Synthesis of conjugates of closo-dodecaborate dianion with cholesterol using a "click" reaction

被引：17

作者：

Druzina, A. A. ^{[1
]}

Zhidkova, O. B. ^{[1
]}

Kosenko, I. D. ^{[1
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, 28 Ul Vavilova, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2020年 / 69卷 / 06期

基金：

俄罗斯科学基金会;

关键词：

closo-dodecaborate dianion; cyclic oxonium derivatives of polyhedral boron hydrides; cholesterol; conjugates; lipids; liposomes; boron neutron capture therapy of cancer; click" reaction; BORON-RICH LIPOSOMES; THERAPEUTIC-EFFICACY; OXONIUM DERIVATIVES; ANION; TUMOR; DELIVERY; COBALT;

D O I：

10.1007/s11172-020-2870-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The nucleophilic ring-opening reaction of tetrahydropyran derivative of thecloso-dode-caborate dianion with sodium azide in the presence of tetrabutylammonium bromide led to the novel azido-derivatives of[B12H12](2-). A Cu-catalyzed 1,3-dipolar [3+2] cycloaddition reaction of the closo-dodecaborate dianion azido-derivatives with alkynyl-cholesterol led to 1,4-disubstituted 1,2,3-triazoles with the closo-dodecaborate fragment at position 1. The resulting conjugates are potentially suitable for the development of liposomal drugs to selectively deliver boron into a tumor cell for boron neutron capture therapy of cancer.

引用

页码：1080 / 1084

页数：5

共 33 条

[1]

Alavi M, 2019, PERS THER, V34, P1

[2] Click reaction based synthesis, antimicrobial, and cytotoxic activities of new 1,2,3-triazoles [J].

Aly, Mohamed Ramadan El Sayed ;

Saad, Hosam Ali ;

Mohamed, Mosselhi Abdelnabi Mosselhi .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (14) :2824-2830

[3] Nanoparticles in the clinic [J].

Anselmo, Aaron C. ;

Mitragotri, Samir .

BIOENGINEERING & TRANSLATIONAL MEDICINE, 2016, 1 (01) :10-29

[4] Towards new boron carriers for boron neutron capture therapy: Metallacarboranes bearing cobalt, iron and chromium and their cholesterol conjugates [J].

Bialek-Pietras, Magdalena ;

Olejniczak, Agnieszka B. ;

Tachikawa, Shoji ;

Nakamura, Hiroyuki ;

Lesnikowski, Zbigniew J. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (05) :1136-1142

[5] Novel types of boronated chlorin e6 conjugates via 'click chemistry' [J].

Bregadze, Vladimir I. ;

Semioshkin, Andrey A. ;

Las'kova, Julia N. ;

Berzina, Maria Ya. ;

Lobanova, Irina A. ;

Sivaev, Igor B. ;

Grin, Mikhail A. ;

Titeev, Rustam A. ;

Brittal, Dmitry I. ;

Ulybina, Olga V. ;

Chestnova, Anastasija V. ;

Ignatova, Anastasija A. ;

Feofanov, Alexey V. ;

Mironov, Andrey F. .

APPLIED ORGANOMETALLIC CHEMISTRY, 2009, 23 (09) :370-374

[6] 'Click' synthesis of cobalt bis(dicarbollide)-cholesterol conjugates [J].

Druzina, Anna A. ;

Shmalko, Akim, V ;

Andreichuk, Ekaterina P. ;

Zhidkova, Olga B. ;

Kosenko, Irina D. ;

Semioshkin, Andrey ;

Sivaev, Igor B. ;

Mandal, Swadhin ;

Shen, Zheyu ;

Bregadze, Vladimir, I .

MENDELEEV COMMUNICATIONS, 2019, 29 (06) :628-630

[7] Synthesis of boron-containing cholesterol derivatives for incorporation into unilamellar liposomes and evaluation as potential agents for BNCT [J].

Feakes, DA ;

Spinler, JK ;

Harris, FR .

TETRAHEDRON, 1999, 55 (37) :11177-11186

[8] NA3[B20H17NH3] - SYNTHESIS AND LIPOSOMAL DELIVERY TO MURINE TUMORS [J].

FEAKES, DA ;

SHELLY, K ;

KNOBLER, CB ;

HAWTHORNE, MF .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (08) :3029-3033

[9]

Hawthorne MF, 1996, CANCER NEUTRON CAPTURE THERAPY, P27

[10] New horizons for therapy based on the boron neutron capture reaction [J].

Hawthorne, MF .

MOLECULAR MEDICINE TODAY, 1998, 4 (04) :174-181

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