Cobalt and iron bis(dicarbollide) conjugates with cholesterol: synthesis and evaluation of antiproliferative activity

被引：3
作者：
Erdelyi, K. E. [1 ,2 ]
Antonets, A. A. [3 ]
Zhidkova, O. B. [1 ]
Druzina, A. A. [1 ]
Nazarov, A. A. [3 ]
Timofeev, S. V. [1 ,3 ]
Sivaev, I. B. [1 ]
Bregadze, V. I. [1 ]
机构：
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, 28-1 Ul Vavilova, Moscow 119334, Russia
[2] Natl Res Univ Higher Sch Econ, 20 Ul Myasnitskaya, Moscow 101000, Russia
[3] Moscow MV Lomonosov State Univ, 1-3 Leninskiye Gory, Moscow 119991, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2023年 / 72卷 / 04期
关键词：
cobalt; iron bis(dicarbollide); cholesterol; lipids; click reaction; boron neutron capture therapy; BORON-RICH LIPOSOMES; THERAPEUTIC-EFFICACY; NIDO-CARBORANE; DRUG-DELIVERY; LIVING CELLS; DERIVATIVES; COSAN; TRANSITION;
D O I：
10.1007/s11172-023-3871-8
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Boron-containing conjugates of cholesterol were synthesized by the copper(i)-catalyzed 1,3-dipolar [3+2] cycloaddition reactions of cobalt and iron bis(dicarbollide) azide derivatives with alkynyl cholesterol. The antiproliferative activity (IC50) of the conjugates was evaluated against a series of human cell lines by the MTT assay. All conjugates were shown to be nontoxic (IC50 >200 mu mol L-1) and to be applicable for the preparation of boron-containing liposomes as potential drugs for boron-neutron capture therapy (BNCT) of cancer.
引用
收藏
页码：1059 / 1065
页数：7
相关论文
共 57 条
  • [1] Click reaction based synthesis, antimicrobial, and cytotoxic activities of new 1,2,3-triazoles
    Aly, Mohamed Ramadan El Sayed
    Saad, Hosam Ali
    Mohamed, Mosselhi Abdelnabi Mosselhi
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (14) : 2824 - 2830
  • [2] High-Affinity Binding of Metallacarborane Cobalt Bis(dicarbollide) Anions to Cyclodextrins and Application to Membrane Translocation
    Assaf, Khaleel I.
    Begaj, Barbara
    Frank, Angelina
    Nilam, Mohamed
    Mougharbel, Ali S.
    Kortz, Ulrich
    Nekvinda, Jan
    Gruner, Bohumir
    Gabel, Detlef
    Nau, Werner M.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (18) : 11790 - 11798
  • [3] A Theta-Shaped Amphiphilic Cobaltabisdicarbollide Anion: Transition From Monolayer Vesicles to Micelles
    Bauduin, Pierre
    Prevost, Sylvain
    Farras, Pau
    Teixidor, Francesc
    Diat, Olivier
    Zemb, Thomas
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (23) : 5298 - 5300
  • [4] Water soluble organometallic small molecules as promising antibacterial agents: synthesis, physical-chemical properties and biological evaluation to tackle bacterial infections
    Bennour, Ines
    Nuria Ramos, M.
    Nuez-Martinez, Miquel
    Maria Xavier, Jewel Ann
    Buades, Ana B.
    Sillanpaa, Reijo
    Teixidor, Francesc
    Choquesillo-Lazarte, Duane
    Romero, Isabel
    Martinez-Medina, Margarita
    Vinas, Clara
    [J]. DALTON TRANSACTIONS, 2022, 51 (18) : 7188 - 7209
  • [5] Towards new boron carriers for boron neutron capture therapy: Metallacarboranes bearing cobalt, iron and chromium and their cholesterol conjugates
    Bialek-Pietras, Magdalena
    Olejniczak, Agnieszka B.
    Tachikawa, Shoji
    Nakamura, Hiroyuki
    Lesnikowski, Zbigniew J.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (05) : 1136 - 1142
  • [6] Boron-Containing Lipids and Liposomes: New Conjugates of Cholesterol with Polyhedral Boron Hydrides
    Bregadze, Vladimir I.
    Sivaev, Igor B.
    Dubey, Ravindra Dhar
    Semioshkin, Andrey
    Shmal'ko, Akim V.
    Kosenko, Irina D.
    Lebedeva, Kseniya V.
    Mandal, Swadhin
    Sreejyothi, Prasannakumar
    Sarkar, Arindam
    Shen, Zheyu
    Wu, Aiguo
    Hosmane, Narayan S.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (61) : 13832 - 13841
  • [7] Novel types of boronated chlorin e6 conjugates via 'click chemistry'
    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.
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2009, 23 (09) : 370 - 374
  • [8] Cancer prevention and therapy through the modulation of the tumor microenvironment
    Casey, Stephanie C.
    Amedei, Amedeo
    Aquilano, Katia
    Azmi, Asfar S.
    Benencia, Fabian
    Bhakta, Dipita
    Bilsland, Alan E.
    Boosani, Chandra S.
    Chen, Sophie
    Ciriolo, Maria Rosa
    Crawford, Sarah
    Fujii, Hiromasa
    Georgakilas, Alexandros G.
    Guha, Gunjan
    Halicka, Dorota
    Helferich, William G.
    Heneberg, Petr
    Honoki, Kanya
    Keith, W. Nicol
    Kerkar, Sid P.
    Mohammed, Sulma I.
    Niccolai, Elena
    Nowsheen, Somaira
    Rupasinghe, H. P. Vasantha
    Samadi, Abbas
    Singh, Neetu
    Talib, Wamidh H.
    Venkateswaran, Vasundara
    Whelan, Richard L.
    Yang, Xujuan
    Felsher, Dean W.
    [J]. SEMINARS IN CANCER BIOLOGY, 2015, 35 : S199 - S223
  • [9] Bimodal Therapeutic Agents Against Glioblastoma, One of the Most Lethal Forms of Cancer
    Couto, Marcos
    Alamon, Catalina
    Nievas, Susana
    Perona, Marina
    Alejandra Dagrosa, Maria
    Teixidor, Francesc
    Cabral, Pablo
    Vinas, Clara
    Cerecetto, Hugo
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (63) : 14335 - 14340
  • [10] Closo-Carboranyl- and Metallacarboranyl [1,2,3]triazolyl-Decorated Lapatinib-Scaffold for Cancer Therapy Combining Tyrosine Kinase Inhibition and Boron Neutron Capture Therapy
    Couto, Marcos
    Alamon, Catalina
    Fernanda Garcia, Maria
    Kovacs, Mariangeles
    Trias, Emiliano
    Nievas, Susana
    Pozzi, Emiliano
    Curotto, Paula
    Thorp, Silvia
    Alejandra Dagrosa, Maria
    Teixidor, Francesc
    Vinas, Clara
    Cerecetto, Hugo
    [J]. CELLS, 2020, 9 (06) : 1 - 18
123456