A Potent and Orally Active Antagonist (SM-406/AT-406) of Multiple Inhibitor of Apoptosis Proteins (IAPs) in Clinical Development for Cancer Treatment
We report the discovery and characterization of SM-406 (compound 2), a potent and orally bioavailable Smac mimetic and an antagonist of the inhibitor of apoptosis proteins (IAPs). This compound binds to XIAP, cIAP1, and cIAP2 proteins with K i of 66.4, 1.9, and 5.1 nM, respectively. Compound 2 effec...
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| Published in | Journal of medicinal chemistry Vol. 54; no. 8; pp. 2714 - 2726 |
|---|---|
| Main Authors | , , , , , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
28.04.2011
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | We report the discovery and characterization of SM-406 (compound 2), a potent and orally bioavailable Smac mimetic and an antagonist of the inhibitor of apoptosis proteins (IAPs). This compound binds to XIAP, cIAP1, and cIAP2 proteins with K i of 66.4, 1.9, and 5.1 nM, respectively. Compound 2 effectively antagonizes XIAP BIR3 protein in a cell-free functional assay, induces rapid degradation of cellular cIAP1 protein, and inhibits cancer cell growth in various human cancer cell lines. It has good oral bioavailability in mice, rats, non-human primates, and dogs, is highly effective in induction of apoptosis in xenograft tumors, and is capable of complete inhibition of tumor growth. Compound 2 is currently in phase I clinical trials for the treatment of human cancer. |
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| AbstractList | We report the discovery and characterization of SM-406 (compound
2
), a potent and orally bioavailable Smac mimetic and an antagonist of the inhibitor of apoptosis proteins (IAPs). This compound binds to XIAP, cIAP1 and cIAP2 proteins with K
i
values of 66.4 nM, 1.9 nM and 5.1 nM, respectively. Compound
2
effectively antagonizes XIAP BIR3 protein in a cell-free functional assay, induces rapid degradation of cellular cIAP1 protein and inhibits cancer cell growth in various human cancer cell lines. It has good oral bioavailability in mice, rats, non-human primates and dogs, is highly effective in induction of apoptosis in xenograft tumors and is capable of complete inhibition of tumor growth. Compound
2
is currently in Phase I clinical trials for the treatment of human cancer. We report the discovery and characterization of SM-406 (compound 2), a potent and orally bioavailable Smac mimetic and an antagonist of the inhibitor of apoptosis proteins (IAPs). This compound binds to XIAP, cIAP1, and cIAP2 proteins with K(i) of 66.4, 1.9, and 5.1 nM, respectively. Compound 2 effectively antagonizes XIAP BIR3 protein in a cell-free functional assay, induces rapid degradation of cellular cIAP1 protein, and inhibits cancer cell growth in various human cancer cell lines. It has good oral bioavailability in mice, rats, non-human primates, and dogs, is highly effective in induction of apoptosis in xenograft tumors, and is capable of complete inhibition of tumor growth. Compound 2 is currently in phase I clinical trials for the treatment of human cancer. |
| Author | Wang, Shaomeng Yi, Han Cai, Qian Sun, Haiying Yang, Chao-Yie Liu, Liu Peng, Yuefeng Kang, Sanmao McEachern, Donna Leopold, Lance Sun, Duxin Lu, Jianfeng Qiu, Su Miller, Rebecca Guo, Ming Yang, Dajun Nikolovska-Coleska, Zaneta Zhang, Tao |
| AuthorAffiliation | Ascenta Therapeutics University of Michigan |
| AuthorAffiliation_xml | – name: University of Michigan – name: Ascenta Therapeutics – name: Ascenta Therapeutics, 101 Lindenwood Drive, Malvern, PA 19355, USA – name: Comprehensive Cancer Center and Departments of Internal Medicine, Pharmacology and Medicinal Chemistry, University of Michigan, Ann Arbor, MI 48109, USA – name: Δ Department of Pharmaceutical Sciences, College of Pharmacy, University of Michigan, Ann Arbor, MI 48109, USA |
| Author_xml | – sequence: 1 givenname: Qian surname: Cai fullname: Cai, Qian – sequence: 2 givenname: Haiying surname: Sun fullname: Sun, Haiying – sequence: 3 givenname: Yuefeng surname: Peng fullname: Peng, Yuefeng – sequence: 4 givenname: Jianfeng surname: Lu fullname: Lu, Jianfeng – sequence: 5 givenname: Zaneta surname: Nikolovska-Coleska fullname: Nikolovska-Coleska, Zaneta – sequence: 6 givenname: Donna surname: McEachern fullname: McEachern, Donna – sequence: 7 givenname: Liu surname: Liu fullname: Liu, Liu – sequence: 8 givenname: Su surname: Qiu fullname: Qiu, Su – sequence: 9 givenname: Chao-Yie surname: Yang fullname: Yang, Chao-Yie – sequence: 10 givenname: Rebecca surname: Miller fullname: Miller, Rebecca – sequence: 11 givenname: Han surname: Yi fullname: Yi, Han – sequence: 12 givenname: Tao surname: Zhang fullname: Zhang, Tao – sequence: 13 givenname: Duxin surname: Sun fullname: Sun, Duxin – sequence: 14 givenname: Sanmao surname: Kang fullname: Kang, Sanmao – sequence: 15 givenname: Ming surname: Guo fullname: Guo, Ming – sequence: 16 givenname: Lance surname: Leopold fullname: Leopold, Lance – sequence: 17 givenname: Dajun surname: Yang fullname: Yang, Dajun – sequence: 18 givenname: Shaomeng surname: Wang fullname: Wang, Shaomeng email: shaomeng@umich.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/21443232$$D View this record in MEDLINE/PubMed |
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| Keywords | SMALL-MOLECULE MIMETICS X-LINKED INHIBITOR MITOCHONDRIA-DERIVED ACTIVATOR XIAP BIR3 DOMAIN STRUCTURAL BASIS ALPHA-DEPENDENT APOPTOSIS CASPASE INHIBITION CONSTRAINED SMAC MIMETICS NF-KAPPA-B STRUCTURE-BASED DESIGN |
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| Notes | NIH RePORTER These authors contributed equally. Present address: For Qian Cai: Guangzhou Institute of Biomedicine and Health, Chinese Academy of Sciences, 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510663, China For Yuefeng Peng: Drug Design and Synthesis Section, Chemical Biology Research Branch, National Institute on Drug Abuse, National Institutes of Health, 5625 Fishers Lane, Bethesda, Maryland 20892, USA. |
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| Snippet | We report the discovery and characterization of SM-406 (compound 2), a potent and orally bioavailable Smac mimetic and an antagonist of the inhibitor of... We report the discovery and characterization of SM-406 (compound 2 ), a potent and orally bioavailable Smac mimetic and an antagonist of the inhibitor of... |
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| SubjectTerms | Administration, Oral Animals Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Antineoplastic Agents - therapeutic use Apoptosis - drug effects Area Under Curve Azocines - pharmacokinetics Azocines - pharmacology Azocines - therapeutic use Benzhydryl Compounds - pharmacokinetics Benzhydryl Compounds - pharmacology Benzhydryl Compounds - therapeutic use Biological Availability Cell Line, Tumor Chemistry, Medicinal Humans Inhibitor of Apoptosis Proteins - antagonists & inhibitors Life Sciences & Biomedicine Models, Molecular Neoplasms - drug therapy Pharmacology & Pharmacy Science & Technology |
| Title | A Potent and Orally Active Antagonist (SM-406/AT-406) of Multiple Inhibitor of Apoptosis Proteins (IAPs) in Clinical Development for Cancer Treatment |
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