Highly efficient, solvent-free esterification of testosterone promoted by a recyclable polymer-supported tosylic acid catalyst under microwave irradiation

Borowiecki, Paweł; Kraszewski, Maciej

doi:10.24820/ark.5550190.p011.059

Cited by 1 publication

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“…In general, in the literature, there are reports on ester prodrugs with different properties modified, which are metabolically transformed into hydroxyl-containing biologically active compounds. The most prominent examples of such a strategy and likely the most common prodrugs ever used in pharmacy are the esters of sex hormones (i.e., 17β-Oacylated testosterone) [36,37] and vitamins (i.e., α-tocopheryl acetate) [38]. The other prime example of derivatized therapeutic agent concerns chloramphenicol palmitate, which was designed to improve very poor pharmacokinetic profile of the original antibiotic [39].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Acyl Derivatives of 3-(4,5,6,7-Tetrabromo-1H-benzimidazol-1-yl)propan-1-ols—Intracellular TBBi-Based CK2 Inhibitors with Proapoptotic Properties

Chojnacki

Wińska

Karatsai

et al. 2021

IJMS

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Protein kinase CK2 has been considered as an attractive drug target for anti-cancer therapy. The synthesis of N-hydroxypropyl TBBi and 2MeTBBi derivatives as well as their respective esters was carried out by using chemoenzymatic methods. Concomitantly with kinetic studies toward recombinant CK2, the influence of the obtained compounds on the viability of two human breast carcinoma cell lines (MCF-7 and MDA-MB-231) was evaluated using MTT assay. Additionally, an intracellular inhibition of CK2 as well as an induction of apoptosis in the examined cells after the treatment with the most active compounds were studied by Western blot analysis, phase-contrast microscopy and flow cytometry method. The results of the MTT test revealed potent cytotoxic activities for most of the newly synthesized compounds (EC50 4.90 to 32.77 µM), corresponding to their solubility in biological media. We concluded that derivatives with the methyl group decrease the viability of both cell lines more efficiently than their non-methylated analogs. Furthermore, inhibition of CK2 in breast cancer cells treated with the tested compounds at the concentrations equal to their EC50 values correlates well with their lipophilicity since derivatives with higher values of logP are more potent intracellular inhibitors of CK2 with better proapoptotic properties than their parental hydroxyl compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Acyl Derivatives of 3-(4,5,6,7-Tetrabromo-1H-benzimidazol-1-yl)propan-1-ols—Intracellular TBBi-Based CK2 Inhibitors with Proapoptotic Properties

Chojnacki

Wińska

Karatsai

et al. 2021

IJMS

Self Cite

View full text Add to dashboard Cite

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Highly efficient, solvent-free esterification of testosterone promoted by a recyclable polymer-supported tosylic acid catalyst under microwave irradiation

Abstract: Dedicated to Professor Michał Fedoryński -a fabulous academic tutor and propagator of organic chemistryamong talented young people -on the occasion of his 73 nd birthday and retirement

Cited by 1 publication

References 69 publications

Synthesis of Novel Acyl Derivatives of 3-(4,5,6,7-Tetrabromo-1H-benzimidazol-1-yl)propan-1-ols—Intracellular TBBi-Based CK2 Inhibitors with Proapoptotic Properties

Synthesis of Novel Acyl Derivatives of 3-(4,5,6,7-Tetrabromo-1H-benzimidazol-1-yl)propan-1-ols—Intracellular TBBi-Based CK2 Inhibitors with Proapoptotic Properties

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