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

Year 2017, , 49 - 54, 22.05.2017

Gühergül Uluçam

https://doi.org/10.23902/trkjnat.291076

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

Abstract

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.

Keywords

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

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