The development of photometric sensors for boronic acids

Greg Springsteen, C. Eric Ballard, Shouhai Gao, Wei Wang, Binghe Wang

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Boronic acids bind certain 1,2- and 1,3-diols with high affinity through reversible formation of boronate esters. They have been utilized as the recognition moiety for artificial receptors, particularly receptors for carbohydrates that have cis-diol moieties. Therefore, sensors for boronic acids could serve as universal reporters for monitoring boronate formation. This paper reports the design and synthesis of a series of photometric chemosensors for phenylboronic acid using diethanolamine as the recognition moiety. Diethanolamine, which binds strongly to boronic acids, has been linked to three different types of optical reporters. A photoinduced electron transfer system based on the anthracene fluorophore has been used to create sensors that show up to a fivefold increase in fluorescent intensity in the presence of millimolar concentrations of phenylboronic acid. Sensor designs based on the restriction of free rotation of extended π systems and on the perturbed electronic properties of azo dyes are also included. This work demonstrates that sensors based on several different designs can be used for the detection of boronic acids.

Original languageEnglish (US)
Pages (from-to)259-270
Number of pages12
JournalBioorganic Chemistry
Volume29
Issue number5
DOIs
StatePublished - 2001
Externally publishedYes

Keywords

  • Boron
  • Boronic acid
  • Diethanolamine
  • PET
  • Sensor

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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