Synthesis of new 7-amino-3,4-dihydroquinolin-2(1H)-one-peptide derivatives and their carbonic anhydrase enzyme inhibition, antioxidant, and cytotoxic activities

KÜÇÜKBAY H., Gonul Z., KÜÇÜKBAY F., Tekin Z., Angeli A., Bartolucci G., ...Daha Fazla

ARCHIV DER PHARMAZIE, cilt.354, sa.11, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 354 Sayı: 11
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1002/ardp.202100122
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, CAB Abstracts, Chemical Abstracts Core, Chimica, EMBASE, International Pharmaceutical Abstracts, MEDLINE, Veterinary Science Database
  • Anahtar Kelimeler: antioxidant, carbonic anhydrase, cytotoxicity, peptide, peptide-dihydroquinolin-2-one conjugates, quinolones, IN-VITRO, INCORPORATING GLYCINE, QUINOLINE DERIVATIVES, ANTIBACTERIAL, COMPLEXES, ALANINE
  • İnönü Üniversitesi Adresli: Evet

Özet

Six new monopeptides, seven new dipeptides, and two deprotected monopeptide dihydroquinolinone conjugates were prepared by the benzothiazole-mediated method and their structures were confirmed by nuclear magnetic resonance, mass, infrared spectroscopy, and elemental analysis methods. The human carbonic anhydrase (hCA) I and hCA II enzyme inhibition activities of the compounds were determined using the stopped-flow instrument. The synthesized peptide-dihydroquinolinone conjugates 2, 3, 6, 10, 13, and 15 showed inhibition against the hCA II enzyme in the range of 15.7-65.7 mu M. However, none of the compounds showed inhibition of hCA I at a concentration of 100 mu M. The antioxidant activities of the compounds were also examined using the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical scavenging method at concentrations of 12.5-125 mu g/ml, but when compared with the standard antioxidant compounds alpha-tocopherol and butylated hydroxyanisole (BHA), weak antioxidant activities were detected. The cytotoxic effects of four compounds against the A549 and BEAS-2B cell lines were also investigated. Among the compounds studied, compound 7 was found to be most effective, with the IC50 values on the A549 cells for 48 and 72 h being 26.87 and 9.979 mu g/ml, respectively, and the IC50 values on the BEAS-2B cells being >100 mu g/ml. None of the tested compounds showed antimicrobial activity in the concentration range (800-1.56 mu g/ml) studied.