Synthesis, characterization, photo-physicochemical and biological properties of water-soluble tetra-substituted phthalocyanines: Antidiabetic, anticancer and anticholinergic potentials

GÜNSEL A., YAŞA ATMACA G., Taslimi P., BİLGİÇLİ A. T., GÜLÇİN İ., ERDOĞMUŞ A., ...Daha Fazla

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, cilt.396, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 396
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.jphotochem.2020.112511
  • Dergi Adı: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Agricultural & Environmental Science Database, BIOSIS, Chemical Abstracts Core, Chimica, INSPEC
  • Anahtar Kelimeler: Phthalocyanine, synthesis, water-soluble, photochemistry, enzyme inhibition, METAL-FREE, INHIBITORY PROPERTIES, CRYSTAL-STRUCTURE, PHOTOPHYSICOCHEMICAL PROPERTIES, CARBONIC-ANHYDRASE, IN-VITRO, BEARING, DERIVATIVES, ZINC(II), GALLIUM
  • Yıldız Teknik Üniversitesi Adresli: Evet

Özet

In this study, we have reported on the synthesis and characterization of water-soluble phthalocyanines [M = 2H (2), Zn(II) (3), Ga(III)Cl (4)], containing sodium 2-mercaptoethanesulfonate substituents at the non-peripheral positions. All compounds were characterized by UV-vis, FT-IR and NMR spectroscopies, and MALDI-TOF mass spectra. Besides, spectral, photophysical (fluorescence quantum yields) and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of newly synthesized phthalocyanines were investigated in DMSO. These synthesized phthalocyanines [M = 2H (2), Zn(II) (3), Ga(III)Cl (4)] were found to be effective inhibitor compounds for the a-glycosidase, human carbonic anhydrase I and II (cytosolic, ubiquitous isozymes), hCA IX (transmembrane, cancerassociated isozyme), and cholinesterase enzymes with Ki values in the range of 0.66 +/- 0.08-2.31 +/- 0.24 mu M for alpha-glycosidase, 8.54 +/- 1.63 - 14.93 +/- 2.05 mu M for hCA I, 10.77 +/- 1.55 -13.74 +/- 0.97 mu M for hCA II, 10.55 +/- 0.98 -15.96 +/- 1.54 mu M for hCA IX, 102.77 +/- 16.04-158.43 +/- 26.95 mu M for BChE, and 114.75 +/- 15.05-174.31 +/- 35.43 mu M for AChE, respectively. Additionally, this work is also the first example of cancer-associated isozyme hCA IX inhibition by these novel phthalocyanines.