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Open AccessArticle

Zinc(II) Terpyridine Complexes: Substituent Effect on Photoluminescence, Antiproliferative Activity, and DNA Interaction

1
School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, Guangxi, China
2
Centro de Química Estrutural, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisbon, Portugal
3
National Engineering Research Center for Non-Food Biorefinery, State Key Laboratory of Non-Food Biomass and Enzyme Technology, Guangxi Academy of Sciences, Nanning 530004, Guangxi, China
4
School of Animal Science and Technology, Guangxi University, Nanning 530004, Guangxi, China
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(24), 4519; https://doi.org/10.3390/molecules24244519
Received: 19 November 2019 / Revised: 2 December 2019 / Accepted: 6 December 2019 / Published: 10 December 2019
(This article belongs to the Section Inorganic Chemistry)
A series of ZnCl2 complexes (compounds 110) with 4′-(substituted-phenyl)-2,2′:6′,2′′-terpyridine that bears hydrogen (L1), p-methyl (L2), p-methoxy (L3), p-phenyl (L4), p-tolyl (L5), p-hydroxyl (L6), m-hydroxyl (L7), o-hydroxyl (L8), p-carboxyl (L9), or p-methylsulfonyl (L10) were prepared and then characterized by 1H NMR, electrospray mass-spectra (ESI-MS), IR, elemental analysis, and single crystal X-ray diffraction. In vitro cytotoxicity assay was used to monitor the antiproliferative activities against tumor cells. Absorption spectroscopy, fluorescence titration, circular dichroism spectroscopy, and molecular modeling studied the DNA interactions. All of the compounds display interesting photoluminescent properties and different maximal emission peaks due to the difference of the substituent groups. The cell viability studies indicate that the compounds have excellent antiproliferative activity against four human carcinoma cell lines, A549, Bel-7402, MCF-7, and Eca-109, with the lowest IC50 values of 0.33 (10), 0.66 (6), 0.37 (7), and 1.05 (7) μM, respectively. The spectrophotometric results reveal that the compounds have strong affinity binding with DNA as intercalator and induce DNA conformational transition. Molecular docking studies indicate that the binding is contributed by the π…π stacking and hydrogen bonds, providing an order of nucleotide sequence binding selectivity as ATGC > ATAT > GCGC. These compounds intercalate into the base pairs of the DNA of the tumor cells to affect their replication and transcription, and the process is supposed to play an important role in the anticancer mechanism. View Full-Text
Keywords: terpyridine complex; photoluminescence; anti-tumor activity; DNA interaction; molecular docking terpyridine complex; photoluminescence; anti-tumor activity; DNA interaction; molecular docking
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MDPI and ACS Style

Li, J.; Liu, R.; Jiang, J.; Liang, X.; Huang, L.; Huang, G.; Chen, H.; Pan, L.; Ma, Z. Zinc(II) Terpyridine Complexes: Substituent Effect on Photoluminescence, Antiproliferative Activity, and DNA Interaction. Molecules 2019, 24, 4519.

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