Synthesis, characterization, and inhibitory properties of novel N-benzylbenzimidazole-silver(I) complexes on carbonic anhydrase and polyphenol oxidase enzymes

Abstract

The biological properties of silver complexes are well known but the studies about the enzyme inhibitory properties of them are very rare. On the other hand, it is known that one of the anticancer mechanisms of action of benzimidazole derivatives is enzyme inhibition. Therefore, in this study, five novel N-benzylbenzimidazole-silver(I) complexes were synthesized and fully characterized by 1H NMR, 13C NMR, IR, mass spectroscopic methods and elemental analyses. The inhibitory properties of the synthesized complexes were tested on the activity of human carbonic anhydrase I - II and polyphenol oxidase, and it was observed that the complexes inhibited the activity of these enzymes with the IC50 values of 29.58-32.65 µM, 21.05-23.65 µM and 30.38-44.45 µM, respectively. We suggest that by also considering the low toxicity of silver compounds to human body at low concentrations, the evaluated complexes in this study are promising agents in the treatment of glaucoma and hyperpigmentation as carbonic anhydrase and polyphenol oxidase inhibitors.

Keywords

• benzimidazole
• silver
• carbonic anhydrase
• polyphenol oxidase

Yeni N-benzilbenzimidazol-gümüş(I) komplekslerinin sentezi, karakterizasyonu, karbonik anhidraz ve polifenol oksidaz enzimleri üzerindeki inhibitör özellikleri

Abstract

Gümüş komplekslerinin biyolojik özellikleri çok iyi bilinmesine rağmen enzim inhibisyonu özelliklerine yönelik çalışmalar oldukça sınırlıdır. Diğer taraftan benzimidazol türevlerinin anti-kanser etki mekanizmalarından birinin enzim inhibisyonu olduğu bilinmektedir. Bu nedenle bu çalışmada, beş yeni N-benzilbenzimidazol-gümüş(I) kompleksi sentezlendi, 1H NMR, 13C NMR, IR ve kütle spektroskopik yöntemleri ve elementel analiz sonuçları ile tamamen karakterize edildi. Elde edilen komplekslerin insan karbonik anhidraz I - II ve polifenol oksidaz enzimleri üzerindeki inhibisyon etkileri incelendi ve komplekslerin bu enzimlerin aktivitelerini sırasıyla 29.58-32.65 µM, 21.05-23.65 µM ve 30.38-44.45 µM’lık IC50 değerleri ile inhibe ettiği gözlendi. Gümüş bileşiklerinin insan vücudunda düşük konsantrasyonlarda toksik etki göstermediği de göz önüne alınırsa, bu çalışmada test edilen kompleksler karbonik anhidraz inhibitörü olarak glokom tedavisinde ve polifenol oksidaz inhibitörü olarak ise hiper-pigmentasyon hastalığı tedavisinde kullanılmak için umut verici adaylardır.      

Keywords

• Benzimidazol
• gümüş
• karbonik anhidraz
• polifenol oksidaz

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