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Open AccessFeature PaperArticle

Multicharged Phthalocyanines as Selective Ligands for G-Quadruplex DNA Structures

1
QOPNA & LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal
2
Coimbra Institute for Clinical and Biomedical Research (iCBR), Faculty of Medicine, University of Coimbra, 3000-548 Coimbra, Portugal
3
CNC.IBILI Consortium, University of Coimbra, 3000-548 Coimbra, Portugal
4
CQE & Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, n1, 1049-001 Lisboa, Portugal
5
CICS-UBI—Centro de Investigação em Ciências da Saúde, Universidade da Beira Interior, Av. Infante D. Henrique, 6200-506 Covilhã, Portugal
*
Authors to whom correspondence should be addressed.
Molecules 2019, 24(4), 733; https://doi.org/10.3390/molecules24040733
Received: 17 January 2019 / Revised: 12 February 2019 / Accepted: 13 February 2019 / Published: 18 February 2019
The stabilization of G-Quadruplex DNA structures by ligands is a promising strategy for telomerase inhibition in cancer therapy since this enzyme is responsible for the unlimited proliferation of cancer cells. To assess the potential of a compound as a telomerase inhibitor, selectivity for quadruplex over duplex DNA is a fundamental attribute, as the drug must be able to recognize quadruplex DNA in the presence of a large amount of duplex DNA, in the cellular nucleus. By using different spectroscopic techniques, such as ultraviolet-visible, fluorescence and circular dichroism, this work evaluates the potential of a series of multicharged phthalocyanines, bearing four or eight positive charges, as G-Quadruplex stabilizing ligands. This work led us to conclude that the existence of a balance between the number and position of the positive charges in the phthalocyanine structure is a fundamental attribute for its selectivity for G-Quadruplex structures over duplex DNA structures. Two of the studied phthalocyanines, one with four peripheral positive charges (ZnPc1) and the other with less exposed eight positive charges (ZnPc4) showed high selectivity and affinity for G-Quadruplex over duplex DNA structures and were able to accumulate in the nucleus of UM-UC-3 bladder cancer cells. View Full-Text
Keywords: multicharged phthalocyanines; G-Quadruplexes; telomerase inhibition; selectivity; salmon sperm DNA; UV-Vis; hyperchromism; G4-FID; circular dichroism multicharged phthalocyanines; G-Quadruplexes; telomerase inhibition; selectivity; salmon sperm DNA; UV-Vis; hyperchromism; G4-FID; circular dichroism
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MDPI and ACS Style

Ramos, C.I.V.; Almeida, S.P.; Lourenço, L.M.O.; Pereira, P.M.R.; Fernandes, R.; Faustino, M.A.F.; Tomé, J.P.C.; Carvalho, J.; Cruz, C.; Neves, M.G.P.M.S. Multicharged Phthalocyanines as Selective Ligands for G-Quadruplex DNA Structures. Molecules 2019, 24, 733.

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