Synthesis, cytotoxicity and antiviral activity studies of the conjugates of cobalt bis(1,2-dicarbollide)(-I) with 5-ethynyl-2′-deoxyuridine and its cyclic derivatives

Ilinova, Anna; Semioshkin, Andrey; Lobanova, I. A.; Bregadze, V. I.; Mironov, A. F.; Paradowska, Edyta; Studzińska, Mirosława; Jabłońska, Agnieszka; Białek‐Pietras, Magdalena; Leśnikowski, Zbigniew J.

doi:10.1016/j.tet.2014.06.072

Cited by 21 publications

(5 citation statements)

References 29 publications

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“…Despite the successful exploitation of icosahedral dicarbaboranes in drug design, relatively little attention has been paid to metallacarboranes and other chemically and thermally stable boron cage compounds. ,,, Some smaller metallacarboranes have a cytostatic effect, ,− and derivatives of icosahedral cobalt bis(dicarbollide) ion [(1,2-C 2 B 9 H 11 ) 2 -3,3′-Co] − can specifically inhibit HIV protease. − Antiviral, antifungal, and antibacterial activity and the ability to penetrate artificial lipid bilayers and cellular membranes have been reported for some metallacarborane derivatives. ,− …”

Section: Introductionmentioning

confidence: 99%

Metallacarborane Sulfamides: Unconventional, Specific, and Highly Selective Inhibitors of Carbonic Anhydrase IX

et al. 2019

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Carbonic anhydrase IX (CAIX) is a transmembrane enzyme that regulates pH in hypoxic tumors and promotes tumor cell survival. Its expression is associated with the occurrence of metastases and poor prognosis. Here, we present nine derivatives of the cobalt bis(dicarbollide)(1−) anion substituted at the boron or carbon sites by alkysulfamide group(s) as highly specific and selective inhibitors of CAIX. Interactions of these compounds with the active site of CAIX were explored on the atomic level using protein crystallography. Two selected derivatives display subnanomolar or picomolar inhibition constants and high selectivity for the tumor-specific CAIX over cytosolic isoform CAII. Both derivatives had a time-dependent effect on the growth of multicellular spheroids of HT-29 and HCT116 colorectal cancer cells, facilitated penetration and/or accumulation of doxorubicin into spheroids, and displayed low toxicity and showed promising pharmacokinetics and a significant inhibitory effect on tumor growth in syngenic breast 4T1 and colorectal HT-29 cancer xenotransplants.

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Section: Introductionmentioning

confidence: 99%

Metallacarborane Sulfamides: Unconventional, Specific, and Highly Selective Inhibitors of Carbonic Anhydrase IX

et al. 2019

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“…dodecaborate (-2) tethered with 5-ethynyl-2'-deoxyuridine through an ether or ether/amine spacer and tested their cytotoxicity and antiviral activity [27,28]. Most of the tested compounds demonstrated low toxicity, though, on average, the molecules bearing metallacarborane modifications exhibited higher toxicity than the dodecarborate derivatives did.…”

Section: Discussionmentioning

confidence: 99%

Synthesis and in vitro antiviral activity of lipophilic pyrimidine nucleoside/carborane conjugates

Białek‐Pietras

Olejniczak

Paradowska

et al. 2015

Journal of Organometallic Chemistry

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“…Studies on medicinal applications of polyhedral boron hydrides have mostly focused on agents for boron neutron capture therapy (BNCT) [16,17], contrast agents for MRI diagnostics [18] and compounds with antiviral activity [19,20]. However, their antimicrobial properties have been investigated only to a limited degree [21].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Activity Studies of the Conjugates of Curcumin with closo-Dodecaborate and Cobalt Bis(Dicarbollide) Boron Clusters

et al. 2022

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A series of novel conjugates of cobalt bis(dicarbollide) and closo-dodecaborate with curcumin were synthesized by copper(I)-catalyzed azide-alkyne cycloaddition. These conjugates were tested for antibacterial activity. It was shown that all derivatives are active when exposed to Bacillus cereus ATCC 10702 and are not active against Gram-negative microorganisms and Candida albicans at the maximum studied concentration of 1000 mg/L. The conjugate of alkynyl-curcumin with azide synthesized from the tetrahydropyran derivative of cobalt bis(dicarbollide) exhibited activity against Gram-positive microorganisms: Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212 and the clinical isolate MRSA 17, that surpassed curcumin by 2–4 times.

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Synthesis, cytotoxicity and antiviral activity studies of the conjugates of cobalt bis(1,2-dicarbollide)(-I) with 5-ethynyl-2′-deoxyuridine and its cyclic derivatives

Cited by 21 publications

References 29 publications

Metallacarborane Sulfamides: Unconventional, Specific, and Highly Selective Inhibitors of Carbonic Anhydrase IX

Metallacarborane Sulfamides: Unconventional, Specific, and Highly Selective Inhibitors of Carbonic Anhydrase IX

Synthesis and in vitro antiviral activity of lipophilic pyrimidine nucleoside/carborane conjugates

Synthesis and Antibacterial Activity Studies of the Conjugates of Curcumin with closo-Dodecaborate and Cobalt Bis(Dicarbollide) Boron Clusters

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