| Screening of bitterness-suppressing agents for quinine: the use of molecularly imprinted polymers. | |
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MedLine Citation:
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PMID: 15614815 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The purpose of the present study was to examine the possibility of using molecularly imprinted polymers (MIPs) to screen for bitterness-suppressing agents. Quinine was selected as the bitter substance standard. L-arginine (L-Arg), L-ornithine (L-Orn), L-lysine (L-Lys), and L-citrulline (L-Ctr) were tested as bitterness suppressant candidates. In a high-performance liquid chromatography study using a uniformly sized MIP for cinchonidine, which has a very similar structure to quinine, the retention factor (k) of quinine was significantly shortened by the addition of L-Arg or L-Orn to the mobile phase, whereas slight or no decrease was observed when L-Ctr and L-Lys were added. The abilities of these amino acids to decrease the k of quinine were ranked in the following order: L-Arg = (L-Orn >(L-Ctr >>(L-Lys. A linear relationship between the reciprocal of k and the concentration of the amino acids indicated a single competitive model at a single site. The magnitude of the association constants obtained seemed to be directly related to the inhibitory effect of the test substances on the affinity of quinine for the receptor site. Nuclear magnetic resonance and molecular modeling studies suggested a one-to-two hydrogen-bonding-based complex formation of one quinine molecule with two methacrylic acid molecules (Q-2MAA) in chloroform. In the molecular modeling studies, the N--N distance of the quinine molecule in the assumed Q-2MAA complex was calculated to be 5.12 angstroms, similar to the N - N distances of the two amino acid complexes (L-Arg-2MAA, L-Orn-2MAA), which were 4.84 and 5.30 angstroms, respectively. This suggests that L-Arg and L-Orn may compete with the quinine molecule in the cinchonidine-imprinted space. Finally, the results of human gustatory sensation tests correlated well with the MIP data. The proposed method using MIPs seems to have a potential for screening bitterness-suppressing agents for quinine. |
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Authors:
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Tazuko Ogawa; Kaori Hoshina; Jun Haginaka; Chie Honda; Toshiko Tanimoto; Takahiro Uchida |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Journal of pharmaceutical sciences Volume: 94 ISSN: 0022-3549 ISO Abbreviation: J Pharm Sci Publication Date: 2005 Feb |
Date Detail:
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Created Date: 2005-01-04 Completed Date: 2005-06-08 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985195R Medline TA: J Pharm Sci Country: United States |
Other Details:
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Languages: eng Pagination: 353-62 Citation Subset: IM |
Copyright Information:
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Copyright 2004 Wiley-Liss, Inc. |
Affiliation:
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School of Pharmaceutical Sciences, Mukogawa Women's University, 11-68, Koshien 9-Bancho, Nishinomiya City 663-8179, Japan. mwu29310@mwu.mukogawa-u.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Arginine
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chemistry,
pharmacology Chromatography, High Pressure Liquid Citrulline / chemistry, pharmacology Drug Evaluation, Preclinical Drug Interactions Humans Lysine / chemistry, pharmacology Models, Biological Models, Molecular Ornithine / chemistry, pharmacology Quinine / chemistry, pharmacology* Reference Standards Sweetening Agents / chemistry, pharmacology Taste / drug effects* Taste Threshold / drug effects |
| Chemical | |
Reg. No./Substance:
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0/Sweetening Agents; 130-95-0/Quinine; 372-75-8/Citrulline; 56-87-1/Lysine; 7006-33-9/Ornithine; 74-79-3/Arginine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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