8-(ω-aminoalkyl)theophyllines and their use in preparing fluorescently labeled derivatives for applications in immunoassay

Fulya Yahioglu, Colin W. Pouton, Michael D. Threadgill

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Abstract

Reaction of alkane-1,ω-diamines with 6-chloro-1,3-dimethylpyrimidine-2,4-dione under carefully controlled conditions gives 6-(ω-aminoalkylamino)-1,3-dimethylpyrimidine-2,4-diones, which can be readily separated from traces of products of disubstitution after benzyloxycarbonyl protection. A sequence of nitrosation at the pyrimidine 5-position, thermal cyclization, and deprotection affords 8-(ω-aminoalkyl) derivatives of theophylline, an important drug in the treatment of asthma and related diseases. These 8-(ω-aminoalkyl)theophyllines can be coupled to fluorescein-5-isothiocyanate and to dansyl chloride, giving fluorescent derivatives of theophylline with applications in automated immunoassay of the drug in biofluids using the fluorescence capillary fill device.

Original languageEnglish
Pages (from-to)611-616
Number of pages6
JournalBioconjugate Chemistry
Volume8
Issue number4
DOIs
Publication statusPublished - 1 Jul 1997
Externally publishedYes

Keywords

  • Fluorescent Dyes/*chemistry *Immunoassay Isothiocyanates/chemistry Magnetic Resonance Spectroscopy Mass Spectrometry Sulfinic Acids/chemistry Theophylline/*analogs & derivatives/chemistry

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