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Host-guest complexation of oxicam NSAIDs with beta-cyclodextrin.
Biopolymers. 2004 Nov; 75(4):355-65.B

Abstract

Spectroscopic and molecular modeling techniques have been employed to study the interaction of the oxicam group of nonsteroidal antiinflammatory drugs (NSAIDs) with a polysaccharide such as beta-cyclodextrin (beta-cd). beta-cd is a good drug delivery system and is known to reduce harmful side effects of these drugs in the gastrointestinal tract and to increase their clinical efficacy. A detailed understanding of such host-guest interaction helps in designing a better drug delivery system coupled with increased therapeutic potential. However, there exists a controversy as to which prototropic form of piroxicam, a drug belonging to the oxicam group, becomes encapsulated in the host and also the stoichiometry of binding. In this study, we have revisited that controversy using steady state fluorescence, absorption, fluorescence anisotropy measurements, and molecular modeling techniques. In addition, we have for the first time studied the interactions of two other oxicam drugs, viz. tenoxicam and meloxicam, with beta-cd in aqueous solution. In all cases the neutral forms of these drugs were incorporated in the beta-cd cavity with a binding stoichiometry of 1:1 host : guest. The values of the binding constants for piroxicam, meloxicam, and tenoxicam with beta-cyclodextrin are 134 +/- 21, 114 +/- 15, and 115 +/- 13 M(-1), respectively. Molecular modeling studies show that the minimum energy configuration gives favorable interaction energy between the host and the guest in the complex with 1:1 stoichiometry when the conjugated rings of the drugs are inside the hydrophobic bucket-like cavity of beta-cd and the third ring is exposed to the solvent.

Authors+Show Affiliations

Chemical Sciences Division, Saha Institute of Nuclear Physics, 1/AF, Bidhannagar, Calcutta, 700 064, India.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

15372483

Citation

Banerjee, Rona, et al. "Host-guest Complexation of Oxicam NSAIDs With Beta-cyclodextrin." Biopolymers, vol. 75, no. 4, 2004, pp. 355-65.
Banerjee R, Chakraborty H, Sarkar M. Host-guest complexation of oxicam NSAIDs with beta-cyclodextrin. Biopolymers. 2004;75(4):355-65.
Banerjee, R., Chakraborty, H., & Sarkar, M. (2004). Host-guest complexation of oxicam NSAIDs with beta-cyclodextrin. Biopolymers, 75(4), 355-65.
Banerjee R, Chakraborty H, Sarkar M. Host-guest Complexation of Oxicam NSAIDs With Beta-cyclodextrin. Biopolymers. 2004;75(4):355-65. PubMed PMID: 15372483.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Host-guest complexation of oxicam NSAIDs with beta-cyclodextrin. AU - Banerjee,Rona, AU - Chakraborty,Hirak, AU - Sarkar,Munna, PY - 2004/9/17/pubmed PY - 2004/12/16/medline PY - 2004/9/17/entrez SP - 355 EP - 65 JF - Biopolymers JO - Biopolymers VL - 75 IS - 4 N2 - Spectroscopic and molecular modeling techniques have been employed to study the interaction of the oxicam group of nonsteroidal antiinflammatory drugs (NSAIDs) with a polysaccharide such as beta-cyclodextrin (beta-cd). beta-cd is a good drug delivery system and is known to reduce harmful side effects of these drugs in the gastrointestinal tract and to increase their clinical efficacy. A detailed understanding of such host-guest interaction helps in designing a better drug delivery system coupled with increased therapeutic potential. However, there exists a controversy as to which prototropic form of piroxicam, a drug belonging to the oxicam group, becomes encapsulated in the host and also the stoichiometry of binding. In this study, we have revisited that controversy using steady state fluorescence, absorption, fluorescence anisotropy measurements, and molecular modeling techniques. In addition, we have for the first time studied the interactions of two other oxicam drugs, viz. tenoxicam and meloxicam, with beta-cd in aqueous solution. In all cases the neutral forms of these drugs were incorporated in the beta-cd cavity with a binding stoichiometry of 1:1 host : guest. The values of the binding constants for piroxicam, meloxicam, and tenoxicam with beta-cyclodextrin are 134 +/- 21, 114 +/- 15, and 115 +/- 13 M(-1), respectively. Molecular modeling studies show that the minimum energy configuration gives favorable interaction energy between the host and the guest in the complex with 1:1 stoichiometry when the conjugated rings of the drugs are inside the hydrophobic bucket-like cavity of beta-cd and the third ring is exposed to the solvent. SN - 0006-3525 UR - https://www.unboundmedicine.com/medline/citation/15372483/Host_guest_complexation_of_oxicam_NSAIDs_with_beta_cyclodextrin_ L2 - https://doi.org/10.1002/bip.20147 DB - PRIME DP - Unbound Medicine ER -