Protocols for lysine conjugation

Methods in Molecular Biology

Volumn 1045, Issue , 2013, Pages 173-187

  Brun, Marie Priscille ^a   Gauzy Lazo, Laurence ^a  

^a SANOFI   (France)

Author keywords

Activated ester; Disulfide cross linker; Iminothiolane; Iodoacetamido cross linker; Lysine conjugation; Maleimido cross linker; One and two step conjugation

Indexed keywords

BENZENE DERIVATIVE; BENZODIAZEPINE; CANTUZUMAB RAVTANSINE; CYSTEINE; CYTOTOXIC AGENT; DISULFIDE; DRUG ANTIBODY; GLYCERYL TRINITRATE; INOTUZUMAB OZOGAMICIN; LYSINE; MAYTANSINE; MONOCLONAL ANTIBODY; SAR 3419; SUCCINIMIDE DERIVATIVE; TOMAYMYCIN; TRASTUZUMAB; TRASTUZUMAB EMTANSINE; TUBULIN; UNCLASSIFIED DRUG;

ARTICLE; CLINICAL PROTOCOL; DRUG CONJUGATION; DRUG STRUCTURE; GENE TARGETING; HYDROPHOBIC INTERACTION CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL;

EID: 84934441628     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-62703-541-5_10     Document Type: Article

References (33)

1. Traut RR, Bollen A, Sun T-T, Hershey WB, Sundberg J, Pierce LR (1973) Methyl 4-mercaptobutyrimidate as a cleavable crosslinking reagent and its application to Escherichia coli 30S ribosome. Biochemistry 12:3266-3273
2. Wilbur DS (1992) Radiohalogenation of proteins: An overview of radionuclides, labeling methods, and reagents for conjugate labeling. Bioconjugate Chem 3:433-470
3. Wang L, Amphlett G, Blattler WA, Lambert JM, Zhang W (2005) Structural characterization of the maytansinoid-monoclonal antibody conjugate, huN901-DM1, by mass spectroscopy. Protein Sci 14:2436-2446
4. Jobbagy A, Kiraly K (1966) Chemical characterization of fluorescein isothiocyanate-protein conjugates. Biochim Biophys Acta 124:166
5. Chen Q, Sowa D, Gabathuler R (2004) The use of isocyanate linkers to make hydrolyzable active agent biopolymer conjugates. WO2004/008101
6. Wilbur DS, Chyan M-K, Nakamae H, Chen Y, Hamlin DK, Santos EB, Kornblit BT, Sandmaier BM (2012) Reagents for astatination of biomolecules. 6. An intact antibody conjugated with a maleimido-closo-decaborate(2-) reagent via sulfhydryl groups had considerably higher kidney concentrations than the same antibody conjugated with an isothiocyanatocloso-decaborate(2-) reagent via lysine amines. Bioconjugate Chem 23:409-420
7. Gavrilyuk JI, Wuellner U, Barbas CF III (2009) β-Lactam-based approach for the chemical programming of aldolase antibody 38C2. Bioorg Med Chem Lett 19:1421-1424
8. Gavrilyuk JI, Wuellner U, Salahuddin S, Goswami RK, Sinha SC, Barbas CF III (2009) An efficient chemical approach to bispecific antibodies and antibodies of high valency. Bioorg Med ChemLett 19:3716-3720
9. Tietze LF, Goerlach A, Beller M (1988) Glycosidation, X. Synthesis of glycoconjugates of acetal-glycosides with lysine and tripeptides for selective cancer therapy. Liebigs Ann Chem 565-577
10. Mier W, Hoffend J, Kramer S, Schuhmacher J, Hull WE, Eisenhut M, Haberkorn U (2005) Conjugation of DOTA using isolated phenolic active esters: The labeling and biodistribution of albumin as blood pool marker. Bioconjugate Chem 16:237-240
11. Singh R, Kovtun Y, Wilhelm SD, Chari R (2010) Potent conjugates and hydrophilic linkers. WO2010/126551
12. Bouchard H, Commerçon A, Fromond C, Mikol V, Parker F, Sassoon I, Tavares D (2011) New maytansinoids and the use of said maytansinoids to prepare conjugates with an antibody. WO2011/039721
13. Bouchard H, Chari RVJ, Commerçon A, Deng Y (2009) Cytotoxic agents comprising new tomaymycin derivatives and their therapeutic use. WO2009/016516
14. Li W, Fishkin NE, Zhao RY, Miller ML, Chari RVJ (2010) Novel benzodiazepine derivatives. WO2010/091150
15. Commerçon A, Gauzy-Lazo L (2011) Conjugates of pyrrolo[1,4]benzodiazepine dimers as anticancer agents. WO2011/023883
16. Hinman LM, Hamann PR, Wallace R, Menendez AT, Durr FE, Upeslacis J (1993) Preparation and characterization of monoclonal antibody conjugates of the calicheamicins: A novel and potent family of antitumor antibiotics. Cancer Res 53:3336-3342
17. Hamann PR, Hinman LM, Beyer CF, Lindh D, Upeslacis J, Flowers DA, Bernstein I (2002) An anti-CD33 antibody-calicheamicin conjugate for treatment of acute myeloid leukemia. Choice of linker. Bioconjugate Chem 13:40-46
18. Hamann PR, Hinman LM, Hollander I, Beyer CF, Lindh D, Holcomb R, Hallett W, Tsou HR, Upeslacis J, Shochat D, Mountain A, Flowers DA, Bernstein I (2002) Gemtuzumab ozogamicin, a potent and selective anti-CD33 antibody-calicheamicin conjugate for treatment of acute myeloid leukemia. Bioconjugate Chem 13:47-58
19. Lewis Phillips GD, LiG,Dugger DL,Crocker LM, Parsons KL, Elaine Mai E, Blattler WA, Lambert JM, Chari RVJ, Lutz RJ,WongWLT, Jacobson FS, Koeppen H, Schwall RH, Kenkare-Mitra SR, Spencer SD, Sliwkowski MX (2008) Targeting HER2-positive breast cancer with Trastuzumab-DM1, an antibody-cytotoxic drug conjugate. Cancer Res 68:9280-9290
20. Gauzy L, Zhao R, Deng Y, Li W, Bouchard H, Chari RVJ, Commerçon A (2007) Cytotoxic agents comprising new tomaymycin derivatives and their therapeutic use. WO2007/085930
21. Chari RVJ, Zhao RY, Kovtun Y, Singh R, Widdison WC (2009) Cross-linkers and their uses. WO2009/134977
22. Singh R, Kovtun Y, Wilhelm SD, Chari RVJ (2009) Potent conjugates and hydrophilic linkers. WO2009/134976
23. Zhao RY, Wilhelm SD, Audette C, Jones G, Leece BA, Lazar AC, Goldmacher VS, Singh R, Kovtun Y, Widdison WC, Lambert JM, Chari RVJ (2011) Synthesis and evaluation of hydrophilic linkers for antibody maytansinoid conjugates. J Med Chem 54:3606-3623
24. Steeves R, Lutz R, Chari R, Xie H, Kovtun Y (2005) Method of targeting specific cell populations using cell-binding agent maytansinoids conjugates linked via a non-cleavable linker, said conjugates, and methods of making said conjugates. WO2005/037992
25. Chari RVJ, Widdison WC (2004) Cytotoxic agents comprising new maytansinoids. US2004/0235840
26. Widdison WC, Wilhelm SD, Cavanagh EE, Whiteman KR, Leece BA, Kovtun Y, Goldmacher VS, Xie H, Steeves RM, Lutz RJ, Zhao R, Wang L, Blattler WA, Chari RVJ (2006) Semisynthetic maytansine analogues for the targeted treatment of cancer. J Med Chem 49:4392-4408
27. Lambert JM (2010) Antibody-maytansinoid conjugates: A new strategy for the treatment of cancer. Drugs Future 35:471-480
28. Blanc V, Bousseau A, Caron A, Carrez C, Lutz RJ, Lambert JL (2011) SAR3419: An anti-CD19-maytansinoid immunoconjugate for the treatment of B-cell malignancies. Clin Cancer Res 17:6448-6458
29. Bouchard H, Brun M-P, Commerçon A, Zhang J (2011) Novel conjugates, preparation thereof, and therapeutic use thereof. WO2011/001052
30. Widdison WC (2004) Cross-linkers with high reactivity and solubility and their use in the preparation of conjugates for targeted delivery of small molecule drugs. WO2004/016801
31. Kellogg BA, Garrett L, Kovtun Y, Lai KC, Leece B, Miller M, Payne G, Steeves R, Whiteman KR, Widdison W, Xie H, Singh R, Chari RVJ, Lambert JM, Lutz RJ (2011) Disulfidelinked antibody-maytansinoid conjugates: Optimization of in vivo activity by varying the steric hindrance at carbon atoms adjacent to the disulfide linkage. Bionconjugate Chem 22:717-727
32. Carroll SF, Goff DA (1990) Hindered linking agents and methods. WO1990/06774
33. King DJ, Terrett JA, Gangwar S, Cardarelli JM, Raonaik C, Pan C (2009) Conjugates of anti-RG1 antibodies. WO2009/073524