SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITIES OF 3-(2-HYDROXYETHYL)-1-(3-AMINOPROPYL)-1H-IMIDAZOLE-3-IUM BROMIDE

Abstract

3-(2-hydroxyethyl)-1-(3-aminopropyl)-1H-imidazole-3-ium bromide as an N-heterocyclic carbene salt was synthesized by the reaction of 3-(1H-imidazole-1-yl )propane -1-amine with 2-bromoethanol. The salt can also be named as imidazole salt which is one of the most stable group of N-heterocyclic carbenes.  The molecular structure of the product was elucidated by FTIR, ¹H NMR, ¹³C NMR, GS-MS and elemental analysis. The antimicrobial, antifungal and anticancer activities of the imidazole salt were also examined. The probit analysis revealed that IC₅₀ values on HeLa and HepG2 cell lines were 155.955μM and 76.769μM, respectively, at the end of 24 hours treatment. It also was determined that the product has no harmful effect on healthy mouse embryonic fibroblasts (MEF) cells. Significant antimicrobial and antifungal activities of the salt on Escherichia coli (Migula, 1895) O157:H7 and Listeria monocytogenes (Pirie, 1940) ATCC 19115 bacteria and the yeast Candida albicans (Berhout, 1923) ATCC 10231 were determined at a concentration value of 32μM.

Keywords

• Imidazole,carbene,antibacterial activity,antifungal activity,anticancer activity

3-(2-HİDROKSİETİL)-1-(3-AMİNOPROPİL)-1H-İMİDAZOL-3-İUM BROMİD SENTEZİ, KARAKTERİZASYONU VE BİYOLOJİK AKTİVİTELERİ

Öz

Bir N-heterohalka karben tuzu olarak, 3-(2-hidroksietil)-1-(3-aminopropil)-1H-imidazol-3-ium bromid, 3-(1H-imidazol-1-il)propan-1-amin ile 2-bromoetanol’ün reaksiyonu sonucunda sentezlenmiştir. Tuz, N-heterohalka karbenlerin en kararlı gruplarından biri olan imidazol tuzu olarak da isimlendirilebilir. Ürünün moleküler yapısı FTIR, ¹HNMR, ¹³C NMR, GS-MS, elemental analiz yöntemleri ile aydınlatılmıştır. Ayrıca, antimikrobiyal, antifungal ve antikanser aktiviteleri incelenmiştir. Probit analizi yapılarak, HeLa ve HepG2 kanser hücre serileri üzerinde 24 saatlik uygulama sonrası IC₅₀ değerlerinin sırasıyla 155,955µM ve 76,769µM olduğu saptanmıştır. Sentezlenen maddenin sağlıklı fare embriyonik fibroblast (MEF) hücreleri üzerinde zararlı bir etkisine rastlanmamıştır. Escherichia coli (Migula, 1895) O157:H7, Listeria monocytogenes (Pirie, 1940) ATCC 19115 bakterileri ve Candida albicans (Berhout, 1923) ATCC 10231 mayası üzerinde ise 32µM’lık konsantrasyonda kayda değer antimikrobiyal ve antifungal aktivitesinin de olduğu belirlenmiştir.

Anahtar Kelimeler

• Imidazol,karben,antibakterial aktivite,antifungal aktivite,antikanser aktivite

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