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DNA-binding and anticancer activity of binuclear gold(I) alkynyl complexes with a phenanthrenyl bridging ligand

Alsaeedi, Mona S; Babgi, Bandar A; Hussien, Mostafa A; Abdellattif, Magda H; Humphrey, Mark

Description

3,6-Diethynyl-9,10-diethoxyphenanthrene (4) was synthesized from phenanthrene and employed in the synthesis of the binuclear gold(I) alkynyl complexes (R3P)Au(C≡C-3-[C14H6-9, 10-diethoxy]-6-C≡C)Au(PR3) (R = Ph (5a), Cy (5b)). The diyne 4 and complexes 5a and 5b were characterized by NMR spectroscopy, mass spectrometry, and elemental analysis. UV-Vis spectroscopy studies of the metal complexes and precursor diyne show strong π → π* transitions in the near UV region that red shift by ca. 50 nm...[Show more]

dc.contributor.authorAlsaeedi, Mona S
dc.contributor.authorBabgi, Bandar A
dc.contributor.authorHussien, Mostafa A
dc.contributor.authorAbdellattif, Magda H
dc.contributor.authorHumphrey, Mark
dc.date.accessioned2022-06-29T00:18:46Z
dc.date.available2022-06-29T00:18:46Z
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/1885/268558
dc.description.abstract3,6-Diethynyl-9,10-diethoxyphenanthrene (4) was synthesized from phenanthrene and employed in the synthesis of the binuclear gold(I) alkynyl complexes (R3P)Au(C≡C-3-[C14H6-9, 10-diethoxy]-6-C≡C)Au(PR3) (R = Ph (5a), Cy (5b)). The diyne 4 and complexes 5a and 5b were characterized by NMR spectroscopy, mass spectrometry, and elemental analysis. UV-Vis spectroscopy studies of the metal complexes and precursor diyne show strong π → π* transitions in the near UV region that red shift by ca. 50 nm upon coordination at the gold centers. The emission spectrum of 4 shows an intense fluorescence band centered at 420 nm which red shifts, slightly upon coordination of 4 to gold. Binding studies of 4, 5a, and 5b against calf thymus DNA were carried out, revealing that 4, 5a, and 5b have ≥40% stronger binding affinities than the commonly used intercalating agent ethidium bromide. The molecular docking scores of 4, 5a, and 5b with B-DNA suggest a similar trend in behavior to that observed in the DNA-binding study. Unlike the ligand 4, promising anticancer properties for 5a and 5b were observed against several cell lines; the DNA binding capability of the precursor alkyne was maintained, and its anticancer efficacy enhanced by the gold centers. Such phenanthrenyl complexes could be promising candidates in certain biological applications because the two components (phenanthrenyl bridge and metal centers) can be altered independently to improve the targeting of the complex, as well as the biological and physicochemical properties.
dc.description.sponsorshipThis project was funded by the Deanship of Scientific Research (DSR), King Abdulaziz University, Jeddah, Saudi Arabia under grant no. (KEP-44-130-40). The authors, therefore, acknowledge with thanks DSR technical and financial support.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherMolecular Diversity Preservation International
dc.rights© 2020 by the authors. Licensee MDPI, Basel, Switzerland.
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.sourceMolecules
dc.subjectgold(I) alkynyls
dc.subjectphenanthrene
dc.subjectDNA-binding
dc.subjectanticancer activity
dc.titleDNA-binding and anticancer activity of binuclear gold(I) alkynyl complexes with a phenanthrenyl bridging ligand
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume25
dc.date.issued2020
local.identifier.absfor340201 - Bioinorganic chemistry
local.identifier.ariespublicationa383154xPUB11287
local.publisher.urlhttp://www.mdpi.com/journal/molecules
local.type.statusPublished Version
local.contributor.affiliationAlsaeedi, Mona S, King Abdulaziz University
local.contributor.affiliationBabgi, Bandar A, King Abdulaziz University
local.contributor.affiliationHussien, Mostafa A, King Abdulaziz University
local.contributor.affiliationAbdellattif, Magda H, Taif University
local.contributor.affiliationHumphrey, Mark, College of Science, ANU
local.bibliographicCitation.issue5
local.bibliographicCitation.startpage1
local.bibliographicCitation.lastpage15
local.identifier.doi10.3390/molecules25051033
dc.date.updated2021-08-01T08:21:33Z
local.identifier.scopusID2-s2.0-85081218594
dcterms.accessRightsOpen Access
dc.provenanceThis article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
dc.rights.licenseCreative Commons Attribution License
CollectionsANU Research Publications

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