Structural studies of five novel bile acid-4-aminopyridine conjugates

Kari V. Ahonen*, Manu K. Lahtinen, Miika S. Lofman, Anniina M. Kiesila, Arto M. Valkonen, Elina I. Sievanen, Nonappa Nonappa, Erkki T. Kolehmainen

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

7 Citations (Scopus)

Abstract

Synthesis and solid-state structural characterization of five bile acid amides of 4-aminopyridine (4-AP) are reported. Systematic crystallization experiments revealed a number of structural modifications and/or solvate/hydrate systems for these conjugates. Particularly, cholic acid conjugate exhibited five distinct structure modifications, including one anhydrous form, mono- and dihydrates, as well as ethanol and 2-butanol solvates. The obtained crystal forms were examined extensively with various analytical methods, including solid-state NMR, Raman. and IR spectroscopies, powder and single crystal X-ray diffraction methods, thermogravimetry, and differential scanning calorimetry. After releasing their crystal solvent molecules, the resulted non-solvated structure forms showed 50-75 degrees C higher melting points than corresponding bile acids, and thermal degradation occurred for all conjugates at about 300-330 degrees C. Moreover, the single crystal X-ray structure of the ursodeoxycholic acid-4-aminopyridine conjugate is reported. (C) 2012 Elsevier Inc. All rights reserved.

Original languageEnglish
Pages (from-to)1141-1151
Number of pages11
JournalSTEROIDS
Volume77
Issue number11
DOIs
Publication statusPublished - Sep 2012
MoE publication typeA1 Journal article-refereed

Keywords

  • 4-Aminopyridine
  • Bile acids
  • Optical spectroscopy
  • X-ray diffraction
  • Solid-state NMR
  • Thermoanalysis
  • RESTORES AXONAL CONDUCTION
  • POTASSIUM CHANNEL BLOCKER
  • MULTIPLE-SCLEROSIS
  • NUCLEAR RECEPTOR
  • SPINAL-CORD
  • ALZHEIMERS-DISEASE
  • ACIDS
  • 4-AMINOPYRIDINE
  • MODEL
  • POLYMORPHISM

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