Siklopentil fonksiyonlu benzimidazol-2-selenon bileşiklerinin sentezi ve biyolojik özellikleri
Küçük Resim Yok
Tarih
2025
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
İnönü Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Kanser ve antimikrobiyal direnç giderek yaygınlaşan küresel bir sağlık sorunu olarak önemini korumaktadır. Başta kataliz olmak üzere antimikrobiyal ve antioksidan özellikleriyle tanınan N-Heterosiklik karben kompleksleri üzerine çalışmalar artış göstermektedir. Düşük toksisite ve yüksek biyolojik aktivite potansiyelleri nedeniyle, NHC bileşikleri kanser araştırmalarında önemli bir yer edinmiştir. Selenyum, glutatyon ve tiyoredoksin redüktaz gibi enzimlerin bileşenine katılarak immün sistemini desteklemektedir. Selenyumun, biyolojik aktiviteye sahip bir eser element olması nedeniyle hazırlanan Se-NHC bileşiklerinin biyolojik aktiviteleri de ilgi çekmektedir. Bu çalışmada, yeni Se-NHC bileşikleri sentezlenerek antimikrobiyal ve antikanser aktiviteleri araştırıldı. Çalışma kapsamında, azota bağlı farklı hacimli ve fonksiyonel grup içeren alkil grupları ile siklopentil grubu taşıyan benzimidazol türevleri kullanılarak yeni karben öncülleri (2a-2j) sentezlendi. Bu öncül benzimidazolyum tuzlarının selenyum ile etkileştirilmesiyle Se-NHC bileşikleri (3a-3j) elde edilmiş olup, tüm bileşiklerin yapıları 1H NMR, 13C NMR ve FT-IR, HR-MS teknikleri ile karakterize edildi. Sentezlenen bileşiklerin disk difüzyon yöntemi ile C. albicans ve C. glabrata mayalarına karşı antifungal aktiviteleri; S. aureus, P. aeruginosa ve E. coli bakterilerine karşı antibakteriyal aktiviteleri incelendi. Ayrıca MTT testi kullanılarak BEAS-2B (insan sağlıklı akciğer hücresi), SH-SY5Y (insan beyin kanseri hücresi), HCT-116 (insan kolon kanseri hücresi), MCF-7 (insan meme kanseri hücresi) ve A549 (insan akciğer kanseri hücresi) hücre hatları üzerindeki antikanser aktiviteleri belirlenerek IC50 değerleri hesaplandı.
Cancer and antimicrobial resistance continue to pose significant global health challenges. Recently, there has been an increasing interest in N-heterocyclic carbene (NHC) complexes, primarily because of their established catalytic, antibacterial, and antioxidant capabilities. Owing to their low toxicity and high potential for biological activity, NHC compounds have gained considerable attention in cancer research. Selenium supports the immune system by participating within the composition of essential enzymes like glutathione and thioredoxin reductases. Given its role as a biologically active trace element, the biological activity of Se-NHC compounds has also attracted significant interest. This study involved the synthesis of novel Se-NHC compounds and the examination of their antibacterial and anticancer properties. A series of new carbene precursors (2a–2j) were synthesized using benzimidazole derivatives bearing cyclopentyl groups and alkyl substituents with varying steric and functional properties attached to the nitrogen atom. The corresponding Se-NHC compounds (3a–3j) were then obtained by reacting these benzimidazolium salts with selenium. The structures of all synthesized compounds were characterized using 1H NMR, 13C NMR, FT-IR, and HR-MS techniques. The antifungal activities of the compounds were evaluated against Candida albicans and Candida glabrata using the disk diffusion method, while their antibacterial activities were tested against Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli. Furthermore, the anticancer activities of the compounds were assessed using the MTT assay on several cell lines, including BEAS-2B (normal human lung cells), SH-SY5Y (human neuroblastoma), HCT-116 (human colon cancer), MCF-7 (human breast cancer), and A549 (human lung cancer), and their IC50 values were calculated.
Cancer and antimicrobial resistance continue to pose significant global health challenges. Recently, there has been an increasing interest in N-heterocyclic carbene (NHC) complexes, primarily because of their established catalytic, antibacterial, and antioxidant capabilities. Owing to their low toxicity and high potential for biological activity, NHC compounds have gained considerable attention in cancer research. Selenium supports the immune system by participating within the composition of essential enzymes like glutathione and thioredoxin reductases. Given its role as a biologically active trace element, the biological activity of Se-NHC compounds has also attracted significant interest. This study involved the synthesis of novel Se-NHC compounds and the examination of their antibacterial and anticancer properties. A series of new carbene precursors (2a–2j) were synthesized using benzimidazole derivatives bearing cyclopentyl groups and alkyl substituents with varying steric and functional properties attached to the nitrogen atom. The corresponding Se-NHC compounds (3a–3j) were then obtained by reacting these benzimidazolium salts with selenium. The structures of all synthesized compounds were characterized using 1H NMR, 13C NMR, FT-IR, and HR-MS techniques. The antifungal activities of the compounds were evaluated against Candida albicans and Candida glabrata using the disk diffusion method, while their antibacterial activities were tested against Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli. Furthermore, the anticancer activities of the compounds were assessed using the MTT assay on several cell lines, including BEAS-2B (normal human lung cells), SH-SY5Y (human neuroblastoma), HCT-116 (human colon cancer), MCF-7 (human breast cancer), and A549 (human lung cancer), and their IC50 values were calculated.
Açıklama
Anahtar Kelimeler
Biyokimya, Biochemistry
