Physicochemical Characterization of α-, β-, and γ-Cyclodextrins Bioesterified with Decanoate Chains Used As Building Blocks of Colloidal Nanoparticles

Abstract

Nanoparticles of amphiphilic α-, β-, and γ-cyclodextrins were obtained by formulation of cyclodextrins enzymatically transesterified with vinyl decanoate. The product of this synthesis is a mixture of bioesterified cyclodextrins with various degrees of substitution (DS) presenting for a same DS different regio-isomers. In a first step, the efficiency of a MALDI-TOF procedure to characterize the average molecular weight of the derivative bulk mixture was demonstrated by comparing the results with those obtained from complementary NMR and HPLC techniques. In a second step, the ultrastructure of nanoparticles prepared from three different batches of synthesis was investigated and correlated with the average molecular weight and DS of the parent derivative.

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

“…Use for molecular dynamics simulations of hydrophobic 1,2,4-trichlorobenzene on hydrophilic TiO 2 (Horikoshi et al, 2011) Glucose monomycolate TOF Condensation of protected glucose-6-tosylate with mycolic acids from M. tuberculosis (Prandi, 2012) Lipid II phosphonate analogues -and -cyclodextrin with phenylalkylamides TOF DCC condensation between 3-manomino-3-monodeoxy-cyclodextrin and benzoic acid, phenylpropionic acid and phenylbutylic acid (Fujiwara & Takahashi, 2011) -, -, and -cyclodextrins bioesterified with decanoate chains TOF (DHB) Used as building blocks for colloidal nanoparticles (Choisnard et al, 2011) Cyclodextrin-based nanotubes TOF (DHP) Use of disulfide bonds at all primary OH groups to link -cyclodextrin s Cyclodextrin-centered polyesters…”

Synthesis of Sulfated Cyclodextrin Amphiphiles with Liposomal Encapsulation Properties

“…For example, a Medusa-like CD was obtained by grafting hydrophobic groups onto all the primary hydroxyl groups of a β-CD [15]- [19]. Skirt-shaped CDs were obtained corresponding to esterification or alkylation of all the secondary hydroxyl groups [20] [21]. These various CD derivatives do not differ only in the position and length of the alkyl chains, but also in the nature of the chemical bond.…”

Bioesterified polysubstituted-cyclodextrin/surfactant nanoparticles obtained by multilevel self-assembly

“…This feature is being used to improve drug stability and bioavailability by increasing the drug permeability properties, solubility and/or dissolution through inclusion complexation, as well as to reduce the drug toxicity and side effects [1][2][3][4][5][6][7][8][9]. The formation of complexes between CDs and drug molecules via dynamic noncovalent interactions, in a host-guest model, has drawn considerable interest [1,[9][10][11][12].…”

“…A recent methodology for grafting of alkyl chains on the secondary face of native CDs by enzymatic transesterification, using thermolysin as a biocatalyzer, has opened new possibilities for the design of drug nanocarriers with colloidal behaviour [8,9]. Amphiphilic CD derivatives with grafted decanoyl chains (CD-C 10 ) may self-assemble into nanospheres with multilamellar inner organization or into reservoir-type particles, which can embed lipophilic drugs [5,[7][8][9].…”

“…Amphiphilic CD derivatives with grafted decanoyl chains (CD-C 10 ) may self-assemble into nanospheres with multilamellar inner organization or into reservoir-type particles, which can embed lipophilic drugs [5,[7][8][9]. However, the unmodified CD-C 10 particles may readily aggregate depending on the surroundings.…”