Biological properties of hexadeca-substituted metal phthalocyanines bearing different functional groups

• Published in: Journal of inorganic biochemistry Vol. 234; p. 111888
• Main Authors: Farajzadeh, Nazli, Özdemir, Sadin, Tollu, Gülşah, Altuntaş Bayır, Zehra, Burkut Koçak, Makbule
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01-09-2022
• Subjects: Biofilm inhibition; Cell viability; Hexadeca-substituted phthalocyanine; Malonic ester; Transesterfication; Biofilm inhibition; Cell viability; Hexadeca-substituted phthalocyanine; Malonic ester; Transesterfication
• ISSN: 0162-0134; 1873-3344
• DOI: 10.1016/j.jinorgbio.2022.111888

In this study, a new tetra-substituted phthalonitrile (diethyl 2-(2-chloro-4,5-dicyano-3,6-bis(hexyloxy)phenyl)malonate) bearing three different substituents was synthesized and characterized. Due to the basic medium, transesterification occurred during the synthesis of the target phthalocyanines [M = Zn (II), Cu (II), Co (II), In (III), Lu (III)] in n-pentanol and the ethyl groups were replaced with pentyl groups. The biological features of the resultant compounds were studied for the first time in this study. All the compounds exhibited high antioxidant, antimicrobial, and DNA cleavage activities. The highest antioxidant activity was obtained 90.39% for lutetium phthalocyanine at 100 mg/L. The most effective MIC value was obtained 8 mg/L against Candida parapisilosis. The most effective microbial cell viability inhibition was obtained 100% for cobalt and lutetium phthalocyanines. They exhibited excellent biofilm inhibiton activities. Higher biofilm inhibition was achieved using light irradiation. The compounds exhibited higher biofilm inhibition activities with photodynamic against Staphylococcus aureus compared with Pseudo aureginosa.
This study presents the preparation of a novel tetra-substituted phthalonitrile and its metal phthalocyanine derivatives bearing three different substituents (hexyloxy, chlorine, and diethyl malonyl groups). The newly synthesized compounds can be extensively utilized as efficient multidisciplinary agents for biological applications. All the compounds exhibited excellent biofilm inhibition. [Display omitted]
•The synthesis and characterization of a new tetra-substituted phthalonitrile.•The synthesis and characterization of novel metallophthalocyanines bearing transesterification.•The study of the biological properties of all the resultant compounds.•The design of the compounds with excellent biofilm inhibition activities against S. aureus and P. aureginosa.