Comparative lipophilicity of morphine derivatives

H. Kalász, Rafael Doležal, K. Tekes, K. Magyar, Tamás Csermely, Sándor Hosztafi

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Lipophilicity is an important physicochemical characteristic of compounds having potential use in the treatment of humans and animals. Morphine and its semisynthetic derivatives have effects on mu (μ), kappa (κ), and delta (δ) opioid receptors, and their physiological, pharmacological, and therapeutic effects mainly depend on their distribution in the body. The progress in separation techniques has made it possible to use modern methods to determine lipophilic/hydrophilic character of small amounts of organic compounds in just a few minutes. In addition to the classical determination of lipophilicity (shaken-flask method), other experimental methods (such as reversed-phase thin-layer chromatography, distribution-pH profile, etc.) and calculations based on the molecular composition are widely used. The lipophilic character of several morphine derivatives was determined using reversed-phase thin-layer chromatography and also high-performance liquid chromatography (HPLC) method. The results are graphically compared. Lipophilicity (log P) calculation using Pallas 3.8 program was successful only for certain morphine derivatives. Parameters derived from the experimental results of reversed-phase thin-layer chromatography and those of a special HPLC column were well comparable.

Original languageEnglish
Pages (from-to)126-132
Number of pages7
JournalJournal of Planar Chromatography - Modern TLC
Volume28
Issue number2
DOIs
Publication statusPublished - Apr 1 2015

Fingerprint

Morphine Derivatives
Thin layer chromatography
Reverse-Phase Chromatography
Thin Layer Chromatography
High performance liquid chromatography
kappa Opioid Receptor
delta Opioid Receptor
High Pressure Liquid Chromatography
Organic compounds
Morphine
Animals
Therapeutic Uses
Derivatives
Pharmacology
Chemical analysis

Keywords

  • Immobilized artificial membrane column
  • Lipophilicity
  • Morphine
  • Morphine derivatives
  • R values
  • Reversed-phase thin-layer chromatography

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Clinical Biochemistry

Cite this

Comparative lipophilicity of morphine derivatives. / Kalász, H.; Doležal, Rafael; Tekes, K.; Magyar, K.; Csermely, Tamás; Hosztafi, Sándor.

In: Journal of Planar Chromatography - Modern TLC, Vol. 28, No. 2, 01.04.2015, p. 126-132.

Research output: Contribution to journalArticle

Kalász, H. ; Doležal, Rafael ; Tekes, K. ; Magyar, K. ; Csermely, Tamás ; Hosztafi, Sándor. / Comparative lipophilicity of morphine derivatives. In: Journal of Planar Chromatography - Modern TLC. 2015 ; Vol. 28, No. 2. pp. 126-132.
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