title: N-Sulfonyl-β-lactam hapten as an effective labeling reagent for aldolase mAb.
abstract: Utilization of chemically programmed antibodies (cpAbs) is regarded to be one of the most efficient methods for the development of therapeutic systems. cpAbs can extend the half-life of programming reagents, activate immune systems via the Fc region of antibodies and achieve universal vaccination by attaching varieties of small, programmed molecules. In the current study, we aimed to develop a novel labeling reagent for the preparation of cpAbs and found that N-sulfonyl-β-lactams (NSBLs) were optimal. NSBL can be synthesized from readily available 4-(bromomethyl)benzenesulfonyl chloride via few simple manipulations and can label the aldolase monoclonal antibody (mAb) 84G3, which could not be labeled effectively by the conventional labeling reagent, N-acyl-β-lactam (NABL). We also demonstrated that the conjugate, which consists of mAb 84G3 and an NSBL bearing a biotin moiety, maintained strong binding activity to streptavidin. In addition, the stability assay of NSBL revealed that NSBLs can tolerate aqueous media without significant decomposition over 24h.
authors: The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States. Electronic address: tinokuma@tokushima-u.ac.jp.
authors: Tsubasa
authors: T
authors: Inokuma
authors: The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States.
authors: Roberta P
authors: RP
authors: Fuller
authors: The Skaggs Institute for Chemical Biology and the Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States.
authors: Carlos F
authors: CF
authors: Barbas
mesh_terms: D000911:Antibodies, Monoclonal / Q000737:chemistry* / Q000276:immunology; D000937:Antigen-Antibody Reactions; D001710:Biotin / Q000737:chemistry / Q000378:metabolism; D005634:Fructose-Bisphosphate Aldolase / Q000737:chemistry* / Q000276:immunology; D006241:Haptens / Q000737:chemistry*; D007140:Immunoglobulin Fab Fragments / Q000737:chemistry* / Q000276:immunology; D011485:Protein Binding; D055550:Protein Stability; D019809:Streptavidin / Q000737:chemistry / Q000378:metabolism; D047090:beta-Lactams / Q000737:chemistry*
chemical_list: D000911:Antibodies, Monoclonal; D006241:Haptens; D007140:Immunoglobulin Fab Fragments; D047090:beta-Lactams; D001710:Biotin; D019809:Streptavidin; C109536:antibody aldolase; D005634:Fructose-Bisphosphate Aldolase
keywords: Aldolase antibody; Bioconjugation; Chemically programmed antibody; N-Sulfonyl-β-lactam