Synthesis, DNA interaction, topoisomerase I, II inhibitory and cytotoxic effects of water soluble silicon (IV) phthalocyanine and napthalocyanines bearing 1-acetylpiperazine units

BAS H., Barut B., BIYIKLIOĞLU Z., ÖZEL A.

DYES AND PIGMENTS, cilt.160, ss.136-144, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 160
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.dyepig.2018.08.005
  • Dergi Adı: DYES AND PIGMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.136-144
  • Anahtar Kelimeler: Synthesis, Silicon, Water solubility, Cytotoxicity, DNA cleavage, Topoisomerases, VITRO PHOTODYNAMIC ACTIVITIES, DNA/BSA BINDING, PHOTOCLEAVAGE PROPERTIES, PIPERAZINE DERIVATIVES, BIOLOGICAL-PROPERTIES, MOLECULAR DOCKING, COMPLEXES, ZINC(II), TETRA
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

In this study, axially 1-acetylpiperazine substituted silicon (IV) phthalocyanine, naphthalocyanine 2, 3 and their water soluble derivatives 2a, 3a were synthesized for the first time and their DNA binding modes (absorption spectral, thermal denaturation and electrophoresis studies), DNA cleavage activities, topoisomerases inhibitory and cytotoxicity effects were investigated. Compounds 2a and 3a showed good binding propensity to CT-DNA with K-b values of 1.25 +/- (0.01) x 10(4) and 1.13 +/- (0.03) x 10(4) M-1. In DNA cleavage studies revealed that the compounds cleaved to supercoiled pBR322 plasmid DNA via the oxidative pathway at irradiation. The compounds inhibited topoisomerase I enzyme in a concentration-dependent manner whilst they had low inhibitory effects against topoisomerase II compared to doxorubicin as a positive control. In vitro studies of the cytotoxicity of the compounds on five carcinoma cell lines indicated that compound 3a had the potential to act as an anticancer drug with CC50 values of 7.83, 3.36, 3.18 and 3.36 mu M toward BT-20, SNU-398, DU-145 and SKMEL 128 compared to cis-platin as a positive control.