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


KARATAVUK A. O., KARABULUT H.

Monatshefte fur Chemie, cilt.151, sa.5, ss.837-844, 2020 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 151 Sayı: 5
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1007/s00706-020-02594-6
  • Dergi Adı: Monatshefte fur Chemie
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.837-844
  • Anahtar Kelimeler: Anti-proliferative effects, Cholesterol, Click chemistry, Dimeric sterols, Ergosterol
  • Trakya Üniversitesi Adresli: Evet

Özet

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. Graphic abstract: [Figure not available: see fulltext.].