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Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine
Department of Pharmacy and Pharmaceutical Technology, Faculty of Pharmacy, University of Santiago de Compostela, Santiago de Compostela 15782, Spain
Faculty of Sciences, University of Valparaíso, Valparaíso 33449, Chile
Faculty of Pharmacy, University of Valparaíso, Valparaíso 33449, Chile
* Authors to whom correspondence should be addressed.
Received: 6 June 2012; in revised form: 27 August 2012 / Accepted: 6 September 2012 / Published: 12 September 2012
Abstract: The aim of this study was to determine the electronic influence of substituent groups and annelated rings such as oxazole-oxazinone on the physicochemical and photoprotection, antioxidant capacity, toxicity and singlet oxygen photosensitization biological properties of isoquinoline alkaloid frameworks. Thus, oxoisoaporphine derivatives 1–5 and 3-azaoxoisoaporphine (6), some of them with phenolic structures, did not present any antioxidant capacity, possibly either by formation of keto-enol tautomerism species or the formation of unstable free radicals. Due to the singlet oxygen quantum yields (FD) near to unity, and greater photostability than phenalenone, oxoisoaporphines 4–6 may be considered as photosensitizers for singlet oxygen production and can be used as new universal study tools. The biological application as antibacterial agents is an important and possible tool in the study of compounds with low cytotoxicity and high reactivity in antineoplastic chemotherapy. On the other hand, when boldine and its annelated derivatives B1–4 are irradiated, a photoprotector effect is observed (SPF = 2.35), even after 30 minutes of irradiation. They also act as photoprotectors in cell fibroblast cultures. No hemolysis was detected for boldine hydrochloride and its salts without irradiation. In solutions irradiated before incubation (at concentrations over 200 ppm) photoproducts were toxic to the nauplii of Artemia salina.
Keywords: antioxidant capacity; oxoisoaporphines; photoprotection; toxicity; singlet oxygen
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Sobarzo-Sánchez, E.; Soto, P.G.; Valdés Rivera, C.; Sánchez, G.; Hidalgo, M.E. Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine. Molecules 2012, 17, 10958-10970.
Sobarzo-Sánchez E, Soto PG, Valdés Rivera C, Sánchez G, Hidalgo ME. Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine. Molecules. 2012; 17(9):10958-10970.
Sobarzo-Sánchez, Eduardo; Soto, Patricio González; Valdés Rivera, Cristóbal; Sánchez, Georgina; Hidalgo, María Eliana. 2012. "Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and Boldine." Molecules 17, no. 9: 10958-10970.