Improved synthesis of 6-[p-(bromoacetamido)benzyl]-1,4,8,11-tetraazacyclotetradecane-N,N′, N″,N‴-tetraacetic acid and development of a thin-layer assay for thiol-reactive bifunctional chelating agents

Justin K. Moran, Douglas P. Greiner, Claude F. Meares

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Monoclonal antibodies labeled with radiometals such as copper-67 have applications in radioimmunodiagnosis and radioimmunotherapy. Moi et al. [(1985) Anal. Biochem. 148, 249-253] showed that 6-[p-(bromoacetamido)benzyl]-1,4,8,11-tetraazacyclotetradecane-N,N′, N″,N‴-tetraacetic acid (BAT) is an effective reagent for linking copper to proteins, and antibodies labeled with copper radionuclides are currently undergoing clinical trials. Here we describe improvements in the original synthesis that increase the overall yield of BAT to 23%. We also describe a new assay useful to determine the activity of bifunctional chelating agents with thiol-reactive functional groups.

Original languageEnglish (US)
Pages (from-to)296-301
Number of pages6
JournalBioconjugate Chemistry
Volume6
Issue number3
StatePublished - 1995

Fingerprint

Chelating Agents
Chelation
Sulfhydryl Compounds
Copper
Assays
Acids
Radioimmunotherapy
Monoclonal antibodies
Radioisotopes
Antibodies
Functional groups
Monoclonal Antibodies
Clinical Trials
Proteins
cyclam

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Clinical Biochemistry
  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

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title = "Improved synthesis of 6-[p-(bromoacetamido)benzyl]-1,4,8,11-tetraazacyclotetradecane-N,N′, N″,N‴-tetraacetic acid and development of a thin-layer assay for thiol-reactive bifunctional chelating agents",
abstract = "Monoclonal antibodies labeled with radiometals such as copper-67 have applications in radioimmunodiagnosis and radioimmunotherapy. Moi et al. [(1985) Anal. Biochem. 148, 249-253] showed that 6-[p-(bromoacetamido)benzyl]-1,4,8,11-tetraazacyclotetradecane-N,N′, N″,N‴-tetraacetic acid (BAT) is an effective reagent for linking copper to proteins, and antibodies labeled with copper radionuclides are currently undergoing clinical trials. Here we describe improvements in the original synthesis that increase the overall yield of BAT to 23{\%}. We also describe a new assay useful to determine the activity of bifunctional chelating agents with thiol-reactive functional groups.",
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year = "1995",
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T1 - Improved synthesis of 6-[p-(bromoacetamido)benzyl]-1,4,8,11-tetraazacyclotetradecane-N,N′, N″,N‴-tetraacetic acid and development of a thin-layer assay for thiol-reactive bifunctional chelating agents

AU - Moran, Justin K.

AU - Greiner, Douglas P.

AU - Meares, Claude F.

PY - 1995

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AB - Monoclonal antibodies labeled with radiometals such as copper-67 have applications in radioimmunodiagnosis and radioimmunotherapy. Moi et al. [(1985) Anal. Biochem. 148, 249-253] showed that 6-[p-(bromoacetamido)benzyl]-1,4,8,11-tetraazacyclotetradecane-N,N′, N″,N‴-tetraacetic acid (BAT) is an effective reagent for linking copper to proteins, and antibodies labeled with copper radionuclides are currently undergoing clinical trials. Here we describe improvements in the original synthesis that increase the overall yield of BAT to 23%. We also describe a new assay useful to determine the activity of bifunctional chelating agents with thiol-reactive functional groups.

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