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Article ; Online: Development of a Novel DNA Mono-alkylator Platform for Antibody-Drug Conjugates.

2024 Volume 23, Issue 4, Page(s) 541–551

Abstract: Although microtubule inhibitors (MTI) remain a therapeutically valuable payload option for antibody-drug conjugates (ADC), some cancers do not respond to MTI-based ADCs. Efforts to fill this therapeutic gap have led to a recent expansion of the ADC ... ...

Abstract	Although microtubule inhibitors (MTI) remain a therapeutically valuable payload option for antibody-drug conjugates (ADC), some cancers do not respond to MTI-based ADCs. Efforts to fill this therapeutic gap have led to a recent expansion of the ADC payload "toolbox" to include payloads with novel mechanisms of action such as topoisomerase inhibition and DNA cross-linking. We present here the development of a novel DNA mono-alkylator ADC platform that exhibits sustained tumor growth suppression at single doses in MTI-resistant tumors and is well tolerated in the rat upon repeat dosing. A phosphoramidate prodrug of the payload enables low ADC aggregation even at drug-to-antibody ratios of 5:1 while still delivering a bystander-capable payload that is effective in multidrug resistant (MDR)-overexpressing cell lines. The platform was comparable in xenograft studies to the clinical benchmark DNA mono-alkylator ADC platform DGN459 but with a significantly better tolerability profile in rats. Thus, the activity and tolerability profile of this new platform make it a viable option for the development of ADCs.
MeSH term(s)	Humans ; Rats ; Animals ; Immunoconjugates/pharmacology ; Immunoconjugates/therapeutic use ; Alkylating Agents ; Neoplasms/drug therapy ; DNA/metabolism ; Cell Line, Tumor ; Antineoplastic Agents/pharmacology
Chemical Substances	Immunoconjugates ; Alkylating Agents ; DNA (9007-49-2) ; Antineoplastic Agents
Language	English
Publishing date	2024-02-14
Publishing country	United States
Document type	Journal Article
ZDB-ID	2063563-1
ISSN	1538-8514 ; 1535-7163
ISSN (online)	1538-8514
ISSN	1535-7163
DOI	10.1158/1535-7163.MCT-23-0622
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Article ; Online: Site-Specific Dolasynthen Antibody-Drug Conjugates Exhibit Consistent Pharmacokinetic Profiles across a Wide Range of Drug-to-Antibody Ratios.

Clardy, Susan M / Uttard, Alex / Du, Bingfan / Catcott, Kalli C / Lancaster, Kelly L / Ditty, Elizabeth / Sadowsky, Jack / Zurita, Jeffrey / Malli, Naniye / Qin, LiuLiang / Bradley, Stephen P / Avocetien, Kenneth / Carter, Tyler / Kim, Dokyong / Nazzaro, Mark / Xu, Ling / Pillow, Thomas H / Zacharias, Neelie T / Lewis, Gail D /

Rowntree, Rebecca K / Iyengar, Radha / Lee, David H / Damelin, Marc / Toader, Dorin / Lowinger, Timothy B

Molecular cancer therapeutics

2023 Volume 23, Issue 1, Page(s) 84–91

Abstract: Key defining attributes of an antibody-drug conjugate (ADC) include the choice of the targeting antibody, linker, payload, and the drug-to-antibody ratio (DAR). Historically, most ADC platforms have used the same DAR for all targets, regardless of target ...

Abstract	Key defining attributes of an antibody-drug conjugate (ADC) include the choice of the targeting antibody, linker, payload, and the drug-to-antibody ratio (DAR). Historically, most ADC platforms have used the same DAR for all targets, regardless of target characteristics. However, recent studies and modeling suggest that the optimal DAR can depend on target expression level and intratumoral heterogeneity, target internalization and trafficking, and characteristics of the linker and payload. An ADC platform that enables DAR optimization could improve the success rate of clinical candidates. Here we report a systematic exploration of DAR across a wide range, by combining THIOMAB protein engineering technology with Dolasynthen, an auristatin-based platform with monomeric and trimeric variants. This approach enabled the generation of homogeneous, site-specific ADCs spanning a discrete range of DARs 2, 4, 6, 12, and 18 by conjugation of trastuzumab IgG1 THIOMAB constructs with 1, 2, or 3 engineered cysteines to monomeric or trimeric Dolasynthen. All ADCs had physicochemical properties that translated to excellent in vivo pharmacology. Following a single dose of ADCs in a HER2 xenograft model with moderate antigen expression, our data demonstrated comparable pharmacokinetics for the conjugates across all DARs and dose-dependent efficacy of all test articles. These results demonstrate that the Dolasynthen platform enables the generation of ADCs with a broad range of DAR values and with comparable physiochemical, pharmacologic, and pharmacokinetics profiles; thus, the Dolasynthen platform enables the empirical determination of the optimal DAR for a clinical candidate for a given target.
MeSH term(s)	Humans ; Immunoconjugates/chemistry ; Xenograft Model Antitumor Assays ; Trastuzumab/pharmacology ; Trastuzumab/chemistry ; Receptor, ErbB-2/metabolism ; Cysteine
Chemical Substances	Immunoconjugates ; Trastuzumab (P188ANX8CK) ; Receptor, ErbB-2 (EC 2.7.10.1) ; Cysteine (K848JZ4886)
Language	English
Publishing date	2023-09-01
Publishing country	United States
Document type	Journal Article
ZDB-ID	2063563-1
ISSN	1538-8514 ; 1535-7163
ISSN (online)	1538-8514
ISSN	1535-7163
DOI	10.1158/1535-7163.MCT-23-0262
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Article ; Online: Discovery and Optimization of a STING Agonist Platform for Application in Antibody Drug Conjugates.

Duvall, Jeremy R / Thomas, Joshua D / Bukhalid, Raghida A / Catcott, Kalli C / Bentley, Keith W / Collins, Scott D / Eitas, Timothy / Jones, Brian D / Kelleher, Eugene W / Lancaster, Kelly / Protopopova, Marina / Ray, Soumya S / Ter-Ovanesyan, Elena / Xu, Ling / Yang, Liping / Zurita, Jeffrey / Damelin, Marc / Toader, Dorin / Lowinger, Timothy B

Journal of medicinal chemistry

2023 Volume 66, Issue 15, Page(s) 10715–10733

Abstract: While STING agonists have proven to be effective preclinically as anti-tumor agents, these promising results have yet to be translated in the clinic. A STING agonist antibody-drug conjugate (ADC) could overcome current limitations by improving tumor ... ...

Abstract	While STING agonists have proven to be effective preclinically as anti-tumor agents, these promising results have yet to be translated in the clinic. A STING agonist antibody-drug conjugate (ADC) could overcome current limitations by improving tumor accessibility, allowing for systemic administration as well as tumor-localized activation of STING for greater anti-tumor activity and better tolerability. In line with this effort, a STING agonist ADC platform was identified through systematic optimization of the payload, linker, and scaffold based on multiple factors including potency and specificity in both in vitro and in vivo evaluations. The platform employs a potent non-cyclic dinucleotide STING agonist, a cleavable ester-based linker, and a hydrophilic PEG8-bisglucamine scaffold. A tumor-targeted ADC built with the resulting STING agonist platform induced robust and durable anti-tumor activity and demonstrated high stability and favorable pharmacokinetics in nonclinical species.
MeSH term(s)	Humans ; Immunoconjugates/pharmacokinetics ; Antibodies, Monoclonal ; Antineoplastic Agents/pharmacokinetics ; Neoplasms/drug therapy
Chemical Substances	Immunoconjugates ; Antibodies, Monoclonal ; Antineoplastic Agents
Language	English
Publishing date	2023-07-24
Publishing country	United States
Document type	Journal Article
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.3c00907
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Article ; Online: Structural approaches to obtain kinase selectivity.

Norman, Richard A / Toader, Dorin / Ferguson, Andrew D

Trends in pharmacological sciences

2012 Volume 33, Issue 5, Page(s) 273–278

Abstract: One of the grand challenges in kinase drug discovery is the design of small-molecule inhibitors with selectivity profiles that will ultimately be efficacious in the clinic. Current medicinal chemistry strategies make heavy use of structural, biophysical ... ...

Abstract	One of the grand challenges in kinase drug discovery is the design of small-molecule inhibitors with selectivity profiles that will ultimately be efficacious in the clinic. Current medicinal chemistry strategies make heavy use of structural, biophysical and computational approaches to achieve this multi-faceted goal. Here we review structure-based approaches underlying the development of several molecules that are currently in clinical trials, including the cMet inhibitor ARQ197 and the Bcr-Abl inhibitor ponatinib. We highlight the challenge posed by the emergence of resistance mutants and discuss promising lead generation strategies to obtain selective inhibitors of protein and lipid kinases such as targeting of specific sites, the use of fragment-based approaches and new chemical probes based on metal complexes.
MeSH term(s)	Adenosine Triphosphate/chemistry ; Binding Sites ; Drug Design ; Humans ; Protein Binding ; Protein Conformation ; Protein Kinase Inhibitors/chemistry ; Protein Kinase Inhibitors/metabolism ; Protein Kinases/chemistry ; Protein Kinases/metabolism
Chemical Substances	Protein Kinase Inhibitors ; Adenosine Triphosphate (8L70Q75FXE) ; Protein Kinases (EC 2.7.-)
Language	English
Publishing date	2012-05
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	282846-7
ISSN	1873-3735 ; 0165-6147
ISSN (online)	1873-3735
ISSN	0165-6147
DOI	10.1016/j.tips.2012.03.005
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Article: Structural approaches to obtain kinase selectivity

Norman, Richard A / Toader, Dorin / Ferguson, Andrew D

Trends in pharmacological sciences. 2012 May, v. 33, no. 5

2012

Abstract	One of the grand challenges in kinase drug discovery is the design of small-molecule inhibitors with selectivity profiles that will ultimately be efficacious in the clinic. Current medicinal chemistry strategies make heavy use of structural, biophysical and computational approaches to achieve this multi-faceted goal. Here we review structure-based approaches underlying the development of several molecules that are currently in clinical trials, including the cMet inhibitor ARQ197 and the Bcr–Abl inhibitor ponatinib. We highlight the challenge posed by the emergence of resistance mutants and discuss promising lead generation strategies to obtain selective inhibitors of protein and lipid kinases such as targeting of specific sites, the use of fragment-based approaches and new chemical probes based on metal complexes.
Keywords	chemistry ; clinical trials ; drugs ; mutants ; phosphotransferases (kinases)
Language	English
Dates of publication	2012-05
Size	p. 273-278.
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	282846-7
ISSN	1873-3735 ; 0165-6147
ISSN (online)	1873-3735
ISSN	0165-6147
DOI	10.1016/j.tips.2012.03.005
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Discovery and Preclinical Characterization of XMT-1660, an Optimized B7-H4-Targeted Antibody-Drug Conjugate for the Treatment of Cancer.

Toader, Dorin / Fessler, Shawn P / Collins, Scott D / Conlon, Patrick R / Bollu, Reddy / Catcott, Kalli C / Chin, Chen-Ni / Dirksen, Anouk / Du, Bingfan / Duvall, Jeremy R / Higgins, Stacy / Kozytska, Mariya V / Bellovoda, Kamela / Faircloth, Chelsey / Lee, David / Li, Fu / Qin, Liuliang / Routhier, Caitlin / Shaw, Pamela /

Stevenson, Cheri A / Wang, Jason / Wongthida, Phonphimon / Ter-Ovanesyan, Elena / Ditty, Elizabeth / Bradley, Stephen P / Xu, Ling / Yin, Mao / Yurkovetskiy, Alexandr V / Mosher, Rebecca / Damelin, Marc / Lowinger, Timothy B

Molecular cancer therapeutics

2023 Volume 22, Issue 9, Page(s) 999–1012

Abstract: Antibody-drug conjugates (ADC) achieve targeted drug delivery to a tumor and have demonstrated clinical success in many tumor types. The activity and safety profile of an ADC depends on its construction: antibody, payload, linker, and conjugation method, ...

Abstract	Antibody-drug conjugates (ADC) achieve targeted drug delivery to a tumor and have demonstrated clinical success in many tumor types. The activity and safety profile of an ADC depends on its construction: antibody, payload, linker, and conjugation method, as well as the number of payload drugs per antibody [drug-to-antibody ratio (DAR)]. To allow for ADC optimization for a given target antigen, we developed Dolasynthen (DS), a novel ADC platform based on the payload auristatin hydroxypropylamide, that enables precise DAR-ranging and site-specific conjugation. We used the new platform to optimize an ADC that targets B7-H4 (VTCN1), an immune-suppressive protein that is overexpressed in breast, ovarian, and endometrial cancers. XMT-1660 is a site-specific DS DAR 6 ADC that induced complete tumor regressions in xenograft models of breast and ovarian cancer as well as in a syngeneic breast cancer model that is refractory to PD-1 immune checkpoint inhibition. In a panel of 28 breast cancer PDXs, XMT-1660 demonstrated activity that correlated with B7-H4 expression. XMT-1660 has recently entered clinical development in a phase I study (NCT05377996) in patients with cancer.
MeSH term(s)	Humans ; Female ; Immunoconjugates/pharmacology ; Immunoconjugates/therapeutic use ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/therapeutic use ; Antibodies ; Breast Neoplasms ; Cell Line, Tumor ; Xenograft Model Antitumor Assays
Chemical Substances	Immunoconjugates ; Antineoplastic Agents ; Antibodies
Language	English
Publishing date	2023-06-09
Publishing country	United States
Document type	Clinical Trial, Phase I ; Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2063563-1
ISSN	1538-8514 ; 1535-7163
ISSN (online)	1538-8514
ISSN	1535-7163
DOI	10.1158/1535-7163.MCT-22-0786
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Article ; Online: Adventures in Scaffold Morphing: Discovery of Fused Ring Heterocyclic Checkpoint Kinase 1 (CHK1) Inhibitors.

Yang, Bin / Vasbinder, Melissa M / Hird, Alexander W / Su, Qibin / Wang, Haixia / Yu, Yan / Toader, Dorin / Lyne, Paul D / Read, Jon A / Breed, Jason / Ioannidis, Stephanos / Deng, Chun / Grondine, Michael / DeGrace, Nancy / Whitston, David / Brassil, Patrick / Janetka, James W

Journal of medicinal chemistry

2018 Volume 61, Issue 3, Page(s) 1061–1073

Abstract: Checkpoint kinase 1 (CHK1) inhibitors are potential cancer therapeutics that can be utilized for enhancing the efficacy of DNA damaging agents. Multiple small molecule CHK1 inhibitors from different chemical scaffolds have been developed and evaluated in ...

Abstract	Checkpoint kinase 1 (CHK1) inhibitors are potential cancer therapeutics that can be utilized for enhancing the efficacy of DNA damaging agents. Multiple small molecule CHK1 inhibitors from different chemical scaffolds have been developed and evaluated in clinical trials in combination with chemotherapeutics and radiation treatment. Scaffold morphing of thiophene carboxamide ureas (TCUs), such as AZD7762 (1) and a related series of triazoloquinolines (TZQs), led to the identification of fused-ring bicyclic CHK1 inhibitors, 7-carboxamide thienopyridines (7-CTPs), and 7-carboxamide indoles. X-ray crystal structures reveal a key intramolecular noncovalent sulfur-oxygen interaction in aligning the hinge-binding carboxamide group to the thienopyridine core in a coplanar fashion. An intramolecular hydrogen bond to an indole NH was also effective in locking the carboxamide in the preferred bound conformation to CHK1. Optimization on the 7-CTP series resulted in the identification of lead compound 44, which displayed respectable drug-like properties and good in vitro and in vivo potency.
MeSH term(s)	Cell Line, Tumor ; Cell Proliferation/drug effects ; Checkpoint Kinase 1/antagonists & inhibitors ; Checkpoint Kinase 1/chemistry ; DNA Damage ; Drug Discovery ; Heterocyclic Compounds/chemistry ; Heterocyclic Compounds/pharmacology ; Humans ; Indoles/chemistry ; Models, Molecular ; Protein Domains ; Protein Kinase Inhibitors/chemistry ; Protein Kinase Inhibitors/pharmacology ; Pyridines/chemistry
Chemical Substances	Heterocyclic Compounds ; Indoles ; Protein Kinase Inhibitors ; Pyridines ; thienopyridine ; indole (8724FJW4M5) ; Checkpoint Kinase 1 (EC 2.7.11.1)
Language	English
Publishing date	2018-01-19
Publishing country	United States
Document type	Journal Article
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.7b01490
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Article: Straightforward Glycoengineering Approach to Site-Specific Antibody-Pyrrolobenzodiazepine Conjugates.

Thompson, Pamela / Ezeadi, Ebele / Hutchinson, Ian / Fleming, Ryan / Bezabeh, Binyam / Lin, Jia / Mao, Shenlan / Chen, Cui / Masterson, Luke / Zhong, Haihong / Toader, Dorin / Howard, Philip / Wu, Herren / Gao, Changshou / Dimasi, Nazzareno

ACS medicinal chemistry letters

2016 Volume 7, Issue 11, Page(s) 1005–1008

Abstract: Antibody-drug conjugates (ADCs) have become a powerful platform to deliver cytotoxic agents selectively to cancer cells. ADCs have traditionally been prepared by stochastic conjugation of a cytotoxic drug using an antibody's native cysteine or lysine ... ...

Abstract	Antibody-drug conjugates (ADCs) have become a powerful platform to deliver cytotoxic agents selectively to cancer cells. ADCs have traditionally been prepared by stochastic conjugation of a cytotoxic drug using an antibody's native cysteine or lysine residues. Through strategic selection of the mammalian expression host, we were able to introduce azide-functionalized glycans onto a homogeneously glycosylated anti-EphA2 monoclonal antibody in one step. Conjugation with an alkyne-bearing pyrrolobenzodiazepine dimer payload (SG3364) using copper-catalyzed click chemistry yielded a site-specific ADC with a drug-to-antibody ratio (DAR) of four. This ADC was compared with a glycoengineered DAR two site-specific ADC, and both were found to be highly potent against EphA2-positive human prostate cancer cells in both an
Language	English
Publishing date	2016-09-20
Publishing country	United States
Document type	Journal Article
ISSN	1948-5875
ISSN	1948-5875
DOI	10.1021/acsmedchemlett.6b00278
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Article ; Online: Structure-Cytotoxicity Relationships of Analogues of N

Toader, Dorin / Wang, Fengjiang / Gingipalli, Lakshmaiah / Vasbinder, Melissa / Roth, Mark / Mao, Shenlan / Block, Michael / Harper, Jay / Thota, Sambaiah / Su, Mei / Ma, Jianquo / Bedian, Vahe / Kamal, Adeela

Journal of medicinal chemistry

2016 Volume 59, Issue 23, Page(s) 10781–10787

Abstract: Herein we report structure-cytotoxicity relationships for analogues of ... ...

Abstract	Herein we report structure-cytotoxicity relationships for analogues of N
MeSH term(s)	Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Cell Line, Tumor ; Cell Proliferation/drug effects ; Dose-Response Relationship, Drug ; Drug Screening Assays, Antitumor ; Humans ; Molecular Structure ; Oligopeptides/chemical synthesis ; Oligopeptides/chemistry ; Oligopeptides/pharmacology ; Structure-Activity Relationship
Chemical Substances	Antineoplastic Agents ; N14-desacetoxytubulysin H ; Oligopeptides
Language	English
Publishing date	2016-11-16
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.6b01023
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Article ; Online: A Biparatopic HER2-Targeting Antibody-Drug Conjugate Induces Tumor Regression in Primary Models Refractory to or Ineligible for HER2-Targeted Therapy.

Cancer cell

2019 Volume 35, Issue 6, Page(s) 948–949

Language	English
Publishing date	2019-06-13
Publishing country	United States
Document type	Published Erratum
ZDB-ID	2078448-X
ISSN	1878-3686 ; 1535-6108
ISSN (online)	1878-3686
ISSN	1535-6108
DOI	10.1016/j.ccell.2019.05.010
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