| Fluorescence emission properties of 8-aza analogues of caffeine, theophylline, and related N-alkyl xanthines. | |
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MedLine Citation:
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PMID: 19250833 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Fluorescence emission properties of 8-azacaffeine, 8-azatheophylline and other N-alkylated 8-azaxanthines (8-azaXan) have been examined. It is shown that N-methylated 8-azaxanthines, as well as 8-azatheophylline, are highly fluorescent in aqueous medium as the neutral, and, in some instances, also as the monoanionic, forms. 8-Azacaffeine exhibits moderate emission, but its isomer, 1,3,8-trimethyl-8-azaXan, is highly fluorescent. All three 8-azaxanthines monomethylated on the triazole ring, as well as 8-azaxanthosine, exhibit increased acidity in the excited state. Some fluorescent pyrazolo[4,3-d]pyrimidine-5,7-diones, xanthine congeners of pyrazolo[4,3-d]pyrimidines, are also reported. Many of these are good fluorescent probes in enzymatic, receptor binding, and nucleic acid systems, some examples of which are presented. In particular, 8-azaXan is an excellent fluorescent probe for purine nucleoside phosphorylases, as a fluorogenic substrate in the reverse, synthetic pathway. |
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Authors:
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Grzegorz Medza; Jacek Wierzchowski; Borys Kierdaszuk; David Shugar |
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Publication Detail:
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Type: Journal Article Date: 2009-01-14 |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 17 ISSN: 1464-3391 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2009 Mar |
Date Detail:
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Created Date: 2009-03-20 Completed Date: 2009-06-04 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 2585-91 Citation Subset: IM |
Affiliation:
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Department of Biophysics, University of Warmia and Mazury, 4 Oczapowskiego Street, PL-10-719 Olsztyn, Poland. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Aza Compounds
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chemistry* Caffeine / analogs & derivatives*, chemistry Spectrometry, Fluorescence / methods* Spectrophotometry, Ultraviolet Theophylline / analogs & derivatives*, chemistry Xanthines / chemistry* |
| Chemical | |
Reg. No./Substance:
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0/Aza Compounds; 0/Xanthines; 58-08-2/Caffeine; 58-55-9/Theophylline |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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