyrins were synthesised by the sol-gel polymerisation of tetraethylorthosilicate (TEOS). Porphyrin dimer formation in sol-gel matrices was studied in the function of gelation time, over the porphyrin concentration range up to 10 − 5 M. The deviation from the linearity of Beer-Lambert law starts with porphyrin concentration about 5 ×10 − 6 M. The dimerization constants were estimated. The similar dependence could be observed for the aerogels and the solid thin films.

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Section: Discussionsupporting

confidence: 57%

Spectroscopic characterization of water-soluble cationic porphyrins in sol–gel silica matrices and coatings

Dargiewicz¹,

Makarska²,

Radzki³

2002

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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“…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. Previous work has shown that this measurement gives data allowing a good estimate of the relative ease of porphyrin stacking (17). The TPPS derivatives evaluated stacked the order TPPS Ϸ Ni Ϸ Pd Ͼ Cu Ͼ VO Ͼ Mn, Sn Ͼ Co, Gd, Ru, TiO (data not shown).…”

Section: Resultsmentioning

confidence: 77%

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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“…8,[41][42][43][44] Therefore, the characterization in the solution state of these cationic bis-porphyrins was first done by visible spectrometry. The value of the e ).…”

Section: Discussionmentioning

confidence: 99%

Solution Properties and Photonuclease Activity of Cationic Bis-porphyrins Linked with a Series of Aliphatic Diamines.

Yamakawa

Ishikawa

Uno

2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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The development of efficient photo-induced DNA cleavage agents has been of particular interest for biomedical applications such as cancer photodynamic therapy (PDT). Toward this objective, we synthesized a series of cationic bis-porphyrins with various lengths of diamino alkyl linkage, N,N-bis{4-[10,15,20-tris(1-methylpyridinium-4-yl)porphyrin-5-yl]benzoyl}oligomethylenediamine hexaiodide. They were expected to show more efficient photocleavage of DNA than unichromophore meso-tetrakis(4-N-methylpyridiniumyl)porphine (TMPyP), which is well known to cleave DNA effectively on illumination. The cationic bis-porphyrins were found to self-aggregate in aqueous solution, and the aggregation property was accounted for by the formation of an intermolecular dimer. Because conservative-type circular dichroism spectra of the bis-porphyrins were induced in the Soret region on binding to calf thymus DNA, we assigned their binding mode to outside self-stacking on the DNA surface. Their photonuclease activity using plasmid DNA decreased as the number of their linker hydrocarbons increased, and was well correlated with their tendency for dimerization. The inhibitory effect of azide anion, N 3 ؊ , and the enhancement effect of D 2 O suggest that singlet oxygen was probably involved in the photocleavage of DNA.Key words porphyrin; DNA; photocleavage; aggregation; singlet oxygen plex DNA, and photonuclease activity. We show that these cationic bis-porphyrins formed intermolecular dimers in aqueous solution, and bound to calf thymus DNA (CTDNA) with outside self-stacking. Their photocleavage efficiency of plasmid DNA diminished as the number of their linker hydrocarbons increased, and correlated with their tendency for dimerization. ExperimentalInstrumentation The 1 H-NMR spectra were recorded on a JEOL GX-400 or JNM-A-500 spectrometer. The MALDI-TOF (matrix-assisted laser desorption/ionization time-of-flight) mass spectra (MS) were measured on a Bruker REFLEX TM . The UV-visible absorption measurement was performed on a Beckman DU650 spectrophotometer. The CD spectra were recorded on a JASCO J-720 spectropolarimeter. Elemental analyses were performed at the Analytical Center, Kumamoto University. Materials and MethodsReagents for the synthesis of cationic bis-porphyrins were purchased from Tokyo Kasei Chemical Co. Thionyl chloride was distilled before use. Hexane, methylene chloride, and triethylamine were distilled in the presence of P 2 O 5 .24) 5-(4-methoxycarbonylphenyl)-10,15,20-tris(4-pyridyl)porphine (TPyPCOOCH 3 ) and 5-(4-carboxyphenyl)-10,15,20-tris(4-pyridyl)porphine (TPyPCOOH) were synthesized according to the previous method.25) CTDNA was purchased from Sigma Chemical Co., and the solution was quantitated spectrophotometrically using e 260 ϭ13200 M (base pairs) Ϫ1 · cm Ϫ1 . The tosylate salt of TMPyP was purchased from Dojin Chemical Co.General Procedure for the Synthesis of Non-charged Bis-porphyrins Linked with a Series of Aliphatic Diamines TPyPCOOH (250 mg, 0.378 mmol) was dissolved in 35 ml of thionyl chloride unde...

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Dimerization of tetracationic porphyrins: ionic strength dependence

Cited by 56 publications

References 74 publications

Spectroscopic characterization of water-soluble cationic porphyrins in sol–gel silica matrices and coatings

Spectroscopic characterization of water-soluble cationic porphyrins in sol–gel silica matrices and coatings

Inactivation of Human Immunodeficiency Virus Type 1 by Porphyrins

Solution Properties and Photonuclease Activity of Cationic Bis-porphyrins Linked with a Series of Aliphatic Diamines.

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