Positively charged cyclodextrins as effective molecular transporters of active phosphorylated forms of gemcitabine into cancer cells View Full Text


Ontology type: schema:ScholarlyArticle      Open Access: True


Article Info

DATE

2017-12

AUTHORS

Violeta Rodriguez-Ruiz, Andrey Maksimenko, Giuseppina Salzano, Maria Lampropoulou, Yannis G. Lazarou, Valentina Agostoni, Patrick Couvreur, Ruxandra Gref, Konstantina Yannakopoulou

ABSTRACT

Positively charged cyclodextrins (PCCDs) are molecular carriers of particular interest for their ability to readily enter into cancer cells. Of main interest, guanidino- and aminoalkyl- PCCDs can be conveniently synthesized and form stable and strong inclusion complexes with various active molecules bearing phosphate groups. We have addressed here the challenge to deliver into cancer cells phosphorylated gemcitabine drugs well known for their instability and inability to permeate cell membranes. NMR data corroborated by semiempirical theoretical calculations have shown that aminoalkyl-CDs form sufficiently stable complexes with both mono- and tri-phosphate forms of gemcitabine by simple mixing of the compounds in aqueous solution at physiological pH. Confocal microscopy and radioactivity counting experiments revealed that the developed systems enabled phosphorylated gemcitabine to penetrate efficiently into aggressive human breast cancer cells (MCF7), eventually leading to a substantial reduction of IC50 values. Moreover, compared to free drugs, phosphorylated metabolites of gemcitabine encapsulated in PCCDs displayed improved in vitro activities also on the aggressive human cancer cells CCRF-CEM Ara-C/8 C, a nucleoside transport-deficient T leukemia cell line. The current study offers the proof-of-principle that phosphorylated nucleoside drugs could be efficiently transported by PCCDs into cancer cells. More... »

PAGES

8353

Identifiers

URI

http://scigraph.springernature.com/pub.10.1038/s41598-017-08727-y

DOI

http://dx.doi.org/10.1038/s41598-017-08727-y

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https://app.dimensions.ai/details/publication/pub.1091148356

PUBMED

https://www.ncbi.nlm.nih.gov/pubmed/28827534


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