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

Antonio Clementi; Maria Chiara Aversa; Carmelo Corsaro; Jeroen Spooren; Rosanna Stancanelli; Christine O'Connor; Mary McNamara; Antonino Mazzaglia

doi:10.1007/s10847-010-9738-z

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

Antonio Clementi, Maria Chiara Aversa, Carmelo Corsaro, Jeroen Spooren, Rosanna Stancanelli, Christine O'Connor, Mary McNamara, Antonino Mazzaglia

School of Chemical and BioPharmaceutical Science

Research output: Contribution to journal › Article › peer-review

Abstract

A novel folic acid-β-cyclodextrin (β-CD) conjugate was synthesized and preliminarily characterized by ¹H NMR, ESI-MS, and MALDI-MS. ¹H 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 (T₁ and T₂) is reported to tentatively explain the colloidal behaviour of the new species in an aqueous solution.

Original language	English
Pages (from-to)	321-325
Number of pages	5
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume	69
Issue number	3-4
DOIs	https://doi.org/10.1007/s10847-010-9738-z
Publication status	Published - Apr 2011

Keywords

Colloids
Conjugates
Cyclodextrin
Dynamic NMR
Folic acid

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title = "Synthesis and characterization of a colloidal novel folic acid-β-cyclodextrin conjugate for targeted drug delivery",

abstract = "A novel folic acid-β-cyclodextrin (β-CD) conjugate was synthesized and preliminarily characterized by 1H NMR, ESI-MS, and MALDI-MS. 1H 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 (Ds) of the three species (α-, γ-conjugates, and free folic acid) and relaxation times (T1 and T2) is reported to tentatively explain the colloidal behaviour of the new species in an aqueous solution.",

keywords = "Colloids, Conjugates, Cyclodextrin, Dynamic NMR, Folic acid",

author = "Antonio Clementi and Aversa, \{Maria Chiara\} and Carmelo Corsaro and Jeroen Spooren and Rosanna Stancanelli and Christine O'Connor and Mary McNamara and Antonino Mazzaglia",

year = "2011",

month = apr,

doi = "10.1007/s10847-010-9738-z",

language = "English",

volume = "69",

pages = "321--325",

journal = "Journal of Inclusion Phenomena and Macrocyclic Chemistry",

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T1 - Synthesis and characterization of a colloidal novel folic acid-β-cyclodextrin conjugate for targeted drug delivery

AU - Clementi, Antonio

AU - Aversa, Maria Chiara

AU - Corsaro, Carmelo

AU - Spooren, Jeroen

AU - Stancanelli, Rosanna

AU - O'Connor, Christine

AU - McNamara, Mary

AU - Mazzaglia, Antonino

PY - 2011/4

Y1 - 2011/4

N2 - A novel folic acid-β-cyclodextrin (β-CD) conjugate was synthesized and preliminarily characterized by 1H NMR, ESI-MS, and MALDI-MS. 1H 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 (Ds) of the three species (α-, γ-conjugates, and free folic acid) and relaxation times (T1 and T2) is reported to tentatively explain the colloidal behaviour of the new species in an aqueous solution.

AB - A novel folic acid-β-cyclodextrin (β-CD) conjugate was synthesized and preliminarily characterized by 1H NMR, ESI-MS, and MALDI-MS. 1H 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 (Ds) of the three species (α-, γ-conjugates, and free folic acid) and relaxation times (T1 and T2) is reported to tentatively explain the colloidal behaviour of the new species in an aqueous solution.

KW - Colloids

KW - Conjugates

KW - Cyclodextrin

KW - Dynamic NMR

KW - Folic acid

UR - https://www.scopus.com/pages/publications/78650097027

U2 - 10.1007/s10847-010-9738-z

DO - 10.1007/s10847-010-9738-z

M3 - Article

AN - SCOPUS:78650097027

SN - 0923-0750

VL - 69

SP - 321

EP - 325

JO - Journal of Inclusion Phenomena and Macrocyclic Chemistry

JF - Journal of Inclusion Phenomena and Macrocyclic Chemistry

IS - 3-4

ER -

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

Abstract

Keywords

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