The results of studies on the synthesis of photosensitizers conducted the last 10 years in frame of health care programs funded by the Moscow Government are reported.
A new photosensitizer, monoconjugate of zinc octa-4,5-carboxy-phthalocyanine with L-cysteine, which is rather readily soluble in water, has been synthesized and characterized. The chemisorption of its molecules on the surface of gold nanoparticles with different sizes has been studied. A comparative analysis of the spectral characteristics of the synthesized conjugates of gold nanoparticles with the photosensitizer has shown that the photosensitizer grafted to gold nanoparticles exhibits rather intense fluorescence. Therefore, such conjugates can be used for photodynamic therapy of tumors.
Синтезирован и охарактеризован новый фотосенсибилизатор моноконъюгат окта-4,5-карбоксифталоцианина цинка с L-цистеином, достаточно хорошо растворимый в фосфатном буфере. Исследована хемосорбция молекул этого соединения на поверхности наночастиц золота разного размера. Проведен сравнительный анализ спектральных характеристик синтезированных конъюгатов наночастиц Au и фотосенсибилизатора, и установлено, что привитый на наночастицы золота фотосенсибилизатор характеризуется достаточно интенсивной флуоресценцией. Это открывает перспективы использования таких конъюгатов в фотодинамической терапии опухолей.
Catalytic oxidative modification of a single-stranded DNA with hydrogen peroxide and molecular oxygen in the presence of a conjugate containing an oligonucleotide complementary to the DNA fragment and tetra-4-carboxyphthalocyanine Fe(II) was studied. The conjugate examined was found to be active in the reaction of oxidative DNA cleavage in the presence of hydrogen peroxide, like the earlier studied oligonucleotide conjugates containing metallocomplexes tetra-4-carboxyphthalocyanine Co(II) and 2,4-di-[2-(2-hydroxyethyl)]deuteroporphyrin IX Fe(III) generating active oxygen forms. The new conjugate was more active in the case of oxidation with molecular oxygen. Kinetic features and optimal regimes of DNA oxidation with hydrogen peroxide were found.
A series of conjugates of sulfo- and carboxy-substituted phthalocyanines with rhodamines were prepared, and their electronic absorption and luminescence spectra were studied. An intramolecular transfer of the excitation energy from the rhodamine moiety (donor) to the phthalocyanine moiety (acceptor) was revealed.
Cobalt, zinc, hydroxoaluminum, and iron complexes of N,N′,N″,N‴-tetrakis(β-diethylaminoethyl) phthalocyanine-2,3 : 9,10 : 16,17 : 23,24-tetrakis(dicarboxamide) were synthesized and were converted into the corresponding water-soluble quaternary salts by treatment with methyl iodide, methyl p-toluenesulfonate, diethyl and dimethyl sulfates, and trimethyl phosphate. The electronic absorption spectra of the quaternary salts indicated their considerable aggregation in aqueous solution; the degree of aggregation decreases in going to solutions in ethanol and disappears in DMSO.
Procedures have been developed for the synthesis of a series of metal complexes derived from water-soluble anionic and cationic octa-4,5-carboxyphthalocyanine-taurine and choline conjugates.
Methods of synthesis of covalent conjugates of metal complexes of octa-4,5-carboxy- and tetra-4-carboxyphthalocyanine, as well as of octa-6,7-carboxy-2,3-naphthalocyanine with α-amino acids, glycine and sarcosine, were developed and certain properties of the products were studied. The prepared conjugates are soluble in organic solvents and water.
The dependence of the quantum yield of photogeneration of singlet oxygen with aluminum sulfophthalocyanines on the degree of their sulfonation was studied. Experiments showed that Fotosens preparation containing, on the average, about three sulfo groups in the macroring in aqueous buffer solution (pH 7.4) exists in the monomeric form and sensitizes singlet oxygen with a quantum yield ϕΔ 0.42±0.06. Aluminum tetra-4-sulfophthalocyanine forms dimers, and correspondingly ϕΔ is lower: 0.22±0.03. Sulfonated aluminum phthalocyanine containing, on the average, about two sulfo groups in the macroring is aggregated to a significant extent. Addition of Triton X-100 detergent results in partial deaggregation of the dye, and ϕΔ increases from ∼0.01 to 0.15±0.02. In the series including previously unknown aluminum phthalocyanines containing residues of phosphonic acids or their esters, and also aluminum and zinc octacarboxyphthalocyanines, the influence of the dye structure on the quantum yield of generation of singlet oxygen suggests participation of axial hydroxy groups in associate formation. These associates are not manifested spectroscopically and generate singlet oxygen inefficiently. The quantum yields ϕΔ for the monomers and associates are 0.3 and 0.1, respectively.
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AbstractThe tetralindicarbonitrile (I), prepared from 1,1,4,4,6,7‐hexamethyltetralin by common methods, is treated with sodium isoamylate to give the phthalocyanine (II).
AbstractAusgehend von den Dinitrilen (I) oder (II) oder den Phlhulimidcn (III) bzw. (IV) wird durch Einwirkung von Harnstoff und Mctallsalzcn mit Natriumsul?il oder Chinolin als Vcrdünnungsmittel eine Reihe von Phthalocyanincn (VIu) ‐ (VIc) W, I) zu hergestellt.
AbstractEs wird eine Reihe von Phthalo cyaninen wie (I) mit vier oder acht Sulfamoylgruppen beschrieben.
Chemischer InformationsdienstVolume 11, Issue 40 Organic Dyes ChemInform Abstract: PHTHALOCYANINES AND RELATED COMPOUNDS. XVII. PHTHALOCYANINETETRA-4- AND -OCTA-4,5-CARBOXYLIC ACIDS AND THEIR FUNCTIONAL DERIVATIVES L. I. SOLOV'EVA, L. I. SOLOV'EVASearch for more papers by this authorE. A. LUK'YANETS, E. A. LUK'YANETSSearch for more papers by this author L. I. SOLOV'EVA, L. I. SOLOV'EVASearch for more papers by this authorE. A. LUK'YANETS, E. A. LUK'YANETSSearch for more papers by this author First published: October 7, 1980 https://doi.org/10.1002/chin.198040300Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume11, Issue40October 7, 1980 RelatedInformation
Chemischer InformationsdienstVolume 7, Issue 51 Isocyclic Compounds ChemInform Abstract: SYNTHESIS OF SUBSTITUTED O-PHTHALONITRILES BY THE ROSENMUND-VON-BRAUN REACTION E. I. KOVSHEV, E. I. KOVSHEVSearch for more papers by this authorL. I. SOLOV'EVA, L. I. SOLOV'EVASearch for more papers by this authorS. A. MIKHALENKO, S. A. MIKHALENKOSearch for more papers by this authorE. A. LUK'YANETS, E. A. LUK'YANETSSearch for more papers by this author E. I. KOVSHEV, E. I. KOVSHEVSearch for more papers by this authorL. I. SOLOV'EVA, L. I. SOLOV'EVASearch for more papers by this authorS. A. MIKHALENKO, S. A. MIKHALENKOSearch for more papers by this authorE. A. LUK'YANETS, E. A. LUK'YANETSSearch for more papers by this author First published: December 21, 1976 https://doi.org/10.1002/chin.197651155Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume7, Issue51December 21, 1976 RelatedInformation