The Synthesis and Singlet Oxygen Generation Study of 13(1)-N-Piperazinyl Chlorin e6-15(2),17(3)-Dimethyl Ester

Abstract

Ключевые слова: Хлорофилл, фотосенсибилизаторы, пиперазин, синтез, фотофизика, синглетный кислород.

Synthesis, Spectral, Luminescence and Photochemical Properties of the Chlorin е6 Tricationic Derivative with Trimethylammonio Groups

“…По результатам исследования фотолюминесценции опреде-лен квантовый выход 1 О 2 , равный 0.59±0.06. Найденная величина соизмерима с γ в растворах хлорина е 6 и дру-гих его производных [19][20][21][22] и близка к квантовому выходу интерконверсии в молекулах этих соединений. [19,20] По-следнее позволяет объяснить фотообразование 1 О 2 вза-имодействием между возбужденными триплетными мо-лекулами 1 и О 2 по механизму переноса энергии.…”

“…Эта величина одного порядка с константа-ми скорости аналогичной реакции других производных хлорина е 6 . [22] Выводы Полученные результаты показывают, что иссле-дованные свойства 1 во многом сходны с известными для других соединений семейства хлорина е 6 . Вместе с тем, обнаружено, что полное превращение 1 при фото-окислении связано не только с 1 O 2 .…”

Biocompatible Supramolecular Systems Based on Chlorin e6: Preparation, Photophysical Properties

“…This method is used in conservative treatment and based on the photosensitizers (PSs, natural or artificially synthesized substances capable of biological tissues photosensitizing) capability to accumulate selectively in tumour or other target tissues and generate singlet oxygen or oxygen-containing free radicals at local exposure of radiation of a certain wavelength corresponding to maximum absorption of PS. [1][2][3][4][5][6] These active oxygen forms are extremely cytotoxic and play a defining role in malignant cell death. Both in the Russian Federation and in other countries there are a number of drugs of the first to third generations with high antitumor activity for use in clinical practice, which can be conditionally combined into three groups: 1) based on porphyrin: a) derivatives of δ-aminolevulinic acid -precursor of endogenous photosensitizer protoporphyrin ("Alasens"); b) benzoporphyrin derivatives ("Visudine"); c) hematoporphyrin derivatives ("Photophrin", Photogem"); 2) chlorophyll-based PS (chlorins and purpurines ("Photolon", "Photoditazin", "Radachlorin", "Foscan"), as well as bacteriochlorins ("Tookad"); 3) dyes (phthalocyanine, naphthalocyanine ("Photosens", "Thiosens", "Octasens").…”

Solubility and Thermodynamics of Dissolution of 13,17-Di-N-(2-aminoethyl)amide of Deuteroporphyrin-IX in Aqueous HCl and Tetraoxalate Buffer at 288-328 K

“…[7] Weighed amounts of the porphyrin (~6 -7 mg) and an aqueous solution of HCl or tetraoxalate buffer (~45 ml) were placed into a 50 ml glass hermetic cell and intensively stirred with a magnetic stirrer usually for two days. The temperature instability inside the cell during the experiment was ±0.05 K. When equilibrium was reached, the stirrer was switched off and one or two milliliters of the liquid content were quickly taken up with a thermostated syringe equipped with a filter (the pore size of 0.45 μm), weighed in a hermetic vessel with analytical balances and diluted by an appropriate solution at a room temperature for a spectrophotometric control.…”

“…Solubility values appear to be one of the most important quantities in this sense. These are, however, scarce and restricted by several organic solvents or their mixtures with water mostly at the standard temperature of 298 K. [4][5][6] During the last several years we have been involved in the intensive and continuing study (see, for example, [7][8][9] and references therein) dealing with the behavior of natural macrocycles in individual and mixed organic solvents modeling their biological environment. Here, we focus on thermodynamics of diamino derivative of deuteroporphyrin-IX in highly aqueous acidic solutions, where protonation of the macrocycle and functional amino groups provides sufficient solubility in water to employ the solute as a natural dye for synthetic or semi-synthetic fabrics.…”