Novel water soluble morpholine substituted Zn(II) phthalocyanine: Synthesis, characterization, DNA/BSA binding, DNA photocleavage and topoisomerase I inhibition

Barut B., DEMIRBAS Ü., ÖZEL A., KANTEKİN H.

INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, cilt.105, ss.499-508, 2017 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 105
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.ijbiomac.2017.07.072
  • Dergi Adı: INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.499-508
  • Anahtar Kelimeler: BSA-binding, DNA-binding, DNA-photocleavage, Phthalocyanines, Topoisomerase I, BOVINE SERUM-ALBUMIN, CALF THYMUS DNA, MOLECULAR DOCKING, PHOTODYNAMIC THERAPY, ZINC(II) PHTHALOCYANINE, ANTIOXIDANT ACTIVITIES, POLYPYRIDYL COMPLEXES, BIOLOGICAL-PROPERTIES, COPPER(II) COMPLEXES, CLEAVAGE PROPERTIES
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

In this study, novel peripherally tetra 3-morpholinophenol substituted zinc(II) phthalocyanine (4) and its water soluble form quaternized zinc(II) phthalocyanine (ZnQ) were synthesized for the first time. These novel compounds were characterized by a combination of different spectroscopic techniques such as FT-IR, H-1 NMR,(CNMR)-C-13, UV-vis and mass. The DNA binding of ZnQ was investigated using UV-vis absorption titration, competitive ethidium bromide, thermal denaturation and viscosity experiments that the ZnQ bound to CT-DNA via intercalation mode. ZnQ indicated photocleavage activity on supercoiled pBR322 plasmid DNA via formation of singlet oxygen under irradiation at 700 nm. Besides, the topoisomerase I inhibitory effect experiments showed that ZnQ inhibited topoisomerase I enzyme in a concentration dependent manner. The bovine serum albumin (BSA) binding experiments indicated that ZnQ bound to proteins through a static quenching mechanism. All of these results claim that ZnQ has potential agent for photodynamic therapy owing to its nucleic acid interactions and photobiological or photochemical properties. (C) 2017 Elsevier B.V. All rights reserved.