Novel zinc(II)phthalocyanines bearing azo-containing schiff base: Determination of pKa values, absorption, emission, enzyme inhibition and photochemical properties

Creative Commons License

Kantar C., Mavi V., Baltas N., Islamoglu F., Sasmaz S.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1122, ss.88-99, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1122
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1016/j.molstruc.2016.05.055
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.88-99
  • Anahtar Kelimeler: Phthalocyanines, Azo, Schiff base, ESIPT, Enzyme inhibition, MICROWAVE-ASSISTED SYNTHESIS, INTRAMOLECULAR PROTON-TRANSFER, XANTHINE-OXIDASE INHIBITORS, ELECTRONICALLY EXCITED-STATE, URIC-ACID LEVELS, ZINC PHTHALOCYANINE, SPECTROSCOPIC CHARACTERIZATION, CHOLINESTERASE-INHIBITORS, TRANSFER MECHANISM, LIGHT-SCATTERING
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

Azo-containing schiff bases are well known and there are many studies about their various properties in literature. However, phthalocyanines bearing azo-containing schiff bases, their spectral, analytical and biological properties are unknown. Therefore, new zinc (II) phthalocyanines bearing azo-containing schiff base were synthesized and investigated to determine pKa values, absorption, emission, enzyme inhibition and photochemical properties. Emission spectra were reported and large Stokes shift values were determined for all compounds, indicating that all molecules exhibit excited state intramolecular proton transfer. These phthalocyanines were the first examples of phthalocyanine showing excited state intramolecular proton transfer. Singlet oxygen quantum yields of zinc (II) phthalocyanines were determined. pKa values and indicator properties of all compounds were investigated by potentiometry. All compounds were assayed for inhibitory activity against bovine milk xanthine oxidase and acetylcholinesterase enzyme in vitro. Compound 2 showed the high inhibitory effect against xanthine oxidase (IC50 = 0.24 +/- 0.01 mu M). However, phthalocyanine compounds did not show enzyme inhibitor behavior. (C) 2016 Elsevier B.V. All rights reserved.