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Molecules 2019, 24(3), 409; https://doi.org/10.3390/molecules24030409

Discovery of a New Xanthone against Glioma: Synthesis and Development of (Pro)liposome Formulations

1
UCIBIO, REQUIMTE, Laboratory of Pharmaceutical Technology, Faculty of Pharmacy, University of Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
2
Laboratory of Organic and Pharmaceutical Chemistry, Department of Chemical Sciences, Faculty of Pharmacy, University of Porto, Rua Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugal
3
Interdisciplinary Centre of Marine and Environmental Research (CIIMAR), University of Porto, Terminal de Cruzeiros do Porto de Leixões Avenida General Norton de Matos P 4450-208 Matosinhos, Portugal
4
LAQV, REQUIMTE, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira, 228, 4050-313 Porto, Portugall
5
CESPU, Institute of Research and Advanced Training in Health Sciences and Technologies (IINFACTS), Rua Central de Gandra, 1317, 4585-116 Gandra, Portugal
6
REQUIMTE/LAQV, Instituto Superior de Engenharia do Porto, Instituto Politécnico do Porto, Portugal
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 28 December 2018 / Revised: 18 January 2019 / Accepted: 22 January 2019 / Published: 23 January 2019
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Abstract

Following our previous work on the antitumor activity of acetylated flavonosides, a new acetylated xanthonoside, 3,6-bis(2,3,4,6-tetra-O-acetyl-β-glucopyranosyl)xanthone (2), was synthesized and discovered as a potent inhibitor of tumor cell growth. The synthesis involved the glycosylation of 3,6-di-hydroxyxanthone (1) with acetobromo-α-d-glucose. Glycosylation with silver carbonate decreased the amount of glucose donor needed, comparative to the biphasic glycosylation. Xanthone 2 showed a potent anti-growth activity, with GI50 < 1 μM, in human cell lines of breast, lung, and glioblastoma cancers. Current treatment for invasive brain glioma is still inadequate and new agents against glioblastoma with high brain permeability are urgently needed. To overcome these issues, xanthone 2 was encapsulated in a liposome. To increase the well-known low stability of these drug carriers, a proliposome formulation was developed using the spray drying method. Both formulations were characterized and compared regarding three months stability and in vitro anti-growth activity. While the proliposome formulation showed significantly higher stability, it was at the expense of losing its biocompatibility as a drug carrier in higher concentrations. More importantly, the new xanthone 2 was still able to inhibit the growth of glioblastoma cells after liposome formulation. View Full-Text
Keywords: xanthone; acetylated; glycosylation; synthesis; glioblastoma; tumor cell lines; nanotechnology; liposomes; proliposomes xanthone; acetylated; glycosylation; synthesis; glioblastoma; tumor cell lines; nanotechnology; liposomes; proliposomes
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Alves, A.; Correia-da-Silva, M.; Nunes, C.; Campos, J.; Sousa, E.; Silva, P.M.; Bousbaa, H.; Rodrigues, F.; Ferreira, D.; Costa, P.C.; Pinto, M. Discovery of a New Xanthone against Glioma: Synthesis and Development of (Pro)liposome Formulations. Molecules 2019, 24, 409.

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