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Abstract

Prostaglandin E1 is currently marketed as a freeze-dried injectable inclusion complex with alpha-cyclodextrin for the treatment of peripheral arterial diseases. alpha-Cyclodextrin is used as a stabilizing agent and to improve the dissolution characteristics of prostaglandin E1. Upon dilution with the infusion medium, the inclusion complex dissociates almost completely as shown by NMR chemical shift measurements of the complexed and uncomplexed prostaglandin E1. Nuclear Overhauser effect (NOE) measurements of the interacting atoms of alpha-cyclodextrin and prostaglandin E1 provide insight into the structure of the complex.

Determination of the binding constant between alprostadil and alpha-cyclodextrin by capillary electrophoresis: Implications for a freeze-dried formulation

“…7 Results of a prior NMR study on the PGE 1 /a-CD system argue against interaction at the carboxylic site. 13 Work by us utilizing NMR similarly supports a 1:1 stoichiometry for the complex between PGE 1 and a-CD. 34 Hence, we invoke the reasonable hypothesis here that a 1:1 stoichiometry exists between PGE 1 and a-CD, and at the terminal methyl group, as depicted above.…”

“…These studies have utilized kinetics, [4][5][6] spectrophotometry, 6,7 potentiometry, 8 dialysis, 9 circular dichroism, 7 thermal analysis, [10][11][12] and NMR. 7,[13][14][15][16][17][18] Of these, NMR is probably the most generally informative, as it affords high specificity and can yield structural information on the nature of the complex.…”

“…Molecular modeling and NMR measurements utilizing the Nuclear Overhauser effect (NOE) provide support for the structure shown above. 13,33 Most studies on complexes between carboxylic acids and cyclodextrins have concluded that carboxylic groups, regardless of ionization state, are repelled from the apolar interior of cyclodextrins. 7 Results of a prior NMR study on the PGE 1 /a-CD system argue against interaction at the carboxylic site.…”

Pyridylamino‐β‐cyclodextrin as a Molecular Chaperone for Lipopolysaccharide Embedded in a Multilayered Polyelectrolyte Architecture

“…The spectra are also displaced for clarity. As an example of the evaluation of the spectra, the Lorentzian components used in the decomposition of curve a, and the residuals of this fit, are depicted at the bottom of the figure. glandins, [28,29] and linoleic acids, [30] through the formation of molecular inclusion complexes. Lipid insertion into the cavity of CDs is affected, among other things, by the cavity size.…”

Determination of the molecular complexation constant between alprostadil and alpha-cyclodextrin by conductometry

“…As to cyclodextrins, binding studies have been conducted with a wide assortment of compounds. Techniques utilized include kinetics [4][5][6], spectrophotometry [6,7], potentiometry [8], dialysis [9], circular dichroism [7], thermal analysis [10][11][12], and NMR [7,[13][14][15][16][17][18]. NMR is the most generally informative of these various approaches, as it affords high specificity and can yield structural information on the nature of the complex.…”