Introduction：Basic information about CAS 150080-09-4|Talabostat mesylate, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Talabostat mesylate |
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| CAS Number | 150080-09-4 | Molecular Weight | 310.175 |
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| Density | / | Boiling Point | / |
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| Molecular Formula | C10H23BN2O6S | Melting Point | / |
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| MSDS | / | Flash Point | / |
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Names
| Name | [(2R)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid,methanesulfonic acid |
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| Synonym | More Synonyms |
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Talabostat mesylate BiologicalActivity
| Description | Talabostat mesylate is a potent, nonselective and orally available dipeptidyl peptidase IV (DPP-IV) inhibitor with a Ki of 0.18 nM. |
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| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>Dipeptidyl PeptidaseResearch Areas >>CancerResearch Areas >>Inflammation/Immunology |
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| Target | Ki: 0.18 nM (DPP-IV), 1.5 nM (DPP8), 0.76 nM (DPP9)[1] |
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| In Vitro | Talabostat mesylate is a nonselective DPP-IV inhibitor, inhibiting DPP8/9, FAP, DPP2 and some other DASH family enzymes essentially as potently as it inhibits DPP-IV[1]. Talabostat stimulates the immune system by triggering a proinflammatory form of cell death in monocytes and macrophages known as pyroptosis. The inhibition of two serine proteases, DPP8 and DPP9, activates the proprotein form of caspase-1 independent of the inflammasome adaptor ASC[2]. Talabostat competitively inhibits the dipeptidyl peptidase (DPP) activity of FAP and CD26/DPP-IV, and there is a high-affinity interaction with the catalytic site due to the formation of a complex between Ser630/624 and the boron of talabostat[3]. |
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| In Vivo | Talabostat can stimulate immune responses against tumors involving both the innate and adaptive branches of the immune system. In WEHI 164 fibrosarcoma and EL4 and A20/2J lymphoma models, PT-100 causes regression and rejection of tumors. The antitumor effect appears to involve tumor-specific CTL and protective immunological memory. Talabostat treatment of WEHI 164-inoculated mice increases mRNA expression of cytokines and chemokines known to promote T-cell priming and chemoattraction of T cells and innate effector cells[3]. Talabostat treated mice show significant less fibrosis and FAP expression is reduced. Upon PT100 treatment, significant differences in the MMP-12, MIP-1α, and MCP-3 mRNA expression levels in the lungs are also observed. Treatment with PT100 in this murine model of pulmonary fibrosis has an anti-fibro-proliferative effect and increases macrophage activation[4]. |
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| Animal Admin | Mice: BLM (0.5mg/kg/day) is administered on days -7, -6, -5, -2, -1, 0 in the nostrils of male mice. Talabostat (40 µg/mouse) or vehicle (0.9% NaCl) is dosed per os twice daily from day 1-14. MRI is performed before BLM and at days 0, 7 and 14. After the last MRI acquisition, animals are euthanised and the lungs harvested for histological and quantitative real-time polymerase chain reaction (qRT-PCR) analyses[4]. |
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| References | [1]. Connolly BA, et al. Dipeptide boronic acid inhibitors of dipeptidyl peptidase IV: determinants of potencyand in vivo efficacy and safety. J Med Chem. 2008 Oct 9;51(19):6005-13. [2]. Okondo MC, et al. DPP8 and DPP9 inhibition induces pro-caspase-1-dependent monocyte and macrophage pyroptosis. Nat Chem Biol. 2017 Jan;13(1):46-53. [3]. Adams S, et al. PT-100, a small molecule dipeptidyl peptidase inhibitor, has potent antitumor effects and augments antibody-mediated cytotoxicity via a novel immune mechanism. Cancer Res. 2004 Aug 1;64(15):5471-80. [4]. Egger C, et al. Effects of the fibroblast activation protein inhibitor, PT100, in a murine model of pulmonary fibrosis. Eur J Pharmacol. 2017 Aug 15;809:64-72. |
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Chemical & Physical Properties
| Molecular Formula | C10H23BN2O6S |
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| Molecular Weight | 310.175 |
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| Exact Mass | 310.136993 |
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| PSA | 149.54000 |
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| LogP | 0.61560 |
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| InChIKey | OXYYOEIGQRXGPI-WSZWBAFRSA-N |
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| SMILES | CC(C)C(N)C(=O)N1CCCC1B(O)O.CS(=O)(=O)O |
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| Storage condition | 2-8℃ |
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Safety Information
Customs
| HS Code | 2933990090 |
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| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
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Synonyms
| Boronic acid, B-[(2R)-1-[(2S)-2-amino-3-methyl-1-oxobutyl]-2-pyrrolidinyl]-, methanesulfonate (1:1) |
| Talabostat mesylate (USAN) |
| Methanesulfonic acid ((R)-1-((S)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)boronic acid (1:1) |
| [(2R)-1-(L-Valyl)-2-pyrrolidinyl]boronic acid methanesulfonate (1:1) |
| Talabostat mesylate |
| Talabostat (mesylate) |
