Synthesis, isolation, characterization of C3-C11 bridge-bond isomer of paclitaxel and its antitumor effect via inducing A549 cells pyroptosis

被引：2

作者：

Yang, Wen ^{[1
]}

Yin, Qiming ^{[1
]}

Tian, Jing ^{[2
]}

Jia, Qiang ^{[1
]}

Wang, Jifeng ^{[3
]}

Niu, Fengju ^{[1
]}

机构：

[1] Shandong Univ Tradit Chinese Med, Innovat Inst Chinese Med & Pharm, Jinan, Peoples R China

[2] Jinan Vocat Coll Nursing, Dept Nursing, Jinan, Peoples R China

[3] Shandong Canc Hosp & Inst, Dept Pharm, Jinan, Peoples R China

来源：

NATURAL PRODUCT RESEARCH | 2024年 / 38卷 / 18期

关键词：

Paclitaxel; C3-C11 bridge-bond isomer; photodegradation; pyroptosis; CO-DELIVERY; NANOPARTICLES; PRODRUG; RING;

D O I：

10.1080/14786419.2023.2218011

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

During the chemical manufacturing control processing of new paclitaxel formulations, a photodegradation impurity called C3-C11 bridge-bond isomer appeared. Our work describes the synthesis, isolation, purification, and structural characterization methods using four spectroscopies: FT-IR, UV, NMR (1H and 13 C), and LC-MS. In addition, we discovered that the C3-C11 bridge-bond isomer can promote A549 cells pyroptosis, and increase pyroptosis-related proteins, including cleaved-caspase 3, cleaved-PARP, GSDME-N, and lactate dehydrogenase, thus making it anti-tumor effects. The study offered data suggesting that the C3-C11 bridge bond isomer may be used as an anti-tumour drug in the future.

引用

页码：3155 / 3164

页数：10

共 2 条

[1] Synthetic studies of the 18-membered antitumor macrolide, tedanolide.: 3.: Stereocontrolled synthesis of the C1-C12 part via a synthesis of the C1-C7 fragment by a mismatched but efficient sharpless dihydroxylation and its coupling with the C8-C11 fragment
Matsushima, T
Mori, M
Zheng, BZ
Maeda, H
Nakajima, N
Uenishi, J
Yonemitsu, O
CHEMICAL & PHARMACEUTICAL BULLETIN, 1999, 47 (03) : 308 - 321
[2] SYNTHESIS, CHARACTERIZATION, AND ISOMERIZATION BEHAVIOR OF SYN-(MU-ETA-3-1-METHYLALLYL)(MU-BENZENETHIOLATO)BIS(TRICYCLOHEXYLPHOSPHINE)DIPALLADIUM(I), ((C6H11)3P)2PD2(SYN-MU-ETA-3-CH2CHCHCH3)(MU-SC6H5), AND ITS ANTI-ISOMER
OSAKADA, K
CHIBA, T
NAKAMURA, Y
YAMAMOTO, T
YAMAMOTO, A
ORGANOMETALLICS, 1989, 8 (11) : 2602 - 2605

← 1 →