Synthesis and characterization of a colloidal novel folic acid–β-cyclodextrin conjugate for targeted drug delivery

A novel folic acid–β-cyclodextrin (β - CD) conjugate was synthesized and preliminarily characterized by 1 H NMR, ESI-MS, and MALDI-MS. 1 H NMR shows the presence of α- and γ-conjugates which are generated by β - CD linkage in turn with both carboxylic functions of folic acid. Moreover ROESY evidence...

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Published inJournal of Inclusion Phenomena and Macrocyclic Chemistry Vol. 69; no. 3-4; pp. 321 - 325
Main Authors Clementi, Antonio, Aversa, Maria Chiara, Corsaro, Carmelo, Spooren, Jeroen, Stancanelli, Rosanna, O’Connor, Christine, McNamara, Mary, Mazzaglia, Antonino
Format Journal Article
LanguageEnglish
Published Dordrecht Springer Netherlands 01.04.2011
Subjects
Chemistry
Chemistry and Materials Science
Crystallography and Scattering Methods
Food Science
Organic Chemistry
Original Article
Conjugates
Cyclodextrin
Dynamic NMR
Colloids
Folic acid
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Summary:A novel folic acid–β-cyclodextrin (β - CD) conjugate was synthesized and preliminarily characterized by 1 H NMR, ESI-MS, and MALDI-MS. 1 H NMR shows the presence of α- and γ-conjugates which are generated by β - CD linkage in turn with both carboxylic functions of folic acid. Moreover ROESY evidences supramolecular interactions between the benzene ring of the folic acid and the β - CD cavity. DOSY suggests that ethylenediamine derived β - CD–folic acid forms a colloidal dispersion difficult to purify from free folic acid. An analysis of self-diffusion coefficient (D s ) of the three species (α-, γ-conjugates, and free folic acid) and relaxation times (T 1 and T 2 ) is reported to tentatively explain the colloidal behaviour of the new species in an aqueous solution.
ISSN:0923-0750
1573-1111
DOI:10.1007/s10847-010-9738-z