Literature DB >> 8667077

Bifunctional NHS-BAT ester for antibody conjugation and stable technetium-99m labeling: conjugation chemistry, immunoreactivity and kit formulation.

M Eisenhut1, W D Lehmann, W Becker, T Behr, H Elser, W Strittmatter, A Steinsträsser, R P Baum, T Valerius, R Repp, Y Deo.   

Abstract

UNLABELLED: Conjugation chemistry and kit formulated binding of the NHS ester of 6-(4'-(4"-carboxyphenoxy)butyl)-2, 10-dimercapto-2,10-dimethyl-4,8-diazaundecane (NHS-BAT ester) to monoclonal antibodies (MAbs) was investigated. The functionalities of the resulting BAT conjugated and 99mTc-labeled MAbs BW 431/26, MAb 425 and bispecific MDX210 (fragment construct) were tested by immunoreactivity and immunoscintigraphy.
METHODS: The kinetics and chemistry of the conjugation reaction were monitored by high-performance liquid chromatography, size-exclusion chromatography and positive fast-atom-bombardment mass spectra (FAB-MS). The 99mTc BAT-MAbs were tested with various immunoreactivity assays. The biodistribution of 99mTc-BAT-BW 431/26 in rats was compared with directly labeled BW 431/26.
RESULTS: At pH 8.5 and 25 degrees C, the reactivity of the NHS-BAT ester was high with 90% completion after 30 min. The conjugation yield of 19 microM MAb and 228 microM NHS-BAT ester amounted to 30%. Higher NHS-BAT ester concentrations afforded higher BAT-to-MAb ratios. According to FAB-MS, the conjugation competing hydrolysis surprisingly occurred at the NHS ring. Almost quantitative 99mTc labeling was achieved after 5 min at 25 degrees C. Immunoreactivity of the 99mTc-BAT antibodies showed > 90% recovery and proved to be insensitive to BAT-to-MAb ratios of up to 10. The 99mTc-BAT-BW 431/26 showed similar organ distribution but revealed less urinary excretion compared with the directly labeled BW 431/26. Immunoscintigraphy with 99mTc-labeled and BAT-BW 431/26 and BAT-MAb 425 showed the respective biological function in vivo.
CONCLUSION: According to straightforward conjugation chemistry, the ease of 99mTc labeling and the application of a simple ultrafiltration technique, the NHS-BAT ester represents a nondestructive, universally applicable biofunctional ligand to introduce stable 99mTc protein binding sites. Kit formulated conjugation/labeling can be performed with little time requirements and laboratory experience.

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Year:  1996        PMID: 8667077

Source DB:  PubMed          Journal:  J Nucl Med        ISSN: 0161-5505            Impact factor:   10.057


  3 in total

Review 1.  Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides.

Authors:  Shuang Liu
Journal:  Adv Drug Deliv Rev       Date:  2008-04-23       Impact factor: 15.470

2.  NHS-Functionalized THP Derivative for Efficient Synthesis of Kit-Based Precursors for 68Ga Labeled PET Probes.

Authors:  Giuseppe Floresta; George P Keeling; Siham Memdouh; Levente K Meszaros; Rafael T M de Rosales; Vincenzo Abbate
Journal:  Biomedicines       Date:  2021-04-01

3.  Phase I clinical trial of the bispecific antibody MDX-H210 (anti-FcgammaRI x anti-HER-2/neu) in combination with Filgrastim (G-CSF) for treatment of advanced breast cancer.

Authors:  R Repp; H H van Ojik; T Valerius; G Groenewegen; G Wieland; C Oetzel; B Stockmeyer; W Becker; M Eisenhut; H Steininger; Y M Deo; G H Blijham; J R Kalden; J G J van de Winkel; M Gramatzki
Journal:  Br J Cancer       Date:  2003-12-15       Impact factor: 7.640

  3 in total

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