img
New AB3-type porphyrins with piperidine and morpholine motifs; synthesis and photo-physicochemical and biological properties    
Yazarlar
Kevser Harmandar
Türkiye
Dr. Öğr. Üyesi Gülay GİRAY
Kastamonu Üniversitesi, Türkiye
Emel Önal
Doğuş Üniversitesi, Türkiye
İbrahim F. Sengül
Sadin Özdemir
Mersin Üniversitesi, Türkiye
Devrim Atilla
Gebze Teknik Üniversitesi, Türkiye
Özet
In this study, new unsymmetrical meso-tetraaryl AB3-type porphyrins 1 and 2 were successfully synthesized by the reaction of p-bromobenzaldehyde and p-hydroxybenzaldehyde with pyrrole in propionic acid. AB3-type porphyrin building blocks with hydroxyl functionality (1 and 2) were further used to generate both covalently linked metal free and Zn(II) porphyrins 3-6 having piperidine and morpholine heterocyclic units. These novel compounds were characterized by using 1H NMR, 13C NMR, FT-IR and MALDI-TOF spectrophotometry. The photophysical and photochemical properties of compounds 1-6 were investigated by employing UV-vis absorption and fluorescence emission spectroscopy in tetrahydrofuran (THF). From the view of biological properties, the antioxidant capacities of porphyrins were determined by using DPPH radical scavenging activity and 2 was determined as the most potent porphyrin analog with a value of 98.42% at 200 mg L−1. All the targeted compounds displayed significant DNA nuclease activity. In addition, the antimicrobial potential of compounds 1-6 was also investigated by a micro-dilution process and 2 was found to be the most effective candidate against the tested microbial strains. The newly synthesized porphyrins also showed 100% microbial cell viability inhibition against E. coli at all examined concentrations. In terms of biofilm inhibition activity, the best results for the maximum photodynamic antimicrobial biofilm inhibition of S. aureus and P. aeruginosa were obtained by compound 2 with the values of 99.75% and 93.39%, respectively.
Anahtar Kelimeler
Makale Türü Özgün Makale
Makale Alt Türü SSCI, AHCI, SCI, SCI-Exp dergilerinde yayımlanan tam makale
Dergi Adı Dalton Transactions
Dergi ISSN 0000
Dergi Tarandığı Indeksler SCI-Expanded
Dergi Grubu Q2
Makale Dili İngilizce
Basım Tarihi 01-2023
Sayfalar 2672 / 2683
Doi Numarası 10.1039/d2dt03738f
Makale Linki rsc.li/dalton