CBTF: New amine-to-thiol coupling reagent for preparation of antibody conjugates with increased plasma stability

Bioconjugate Chemistry

Volumn 26, Issue 2, 2015, Pages 197-200

  Kolodych, Sergii ^a   Koniev, Oleksandr ^a   Baatarkhuu, Zoljargal ^a   Bonnefoy, Jean Yves ^b   Debaene, François ^a,c   Cianférani, Sarah ^a,c   Van Dorsselaer, Alain ^a,c   Wagner, Alain ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b Syndivia SAS   (France)

^c INSTITUT DE RECHERCHES SUBATOMIQUES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; BLOOD; CHEMICAL REACTIONS;

ACTIVATED ESTER; ANTIBODY CONJUGATE; ANTIBODY-DRUG CONJUGATES; BLOOD CIRCULATION; COUPLING REAGENTS; HUMAN BLOOD PLASMAS; MALEIMIDE GROUP; MALEIMIDES; THERAPEUTIC EFFICACY;

PLASMA STABILITY;

AMINE; ANTIBODY CONJUGATE; MALEIMIDE; MALEIMIDE DERIVATIVE; NITRILE; REAGENT; SODIUM 4 [[4 (CYANOETHYNYL)BENZOYL]OXY] 2,3,5,6 TETRA FLUOROBENZENESULFONATE; THIOL; UNCLASSIFIED DRUG; BENZENE DERIVATIVE; CROSS LINKING REAGENT; THIOL DERIVATIVE;

ARTICLE; CROSS COUPLING REACTION; DRUG STABILITY; HUMAN; BLOOD; CELL LINE; CHEMISTRY; HALOGENATION;

AMINES; BENZENE DERIVATIVES; CELL LINE; CROSS-LINKING REAGENTS; HALOGENATION; HUMANS; IMMUNOCONJUGATES; MALEIMIDES; SULFHYDRYL COMPOUNDS;

EID: 84923225838     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc500610g     Document Type: Article

References (24)

1. Hermanson, G. T. (2008) Bioconjugate Techniques, 2 nd ed, Academic Press.
2. Baslé, E., Joubert, N., and Pucheault, M. (2010) Protein chemical modification on endogenous amino acids Chem. Biol. 17, 213-227
3. Brotzel, F. and Mayr, H. (2007) Nucleophilicities of amino acids and peptides Org. Biomol. Chem. 5, 3814-3820
4. Anderson, G. W., Zimmerman, J. E., and Callahan, F. M. (1964) The use of esters of N-hydroxysuccinimide in peptide synthesis J. Am. Chem. Soc. 86, 1839-1842
5. Kisfaludy, L., Roberts, J. E., Johnson, R. H., Mayers, G. L., and Kovacs, J. (1970) Synthesis of N-carbobenzoxyamino acid and peptide pentafluorophenyl esters as intermediates in peptide synthesis J. Org. Chem. 35, 3563-3565
6. Staros, J. V. (1982) N-Hydroxysulfosuccinimide active esters: bis(N-hydroxysulfosuccinimide) esters of two dicarboxylic acids are hydrophilic, membrane-impermeant, protein cross-linkers Biochemistry 21, 3950-3955
7. Koniev, O., Leriche, G., Nothisen, M., Remy, J.-S., Strub, J.-M., Schaeffer-Reiss, C., Van Dorsselaer, A., Baati, R., and Wagner, A. (2014) Selective irreversible chemical tagging of cysteine with 3-arylpropiolonitriles Bioconjugate Chem. 25, 202-206
8. Shen, B.-Q., Xu, K., Liu, L., Raab, H., Bhakta, S., Kenrick, M., Parsons-Reponte, K. L., Tien, J., Yu, S.-F., and Mai, E. 2012, Conjugation site modulates the in vivo stability and therapeutic activity of antibody-drug conjugates Nat. Biotechnol. 30, 184-189
9. Alley, S. C., Okeley, N. M., and Senter, P. D. (2010) Antibody-drug conjugates: targeted drug delivery for cancer Curr. Opin. Chem. Biol. 14, 529-537
10. Beck, A. and Reichert, J. M. (2014) Antibody-drug conjugates present and future MAbs 6, 15-17
11. Klinguer-Hamour, C., Strop, P., Shah, D. K., Ducry, L., Xu, A., and Beck, A. (2014) World antibody-drug conjugate summit, october 15-16, 2013, San Francisco, CA MAbs 6, 18-29
12. Lu, D., Jin, J. Y., Girish, S., Agarwal, P., Li, D., Prabhu, S., Dere, R. C., Saad, O. M., Nazzal, D., Koppada, N., and Ramanujan, S. 2014, Semi-mechanistic multiple-analyte pharmacokinetic model for an antibody-drug-conjugate in cynomolgus monkeys Pharm. Res. 10.1007/s11095-014-1585-y
13. Xu, K., Liu, L., Dere, R., Mai, E., Erickson, R., Hendricks, A., Lin, K., Junutula, J. R., and Kaur, S. (2013) Characterization of the drug-to-antibody ratio distribution for antibody-drug conjugates in plasma/serum Bioanalysis 5, 1057-1071
14. Bender, B., Leipold, D. D., Xu, K., Shen, B.-Q., Tibbitts, J., and Friberg, L. E. (2014) A mechanistic pharmacokinetic model elucidating the disposition of trastuzumab emtansine (T-DM1), an antibody-drug conjugate (ADC) for treatment of metastatic breast cancer AAPS J. 16, 994-1008
15. Tumey, L. N., Charati, M., He, T., Sousa, E., Ma, D., Han, X., Clark, T., Casavant, J., Loganzo, F., and Barletta, F. 2014, Mild method for succinimide hydrolysis on ADCs: impact on ADC potency, stability, exposure, and efficacy Bioconjugate Chem. 25, 1871-1880
16. Lyon, R. P., Setter, J. R., Bovee, T. D., Doronina, S. O., Hunter, J. H., Anderson, M. E., Balasubramanian, C. L., Duniho, S. M., Leiske, C. I., and Li, F. 2014, Self-hydrolyzing maleimides improve the stability and pharmacological properties of antibody-drug conjugates Nat. Biotechnol. 32, 1059-1062
17. Fontaine, S. D., Reid, R., Robinson, L., Ashley, G. W., and Santi, D. V. (2015) Long-term stabilization of maleimide-thiol conjugates Bioconjugate Chem. 26, 145-152 10.1021/bc5005262
18. Agarwal, P. and Bertozzi, C. R. (2015) Site-specific antibody-drug conjugates: the nexus of bioorthogonal chemistry, protein engineering, and drug development Bioconjugate Chem. 10.1021/bc5004982
19. Patterson, J. T., Asano, S., Li, X., Rader, C., and Barbas, C. F. (2014) Improving the serum stability of site-specific antibody conjugates with sulfone linkers Bioconjugate Chem. 25, 1402-1407
20. Abbas, A., Xing, B., and Loh, T.-P. (2014) Allenamides as orthogonal handles for selective modification of cysteine in peptides and proteins Angew. Chem., Int. Ed. 53, 7491-7494
21. Toda, N., Asano, S., and Barbas, C. F. (2013) Rapid, stable, chemoselective labeling of thiols with Julia-Kocieński-like reagents: a serum-stable alternative to maleimide-based protein conjugation Angew. Chem., Int. Ed. 52, 12592-12596
22. McAllister, G. D., Wilfred, C. D., and Taylor, R. J. (2002) Tandem oxidation processes: the direct conversion of activated alcohols into nitriles Synlett 1291-1292
23. Debaene, F., Bœuf, A., Wagner-Rousset, E., Colas, O., Ayoub, D., Corvaïa, N., Van Dorsselaer, A., Beck, A., and Cianférani, S. (2014) Innovative native MS methodologies for antibody drug conjugate characterization: high resolution native MS and IM-MS for average DAR and DAR distribution assessment Anal. Chem. 86, 10674-10683
24. http://syndivia.com/products.