Inclusion Complexes of ß-Cyclodextrin and Its Silyl Derivative with Some Pharmacologically Important Aromatic Monocarboxylic Acids

Abstract

Stable host-guest complexes of β-cyclodextrin and its silyl derivative with some aromatic monocarboxylic acids of pharmacological interest were prepared. The structure of the β-cyclodextrin complex with nicotinic acid was studied by X-ray diffraction.

Adducts of N-Heterocyclic Drugs, Niacin, Allopurinol, and Amiloride, with 2,4-Pyridinedicarboxylic Acid Coformer

“…The neutral character of only one of three carboxylic groups in 1 is also supported by the difference in the C–O bond distances in this compound (Table S2). Such a location of hydrogen atoms means that both components exist in the zwitterion forms previously reported for both. ,,− …”

“…Contrary to ALP and AMI, niacin and its derivatives, nicotinamide and isonicotinamide, are popular agents for co-crystallization in pharmaceutical co-crystal studies. For NIA, the extended information in the CSD is available, and NIA is reported in four different ionization states, as a pyridinium cation (the mostly frequently met form), as a nicotinate anion in the drug–drug solids with blonanserin, clofazimine, pyrimethamine, tegaserod, and lamotrigine. − In the zwitterion form, due to the intramolecular proton transfer, NIA is reported in adducts with rac- and (+)-hesperetin, hydrochlorothiazide, pyrogallol, ,, and with several carboxylic acids. ,, Finally, only two examples report NIA in the neutral form in adducts with β-cyclodextrin (β-CD) and 4-aminobenzoic acid. , …”

“…44,52,70 Finally, only two examples report NIA in the neutral form in adducts with β-cyclodextrin (β-CD) and 4-aminobenzoic acid. 71,72 Allopurinol (ALP) belongs to a class of purines whose molecules consist of a pyrimidine ring fused to an imidazole ring. Since its approval in 1966 by the FDA, ALP has been prescribed for the treatment of gout and tumor lysis syndrome,…”

Inclusion complexes of β-cyclodextrin with some dicarboxylic acids

“…Apart from protection of the guest molecule from biodegradation and increase of the solubility in water, β-cyclodextrin in some cases favors efficient targeted drug delivery [1][2][3][4][5]. We previously proposed practical procedures for the synthesis of stable inclusion complexes of cyclodextrins with some aromatic monocarboxylic acids and determined the effects of the size of the cavity, solvent nature, and substitution pattern in the cyclodextrin framework on their stability [6][7][8].…”