Synthesis, mechanism and fluorescence properties of 8-(aryl)-3-β-D- ribofuranosylimidazo[2,1-i]purine 5'-phosphate derivatives

Bilha Fischer, Eihab Kabha, Fernand Pierre Gendron, Adrien R. Beaudoin

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The synthesis of new fluorescent nucleotides is described. This synthesis comprises two parallel reactions, the Kornblum oxidation and imidazole formation, which lead to 8-(aryl)-3-β-D-ribofuranosylimidazo[2,1- i]purine 5'-phosphates 2 from AMP or ATP. A detailed mechanism is proposed based on monitoring the reaction by 1H- and 13C-NMR spectroscopy, MS, FAB, HPLC, and pH meter. The spectral and fluorescent properties of the new derivatives at various pH values are described. Excitation and emission maxima for 3 were observed at 290 and 420 nm, respectively, in both basic and neutral media. In acidic media, the emission maximum shifted to 410 nm, however, the fluorescence intensity increased 1.5-fold. ATP analogues 2b and 3b exhibited relative stability regarding hydrolysis by type II ATPDase. Compound 3b is relatively chemically stable at pH 10.4 and 7.4.

Original languageEnglish
Pages (from-to)1033-1054
Number of pages22
JournalNucleosides, Nucleotides and Nucleic Acids
Volume19
Issue number5-6
DOIs
StatePublished - 2000

Bibliographical note

Funding Information:
Acknowledgment. This work was supported in part by German-Israeli Foundation (GIF) grant no. 1-5 13-210.09/96, and the Marcus Center for Pharmaceutical and Medicinal Chemistry. The authors thank Dr. A. Zaban and Mr. A. Falach for their help with the fluorescent measurements.

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