New derivatives of meso-(tetra-4-pyridyl)porphine and their reactions

Madakyan, V. N.; Kazaryan, R. K.; Khachatryan, M. A.; Stepanyan, Ani; Kurtikyan, T. S.; Ordyan, M. B.

doi:10.1007/bf00519937

Cited by 12 publications

(5 citation statements)

References 5 publications

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“…For example, we previously reported synthesis of water-soluble meso-tetra (4-N-oxyethylpyridyl) porphyrin (TOEPyP(4)), its 3-N analog (TOEPyP (3)) and their metallocomplexes with Co, Cu, Ni, Zn, which had been shown to have both antibacterial and antifungal activities (6)(7)(8). Although the anti tumor and viral activities of modified porphyrins have been established, the mechanisms of their interactions with biological macromolecules, in particular with duplex DNA, have not been thoroughly characterized.…”

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confidence: 99%

Interactions of Meso-tetra-(4-N-oxyethylpyridyl) Porphyrin, Its 3-N Analog and Their Metallocomplexes with Duplex DNA

Dalyan

Haroutiunian²,

Ananyan³

et al. 2001

Journal of Biomolecular Structure and Dynamics

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Interactions of meso-tetra-(4-N-oxyethylpyridyl) porphyrin (TOEPyP(4)), its 3-N analog (TOEPyP(3)) and their Co, Cu, Ni, Zn metallocomplexes with duplex DNA have been investigated by uv/visible absorbance and circular dichrosim spectroscopies. Results reveal the interactions of these complexes with duplex DNA are of two types. (1) External binding of duplex DNA by metalloporphyrins containing Zn and Co, and (2) Binding of duplex DNA both externally and internally (by intercalation) by porphyrins not containing metals, and metalloporphyrins containing Cu and Ni. Results indicate that (4N-oxyethylpyridyl) porphyrins intercalate more preferably in the structure of duplex DNA and have weaker external binding than 3N-porphyrins.

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confidence: 99%

Interactions of Meso-tetra-(4-N-oxyethylpyridyl) Porphyrin, Its 3-N Analog and Their Metallocomplexes with Duplex DNA

Dalyan

Haroutiunian²,

Ananyan³

et al. 2001

Journal of Biomolecular Structure and Dynamics

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“…Lando from the Institute of Bioorganic Chemistry (Minsk, Belarus). Porphyrins were synthesized at the Department of Pharmacological Chemistry, Yerevan State Medical University by the method described in [5].…”

Section: Methodsmentioning

confidence: 99%

New Porphyrins/Calf Thymus DNA Complexes - Their Thermostability

Aloyan

Dalyan

Gogolev

2015

AMR

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The paper studies the melting parameters of the complexes of water soluble cationic 3N- and 4N-pyridyl porphyrins with different peripheral substituents (oxyethyl, buthyl, allyl, metallyl) with DNA. The results indicate that the presence of porphyrin changes the shape and parameters of DNA melting curve. The porphyrin concentration increase results in the increase of the melting temperature (Tm) and melting interval (ΔT) of DNA. With the porphyrin-DNA concentration ratio ν = 0.01, changes of melting temperature have not been observed. The melting intervals almost do not change upon the addition of the 4N- porphyrins, while the decrease of ΔT is observed in the presence of 3N-porphyrins. Because of the intercalation binding mechanism occurring in GC-rich regions of DNA, we assume that 3N-porphyrins intercalated in GC-rich regions, reduce the thermal stability of these sites, bringing them closer to the thermal stability of the AT-sites, which is the reason for the decrease in melting interval. While with the relative concentration ν = 0.01 for 4-N porphyrins the external binding mechanism “turns on” and destabilizing effect of porphyrins on GC-pairs compensated by their stabilizing effect on AT-pairs. As a result, no change in the melting parameters of DNA is observed upon complexation with these porphyrins.

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“…To a mixture of ethyl 3-hydroxyimino-1-phenyl-1-cyclopentanecarboxylate (5) (10 g, 0.04 mol) [12] and CoTOEtPyP (3) (0.2 g, 0.0002 mol) as catalyst [10] in methanol (300 ml) at 25-30°C over 2 h we added in small portions sodium borohydride (6.1 g, 0.16 mol). When all the sodium borohydride had been added the stirring was continued for a further 2 h, the methanol was distilled, water (200 ml) was added to the residue, and the product was extracted with ether.…”

Section: Methodsmentioning

confidence: 99%

“…To a mixture of ethyl 1-benzyl-5-oxo-2-phenyl-2-pyrrolidinecarboxylate (8) (3.2 g, 0.01 mol) [13] and CuTOEtPyP (4) (0.2 g, 0.0002 mol) as catalyst [10] in methanol (100 ml) at 25-30°C we added in small portions over 2 h sodium borohydride (1.5 g, 0.04 mol).…”

Section: -Phenyl-1-azabicyclo[221]heptan-2-one (7)mentioning

confidence: 99%

Metal-complex catalysis during the reduction of functional groups by sodium borohydride in the synthesis of pyrrolidine derivatives

Martirosyan

Hovhanesyan

Gasparyan

et al. 2006

Chem Heterocycl Compd

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The development of selective and universal methods for the reduction of functional groups is an important function of organic chemistry.There are many ways of using the mild and readily available reducing agent sodium borohydride in various catalytic systems with the aim of extending its reducing capabilities, the selectivity of its action, and its other properties. Reducing systems containing sodium borohydride and the salts of metals, such as CuCl 2 [1], CoCl 2 [2], NiCl 2 [3], ZrCl 3 [4], and others, are well known and have been well studied. It was demonstrated that the selectivity of reduction depends on the nature of the metal. The mechanism of reduction involving the formation of borides of the respective metals has also been studied [4]. However, the method has a series of important disadvantages, mainly associated with the quantities of the reagents employed. The ratios of the compound being reduced, the metal salt, and sodium borohydride amounted to 1:2:10.The use of metal complexes as catalysts with sodium borohydride significantly simplifies the process, making it suitable for extensive application. Complexes of CuCl 2 [5], CoCl 2 , and NiCl 2 [6] with triphenylphosphine and metal complexes of porphyrins such as iron meso-tetraphenylporphyrinate [ClFe(III)TPP] [7] and cobalt meso-tetra(p-sulfophenyl)porphyrinate [Co(III)TPPS] have been used successfully [8].As catalysts for reduction in a system containing sodium borohydride we used a series of familiar metal complexes, like the complexes of CoCl 2 and CuCl 2 with triethylbenzylammonium chloride (1) and (2) [9] and cobalt and copper meso-tetra [4-(2-hydroxyethyl)pyridyl]porphyrinates (CoTOEtPyP) (3) and (CuTOEtPyP) (4)

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New derivatives of meso-(tetra-4-pyridyl)porphine and their reactions

Cited by 12 publications

References 5 publications

Interactions of Meso-tetra-(4-N-oxyethylpyridyl) Porphyrin, Its 3-N Analog and Their Metallocomplexes with Duplex DNA

Interactions of Meso-tetra-(4-N-oxyethylpyridyl) Porphyrin, Its 3-N Analog and Their Metallocomplexes with Duplex DNA

New Porphyrins/Calf Thymus DNA Complexes - Their Thermostability

Metal-complex catalysis during the reduction of functional groups by sodium borohydride in the synthesis of pyrrolidine derivatives

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