Concise synthesis of ciguatoxin ABC-ring fragments and surface plasmon resonance study of the interaction of their BSA conjugates with monoclonal antibodies

Yoko Nagumo, Hiroki Oguri, Yumi Shindo, Shin ya Sasaki, Tohru Oishi, Masahiro Hirama, Yoshihisa Tomioka, Michinao Mizugaki, Takeshi Tsumuraya

Research output: Contribution to journalArticlepeer-review

39 Citations (Scopus)

Abstract

Monoclonal antibodies (mAbs), 4H2 and 6H7, were prepared previously using a protein conjugate of a 1:1 epimeric mixture of the synthetic ABC-ring fragments of ciguatoxin (CTX), 3 and 4. Here, the interactions of these mAbs with the fragments of CTX and CTX3C, 3 and 5, were investigated by surface plasmon resonance (SPR) spectroscopy in an attempt to clarify an antigenic determinant. Compared with the previous synthesis, the fragment 3 possessing the 2S configuration was synthesized from tri-O-acetyl-D-glucal much more effectively. The mAb 4H2 was already known to show a dose-dependent binding to the bovine serum albumin (BSA) conjugate of 3, but not to that of 5. The present SPR study of 4H2 demonstrates that the A-ring side chain of 3 plays a decisive role as an epitope. Therefore, SPR can effectively replace the ELISA method for the analysis of mAbs.

Original languageEnglish
Pages (from-to)2037-2040
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume11
Issue number15
DOIs
Publication statusPublished - 2001 Aug 6

ASJC Scopus subject areas

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

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