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Synthesis of novel dimers containing cholesterol and ergosterol using click reaction and their anti-proliferative effects

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Abstract

This study aimed to achieve the synthesis of dimers containing cholesterol and ergosterol using click reaction and to perform biologic evaluations. For this purpose, cholesterol and ergosterol were converted to their esters. Three ergosterol esters were reported as novel compounds. To be used as linkers, furan and thiophene derivatives containing azide groups were synthesized. Of these, 2,5-bis(azidomethyl)thiophene was reported to be a novel compound. The obtained compounds were converted to dimers using a click reaction and 12 novel dimers were obtained as a result. The synthesized compounds were examined to evaluate their biologic activity against MCF-7 and HT29 cancer cells and MEF healthy cells. As a result of the biologic evaluation, the most effective compound against the MCF-7 cancer cell line was [2,5-furandiylbis(methylene)]bis(cholest-5-en-3-yl1H-1,2,3-triazole-4-pentanoate) with 205.06 µM concentration and [2,5-furandiylbis(methylene)]bis(ergosta-5,7,22-trien-3-yl1H-1,2,3-triazole-4-propanoate) with 159.5 µM concentration was the most effective for the HT29 cancer cell line.

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Acknowledgements

We thank Trakya University for its support through project number TUBAP 2017/113. We are also grateful to TUBİTAK Department for Support of Scientists (BİDEB) for its support in the framework of a 2211-A national doctoral bursary during this doctoral study. We thank Trakya University Technology Research Development Application and Research Center (TUTAGEM) for performing biologic activity tests.

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  1. Department of Chemistry, Faculty of Science, Trakya University, Edirne, 22030, Turkey

    Ali Osman Karatavuk & H. R. Ferhat Karabulut

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  1. Ali Osman Karatavuk
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  2. H. R. Ferhat Karabulut
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Correspondence to H. R. Ferhat Karabulut.

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Karatavuk, A.O., Karabulut, H.R.F. Synthesis of novel dimers containing cholesterol and ergosterol using click reaction and their anti-proliferative effects. Monatsh Chem 151, 837–844 (2020). https://doi.org/10.1007/s00706-020-02594-6

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  • DOI: https://doi.org/10.1007/s00706-020-02594-6

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