Design and synthesis of a photocleavable biotin-linker for the photoisolation of ligand-receptor complexes based on the photolysis of 8-quinolinyl sulfonates in aqueous solution

Shin Aoki, Nanako Matsuo, Kengo Hanaya, Yasuyuki Yamada, Yoshiyuki Kageyama

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The ability of avidin (Avn) to form strong complex with biotin (Btn) is frequently used in the detection and isolation of biomolecules in biochemical, analytical, and medicinal research. The fact that the binding is nealy irreversible, however, constitutes a drawback in term of the isolation and purification of intact biomolecules. We recently found that 8-quinolinyl esters of aromatic or aliphatic sulfonic acids undergo photolysis when irradiated at 300-330 nm in aqueous solution at neutral pH. In this work, a biotin-dopamine (BD) conjugate containing a photocleavable 8-quinolinyl benzenesulfonate (QB) linker, BDQB, was designed and synthesized for use in the efficient recovery of dopamine-protein (e.g., antibody) complexes from an Avn-Btn system. The complexation of BDQB with a primary anti-dopamine antibody (anti-dopamine IgG1 from mouse) on an Avn-coated plate was confirmed by an enzyme-linked immunosorbent assay (ELISA) utilizing a secondary antibody (anti-IgG1 antibody) conjugated with horseradish peroxidase (HRP). Upon the photoirradiation (at 313 nm) of the BDQB-IgG1 complex, the release of dopamine-IgG1 complex was confirmed by ELISA. Characterization of the resulting photoreleased dopamine-anti-dopamine IgG1 complex was performed by SDS-PAGE and Western blot.

Original languageEnglish
Pages (from-to)3405-3413
Number of pages9
JournalBioorganic and Medicinal Chemistry
Volume17
Issue number9
DOIs
Publication statusPublished - 2009 May 1
Externally publishedYes

Fingerprint

Photolysis
Biotin
Dopamine
Ligands
Immunoglobulin G
Avidin
Immunosorbents
Biomolecules
Anti-Idiotypic Antibodies
Assays
Enzyme-Linked Immunosorbent Assay
Sulfonic Acids
Antibodies
Enzymes
Horseradish Peroxidase
Complexation
Purification
Polyacrylamide Gel Electrophoresis
Esters
Fatty Acids

Keywords

  • Antibody
  • Avidin
  • Biotin
  • Click chemistry
  • Dopamine
  • Photolysis
  • Quinolinol
  • Sulfonate

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

Design and synthesis of a photocleavable biotin-linker for the photoisolation of ligand-receptor complexes based on the photolysis of 8-quinolinyl sulfonates in aqueous solution. / Aoki, Shin; Matsuo, Nanako; Hanaya, Kengo; Yamada, Yasuyuki; Kageyama, Yoshiyuki.

In: Bioorganic and Medicinal Chemistry, Vol. 17, No. 9, 01.05.2009, p. 3405-3413.

Research output: Contribution to journalArticle

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