Publication Type Journal Article
Title Click and go : simple and fast folic acid conjugation
Authors Alexandre F. Trindade Raquel F. M. Frade Ermelinda Macoas Catia Graca C. Rodrigues J. M. G. Martinho Carlos A. M. Afonso
Groups
Journal ORGANIC \& BIOMOLECULAR CHEMISTRY
Year 2014
Month
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Volume 12
Number 20
Pages 3181-3190
Abstract Folic acid targeting by functionalization of the terminal gamma-carboxylic acid is one of the most important strategies to selectively deliver chemotherapeutics and dyes to cancer cells which overexpress folate receptors. However, conjugation of folic acid is limited by its unique solubility and by selectivity issues imposing the need for expensive preparative reverse-phase chromatographic purification to isolate gamma-folate conjugates. Herein is provided a novel synthetic tool for the synthesis of new folic acid conjugates with excellent gamma-purity based on strain-promoted alkyne-azide cycloadditions with a gamma-folate-cyclooctyne conjugate 3. To demonstrate the potential of this methodology several new folate conjugates were synthesized with high gamma-purity and without using any type of chromatographic purification by reacting conjugate 3 with several fluorescent probes, polymers and siliceous materials bearing azide. In addition, the cycloaddition reaction between conjugate 3 and an azido-derived fluorescent dye was successfully performed in cellular media leading to an increase of fluorescence in the cells which overexpress folate receptors (NCI-H460).
DOI http://dx.doi.org/10.1039/c4ob00150h
ISBN
Publisher
Book Title
ISSN 1477-0520
EISSN 1477-0539
Conference Name
Bibtex ID ISI:000335336800006
Observations
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