Tuning the pKa of the antihistaminic drug chlorpheniramine maleate by supramolecular interactions with water-soluble polymers

Ignacio Moreno-Villoslada, Felipe González, Bernabé L. Rivas, Toshimichi Shibue, Hiroyuki Nishide

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

The interaction of the pharmacologically important chlorpheniramine maleate (CPM) with polyanions containing sulfonate groups such as poly(sodium 4-styrenesulfonate) (PSS), poly(sodium vinylsulfonate) (PVS), and the more hydrophobic poly(sodium 2-(N-acrylamido)-2-methyl-propanesulfonate) (PAMPS) has been studied by 1H NMR. It was found that the pKa of the low-molecular weight molecule (LMWM) may be modified by its interaction with the polyanions, changing from 3 to 5, due to electric charge compensation. Interestingly, the interaction of CPM with PSS produces changes in CPM resonances, such as a general broadening and upfield shifts of the signals, and NOE effects between the LMWM and the water-soluble polymer (WSP) that indicate the presence of π-π interactions.

Original languageEnglish
Pages (from-to)799-804
Number of pages6
JournalPolymer
Volume48
Issue number3
DOIs
Publication statusPublished - 2007 Jan 26

Fingerprint

Chlorpheniramine
Polymers
Tuning
Sodium
Water
Molecular weight
Pharmaceutical Preparations
Electric charge
Molecules
Nuclear magnetic resonance
polyanions

Keywords

  • π-π interactions
  • Chlorpheniramine maleate
  • Water-soluble polymers

ASJC Scopus subject areas

  • Organic Chemistry
  • Polymers and Plastics

Cite this

Tuning the pKa of the antihistaminic drug chlorpheniramine maleate by supramolecular interactions with water-soluble polymers. / Moreno-Villoslada, Ignacio; González, Felipe; Rivas, Bernabé L.; Shibue, Toshimichi; Nishide, Hiroyuki.

In: Polymer, Vol. 48, No. 3, 26.01.2007, p. 799-804.

Research output: Contribution to journalArticle

Moreno-Villoslada, Ignacio ; González, Felipe ; Rivas, Bernabé L. ; Shibue, Toshimichi ; Nishide, Hiroyuki. / Tuning the pKa of the antihistaminic drug chlorpheniramine maleate by supramolecular interactions with water-soluble polymers. In: Polymer. 2007 ; Vol. 48, No. 3. pp. 799-804.
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AU - Rivas, Bernabé L.

AU - Shibue, Toshimichi

AU - Nishide, Hiroyuki

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