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

doi:10.1080/15257770008033041

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	1033-1054
Number of pages	22
Journal	Nucleosides, Nucleotides and Nucleic Acids
Volume	19
Issue number	5-6
DOIs	https://doi.org/10.1080/15257770008033041
State	Published - 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.

Funding

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.

Funders	Funder number
German-Israeli Foundation for Scientific Research and Development	1-5 13-210.09/96

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

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.",

author = "Bilha Fischer and Eihab Kabha and Gendron, {Fernand Pierre} and Beaudoin, {Adrien R.}",

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.",

year = "2000",

doi = "10.1080/15257770008033041",

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AU - Fischer, Bilha

AU - Kabha, Eihab

AU - Gendron, Fernand Pierre

AU - Beaudoin, Adrien R.

N1 - 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.

PY - 2000

Y1 - 2000

N2 - 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.

AB - 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.

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

Abstract

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Funding

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