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维生素B和黄素腺嘌呤二核苷酸催化下氮烯咪胺在可见光照射下的光降解作用

Photodegradation of Dacarbazine Catalyzed by Vitamin B and Flavin Adenine Dinucleotide Under Visible-Light Irradiation.

作者信息

Kimura Yuka, Suga Mayuko, Nakamura Kayo, Tabata Hidetsugu, Oshitari Tetsuta, Natsugari Hideaki, Takahashi Hideyo

机构信息

Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641Yamazaki, Noda-Shi, Chiba, 278-8510, Japan.

Department of Medicinal Chemistry, Faculty of Pharma Sciences, Teikyo University, Itabashi-Ku, Tokyo, Japan.

出版信息

Pharm Res. 2024 Dec;41(12):2363-2375. doi: 10.1007/s11095-024-03802-2. Epub 2024 Dec 18.

DOI:10.1007/s11095-024-03802-2
PMID:39695066
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11682012/
Abstract

PURPOSE

Drug photodegradation is a matter of great concern because it can result in potency loss and adverse side effects. This study examines the light-induced degradation of dacarbazine catalyzed by vitamin B and flavin adenine dinucleotide (FAD) under light-emitting diode (LED) or fluorescent light irradiation.

METHODS

Dacarbazine was irradiated with LED (405 nm) or fluorescent light in the presence of various equivalents of vitamin B or FAD. The photodegradation of the drug in DO was monitored by H nuclear magnetic resonance spectroscopy.

RESULTS

Dacarbazine dissolved in DO decomposed in the presence of vitamin B or FAD under irradiation with LED or fluorescent light. The decomposition products were 2-azahypoxanthine 2, which has previously been observed after light irradiation in the absence of vitamin B, and 1H-imidazole-5-carboxamide 6, a new product formed in the presence of vitamin B. Irradiation with LED light was more effective than irradiation with fluorescent light in degrading dacarbazine.

CONCLUSION

Vitamin B and FAD induced dacarbazine photodegradation. Thus, the interfusion of vitamin B or FAD under excessive light exposure should be avoided during the intravenous administration of dacarbazine.

摘要

目的

药物光降解是一个备受关注的问题，因为它可能导致效力丧失和不良副作用。本研究考察了在发光二极管（LED）或荧光照射下，维生素B和黄素腺嘌呤二核苷酸（FAD）催化的达卡巴嗪光致降解。

方法

在不同当量的维生素B或FAD存在下，用LED（405nm）或荧光对达卡巴嗪进行照射。通过氢核磁共振光谱监测药物在重水中的光降解。

结果

溶解在重水中的达卡巴嗪在维生素B或FAD存在下，经LED或荧光照射会发生分解。分解产物为2-氮杂次黄嘌呤2（此前在无维生素B光照后已观察到）和1H-咪唑-5-甲酰胺6（在维生素B存在下形成的一种新产物）。LED光照在降解达卡巴嗪方面比荧光照射更有效。

结论

维生素B和FAD可诱导达卡巴嗪光降解。因此，在静脉注射达卡巴嗪期间，应避免在过度光照下维生素B或FAD的混入。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/22b6f8ccbf41/11095_2024_3802_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/c024aa92694b/11095_2024_3802_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/8575f4cd41be/11095_2024_3802_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/46caf34c6c61/11095_2024_3802_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/f638458f554f/11095_2024_3802_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/76bb977dfd1d/11095_2024_3802_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/8d20de80bee3/11095_2024_3802_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/a2ae1c08e449/11095_2024_3802_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/22b6f8ccbf41/11095_2024_3802_Fig7_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/c024aa92694b/11095_2024_3802_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/8575f4cd41be/11095_2024_3802_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/46caf34c6c61/11095_2024_3802_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/f638458f554f/11095_2024_3802_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/76bb977dfd1d/11095_2024_3802_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/8d20de80bee3/11095_2024_3802_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/a2ae1c08e449/11095_2024_3802_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1ab/11682012/22b6f8ccbf41/11095_2024_3802_Fig7_HTML.jpg

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