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Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
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JoVE Journal Chemistry
Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

DOI:
10.3791/59063-v

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08:47 min

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March 06, 2019

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, , ,
1Department of Chemistry,Hunter College of the City University of New York, 2Ph.D. Program in Chemistry,Graduate Center of the City University of New York, 3Department of Radiology,Memorial Sloan Kettering Cancer Center, 4Department of Radiology,Weill Cornell Medical College

Chapters

  • 00:04Title
  • 00:28Synthesis of 4-[5-(methylthio)-1,3,4-oxadiazol-2-yl]-aniline (1)
  • 01:15Synthesis of Tert-butyl[18-({4-[5-(methylthio)-1,3,4-oxadiazol-2-yl]phenyl}amino)-15,18-dioxo-4,7,10-trioxa-14-azaoctadecyl] Carbamate (2)
  • 03:00Synthesis of Tert-butyl[18-({4-[5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl]phenyl}amino)-15,18-dioxo-4,7,10-trioxa-14-azaoctadecyl] Carbamate (3)
  • 03:55Synthesis of N1-(3-{2-[2-(3-aminopropoxy)ethoxy]-ethoxy}propyl)-N4-{4-[5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl] phenyl}Succinamide (PODS)
  • 04:47Synthesis of PODS-DOTA and Bioconjugation of PODS-DOTA to Trastuzumab
  • 06:05Results: Synthesis of PODS and PODS-DOTA and Conjugation to Trastuzumab
  • 08:01Conclusion

Summary

Automatic Translation

Automatic Translation

In this protocol, we will describe the synthesis of PODS, a phenyoxadiazolyl methyl sulfone-based reagent for the site-selective attachment of cargos to the thiols of biomolecules, particularly antibodies. In addition, we will describe the synthesis and characterization of a PODS-bearing bifunctional chelator and its conjugation to a model antibody.

Tags

Keywords: Thiol-reactive ReagentsSite-specific BioconjugationImmunoconjugatesPODSMaleimide-thiol-based BioconjugationAminophenyl Oxadiazole ThiolDiisopropylethylamineIodomethaneBoc-protected Carboxylic AcidDichloromethaneEDCIAnilineHydrochloric AcidSodium CarbonateMagnesium SulfateEthyl AcetateCyclohexaneCarbamateM-chloroperbenzoic Acid

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