Details

Autor(en) / Beteiligte

• Saifutiarova, Alina E.
• Fedorov, Yuri V.
• Tsvetkov, Vladimir B.
• Rustamova, Dina A.
• Gulakova, Elena N.
• Chmelyuk, Nelly S.
• Abakumov, Maxim A.
• Aliev, Teimur M.
• Fedorova, Olga A.

Titel

Photochemical synthesis, intercalation with DNA and antitumor evaluation in vitro of benzo[d]thiazolo[3,2-a]quinolin-10-ium derivatives

Ist Teil von

• Bioorganic chemistry, 2021-10, Vol.115, p.105267-105267, Article 105267

Ort / Verlag

United States: Elsevier Inc

Erscheinungsjahr

2021

Quelle

MEDLINE

Beschreibungen/Notizen

• [Display omitted] •We have designed and synthesized five novel benzo[d]thiazolo[3,2-a]quinolin-10-ium derivatives.•Prepared ligands showed good DNA binding affinities through the intercalation and different anticancer activity against four cell lines.•Docking and molecular dynamic calculations supported the results of the possible binding interactions of the target compounds with DNA through the intercalation and demonstrated the effect of substituent in the benzothiazole moiety on the structure of the formed DNA-ligand complex.•The negative CD band in the region of absorption of intercalator points on that the rotating occurs by angle θ = 60°. The positive band in CD spectrum upon the intercalation of ligand arises when angle of rotating is θ = − 60°.•When ligands bind to DNA, fluorescence is quenched by more than 20 times. A new anticancer benzo[d]thiazolo[3,2-a]quinolin-10-ium derivatives were synthesized and characterized. Anticancer evaluation in vitro against four cancer cell lines including adenocarcinomic human alveolar basal epithelial cells (A549), hepatocellular carcinoma (HepG2), prostate cancer (PC3) and breast cancer (MCF7) indicated that some of prepared compounds shows higher selectivity in comparison with doxorubicin. DNA interaction studies by optical, CD, NMR spectroscopies showed the high affinity of benzothiazole ligands towards the dsDNA. The ligand-DNA interaction occurs through the intercalation of benzo[d]thiazolo[3,2-a]quinolin-10-ium derivatives with nucleic acid. The investigation of formed ligand – DNA complexes by docking and molecular dynamic calculations was applied for analysis of the relationship between structure and anticancer activity. The results suggested that benzo[d]thiazolo[3,2-a]quinolin-10-ium derivatives might serve as a novel scaffold for the future development to new antitumor agents.