New acetylenic derivatives of bile acids as versatile precursors for the preparation of prodrugs. Synthesis and cytotoxicity study

被引：3

作者：

Pavley, Yu. R. ^{[1
]}

Yamansarov, E. Yu. ^{[1
,2
]}

Evteev, S. A. ^{[1
]}

Lopatukhina, E. V. ^{[1
,2
]}

Zyk, N. V. ^{[1
]}

Erofeev, A. S. ^{[1
,2
]}

Gorelkin, P. V. ^{[1
,2
]}

Beloglazkina, E. K. ^{[1
]}

机构：

[1] Lomonosov Moscow State Univ, 1 Leninskie Gory, Moscow 119991, Russia

[2] Natl Univ Sci & Technol MISIS, 4 Leninskii Prosp, Moscow 119049, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2023年 / 72卷 / 03期

基金：

俄罗斯科学基金会;

关键词：

steroids; alkynes; esterification; bile acids; lithocholic acid; deoxycholic acid; cholic acid; amphiphilicity; surface activity; cytotoxicity; DRUG-DELIVERY; CHEMISTRY;

D O I：

10.1007/s11172-023-3837-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Three groups of bile acid derivatives with acetylenic moieties, such as propargyl, hex-5-ynoyl, and 4,7,10,13-tetraoxahexadec-15-ynoyl ones, were obtained. The cytotoxic activity of the synthesized compounds against hepatocellular carcinoma (HepG2, Huh7), prostate cancer (PC3), and human embryonic kidney (HEK293) cell lines was studied. The parameters enabling estimation of the total lipophilicity of the synthesized bile acid derivatives (logP, TPSA) were calculated. The correlation between the cytotoxic activity and hydrophilic-lipophilic balance of the synthesized compounds was determined. A physicochemical mechanism for the cytotoxic action of bile acid derivatives is proposed.

引用

页码：724 / 739

页数：16

共 35 条

[1] [Anonymous], 2015, Targeted drug delivery: concepts and design, DOI DOI 10.1007/978-3-319-11355-5
[2] A Comprehensive Review on Steroidal Bioconjugates as Promising Leads in Drug Discovery
Bansal, Ranju
Suryan, Amruta
[J]. ACS BIO & MED CHEM AU, 2022, 2 (04): : 340 - 369
[3] Design, Synthesis, and Evaluation of Novel 1,2,3-Triazole-Tethered Glycolipids as Vaccine Adjuvants
Bhunia, Debabrata
Pallavi, Preethi M. C.
Bonam, Srinivasa Reddy
Reddy, Sandeep A.
Verma, Yogesh
Halmuthur, M. Sampath Kumar
[J]. ARCHIV DER PHARMAZIE, 2015, 348 (10) : 689 - 703
[4] GABAkines - Advances in the discovery, development, and commercialization of positive allosteric modulators of GABAA receptors
Cerne, Rok
Lippa, Arnold
Poe, Michael M.
Smith, Jodi L.
Jin, Xiaoming
Ping, Xingjie
Golani, Lalit K.
Cook, James M.
Witkina, JeffreyM.
[J]. PHARMACOLOGY & THERAPEUTICS, 2022, 234
[5] DSouza A A., 2015, ADV DELIV SCI TECHNO, V6, P197, DOI [10.1007/978-3-319-11355-5_6, DOI 10.1007/978-3-319-11355-5_6]
[6] Cholesterol Modified Self-Assemblies and Their Application to Nanomedicine
Ercole, Francesca
Whittaker, Michael R.
Quinn, John F.
Davis, Thomas P.
[J]. BIOMACROMOLECULES, 2015, 16 (07) : 1886 - 1914
[7] Bile acids and bile acid derivatives: use in drug delivery systems and as therapeutic agents
Faustino, Celia
Serafim, Claudia
Rijo, Patricia
Reis, Catarina Pinto
[J]. EXPERT OPINION ON DRUG DELIVERY, 2016, 13 (08) : 1133 - 1148
[8] Targeted drug conjugates: principles and progress
Garnett, MC
[J]. ADVANCED DRUG DELIVERY REVIEWS, 2001, 53 (02) : 171 - 216
[9] Site-Selective Antibody Functionalization via Orthogonally Reactive Arginine and Lysine Residues
Hwang, Dobeen
Nilchan, Napon
Nanna, Alex R.
Li, Xiaohai
Cameron, Michael D.
Roush, William R.
Park, HaJeung
Rader, Christoph
[J]. CELL CHEMICAL BIOLOGY, 2019, 26 (09): : 1229 - +
[10] Lipid-Drug Conjugate for Enhancing Drug Delivery
Irby, Danielle
Du, Chengan
Li, Feng
[J]. MOLECULAR PHARMACEUTICS, 2017, 14 (05) : 1325 - 1338

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