Synthesis, characterization and DNA interaction properties of the novel peripherally tetra 4-(3-methy1-4-(3-morpholinopropyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl) substituted water soluble Zn(II) and Cu(II) phthalocyanines

DEMİRBAŞ Ü., Barut B., ÖZEL A., ÇELİK F., KANTEKİN H., SANCAK K.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1177, ss.571-578, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1177
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.molstruc.2018.10.006
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.571-578
  • Anahtar Kelimeler: Phthalocyanine, CT-DNA, DNA binding, Photo cleavage, BOVINE SERUM-ALBUMIN, PHOTODYNAMIC THERAPY, BINDING-PROPERTIES, TOPOISOMERASE-I, COMPLEXES, PHOTOCLEAVAGE, CLEAVAGE, THIOSEMICARBAZONES, INHIBITION, ZINC(II)
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

The triazol compound 3-methyl-4-(3-morpholinopropyl)-1H-1,2,4-triazol-5(4H)-one (3), phthalonitrile compound 4-(3-methyl-4-(3-morpholinopropyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)phthalonitrile (5), peripherally tetra substituted zinc(II) (6) and copper(II) (7) phthalocyanines and their water soluble quaternized derivatives (6a) and (7a) were synthesized for the first time in this study. These novel compounds were characterized with FT-IR,H- 1 NMR, C-13 NMR, UV-Vis and mass spectroscopy. The absorption titration, and thermal denaturation studies were preferred to investigate the interaction mode of the water soluble quaternized tetra substituted peripherally phthalocyanines zinc(II) (6a) and copper (II) (7a) with CT-DNA. 6a and 7a bound to CT-DNA with K-b values of 6.53 +/- (0.04) x 10(4) M-1 and 1.14 +/- (0.02) x 10(4) M-1, respectively. The observed Delta T-m of CT-DNA with the compounds were elucidated as 7.55 degrees C and 5.75 degrees C. In addition, supercoiled pBR322 plasmid DNA was used to determine cleavage properties of the compounds by agarose gel electrophoresis. The compounds had no cleavage activities in the absence of oxidizing agents in the dark whereas; the both compounds had excellent photo cleavage activities in the absence and presence of oxidizing agents such as H2O2, ME and AA. The results of electrophoresis indicated that singlet oxygen is responsible for the cleavage activities of the water soluble quaternized tetra substituted peripherally phthalocyanines zinc(II) (6a) and copper (II) (7a) with irradiation. These results showed that both compounds may be potential anticancer drug for photodynamic therapy. (C) 2018 Elsevier B.V. All rights reserved.