Publication: Synthesis of flurbiprofen thiadiazole urea derivatives and assessment of biological activities and molecular docking studies
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Date
2023-01-01
Authors
ZENGİN KURT B.
Altundağ Ö.
Tokgöz M. N.
ÖZTÜRK CİVELEK D.
Tuncay F. O.
Cakmak U.
KOLCUOĞLU Y.
Akdemir A.
Sönmez F.
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Abstract
Totally 15 novel flurbiprofen urea derivatives were synthesized bearing the thiadiazole ring. Their inhibition effects on tyrosinase were determined. 3c was found to be the strongest inhibitor with the IC50 value of 68.0 μM against tyrosinase. The enzyme inhibition types of the synthesized compounds were determined by examining the kinetic parameters. The inhibition type of 3c was determined as uncompetitive and the Ki value was calculated as 36.3 μM. Moreover, their cytotoxic effects on hepatocellular carcinoma (HepG2), colorectal carcinoma (HT-29), and melanoma (B16F10) cell lines were evaluated. According to the cytotoxicity results, 3l (IC50 = 14.11 μM) showed the highest cytotoxicity on the HT-29 cells, while 3o (IC50 = 4.22 μM) exhibited the strongest cytotoxic effect on HepG2 cell lines. Also, 3j (IC50 = 7.55 μM strongly affected B16F10. The effects of synthesized compounds on the healthy cell line were evaluated on the CCD-986Sk cell line. Molecular modelling studies have indicated the potential binding interactions of the uncompetitive inhibitor 3c with the enzyme-substrate complex.
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Eczacılık, Temel Eczacılık Bilimleri, Yaşam Bilimleri, Biyoteknoloji, Moleküler Biyoloji ve Genetik, Sitogenetik, Kimya, Biyokimya, Biyoinorganik Kimya, Sağlık Bilimleri, Temel Bilimler, Pharmacology and Therapeutics, Basic Pharmaceutics Sciences, Life Sciences, Biotechnology, Molecular Biology and Genetics, Cytogenetic, Chemistry, Biochemistry, Bioinorganic Chemistry, Health Sciences, Natural Sciences, Temel Bilimler (SCI), Yaşam Bilimleri (LIFE), Farmakoloji ve Toksikoloji, Mikrobiyoloji, KİMYA, ORGANİK, FARMAKOLOJİ VE ECZACILIK, BİYOKİMYA VE MOLEKÜLER BİYOLOJİ, BİYOTEKNOLOJİ VE UYGULAMALI MİKROBİYOLOJİ, Natural Sciences (SCI), Life Sciences (LIFE), CHEMISTRY, PHARMACOLOGY & TOXICOLOGY, MOLECULAR BIOLOGY & GENETICS, MICROBIOLOGY, CHEMISTRY, ORGANIC, PHARMACOLOGY & PHARMACY, BIOCHEMISTRY & MOLECULAR BIOLOGY, BIOTECHNOLOGY & APPLIED MICROBIOLOGY, Moleküler Tıp, Farmakoloji, İlaç Keşfi, Organik Kimya, Fizik Bilimleri, Molecular Medicine, Pharmacology, Drug Discovery, Organic Chemistry, Physical Sciences, cytotoxcity, flurbiprofen, molecular docking, thiadiazole ring, tyrosinase inhibition, urea
Citation
ZENGİN KURT B., Altundağ Ö., Tokgöz M. N., ÖZTÜRK CİVELEK D., Tuncay F. O., Cakmak U., KOLCUOĞLU Y., Akdemir A., Sönmez F., "Synthesis of flurbiprofen thiadiazole urea derivatives and assessment of biological activities and molecular docking studies", Chemical Biology and Drug Design, 2023