Self-Assembled Molecular Complexes of 1,10-Phenanthroline and 2-Aminobenzimidazoles: Synthesis, Structure Investigations, and Cytotoxic Properties

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creativework.keywords1,10-phenanthroline, 2-aminobenzimidazoles, antitumor activity, DFT, in vitro DNA binding, self-assembly, X-ray diffraction analysis
creativework.publisherMultidisciplinary Digital Publishing Institute (MDPI)en
dc.contributor.authorAnichina K.
dc.contributor.authorKaloyanov N.
dc.contributor.authorZasheva D.
dc.contributor.authorRusew R.
dc.contributor.authorNikolova R.
dc.contributor.authorYancheva D.
dc.contributor.authorBakov V.
dc.contributor.authorGeorgiev N.
dc.date.accessioned2024-07-10T14:27:06Z
dc.date.accessioned2024-07-10T14:51:06Z
dc.date.available2024-07-10T14:27:06Z
dc.date.available2024-07-10T14:51:06Z
dc.date.issued2024-02-01
dc.description.abstractThree new molecular complexes (phen)3(2-amino-Bz)2(H+)(BF4−)·3H2O 5, (phen)3(2-amino-5(6)-methyl-Bz)2(H+)(BF4−)·H2O 6, and (phen)(1-methyl-2-amino-Bz)(H+)(BF4−) 7, were prepared by self-assembly of 1,10-phenanthroline (phen) and various substituted 2-aminobenzimidazoles. Confirmation of their structures was established through spectroscopic methods and elemental analysis. The X-ray diffraction analysis revealed that the crystal structure of 7 is stabilized by the formation of hydrogen bonds and short contacts. In addition, the molecular geometry and electron structure of molecules 5 and 6 were theoretically evaluated using density functional theory (DFT) methods. According to the DFT B3LYP/6-311+G* calculations, the protonated benzimidazole (Bz) units act as NH hydrogen bond donors, binding two phenanthrolines and a BF4− ion. Non-protonated Bz unit form hydrogen bonds with the N-atoms of a third molecule phen. The molecular assembly is held together by π-π stacking between benzimidazole and phenanthroline rings, allowing for N-atoms to associate with water molecules. The complexes were tested in vitro for their tumor cell growth inhibitory effects on prostate (PC3), breast (MDA-MB-231 and MCF-7), and cervical (HeLa) cancer cell lines using MTT-dye reduction assay. The in vitro cytotoxicity analysis and spectrophotometric investigation in the presence of ct-DNA, showed that self-assembled molecules 5–7 are promising DNA-binding anticancer agents warranting further in-depth exploration.
dc.identifier.doi10.3390/molecules29030583
dc.identifier.issn1420-3049
dc.identifier.scopusSCOPUS_ID:85184513523en
dc.identifier.urihttps://rlib.uctm.edu/handle/123456789/901
dc.language.isoen
dc.source.urihttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=85184513523&origin=inward
dc.titleSelf-Assembled Molecular Complexes of 1,10-Phenanthroline and 2-Aminobenzimidazoles: Synthesis, Structure Investigations, and Cytotoxic Properties
dc.typeArticle
oaire.citation.issue3
oaire.citation.volume29
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