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Importance of the hydroxyl substituents in the B-ring of plant flavonols on their preferential binding interactions with VEGF G-quadruplex DNA: Multi-spectroscopic and molecular modeling studies
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
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2018 (Engelska)Ingår i: International Journal of Biological Macromolecules, ISSN 0141-8130, E-ISSN 1879-0003, Vol. 118, s. 629-639Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

G-quadruplex (G4) structures are known to be promising anticancer drug targets and flavonols (an important class of fiavonoids) are small molecules reported to possess several health-promoting properties including those of anticancer activities. In this work, we explored the interactions of the structurally related plant flavonols kaempferol (KAE; 3,5,7,4'-OH flavone) and morin (MOR; 3,5,7,2',4'-OH flavone) with various G4-DNA sequences along with duplex DNA using a combination of spectroscopic and molecular docking studies. Our results revealed that KAE shows preferential interaction with VEGF G4-DNA in comparison to the other G4 sequences and duplex DNA. Moreover, KAE enhances the thermal stability of VEGF G4-DNA. In contrast, MOR exhibits an appreciably weaker level of interaction with both duplex and various G4-DNAs, with no significant structural specificity. The contrasting DNA binding behaviors suggest a crucial role of the 2'-OH substituent in the Bring of flavonol moiety. While KAE is relatively planar, MOR adopts a significantly non-planar conformation attributable to steric hindrance from the additional 2'-OH substituent. This small structural difference is apparently very important for the ability of KAE and MOR to interact with VEGF G4-DNA. Thus, KAE (but not MOR) appears to be an effective ligand for VEGF G4-DNA, opening up possibilities of its application for regulation of gene expression in cancer cells. 

Ort, förlag, år, upplaga, sidor
Elsevier, 2018. Vol. 118, s. 629-639
Nyckelord [en]
VEGF G-quadruplex DNA, Kaempferol, Morin, Spectroscopy, Molecular docking, Preferential binding
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:umu:diva-152378DOI: 10.1016/j.ijbiomac.2018.06.115ISI: 000445170200071PubMedID: 29953891Scopus ID: 2-s2.0-85049330598OAI: oai:DiVA.org:umu-152378DiVA, id: diva2:1253742
Forskningsfinansiär
Kempestiftelserna, SMK-1632.2
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Tillgänglig från: 2018-10-05 Skapad: 2018-10-05 Senast uppdaterad: 2023-03-23Bibliografiskt granskad

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Chorell, Erik

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