Stereospecific immuno-recognition of the tetracyclic anti-depressant oxaprotiline

Lotfi Chouchane, A. Donny Strosberg, J. Hoebeke

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Immunization of a rabbit with a racemic mixture of (±)-oxaprotiline, conjugated to bovine serum albumin, resulted in two antibody populations with affinity constants 1.5 × 109 and 2.5 × 106 m-1. Both populations showed a higher affinity for the (-)-isomer than for the ( + )-isomer of the drug. Both stereoisomers of the drug were immunogenic in mice, but only the (-)-isomer was recognized with high affinity. Somatic fusion of the spleen of a mouse, immunized with the (-)-isomer yielded 12 hybridomas secreting monoclonal anti-oxaprotiline antibodies. Five of these monoclonal antibodies (MAbs) recognized both isomers, four bound more specifically to the (-)-isomer, one recognized the (+)-isomer and two were specific for the coupling arm. One of the MAbs was further analyzed to gain insight into the structural features of the drug involved in antibody recognition. This analysis suggested that the stereospecific recognition of oxaprotiline could be directly linked to the position of the hydroxyl group on the asymmetric carbon.

Original languageEnglish
Pages (from-to)1299-1308
Number of pages10
JournalMolecular Immunology
Volume25
Issue number12
DOIs
Publication statusPublished - 1988
Externally publishedYes

Fingerprint

hydroxymaprotilin
Monoclonal Antibodies
Pharmaceutical Preparations
Stereoisomerism
Antibodies
Hybridomas
Bovine Serum Albumin
Hydroxyl Radical
Population
Anti-Idiotypic Antibodies
Immunization
Carbon
Spleen
Rabbits

ASJC Scopus subject areas

  • Immunology
  • Medicine(all)
  • Molecular Biology

Cite this

Stereospecific immuno-recognition of the tetracyclic anti-depressant oxaprotiline. / Chouchane, Lotfi; Strosberg, A. Donny; Hoebeke, J.

In: Molecular Immunology, Vol. 25, No. 12, 1988, p. 1299-1308.

Research output: Contribution to journalArticle

Chouchane, Lotfi ; Strosberg, A. Donny ; Hoebeke, J. / Stereospecific immuno-recognition of the tetracyclic anti-depressant oxaprotiline. In: Molecular Immunology. 1988 ; Vol. 25, No. 12. pp. 1299-1308.
@article{153a64fd585147728765e3494249d5e4,
title = "Stereospecific immuno-recognition of the tetracyclic anti-depressant oxaprotiline",
abstract = "Immunization of a rabbit with a racemic mixture of (±)-oxaprotiline, conjugated to bovine serum albumin, resulted in two antibody populations with affinity constants 1.5 × 109 and 2.5 × 106 m-1. Both populations showed a higher affinity for the (-)-isomer than for the ( + )-isomer of the drug. Both stereoisomers of the drug were immunogenic in mice, but only the (-)-isomer was recognized with high affinity. Somatic fusion of the spleen of a mouse, immunized with the (-)-isomer yielded 12 hybridomas secreting monoclonal anti-oxaprotiline antibodies. Five of these monoclonal antibodies (MAbs) recognized both isomers, four bound more specifically to the (-)-isomer, one recognized the (+)-isomer and two were specific for the coupling arm. One of the MAbs was further analyzed to gain insight into the structural features of the drug involved in antibody recognition. This analysis suggested that the stereospecific recognition of oxaprotiline could be directly linked to the position of the hydroxyl group on the asymmetric carbon.",
author = "Lotfi Chouchane and Strosberg, {A. Donny} and J. Hoebeke",
year = "1988",
doi = "10.1016/0161-5890(88)90045-4",
language = "English",
volume = "25",
pages = "1299--1308",
journal = "Molecular Immunology",
issn = "0161-5890",
publisher = "Elsevier Limited",
number = "12",

}

TY - JOUR

T1 - Stereospecific immuno-recognition of the tetracyclic anti-depressant oxaprotiline

AU - Chouchane, Lotfi

AU - Strosberg, A. Donny

AU - Hoebeke, J.

PY - 1988

Y1 - 1988

N2 - Immunization of a rabbit with a racemic mixture of (±)-oxaprotiline, conjugated to bovine serum albumin, resulted in two antibody populations with affinity constants 1.5 × 109 and 2.5 × 106 m-1. Both populations showed a higher affinity for the (-)-isomer than for the ( + )-isomer of the drug. Both stereoisomers of the drug were immunogenic in mice, but only the (-)-isomer was recognized with high affinity. Somatic fusion of the spleen of a mouse, immunized with the (-)-isomer yielded 12 hybridomas secreting monoclonal anti-oxaprotiline antibodies. Five of these monoclonal antibodies (MAbs) recognized both isomers, four bound more specifically to the (-)-isomer, one recognized the (+)-isomer and two were specific for the coupling arm. One of the MAbs was further analyzed to gain insight into the structural features of the drug involved in antibody recognition. This analysis suggested that the stereospecific recognition of oxaprotiline could be directly linked to the position of the hydroxyl group on the asymmetric carbon.

AB - Immunization of a rabbit with a racemic mixture of (±)-oxaprotiline, conjugated to bovine serum albumin, resulted in two antibody populations with affinity constants 1.5 × 109 and 2.5 × 106 m-1. Both populations showed a higher affinity for the (-)-isomer than for the ( + )-isomer of the drug. Both stereoisomers of the drug were immunogenic in mice, but only the (-)-isomer was recognized with high affinity. Somatic fusion of the spleen of a mouse, immunized with the (-)-isomer yielded 12 hybridomas secreting monoclonal anti-oxaprotiline antibodies. Five of these monoclonal antibodies (MAbs) recognized both isomers, four bound more specifically to the (-)-isomer, one recognized the (+)-isomer and two were specific for the coupling arm. One of the MAbs was further analyzed to gain insight into the structural features of the drug involved in antibody recognition. This analysis suggested that the stereospecific recognition of oxaprotiline could be directly linked to the position of the hydroxyl group on the asymmetric carbon.

UR - http://www.scopus.com/inward/record.url?scp=0024271498&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0024271498&partnerID=8YFLogxK

U2 - 10.1016/0161-5890(88)90045-4

DO - 10.1016/0161-5890(88)90045-4

M3 - Article

VL - 25

SP - 1299

EP - 1308

JO - Molecular Immunology

JF - Molecular Immunology

SN - 0161-5890

IS - 12

ER -