Photodynamic activity of chlorin e6 and chlorin e6 ethylenediamide in vitro and in vivo

Gurinovich, G. P.; Zorina, Tatyana E.; Мельнов, С. Б.; Melnova, N.I.; Gurinovich, I. F.; Grubina, L. A.; Sarzhevskaya, M. V.; Sn, Cherenkevich

doi:10.1016/1011-1344(92)80039-x

Cited by 29 publications

(19 citation statements)

References 7 publications

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“…(46) studied MACE (1) with I4C incorporated into the pyrrolic rings of the sensitizer vs I4C in the aspartyl residue and found similar biodistribution and pharmacokinetics, indicating that MACE (1) was not significantly metabolized during the course of the experiment. A comparison of chlorin e6 (44) with an ethylene diamine (EDA) (45) derivative in which the EDA moiety was attached by an amide linkage to the carboxyl group on the pyrrolic C ring of the chlorin has been made by Gurinivich et al (48). Ten mg kg-' body weight of each chlorin was injected ip in PBS into Af mice bearing transplanted methylcholanthrene-induced sarcomas.…”

Section: Hy Drophlllc Sensitizersmentioning

confidence: 99%

Structure and Biodistribution Relationships of Photodynamic Sensitizers*

Boyle

Dolphin

1996

Photochem & Photobiology

497

339

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e.g. rose bengal and the hypericins, have also been omitted to allow meaningful comparisons to be made between difPhotodynamic therapy (PDT) has, during the last quarter ferent compounds. As the intracellular distribution of phocentury, into a fully fledged lieid tosensitizers to organelles and other subcellular structures with its own association, the International Photodynamic can have a large effect on PDT efficacy, a section will be Association ( P A ) and regular conferences devoted solely devoted to this topic. to this topic. Recent approval of the first PDT sensitizer, Photofrinm (porfimer sodium), by health boards in Canada, Japan, the Netherlands and United States for use against certain types of solid tumors represents, perhaps, the single most significant indicator of the progress of PDT from a laboratory research concept to clinical reality.The approval of Photofrinm will undoubtedly encourage the accelerated development of second-generation photosensitizers, which have recently been the subject of intense study. Many of these second-generation drugs show significant differences, when compared to Photofrinm, in terms of treatment times postinjection, light doses and drug doses required for optimal results. These differences can ultimately be attributed to variations in either the quantum efficiency of the photosensitizer in s h , which is in turn affected by aggregation state, localized concentration of endogenous quenchers and primary photophysics of the dye, or the intratumoral and intracellular localization of the photosensitizer at the time of activation with light. The purpose of this review is to bring together data relating to the biodistribution and pharmacokinetics of second-generation sensitizers and attempt to correlate this with structural and electronic features of these molecules. As this requires a clear knowledge of photosensitizer structure, only chemically well-characterized compounds are included, e.g. PhotofrinB and crude sulfonated phthalocyanines have been excluded as they are known to be complex mixtures. Nonporphyrin-based photosensitizers,

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Section: Hy Drophlllc Sensitizersmentioning

confidence: 99%

Structure and Biodistribution Relationships of Photodynamic Sensitizers*

Boyle

Dolphin

1996

Photochem & Photobiology

497

339

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“…Synthesis of chlorin e 6 13-amide derivatives (19)(20)(21)(22)(23)(24)(25) was carried out by the reaction of methyl pheophorbide a and corresponding amine (Scheme 4). [48,49,[58][59][60] 13-Amide derivatives 30 (Scheme 2) and 34 (Scheme 6) were obtained by the same way.…”

Section: Resultsmentioning

confidence: 99%

“…It was shown that chlorins without exo-cycle (20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35) cause an active photosensitized lysis of erythrocytes regardless of the substituent's nature. The presence of exocycle (compounds 1-19) in the most cases leads to decrease in photohemolysis power and increase in its induction period.…”

Section: Discussionmentioning

confidence: 99%

“…Methylpheophorbide a 13(2)-N,N-dibuthylamide (3) was obtained according to [49] . Methyl-13(2)-N,N-dimethylaminomethylpheophorbide a (4), chlorin e 6 13(1)-N-(n-hexyl)amide-15(2),17(3)-dimethyl ester (22), chlorin e 6 13(1)-N-(n-octyl)amide-15(2),17(3)-dimethyl ester (23), chlorin e 6 3(1),3(2)-bis-(N,N-dimethylaminomethyl)-13(1)-N-methylamide-15(2),17(3)-dimethyl ester (26), chlorin e 6 13(1)-N,N-dimethylamide-15-(1-methoxycarbomoylvinyl)-17(3)-methyl ester (35) were obtained according to [50] . Methylmesopheophorbide a (8), [51] methylpyropheophorbide b (9), [52] methylpheophorbide b (10), [52] methylpyropheophorbide d (11), [53] methylpheophorbide b (12), [54] methyl-3(1),3(2)-bis-(N,N-dimethylaminomethyl)-pyropheophorbide a (15), [55] and Scheme 1.…”

Section: Methodsmentioning

confidence: 99%

“…[15,21,[28][29][30][31][32] Variation of chlorins chemical structure features such as charge, hydrophobicity and steric properties leads to the significant changing of the pigments ability to insert into the cell which can define their photodynamic effectivity. [33,34] The ability of pigments to interact with membrane structures is of a great significance for photosensitizing activity appearance in cell culture and in vivo. [35] It is well known that sub-cell localization of PS defines their biological efficiency.…”

Section: Introductionmentioning

confidence: 99%

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