[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate
- CAS No.
- 150080-09-4
- Chemical Name:
- [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate
- Synonyms
- CS-1219;PT100 mesylate;Unii-V8zg4Y1B51;Talabostat Mesilate;Talabostat mesylate;Val-boroPro mesylate;Adrafinil Impurity 6;Talabostat-mesylate, PT-100;[(2R)-1-(L-Valyl)-2-pyrrolidinyl]boronic acid methanesulfonate (1:1);[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate
- CBNumber:
- CB52128758
- Molecular Formula:
- C10H23BN2O6S
- Molecular Weight:
- 310.17
- MDL Number:
- MFCD13194906
- MOL File:
- 150080-09-4.mol
Melting point | >160°C (dec.) |
---|---|
storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C |
solubility | Soluble in DMSO (up to at least 25 mg/ml) |
form | solid |
color | White |
Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month. |
NCI Dictionary of Cancer Terms | talabostat mesylate |
FDA UNII | V8ZG4Y1B51 |
NCI Drug Dictionary | talabostat mesylate |
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate price More Price(31)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | 5.31465 | Val-boroPro - CAS 150080-09-4 - Calbiochem | 150080-09-4 | 10mg | $260 | 2024-03-01 | Buy |
Cayman Chemical | 29007 | Talabostat (mesylate) | 150080-09-4 | 5mg | $49 | 2024-03-01 | Buy |
Cayman Chemical | 29007 | Talabostat (mesylate) | 150080-09-4 | 10mg | $82 | 2024-03-01 | Buy |
Cayman Chemical | 29007 | Talabostat (mesylate) | 150080-09-4 | 25mg | $190 | 2024-03-01 | Buy |
Cayman Chemical | 29007 | Talabostat (mesylate) | 150080-09-4 | 50mg | $333 | 2024-03-01 | Buy |
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Chemical Properties,Uses,Production
Description
Talabostat is a non-selective inhibitor of dipeptidyl peptidases (DPPs), including DPP-4, DPP-7, DPP-8, DPP-9, fibroblast activation protein (FAP), and prolyl endopeptidase (PREP; IC50s = >4, 310, 4, 11, 560, and 390 nM, respectively). It inhibits proliferation of superantigen-stimulated human peripheral blood mononuclear cells (PBMCs; IC50 = ~10 nM). Talabostat (5 μg twice per day) increases expression of a variety of cytokines, including those encoding IL-1β, IL-6, and G-CSF, and chemokines in tumors and tumor-draining lymph nodes in a WEHI-164 fibrosarcoma mouse model. It reduces tumor growth in WEHI-164, MM45T.Sp, and MM52.T fibrosarcoma, EL-4 and A20/2J lymphoma, B16/F10 melanoma, and P815 mastocytoma syngeneic mouse models. Talabostat also increases the efficacy of the antitumor antibodies rituximab and trastuzumab in Namalwa B cell lymphoma and LS180 colon carcinoma mouse xenograft models, respectively.
Uses
Talabostat Mesylate can be used in biological study and pharmacological activity of treatment of cancer using immunomodulation.
Uses
Treatment of cancer; hematopoetic stimulant.
General Description
A prolineboronic acid-based broad-spectrum DDP IV activity and/or structural homologue (DASH) family dipeptidyl peptidases inhibitor that converts in solution between the protonated active form and a cyclized inactive form due to a reversible intramolecular B-N dative bond formation of the non-protonated Val-boroPro (kinact = 6.4 x 10--4 s- and kcyc = 6.4 x 10-5 s- at pH 7.8). Although equilibrium favors cyclization at basic pH, high affinity binding (kon & koff toward CD26 at pH 7.8 = 5.02 x 106 M-s- and 77.8 x 10-6 s-, respectively) drives the equilibrium away from cyclization and traps the active form in enzyme-bound state with prolonged incubation. Reported to inhibit DPP7/DPPII/QPP (IC50/[Substrate]/rxn time at pH 5.5 = 15 nM/500 μM Lys-Pro-MNA/1 h & 310 nM/50 μM Nle-Pro-AMC/15 min), CD26/DPPIV (IC50 = 26 nM; 500 μM Ala-Pro-MNA for 1 h at pH 7.8), fibroblast activation protein/FAP (IC50 = 40 nM; 250 μM Ala-Pro-AFC at pH 2.0), DPP8 (IC50 = 4 nM; 100 μM Ala-Pro-AFC for 15 min at pH 8.0), DDP9 (IC50 = 11 nM; 100 μM Gly-Pro-AMC for 30 min at pH 7.4) with little potency against 9 other proteases (IC50 >100 μM; aminopeptidase P, chymoptrypsin, leukocyte elastase, plasma kallikrein, plasmin, prolidase, thrombin, trypsin, tryptase), while contradictory reports regarding prolyl endopeptidase/PEP/PREP inhibition exist (e.g. IC50 = 390 nM/50 μM Z-Gly-Pro-AMC/pH 7.5/30 min vs. 25 μM/500 μM Z-Gly-Pro-MNA/pH 7.8/60 min). Shown to promote the propagation of human BM CD34+ cells by stimulating stromal cells cytokine production in vitro (min EC 0.1 nM) and display hematopoietic stimulatory effect in mice in vivo (min ED 2 μg/mouse/12 h; p.o.). Although orally available in mice and rats, caution must be taken not to exceed toxicity levels (MTD = 25 μg/mL using Sprague-Dawley rats; LD50 ~0.5 mg/mL in 24 survival test using Fisher rats; p.o.) for in vivo studies.
Biochem/physiol Actions
Cell permeable: yes
in vitro
by the cleavage of n-terminal xaa-pro or xaa-ala residues, talabostat blocks dipeptidyl peptidases, such as fibroblast activation protein (fap), resulting in inducing the production of cytokine and chemokine (besides specific t-cell immunity and t-cell-dependent activity). this agent may also induce the production of colony stimulating factors, for instance, granulocyte colony stimulating factor (g-csf), resulting in the inducement of hematopoiesis. dipeptidyl peptidases are referred to the activation of polypeptide hormones and chemokines.
IC 50
1 nm
storage
Store at -20°C
References
1) Lankas et al. (2005) Dipeptidyl Peptidase IV Inhibition for the Treatment of Type 2 Diabetes; Diabetes 54 2988 2) Adams et al. (2004) PT-100,a small molecule dipeptidyl peptidase inhibitor, has potent antitumor effects and augments antibody-mediated cytotoxicity via a novel immune mechanism; Cancer Res. 64 5471 3) Walsh et al. (2013) Val-BoroPro Accelerates T Cell Priming via Modulation of Dendritic Cell Trafficking Resulting in Complete Regression of Established Murine Tumors; PLoS One 8 e58860 4) Okondo et al. (2017) DPP8/9 inhibition induces pro-caspase-1-dependent monocyte and macrophage pyroptosis; Nat. Chem. Biol. 13 46 5) Okondo et al. (2018) Inhibition of DPP8/9 Activates the Nlrp1b Inflammasome; Cell Chem. Biol. 25 1
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Preparation Products And Raw materials
Raw materials
Preparation Products
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
Alpha Biopharmaceuticals Co., Ltd | +86-15542445688 | sales@alabiochem.com | China | 888 | 58 |
Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29798 | 60 |
ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32835 | 60 |
BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | sales@chemdad.com | China | 39916 | 58 |
CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49403 | 58 |
career henan chemical co | +86-0371-86658258 +8613203830695 | factory@coreychem.com | China | 29820 | 58 |
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd | +8613580539051 | joe@yuhengpharm.com | CHINA | 21149 | 58 |
Win-Win chemical CO., Limited | +86-0086-577-64498589 +86-15355981851 | sales@win-winchemical.com | China | 14350 | 58 |
Dideu Industries Group Limited | +86-29-89586680 +86-15129568250 | 1026@dideu.com | China | 23430 | 58 |
View Lastest Price from [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
---|---|---|---|---|---|---|---|---|
2022-08-31 | [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate
150080-09-4
|
US $1.10 / g | 1g | 99.00% | 100 Tons Min | Dideu Industries Group Limited | ||
2021-07-13 | Talabostat mesylate
150080-09-4
|
US $15.00-10.00 / KG | 1KG | 99%+ HPLC | Monthly supply of 1 ton | Zhuozhou Wenxi import and Export Co., Ltd | ||
2021-07-10 | Talabostat mesylate
150080-09-4
|
US $15.00-10.00 / KG | 1KG | 99%+ HPLC | Monthly supply of 1 ton | Zhuozhou Wenxi import and Export Co., Ltd |
- [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate
150080-09-4
- US $1.10 / g
- 99.00%
- Dideu Industries Group Limited
- Talabostat mesylate
150080-09-4
- US $15.00-10.00 / KG
- 99%+ HPLC
- Zhuozhou Wenxi import and Export Co., Ltd
- Talabostat mesylate
150080-09-4
- US $15.00-10.00 / KG
- 99%+ HPLC
- Zhuozhou Wenxi import and Export Co., Ltd