Photoisomerization of Sulindac and Ozagrel Hydrochloride by Vitamin B2 Catalyst Under Visible Light Irradiation
Photoisomerization of Sulindac and Ozagrel Hydrochloride by Vitamin B2 Catalyst Under Visible Light Irradiation
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可见光照射下维生素B2催化剂光致异构化舒林酸和盐酸奥扎格雷
DOI：
10.1007/s11095-022-03203-3
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发表时间：
2022
影响因子：
3.7
通讯作者：
Takahashi Hideyo
中科院分区：
文献类型：
--
作者：
Suga Mayuko;Makino Kosho;Tabata Hidetsugu;Oshitari Tetsuta;Natsugari Hideaki;Takahashi Hideyo
目的药物E/Z-烯烃结构的光异构化是一个值得关注的问题，因为它可能导致药效损失和不良副作用。本研究主要研究在发光二极管（LED）或荧光灯下，维生素B2共同催化下盐酸舒林酸和奥扎格雷的光诱导异构化。方法在0.05/0.03当量的维生素B2/黄素腺嘌呤二核苷酸（FAD）存在下，对盐酸舒林酸或奥扎格雷进行辐照。 使用 LED 灯 (405 nm) 或荧光灯。通过 1 H NMR 光谱监测 CD3OD 和 D2O 中的光异构化。结果在催化量的维生素 B2 或 FAD 存在下，在 405 nm LED 灯和荧光灯的照射下，舒林酸和盐酸奥扎格雷发生异构化。发现 LED 灯照射比荧光灯照射更有效。光异构化速率受溶剂影响，CD3OD中的反应比D2O中进行得更快。此外，盐酸奥扎格雷比舒林酸更容易发生异构化。结论维生素B2或FAD在舒林酸和盐酸奥扎格雷的光异构化反应中表现出催化活性。考虑到D2O中光致异构化的速率很慢，临床使用过程中发生光致异构化的可能性较低。然而，本研究提示，静脉注射舒林酸或盐酸奥扎格雷时，应避免在过度光照下输注维生素 B2 或 FAD。
PurposePhotoisomerization of theE/Z-alkene structures of drugs is a matter of concern as it could result in potency loss and adverse side effects. This study focused on light-induced isomerization of sulindac and ozagrel hydrochloride catalyzed by concomitant vitamin B2under light-emitting diode (LED) or fluorescent light.MethodsIn the presence of 0.05/0.03 equivalents of vitamin B2/flavin adenine dinucleotide (FAD), sulindac or ozagrel hydrochloride was irradiated with LED light (405 nm) or fluorescent light. The photoisomerization in CD3OD and D2O was monitored by1H NMR spectroscopy.ResultsSulindac and ozagrel hydrochloride isomerized in the presence of a catalytic amount of vitamin B2or FAD under irradiation of 405 nm LED light and fluorescent light. Irradiation with LED light was found to be more effective than fluorescent light irradiation. The rate of photoisomerization was affected by the solvent, and the reaction in CD3OD proceeded faster than in D2O. Furthermore, ozagrel hydrochloride was more prone to isomerization than sulindac.ConclusionThe catalytic activity of vitamin B2or FAD was demonstrated in the photoisomerization reaction of sulindac and ozagrel hydrochloride. Considering that the rate of photoisomerization in D2O is very slow, the possibility of the occurrence of photoisomerization during clinical use is low. However, this study suggests that the interfusion of vitamin B2or FAD under excessive light exposure should be avoided as a caution during intravenous administration of sulindac or ozagrel hydrochloride.
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