Chemical synthesis of 7-ethyl-10-hydroxycamptothecin derivative

被引:0
|
作者
Kuang, Hao [1 ]
Wang, Jisheng [1 ]
Hong, Zhiming [2 ]
Li, Haisong [1 ]
机构
[1] Beijing Univ Chinese Med, Beijing, Peoples R China
[2] Guangzhou Univ Chinese Med, Shenzhen, Peoples R China
来源
PRZEMYSL CHEMICZNY | 2024年 / 103卷 / 02期
关键词
camptothecin; 7-ethyl-10-hydroxy-camptothecin; ethylene glycol; chemical synthesis; click reaction; CANCER; DRUG; NANOPARTICLES; GLUTATHIONE; IRINOTECAN; RESISTANT;
D O I
10.15199/62.2024.2.6
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An 7-Et-10-hydroxycamptothecin (I) derivative was synthesized with a high yield (up to 88%) by nucleophilic substitution by using ethylene glycol as starting material. The OH group was introduced at the C-10 position of camptothecin structure through nucleophilic substitution and an glucose azide was used for the following click reaction.
引用
收藏
页码:262 / 265
页数:4
相关论文
共 50 条
  • [31] Glucuronidation of 7-ethyl-10-hydroxycamptothecin (SN-38) by the human UDP-glucuronosyltransferases encoded at the UGT1 locus
    Ciotti, M
    Basu, N
    Brangi, M
    Owens, IS
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1999, 260 (01) : 199 - 202
  • [32] High payload nanoparticles composed of 7-ethyl-10-hydroxycamptothecin and chlorin e6 for synergistic chemo-photodynamic combination therapy
    Zhao, Yanna
    Jiang, Xinxin
    Ma, Qisan
    Zhao, Yuping
    Zhang, Huaizhen
    Wang, Qingpeng
    Ding, Zhuang
    Liu, Min
    Wang, Zhengping
    Han, Jun
    DYES AND PIGMENTS, 2021, 184
  • [33] Improved lymphatic targeting: effect and mechanism of synthetic borneol on lymph node uptake of 7-ethyl-10-hydroxycamptothecin nanoliposomes following subcutaneous administration
    Ye, Tiantian
    Wu, Yue
    Shang, Lei
    Deng, Xueqing
    Wang, Shujun
    DRUG DELIVERY, 2018, 25 (01) : 1461 - 1471
  • [34] Common human UGT1A polymorphisms and the altered metabolism of irinotecan active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38)
    Gagné, JF
    Montminy, V
    Belanger, P
    Journault, K
    Gaucher, G
    Guillemette, C
    MOLECULAR PHARMACOLOGY, 2002, 62 (03) : 608 - 617
  • [35] Mechanisms of chitosan-coated poly(lactic-co-glycolic acid) nanoparticles for improving oral absorption of 7-ethyl-10-hydroxycamptothecin
    Guo, Miao
    Rong, Wen-Ting
    Hou, Jie
    Wang, Dong-Fang
    Lu, Yu
    Wang, Ying
    Yu, Shu-Qin
    Xu, Qian
    NANOTECHNOLOGY, 2013, 24 (24)
  • [36] Conversion of irinotecan (CPT-11) to its active metabolite, 7-ethyl-10-hydroxycamptothecin (SN-38), by human liver carboxylesterase
    Rivory, LP
    Bowles, MR
    Robert, J
    Pond, SM
    BIOCHEMICAL PHARMACOLOGY, 1996, 52 (07) : 1103 - 1111
  • [37] INHIBITION OF BETA-GLUCURONIDASE BY NATURAL GLUCURONIDES OF KAMPO MEDICINES USING GLUCURONIDE OF SN-38(7-ETHYL-10-HYDROXYCAMPTOTHECIN) AS A SUBSTRATE
    NARITA, M
    NAGAI, E
    HAGIWARA, H
    ABURADA, M
    YOKOI, T
    KAMATAKI, T
    XENOBIOTICA, 1993, 23 (01) : 5 - 10
  • [38] Transport of 7-ethyl-10-hydroxycamptothecin (SN-38) by breast cancer resistance protein ABCG2 in human lung cancer cells
    Nakatomi, K
    Yoshikawa, M
    Oka, M
    Ikegami, Y
    Hayasaka, S
    Sano, K
    Shiozawa, K
    Kawabata, S
    Soda, H
    Ishikawa, T
    Tanabe, S
    Kohno, S
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2001, 288 (04) : 827 - 832
  • [39] Spectrophotometric and Voltammetric Studies on the Interaction of 7-Ethyl-10-hydroxycamptothecin (SN-38) as the Metabolized Compound of CPT-11 with ds-DNA
    Hajian, Reza
    Tan, Guan H.
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (01) : 436 - 440
  • [40] RAFT-Derived Polymer-Drug Conjugates: Poly(hydroxypropyl methacrylamide) (HPMA)-7-Ethyl-10-hydroxycamptothecin (SN-38) Conjugates
    Williams, Charlotte C.
    Thang, San H.
    Hantke, Tina
    Vogel, Uwe
    Seeberger, Peter H.
    Tsanaktsidis, John
    Lepenies, Bernd
    CHEMMEDCHEM, 2012, 7 (02) : 281 - 291