Applied Biological and Physicochemical Activity of Isoquinoline Alkaloids: Oxoisoaporphine and BoldineReport as inadecuate




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1

Department of Pharmacy and Pharmaceutical Technology, Faculty of Pharmacy, University of Santiago de Compostela, Santiago de Compostela 15782, Spain

2

Faculty of Sciences, University of Valparaíso, Valparaíso 33449, Chile

3

Faculty of Pharmacy, University of Valparaíso, Valparaíso 33449, Chile





*

Authors to whom correspondence should be addressed.



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 antioxidant capacity; oxoisoaporphines; photoprotection; toxicity; singlet oxygen





Author: Eduardo Sobarzo-Sánchez 1,* , Patricio González Soto 2, Cristóbal Valdés Rivera 2, Georgina Sánchez 3 and María Eliana Hidalgo 2,*

Source: http://mdpi.com/



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