Your browser doesn't support javascript.
loading
Effect of Arylazo Sulfones on DNA: Binding, Cleavage, Photocleavage, Molecular Docking Studies and Interaction with A375 Melanoma and Non-Cancer Cells.
Mikra, Chrysoula; Mitrakas, Achilleas; Ghizzani, Virginia; Katsani, Katerina R; Koffa, Maria; Koukourakis, Michael; Psomas, George; Protti, Stefano; Fagnoni, Maurizio; Fylaktakidou, Konstantina C.
Affiliation
  • Mikra C; Laboratory of Organic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
  • Mitrakas A; Laboratory of Cellular Biology and Cell Cycle, Molecular Biology and Genetics Department, Democritus University of Thrace, University Campus, Dragana, 68100 Alexandroupolis, Greece.
  • Ghizzani V; Department of Radiotherapy and Oncology, Democritus University of Thrace, University General Hospital of Alexandroupolis, 68100 Alexandroupolis, Greece.
  • Katsani KR; PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy.
  • Koffa M; Laboratory of Biochemistry and Molecular Virology, Molecular Biology and Genetics Department, Democritus University of Thrace, Dragana, 68100 Alexandroupolis, Greece.
  • Koukourakis M; Laboratory of Cellular Biology and Cell Cycle, Molecular Biology and Genetics Department, Democritus University of Thrace, University Campus, Dragana, 68100 Alexandroupolis, Greece.
  • Psomas G; Department of Radiotherapy and Oncology, Democritus University of Thrace, University General Hospital of Alexandroupolis, 68100 Alexandroupolis, Greece.
  • Protti S; Laboratory of Inorganic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
  • Fagnoni M; PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy.
  • Fylaktakidou KC; PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy.
Int J Mol Sci ; 24(3)2023 Jan 17.
Article in En | MEDLINE | ID: mdl-36768159
ABSTRACT
A set of arylazo sulfones, known to undergo N-S bond cleavage upon light exposure, has been synthesized, and their activity in the dark and upon irradiation towards DNA has been investigated. Their interaction with calf-thymus DNA has been examined, and the significant affinity observed (most probably due to DNA intercalation) was analyzed by means of molecular docking "in silico" calculations that pointed out polar contacts, mainly via the sulfonyl moiety. Incubation with plasmid pBluescript KS II revealed DNA cleavage that has been studied over time and concentration. UV-A irradiation considerably improved DNA damage for most of the compounds, whereas under visible light the effect was slightly lower. Moving to in vitro experiments, irradiation was found to slightly enhance the death of the cells in the majority of the compounds. Naphthylazosulfone 1 showed photo-disruptive effect under UV-A irradiation (IC50 ~13 µΜ) followed by derivatives 14 and 17 (IC50 ~100 µΜ). Those compounds were irradiated in the presence of two non-cancer cell lines and were found equally toxic only upon irradiation and not in the dark. The temporal and spatial control of light, therefore, might provide a chance for these novel scaffolds to be useful for the development of phototoxic pharmaceuticals.
Subject(s)
Key words
Fulltext
Print
XML
PubMed Links
Search on Google

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Sulfones / Melanoma Limits: Humans Language: En Journal: Int J Mol Sci Year: 2023 Type: Article Affiliation country: Greece
Fulltext
Print
XML
PubMed Links
Search on Google

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Sulfones / Melanoma Limits: Humans Language: En Journal: Int J Mol Sci Year: 2023 Type: Article Affiliation country: Greece