On the mechanism of erythrocyte hemolysis induced by photooxidized psoralen

Nevezhin, E V; Vlasova, N. V.; Pyatnitskiy, I. A.; Lysenko, Eugene P.; Malakhov, Mikhail V.

doi:10.1134/s0006297915060115

Cited by 3 publications

(3 citation statements)

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“…Photolysis of psoralens in vitro provides the complex mixtures of biologically active photoproducts comprehensively reviewed by S. Caffieri [ 14 ]. Photoproducts of psoralens were found to induce phototoxic and dark membranolytic effects and apoptosis, as well as affect cell proliferation and differentiation [ 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 ]. More importantly, photoproducts of psoralen photooxidation were able to induce the immunotherapeutic effect in vivo [ 20 , 21 , 22 ] and selectively induce apoptosis in vitro in the transformed T-cell lines ( Jurkat cell line) [ 17 ], suggesting the crucial role of these photoproducts in the realization of the immunotherapeutic effects of psoralen-based phototherapies.…”

Section: Introductionmentioning

confidence: 99%

pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

et al. 2021

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Photo-controlled or photo-regulated molecules, especially biologically active and operating in physiological conditions, are in steady demand. Herein, furocoumaric and furocoumarinic acids being (Z/E)-isomers relative to each other were obtained in two stages starting from psoralen: the alkaline solvolysis of psoralen led to furocoumaric acid, which was further Z → E photoisomerized (365 nm) to furocoumarinic acid. The kinetics of Z → E photoisomerization was monitored by HPLC and UV-vis spectrophotometry. Photophysical characteristics in the aqueous phase for both acids, as well as the reversibility of (Z/E) photoisomerization process, were also assessed. Furocoumarinic acid was found to be visibly fluorescent at pH 2.0–12.0, with the maxima of fluorescence emission spectra being pH-dependent. The reverse E → Z photoisomerization predicted by quantum chemistry calculations as energetically favorable for the monoanionic form of furocoumarinic acid was proved in the experiment while being complicated by pyrone ring closure back to psoralen in acidic and neutral conditions. The preparative synthesis of furocoumarinic acid outlined in this work is particularly valuable in view of a wide range of pharmacological effects previously predicted for this compound.

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Section: Introductionmentioning

confidence: 99%

pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

et al. 2021

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“…Ряд данных указывает на возможную или явную роль гидропероксидов в реализации этих эффектов. Обнаружено, что: а) ионы Fe 2+ активируют гемолиз эритроцитов, индуцированный ФОП [6], и другой тип фотогемолиза, сенсибилизированного псораленом (ПУВА-гемолиз) [7]; б) ФОП вызывает превращения гемоглобина, аналогичные таковым при добавлении H 2 O 2 [8]; в) производные псоралена, содержащие гидропероксидную группу в составе боковой цепи, индуцируют фотогемолиз эритроцитов [9,10]. Также известен факт хемилюминесценции, индуцированной добавлением ионов Fe 2+ к ФОП [11,12].…”

Section: Introductionunclassified

“…Формирование гидропероксидов в процессе фотоокисления псоралена может вовлекать их во вторичные (постлучевые) химические реакции, что важно для понимания механизмов формирования биологически активных ФОП-продуктов. Так, мы предполагаем возможность формирования, по меньшей мере, еще одного гидропероксида (помимо H 2 O 2 ) в качестве промежуточного продукта фотоокисления псоралена [6].…”

Section: Introductionunclassified

Detection of Hydroperoxides in Solutions of Photooxidized Psoralen

et al. 2019

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Photooxidized psoralen solutions possess a variety of biological effects, which implementation mechanism may presumably involve hydroperoxides. Here, the hydroperoxide content in photooxidized psoralen solutions was assessed using photometric FOX assay (from Ferrous Oxidation + Xylenol Orange). FOX reagent with 10× content of Xylenol Orange, modified for quantitative analysis of up to 50 μM of hydroperoxides in aqueous phase was used in experiments. During photooxidation of 0.1 mM psoralen in phosphate buffer solution, hydroperoxide production increases with dose of UVA irradiation (~2.5 μM eq. of H2O2 for dose of 252 kJ/m2 and ~11 μM eq. of H2O2 for dose of 1512 kJ/m2) and reaches ~16.5 μM eq. of H2O2 at the highest dose investigated (3024 kJ/m2). A comparison of kinetics of psoralen photolysis and hydroperoxide generation allows us to suggest that generation of hydroperoxide results from the secondary photochemical processes involving psoralen photoproducts, presumably from photoinduced autooxidation of aldehydic photoproducts of psoralen.

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Prospective pharmacological effects of psoralen photoxidation products and their cycloadducts with aminothiols: chemoinformatic analysis

Skarga

Zadorozhny

Shilov

et al. 2020

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Psoralens are medicinal photosensitizing furocoumarins which are used in photochemotherapy and photoimmunotherapy of dermatoses. Psoralen photooxidation products may be involved in therapeutic effects, but the possible mechanisms of their action remain unclear. The study was aimed to assess the prospective pharmacological effects and mechanisms of activity for six previously identified ortho–hydroxyformyl-containing psoralen photooxidation products and their cycloadducts with aminothiols, as well as for structurally similar compounds (furocoumaric acid and tucaresol). Chemoinformatic analysis of the prospective pharmacological effects and mechanisms of action of these compounds was performed using the PASS and PharmaExpert software. The predicted pharmacological effects partially confirmed by previous studies highlight the possible involvement of psoralen photooxidation products in the effects of PUVA therapy or photopheresis during the course of dermatoses and proliferative disorders treatment. A broad spectrum of pharmacological effects found for furocoumaric acid and cycloadducts of coumarinic and benzofuranic photoproducts of psoralen with cysteine and homocysteine appoints new directions of research relating to therapeutic use of psoralens.

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On the mechanism of erythrocyte hemolysis induced by photooxidized psoralen

Cited by 3 publications

References 30 publications

pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

pH-Dependent Photoinduced Interconversion of Furocoumaric and Furocoumarinic Acids

Detection of Hydroperoxides in Solutions of Photooxidized Psoralen

Prospective pharmacological effects of psoralen photoxidation products and their cycloadducts with aminothiols: chemoinformatic analysis

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