Binding Enhancements of Nicotinic Acid to Water-Soluble Zinc Porphyrins Based on Triple Attractions of Coordination, Coulomb, and CH–π Interactions

The binding of amines to artificial zinc-porphyrin receptors 1—4 was examined in basic aqueous solutions. For nicotinic acid and 3,5-dicarboxypyridine, substantial binding enhancements were observed compared to other amines with no π system or carboxyl group. This observation suggested that interlig...

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Published inChemical & pharmaceutical bulletin Vol. 56; no. 7; pp. 969 - 972
Main Authors Imai, Hiroyasu, Munakata, Hiroki, Uemori, Yoshio
Format Journal Article
LanguageEnglish
Published TOKYO The Pharmaceutical Society of Japan 01.07.2008
Pharmaceutical Soc Japan
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Multidisciplinary
CH–π interaction
coordination
Coulomb interaction
Life Sciences & Biomedicine
Metalloporphyrins - chemistry
molecular recognition
Niacin - chemistry
nicotinic acid
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
water-soluble zinc porphyrin
CH-pi interaction
ARRAY
water-soluble zinc porphyrin
AMINO-ACIDS
OLIGOPEPTIDES
BONDS
CHEMISTRY
molecular recognition
RECEPTORS
Coulomb interaction
nicotinic acid
coordination
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Summary:The binding of amines to artificial zinc-porphyrin receptors 1—4 was examined in basic aqueous solutions. For nicotinic acid and 3,5-dicarboxypyridine, substantial binding enhancements were observed compared to other amines with no π system or carboxyl group. This observation suggested that interligand attractions of Coulomb and CH–π interactions in addition to N-atom coordination can act effectively as recognition factors. The differences in the Coulomb interaction between carboxylate and sulfonate anions were also discussed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.56.969