Evaluation of paclitaxel rearrangement involving opening of the oxetane ring and migration of acetyl and benzoyl groups
- 作者：Sang-Hyun Pyo ; Jin-Suk Cho ; Ho-Joon Choi ; Byung-Hee Han
- 关键词：Paclitaxel ; Oxetane ring opening ; Acetyl migration ; Benzoyl migration ; Rearrangement
- 刊名：Journal of Pharmaceutical and Biomedical Analysis
- 出版年：2007
- 期刊代码：65_07317085
- 类别：ch
- 出版时间：19 February 2007
- 卷：43
- 期：3
- 页码：1141-1145
- 文件大小：440 K
摘要
The stability of drug is a critical factor in quality control, drug efficacy, safety, storage, and production conditions. The rearrangement of paclitaxel, which involves opening of the oxetane ring and migration of acetyl group occurred on heating a powder of purified paclitaxel. Subsequently, the unusual migration of benzoyl groups progressed rapidly in organic solvents. These rearrangement derivatives were isolated carefully. The structures of the intermediate derivative A and the product derivative B were confirmed using 1H NMR, high performance liquid chromatography (HPLC), and mass spectrometry. We proposed the rearrangement pathway here for the first time. Neither derivative exhibited bioactivity in SKOV3 (ovarian cancer) or MDA-MB-435 (breast cancer) cell culture assays.