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Evaluation of paclitaxel rearrangement involving opening of the oxetane ring and migration of acetyl and benzoyl groups

Pyo, Sang-Hyun LU ; Cho, Jin-Suk ; Choi, Ho-Jun and Han, Byung-Hee (2007) In Journal of Pharmaceutical and Biomedical Analysis 43(3). p.1141-1145
Abstract
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... (More)
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. (Less)
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author
; ; and
publishing date
type
Contribution to journal
publication status
published
keywords
Paclitaxel, Oxetane ring opening, Acetyl migration
in
Journal of Pharmaceutical and Biomedical Analysis
volume
43
issue
3
pages
1141 - 1145
publisher
Elsevier
external identifiers
  • scopus:33846590510
ISSN
0731-7085
DOI
10.1016/j.jpba.2006.08.026
language
English
LU publication?
no
id
5cf77db3-c28c-475e-b220-25c42f4c7757
date added to LUP
2024-12-28 10:30:41
date last changed
2025-01-08 12:07:02
@article{5cf77db3-c28c-475e-b220-25c42f4c7757,
  abstract     = {{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.}},
  author       = {{Pyo, Sang-Hyun and Cho, Jin-Suk and Choi, Ho-Jun and Han, Byung-Hee}},
  issn         = {{0731-7085}},
  keywords     = {{Paclitaxel; Oxetane ring opening; Acetyl migration}},
  language     = {{eng}},
  month        = {{02}},
  number       = {{3}},
  pages        = {{1141--1145}},
  publisher    = {{Elsevier}},
  series       = {{Journal of Pharmaceutical and Biomedical Analysis}},
  title        = {{Evaluation of paclitaxel rearrangement involving opening of the oxetane ring and migration of acetyl and benzoyl groups}},
  url          = {{http://dx.doi.org/10.1016/j.jpba.2006.08.026}},
  doi          = {{10.1016/j.jpba.2006.08.026}},
  volume       = {{43}},
  year         = {{2007}},
}