Modulating Antibody–Drug Conjugate Payload Metabolism by Conjugation Site and Linker Modification

This article is cited by 49 publications.

1. Jeremy R. Duvall, Joshua D. Thomas, Raghida A. Bukhalid, Kalli C. Catcott, Keith W. Bentley, Scott D. Collins, Timothy Eitas, Brian D. Jones, Eugene W. Kelleher, Kelly Lancaster, Marina Protopopova, Soumya S. Ray, Elena Ter-Ovanesyan, Ling Xu, Liping Yang, Jeffrey Zurita, Marc Damelin, Dorin Toader, Timothy B. Lowinger. Discovery and Optimization of a STING Agonist Platform for Application in Antibody Drug Conjugates. Journal of Medicinal Chemistry 2023, 66 (15) , 10715-10733. https://doi.org/10.1021/acs.jmedchem.3c00907
2. Mark E. Petersen, Michael G. Brant, Manuel Lasalle, Vincent K. C. Fung, Andrea Hernandez Rojas, Jodi Wong, Samir Das, Stuart D. Barnscher, Jamie R. Rich, Geoffrey C. Winters. Structure–Activity Relationships of Bis-Intercalating Peptides and Their Application as Antibody–Drug Conjugate Payloads. Journal of Medicinal Chemistry 2023, 66 (12) , 8288-8309. https://doi.org/10.1021/acs.jmedchem.3c00760
3. Wei Shi, Jianxin Zhang, Liya Liu, Wanzhen Li, Zhi Liu, Anni Ren, Jie Wang, Caihong Tang, Yang Yang, Dandan Xu, Qianqian Huang, Yongqin Wang, Caili Luo, Wei Huang, Feng Tang. Hiding Payload Inside the IgG Fc Cavity Significantly Enhances the Therapeutic Index of Antibody–Drug Conjugates. Journal of Medicinal Chemistry 2023, 66 (1) , 1011-1026. https://doi.org/10.1021/acs.jmedchem.2c01812
4. Jeremy M. Quintana, David Arboleda, Huiyu Hu, Ella Scott, Gaurav Luthria, Sara Pai, Sareh Parangi, Ralph Weissleder, Miles A. Miller. Radiation Cleaved Drug-Conjugate Linkers Enable Local Payload Release. Bioconjugate Chemistry 2022, 33 (8) , 1474-1484. https://doi.org/10.1021/acs.bioconjchem.2c00174
5. Jorick J. Bruins, Johannes A. M. Damen, Marloes A. Wijdeven, Lianne P. W. M. Lelieveldt, Floris L. van Delft, Bauke Albada. Non-Genetic Generation of Antibody Conjugates Based on Chemoenzymatic Tyrosine Click Chemistry. Bioconjugate Chemistry 2021, 32 (10) , 2167-2172. https://doi.org/10.1021/acs.bioconjchem.1c00351
6. Matthew Giese, Paul D. Davis, Robert H. Woodman, Greg Hermanson, Alex Pokora, Melissa Vermillion. Linker Architectures as Steric Auxiliaries for Altering Enzyme-Mediated Payload Release from Bioconjugates. Bioconjugate Chemistry 2021, 32 (10) , 2257-2267. https://doi.org/10.1021/acs.bioconjchem.1c00429
7. Stepan Chuprakov, Ayodele O. Ogunkoya, Robyn M. Barfield, Maxine Bauzon, Colin Hickle, Yun Cheol Kim, Dominick Yeo, Fangjiu Zhang, David Rabuka, Penelope M. Drake. Tandem-Cleavage Linkers Improve the In Vivo Stability and Tolerability of Antibody–Drug Conjugates. Bioconjugate Chemistry 2021, 32 (4) , 746-754. https://doi.org/10.1021/acs.bioconjchem.1c00029
8. Jennifer J. Schmidt, Yogan Khatri, Scott I. Brody, Catherine Zhu, Halina Pietraszkiewicz, Frederick A. Valeriote, David H. Sherman. A Versatile Chemoenzymatic Synthesis for the Discovery of Potent Cryptophycin Analogs. ACS Chemical Biology 2020, 15 (2) , 524-532. https://doi.org/10.1021/acschembio.9b00998
9. Dian Su, Jinhua Chen, Ely Cosino, Josefa dela Cruz-Chuh, Helen Davis, Geoffrey Del Rosario, Isabel Figueroa, Leanne Goon, Jintang He, Amrita V. Kamath, Surinder Kaur, Katherine R. Kozak, Jeffrey Lau, Donna Lee, M. Violet Lee, Douglas Leipold, Luna Liu, Peter Liu, Guo-Liang Lu, Chris Nelson, Carl Ng, Thomas H. Pillow, Paul Polakis, Andrew G. Polson, Rebecca K. Rowntree, Ola Saad, Brian Safina, Nicola J. Stagg, Moana Tercel, Richard Vandlen, Breanna S. Vollmar, John Wai, Tao Wang, BinQing Wei, Keyang Xu, Juanjuan Xue, Zijin Xu, Gang Yan, Hui Yao, Shang-Fan Yu, Donglu Zhang, Fiona Zhong, Peter S. Dragovich. Antibody–Drug Conjugates Derived from Cytotoxic seco-CBI-Dimer Payloads Are Highly Efficacious in Xenograft Models and Form Protein Adducts In Vivo. Bioconjugate Chemistry 2019, 30 (5) , 1356-1370. https://doi.org/10.1021/acs.bioconjchem.9b00133
10. Zhonghua Pei, Chunjiao Chen, Jinhua Chen, Josefa dela Cruz-Chuh, Reginald Delarosa, Yuzhong Deng, Aimee Fourie-O’Donohue, Isabel Figueroa, Jun Guo, Weiwei Jin, S. Cyrus Khojasteh, Katherine R. Kozak, Brandon Latifi, James Lee, Guangmin Li, Eva Lin, Liling Liu, Jiawei Lu, Scott Martin, Carl Ng, Trung Nguyen, Rachana Ohri, Gail Lewis Phillips, Thomas H. Pillow, Rebecca K. Rowntree, Nicola J. Stagg, David Stokoe, Sheila Ulufatu, Vishal A. Verma, John Wai, Jing Wang, Keyang Xu, Zijin Xu, Hui Yao, Shang-Fan Yu, Donglu Zhang, Peter S. Dragovich. Exploration of Pyrrolobenzodiazepine (PBD)-Dimers Containing Disulfide-Based Prodrugs as Payloads for Antibody–Drug Conjugates. Molecular Pharmaceutics 2018, 15 (9) , 3979-3996. https://doi.org/10.1021/acs.molpharmaceut.8b00431
11. Chi Hun Song, Minchan Jeong, Hyukmin In, Ji Hoe Kim, Chih-Wei Lin, Kyung Ho Han. Trends in the Development of Antibody-Drug Conjugates for Cancer Therapy. Antibodies 2023, 12 (4) , 72. https://doi.org/10.3390/antib12040072
12. Fuzhuo Li, Heping Deng, Hans Renata. Chemoenzymatic approaches for exploring structure–activity relationship studies of bioactive natural products. Nature Synthesis 2023, 2 (8) , 708-718. https://doi.org/10.1038/s44160-023-00358-8
13. Joshua Hurwitz, Lucy Roxana Haggstrom, Elgene Lim. Antibody–Drug Conjugates: Ushering in a New Era of Cancer Therapy. Pharmaceutics 2023, 15 (8) , 2017. https://doi.org/10.3390/pharmaceutics15082017
14. Anupama Samantasinghar, Naina Pullarkat Sunildutt, Faheem Ahmed, Afaque Manzoor Soomro, Abdul Rahim Chethikkattuveli Salih, Pratibha Parihar, Fida Hussain Memon, Kyung Hwan Kim, In Suk Kang, Kyung Hyun Choi. A comprehensive review of key factors affecting the efficacy of antibody drug conjugate. Biomedicine & Pharmacotherapy 2023, 161 , 114408. https://doi.org/10.1016/j.biopha.2023.114408
15. Hany E. Marei, Carlo Cenciarelli, Anwarul Hasan. Potential of antibody–drug conjugates (ADCs) for cancer therapy. Cancer Cell International 2022, 22 (1) https://doi.org/10.1186/s12935-022-02679-8
16. Markus Walles, Michael Berna, Wenying Jian, Simon Hauri, Shawna Hengel, Lloyd King, John C. Tran, Cong Wei, Keyang Xu, Xiaochun Zhu. A Cross Company Perspective on the Assessment of Therapeutic Protein Biotransformation. Drug Metabolism and Disposition 2022, 50 (6) , 846-857. https://doi.org/10.1124/dmd.121.000462
17. Valerie M. Kramlinger, Deepak Dalvie, Carley J.S. Heck, Amit S. Kalgutkar, James O’Neill, Dian Su, Aaron M. Teitelbaum, Rheem A. Totah. Future of Biotransformation Science in the Pharmaceutical Industry. Drug Metabolism and Disposition 2022, 50 (3) , 258-267. https://doi.org/10.1124/dmd.121.000658
18. Jarosław Sączewski, Joanna Fedorowicz. Three Heterocyclic Rings Fused (6-5-6). 2022, 569-596. https://doi.org/10.1016/B978-0-12-409547-2.14881-4
19. Robert S. Foti. ADME of Biologicals and New Therapeutic Modalities. 2022, 716-742. https://doi.org/10.1016/B978-0-12-820472-6.00141-9
20. Yiming Jin, Megan A. Schladetsch, Xueting Huang, Marcy J. Balunas, Andrew J. Wiemer. Stepping forward in antibody-drug conjugate development. Pharmacology & Therapeutics 2022, 229 , 107917. https://doi.org/10.1016/j.pharmthera.2021.107917
21. M. Frigerio, N. Camper. Linker Design and Impact on ADC Properties. 2021, 71-135. https://doi.org/10.1039/9781839165153-00071
22. M. W. Giese, R. H. Woodman, G. T. Hermanson, P. D. Davis. The Use of Uniform PEG Compounds in the Design of ADCs. 2021, 286-376. https://doi.org/10.1039/9781839165153-00286
23. Anna Kaempffe, Stephan Dickgiesser, Nicolas Rasche, Andrea Paoletti, Elisa Bertotti, Ilse De Salve, Federico Riccardi Sirtori, Roland Kellner, Doreen Könning, Stefan Hecht, Jan Anderl, Harald Kolmar, Christian Schröter. Effect of Conjugation Site and Technique on the Stability and Pharmacokinetics of Antibody-Drug Conjugates. Journal of Pharmaceutical Sciences 2021, 110 (12) , 3776-3785. https://doi.org/10.1016/j.xphs.2021.08.002
24. Michael P. Luciano, Ivan Dingle, Saghar Nourian, Martin J. Schnermann. Preferential light-chain labeling of native monoclonal antibodies improves the properties of fluorophore conjugates. Tetrahedron Letters 2021, 75 , 153211. https://doi.org/10.1016/j.tetlet.2021.153211
25. Dian Su, Donglu Zhang. Linker Design Impacts Antibody-Drug Conjugate Pharmacokinetics and Efficacy via Modulating the Stability and Payload Release Efficiency. Frontiers in Pharmacology 2021, 12 https://doi.org/10.3389/fphar.2021.687926
26. K. C. Nicolaou, Stephan Rigol, Emmanuel N. Pitsinos, Dipendu Das, Yong Lu, Subhrajit Rout, Alexander W. Schammel, Dane Holte, Baiwei Lin, Christine Gu, Hetal Sarvaiya, Jose Trinidad, Nicole Barbour, Amanda M. Valdiosera, Joseph Sandoval, Christina Lee, Monette Aujay, Hanan Fernando, Anukriti Dhar, Holger Karsunky, Nicole Taylor, Marybeth Pysz, Julia Gavrilyuk. Uncialamycin-based antibody–drug conjugates: Unique enediyne ADCs exhibiting bystander killing effect. Proceedings of the National Academy of Sciences 2021, 118 (25) https://doi.org/10.1073/pnas.2107042118
27. Breanna S. Vollmar, Chris Frantz, Melissa M. Schutten, Fiona Zhong, Geoffrey del Rosario, Mary Ann T. Go, Shang-Fan Yu, Douglas D. Leipold, Amrita V. Kamath, Carl Ng, Keyang Xu, Josefa dela Cruz-Chuh, Katherine R. Kozak, Jinhua Chen, Zijin Xu, John Wai, Pragya Adhikari, Hans K. Erickson, Peter S. Dragovich, Andrew G. Polson, Thomas H. Pillow. Calicheamicin Antibody–Drug Conjugates with Improved Properties. Molecular Cancer Therapeutics 2021, 20 (6) , 1112-1120. https://doi.org/10.1158/1535-7163.MCT-20-0035
28. Joseph Z. Hamilton, Thomas A. Pires, Jamie A. Mitchell, Julia H. Cochran, Kim K. Emmerton, Margo Zaval, Ivan J. Stone, Martha E. Anderson, Steven Jin, Andrew B. Waight, Robert P. Lyon, Peter D. Senter, Scott C. Jeffrey, Patrick J. Burke. Improving Antibody‐Tubulysin Conjugates through Linker Chemistry and Site‐Specific Conjugation. ChemMedChem 2021, 16 (7) , 1077-1081. https://doi.org/10.1002/cmdc.202000889
29. Shang-Fan Yu, Donna W. Lee, Bing Zheng, Geoffrey del Rosario, Douglas Leipold, Helen Booler, Fiona Zhong, Montserrat Carrasco-Triguero, Kyu Hong, Peter Yan, Rebecca K. Rowntree, Melissa M. Schutten, Thomas Pillow, Jack D. Sadowsky, Peter S. Dragovich, Andrew G. Polson. An Anti–CD22- seco -CBI-Dimer Antibody–Drug Conjugate (ADC) for the Treatment of Non-Hodgkin Lymphoma That Provides a Longer Duration of Response than Auristatin-Based ADCs in Preclinical Models. Molecular Cancer Therapeutics 2021, 20 (2) , 340-346. https://doi.org/10.1158/1535-7163.MCT-20-0046
30. Michele Anselmi, Adina Borbély, Eduard Figueras, Carmela Michalek, Isabell Kemker, Luca Gentilucci, Norbert Sewald. Linker Hydrophilicity Modulates the Anticancer Activity of RGD–Cryptophycin Conjugates. Chemistry – A European Journal 2021, 27 (3) , 1015-1022. https://doi.org/10.1002/chem.202003471
31. Stephan Dickgiesser, Marcel Rieker, Nicolas Rasche. Antibody–Drug Conjugates. 2021, 189-214. https://doi.org/10.1007/978-3-030-54630-4_8
32. Byeong ill Lee, Seo-jin Park, Yuri Park, Seok-Ho Shin, Jang-mi Choi, Min-jae Park, Jeong-hyeon Lim, Sun Young Kim, Hyangsook Lee, Young G. Shin. Assessments of the In Vitro and In Vivo Linker Stability and Catabolic Fate for the Ortho Hydroxy-Protected Aryl Sulfate Linker by Immuno-Affinity Capture Liquid Chromatography Quadrupole Time-of-Flight Mass Spectrometric Assay. Pharmaceutics 2021, 13 (1) , 125. https://doi.org/10.3390/pharmaceutics13010125
33. Dane Holte, Joseph P. Lyssikatos, Amanda M. Valdiosera, Zachary Swinney, Vikram Sisodiya, Joseph Sandoval, Christina Lee, Monette A. Aujay, Robert B. Tchelepi, Omar M. Hamdy, Christine Gu, Baiwei Lin, Hetal Sarvaiya, Marybeth A. Pysz, Amy Laysang, Samuel Williams, Dong Jun Lee, Magda K. Holda, James W. Purcell, Julia Gavrilyuk. Evaluation of PNU-159682 antibody drug conjugates (ADCs). Bioorganic & Medicinal Chemistry Letters 2020, 30 (24) , 127640. https://doi.org/10.1016/j.bmcl.2020.127640
34. Victor Yip, Isabel Figueroa, Brandon Latifi, Shab Masih, Carl Ng, Doug Leipold, Amrita Kamath, Ben-Quan Shen. Anti–Lymphocyte Antigen 6 Complex, Locus E- Seco -Cyclopropabenzindol-4-One-Dimer Antibody-Drug Conjugate That Forms Adduct with α 1-Microglobulin Demonstrates Slower Systemic Antibody Clearance and Reduced Tumor Distribution in Animals. Drug Metabolism and Disposition 2020, 48 (12) , 1247-1256. https://doi.org/10.1124/dmd.120.000145
35. Laurence Gauzy-Lazo, Ingrid Sassoon, Marie-Priscille Brun. Advances in Antibody–Drug Conjugate Design: Current Clinical Landscape and Future Innovations. SLAS Discovery 2020, 25 (8) , 843-868. https://doi.org/10.1177/2472555220912955
36. Qinhuai Lai, Mengdan Wu, Ruixue Wang, Weirong Lai, Yiran Tao, Ying Lu, Yuxi Wang, Lin Yu, Ruirui Zhang, Yujia Peng, Xiaohua Jiang, Yuyin Fu, Xin Wang, Zhixiong Zhang, Cuiyu Guo, Wei Liao, Yiwen Zhang, Tairan Kang, Hao Chen, Yuqin Yao, Lantu Gou, Jinliang Yang. Cryptophycin-55/52 based antibody-drug conjugates: Synthesis, efficacy, and mode of action studies. European Journal of Medicinal Chemistry 2020, 199 , 112364. https://doi.org/10.1016/j.ejmech.2020.112364
37. Donmienne Leung, Jacqueline Wurst, Tao Liu, Ruben Martinez, Amita Datta-Mannan, Yiqing Feng. Antibody Conjugates-Recent Advances and Future Innovations. Antibodies 2020, 9 (1) , 2. https://doi.org/10.3390/antib9010002
38. Linjie Han, Yanqun Zhao, Qunying Zhang. Conjugation Site Analysis by MS/MS Protein Sequencing. 2020, 221-233. https://doi.org/10.1007/978-1-4939-9929-3_15
39. Pragya Adhikari, Neelie Zacharias, Rachana Ohri, Jack Sadowsky. Site-Specific Conjugation to Cys-Engineered THIOMAB™ Antibodies. 2020, 51-69. https://doi.org/10.1007/978-1-4939-9929-3_4
40. Donglu Zhang, Peter S. Dragovich, Shang-Fan Yu, Yong Ma, Thomas H. Pillow, Jack D. Sadowsky, Dian Su, Wei Wang, Andrew Polson, S. Cyrus Khojasteh, Cornelis E.C.A. Hop. Exposure-Efficacy Analysis of Antibody-Drug Conjugates Delivering an Excessive Level of Payload to Tissues. Drug Metabolism and Disposition 2019, 47 (10) , 1146-1155. https://doi.org/10.1124/dmd.119.087023
41. Rongjun He, Brian Finan, John P. Mayer, Richard D. DiMarchi. Peptide Conjugates with Small Molecules Designed to Enhance Efficacy and Safety. Molecules 2019, 24 (10) , 1855. https://doi.org/10.3390/molecules24101855
42. Eduard Figueras, Ana Martins, Adina Borbély, Vadim Le Joncour, Paola Cordella, Raffaella Perego, Daniela Modena, Paolo Pagani, Simone Esposito, Giulio Auciello, Marcel Frese, Paola Gallinari, Pirjo Laakkonen, Christian Steinkühler, Norbert Sewald. Octreotide Conjugates for Tumor Targeting and Imaging. Pharmaceutics 2019, 11 (5) , 220. https://doi.org/10.3390/pharmaceutics11050220
43. Warren Viricel, Guy Fournet, Sabine Beaumel, Emeline Perrial, Sébastien Papot, Charles Dumontet, Benoît Joseph. Monodisperse polysarcosine-based highly-loaded antibody-drug conjugates. Chemical Science 2019, 10 (14) , 4048-4053. https://doi.org/10.1039/C9SC00285E
44. Alain Beck, Valentina D’Atri, Anthony Ehkirch, Szabolcs Fekete, Oscar Hernandez-Alba, Rabah Gahoual, Emmanuel Leize-Wagner, Yannis François, Davy Guillarme, Sarah Cianférani. Cutting-edge multi-level analytical and structural characterization of antibody-drug conjugates: present and future. Expert Review of Proteomics 2019, 16 (4) , 337-362. https://doi.org/10.1080/14789450.2019.1578215
45. Adina Borbély, Eduard Figueras, Ana Martins, Simone Esposito, Giulio Auciello, Edith Monteagudo, Annalise Di Marco, Vincenzo Summa, Paola Cordella, Raffaella Perego, Isabell Kemker, Marcel Frese, Paola Gallinari, Christian Steinkühler, Norbert Sewald. Synthesis and Biological Evaluation of RGD–Cryptophycin Conjugates for Targeted Drug Delivery. Pharmaceutics 2019, 11 (4) , 151. https://doi.org/10.3390/pharmaceutics11040151
46. Stephan Dickgiesser, Roland Kellner, Harald Kolmar, Nicolas Rasche. Site-Specific Conjugation of Thiol-Reactive Cytotoxic Agents to Nonnative Cysteines of Engineered Monoclonal Antibodies. 2019, 1-14. https://doi.org/10.1007/978-1-4939-9654-4_1
47. Madhuri Jayathirtha, Costel C. Darie. Investigation of Antibody-Drug Conjugates by Mass Spectrometry. 2019, 251-263. https://doi.org/10.1007/978-3-030-15950-4_14
48. Amita Datta-Mannan, Hiuwan Choi, David Stokell, Jason Tang, Anthony Murphy, Aaron Wrobleski, Yiqing Feng. The Properties of Cysteine-Conjugated Antibody-Drug Conjugates Are Impacted by the IgG Subclass. The AAPS Journal 2018, 20 (6) https://doi.org/10.1208/s12248-018-0263-0
49. Eshita Khera, Greg M. Thurber. Pharmacokinetic and Immunological Considerations for Expanding the Therapeutic Window of Next-Generation Antibody–Drug Conjugates. BioDrugs 2018, 32 (5) , 465-480. https://doi.org/10.1007/s40259-018-0302-5