Site-Specific Lysine Arylation as an Alternative Bioconjugation Strategy for Chemically Programmed Antibodies and Antibody–Drug Conjugates
By exploiting a uniquely reactive lysine residue (Lys99) for site-specific attachment of small molecules, the humanized catalytic antibody h38C2 has been used as bioconjugation module in the assembly of chemically programmed antibodies and antibody–drug conjugates. Treatment of h38C2 with β-lactam-f...
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Published in | Bioconjugate chemistry Vol. 30; no. 11; pp. 2889 - 2896 |
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Main Authors | , , , , |
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Language | English |
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20.11.2019
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Abstract | By exploiting a uniquely reactive lysine residue (Lys99) for site-specific attachment of small molecules, the humanized catalytic antibody h38C2 has been used as bioconjugation module in the assembly of chemically programmed antibodies and antibody–drug conjugates. Treatment of h38C2 with β-lactam-functionalized small molecules has been previously shown to result in covalent conjugation by selective formation of a stable amide bond with the ε-amino group of the Lys99 residue. Here we report that heteroaryl methylsulfonyl (MS-PODA)-functionalized small molecules represent an alternative bioconjugation strategy through highly efficient, site-specific, and stable arylation of the Lys99 residue. A set of chemically programmed antibodies and antibody–drug conjugates assembled by Lys99 arylation provided proof-of-concept for the therapeutic utility of this alternative bioconjugation strategy. While being equally effective as β-lactam-functionalized ligands for bioconjugation with catalytic antibody h38C2, the MS-PODA moiety offers distinct synthetic advantages, making it highly attractive. |
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AbstractList | By exploiting a uniquely reactive lysine residue (Lys99) for site-specific attachment of small molecules, the humanized catalytic antibody h38C2 has been used as bioconjugation module in the assembly of chemically programmed antibodies and antibody-drug conjugates. Treatment of h38C2 with β-lactam-functionalized small molecules has been previously shown to result in covalent conjugation by selective formation of a stable amide bond with the ε-amino group of the Lys99 residue. Here we report that heteroaryl methylsulfonyl (MS-PODA)-functionalized small molecules represent an alternative bioconjugation strategy through highly efficient, site-specific, and stable arylation of the Lys99 residue. A set of chemically programmed antibodies and antibody-drug conjugates assembled by Lys99 arylation provided proof-of-concept for the therapeutic utility of this alternative bioconjugation strategy. While being equally effective as β-lactam-functionalized ligands for bioconjugation with catalytic antibody h38C2, the MS-PODA moiety offers distinct synthetic advantages, making it highly attractive. By exploiting a uniquely reactive lysine residue (Lys99) for site-specific attachment of small molecules, the humanized catalytic antibody h38C2 has been used as bioconjugation module in the assembly of chemically programmed antibodies and antibody-drug conjugates. Treatment of h38C2 with beta-lactam-functionalized small molecules has been previously shown to result in covalent conjugation by selective formation of a stable amide bond with the epsilon-amino group of the Lys99 residue. Here we report that heteroaryl methylsulfonyl (MS-PODA)-functionalized small molecules represent an alternative bioconjugation strategy through highly efficient, site-specific, and stable arylation of the Lys99 residue. A set of chemically programmed antibodies and antibody-drug conjugates assembled by Lys99 arylation provided proof-of-concept for the therapeutic utility of this alternative bioconjugation strategy. While being equally effective as beta-lactam-functionalized ligands for bioconjugation with catalytic antibody h38C2, the MS-PODA moiety offers distinct synthetic advantages, making it highly attractive. |
Author | Park, HaJeung Burke, Terrence R Tsuji, Kohei Hwang, Dobeen Rader, Christoph |
AuthorAffiliation | Department of Immunology and Microbiology X-ray Crystallography Core Chemical Biology Laboratory, Center for Cancer Research |
AuthorAffiliation_xml | – name: – name: Chemical Biology Laboratory, Center for Cancer Research – name: X-ray Crystallography Core – name: Department of Immunology and Microbiology – name: Department of Immunology and Microbiology, The Scripps Research Institute, Jupiter, FL 33458, USA – name: Chemical Biology Laboratory, Center for Cancer Research, National Cancer Institute, National Institutes of Health, Frederick, MD 21702, USA – name: X-Ray Crystallography Core, The Scripps Research Institute, Jupiter, FL 33458, USA |
Author_xml | – sequence: 1 givenname: Dobeen surname: Hwang fullname: Hwang, Dobeen – sequence: 2 givenname: Kohei surname: Tsuji fullname: Tsuji, Kohei organization: Chemical Biology Laboratory, Center for Cancer Research – sequence: 3 givenname: HaJeung surname: Park fullname: Park, HaJeung – sequence: 4 givenname: Terrence R orcidid: 0000-0001-9925-8586 surname: Burke fullname: Burke, Terrence R organization: Chemical Biology Laboratory, Center for Cancer Research – sequence: 5 givenname: Christoph orcidid: 0000-0001-9955-3454 surname: Rader fullname: Rader, Christoph email: crader@scripps.edu |
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Snippet | By exploiting a uniquely reactive lysine residue (Lys99) for site-specific attachment of small molecules, the humanized catalytic antibody h38C2 has been used... |
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SubjectTerms | Amides Antibodies Biochemical Research Methods Biochemistry & Molecular Biology Chemistry Chemistry, Multidisciplinary Chemistry, Organic Conjugates Conjugation Immunoglobulins Life Sciences & Biomedicine Lysine Organic chemistry Physical Sciences Science & Technology Strategy β-Lactam antibiotics |
Title | Site-Specific Lysine Arylation as an Alternative Bioconjugation Strategy for Chemically Programmed Antibodies and Antibody–Drug Conjugates |
URI | http://dx.doi.org/10.1021/acs.bioconjchem.9b00609 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000499743100018 https://www.ncbi.nlm.nih.gov/pubmed/31675216 https://www.proquest.com/docview/2319471499 https://search.proquest.com/docview/2311656669 https://pubmed.ncbi.nlm.nih.gov/PMC7518637 |
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