Metabolic properties of phosphonate esters

Gabor Somogyi, Peter Buchwald, N. Bodor

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The object of the present work was to investigate the difference in the metabolism of the phosphonate derivatives of primary or secondary hydroxyl groups. To study the phosphorolytic cleavage of such P-O bonds, zidovudine (AZT) hexanoyloxymethyl-methylphosphonate (HOM-AZT-P), an ester of a primary OH functionality, and methyl-pivaloyloxymethyl-testosterylphosphonate (POM-T-P), an ester of a secondary OH functionality, were prepared. The actions of pure enzymes such as alkaline phosphatase and phosphodiesterase on the corresponding phosphonate compounds (AZT-P and T-P) were investigated at various pH values. The phosphonate derivative of the secondary hydroxyl group of testosterone proved completely resistant to such phosphorolytic attacks, and release of free testosterone could not be detected. The phosphonate derivative of the primary hydroxyl group of zidovudine proved resistant to phosphodiesterase, but not to alkaline phosphatase, and in this second case, release of free zidovudine could be detected.

Original languageEnglish
Pages (from-to)378-381
Number of pages4
JournalPharmazie
Volume59
Issue number5
StatePublished - May 1 2004
Externally publishedYes

Fingerprint

Organophosphonates
Zidovudine
Esters
Hydroxyl Radical
Derivatives
Alkaline Phosphatase
Testosterone
Phosphodiesterase I
Phosphoric Diester Hydrolases
Metabolism
Enzymes

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science

Cite this

Somogyi, G., Buchwald, P., & Bodor, N. (2004). Metabolic properties of phosphonate esters. Pharmazie, 59(5), 378-381.

Metabolic properties of phosphonate esters. / Somogyi, Gabor; Buchwald, Peter; Bodor, N.

In: Pharmazie, Vol. 59, No. 5, 01.05.2004, p. 378-381.

Research output: Contribution to journalArticle

Somogyi, G, Buchwald, P & Bodor, N 2004, 'Metabolic properties of phosphonate esters', Pharmazie, vol. 59, no. 5, pp. 378-381.
Somogyi G, Buchwald P, Bodor N. Metabolic properties of phosphonate esters. Pharmazie. 2004 May 1;59(5):378-381.
Somogyi, Gabor ; Buchwald, Peter ; Bodor, N. / Metabolic properties of phosphonate esters. In: Pharmazie. 2004 ; Vol. 59, No. 5. pp. 378-381.
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