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ChemicalBook >> CAS DataBase List >>[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate

[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate

[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Structure
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate structure
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
Last updated:2023-06-30 15:45:59
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[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Properties

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
Product number Packaging Price Buy
5.31465 10mg $260 Buy
29007 5mg $49 Buy
29007 10mg $82 Buy
29007 25mg $190 Buy
29007 50mg $333 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

[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Suppliers

Global( 107)Suppliers
Supplier Tel Email Country ProdList Advantage
Alpha Biopharmaceuticals Co., Ltd 		+86-411-39042497 +8613921981412 sales@alphabiopharm.com China 886 58
Capot Chemical Co.,Ltd. 		571-85586718 +8613336195806 sales@capotchem.com China 29797 60
ATK CHEMICAL COMPANY LIMITED 		+undefined-21-51877795 ivan@atkchemical.com China 32686 60
BOC Sciences 		+1-631-485-4226 inquiry@bocsci.com United States 19553 58
Chongqing Chemdad Co., Ltd 		+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
CONIER CHEM AND PHARMA LIMITED 		+8618523575427 sales@conier.com China 49391 58
career henan chemical co 		+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
Shaanxi Dideu Medichem Co. Ltd 		+86-29-87569266 15319487004 1015@dideu.com China 2263 58
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd 		+8613580539051 joe@yuhengpharm.com CHINA 21149 58
WinWin Chemical CO., Limited 		+86-0577-64498589 +8615325081899 sales@win-winchemical.com China 14145 58
Supplier Advantage
Alpha Biopharmaceuticals Co., Ltd 		58
Capot Chemical Co.,Ltd. 		60
ATK CHEMICAL COMPANY LIMITED 		60
BOC Sciences 		58
Chongqing Chemdad Co., Ltd 		58
CONIER CHEM AND PHARMA LIMITED 		58
career henan chemical co 		58
Shaanxi Dideu Medichem Co. Ltd 		58
Guangzhou Yuheng Pharmaceutical Technology Co., Ltd 		58
WinWin Chemical CO., Limited 		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
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate pictures 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
Talabostat mesylate pictures 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
Talabostat mesylate pictures 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
  • Talabostat mesylate pictures
  • Talabostat mesylate
    150080-09-4
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
  • Talabostat mesylate pictures
  • Talabostat mesylate
    150080-09-4
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Spectrum

[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate(150080-09-4)MS

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[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Boronic acid, ((2R)-1-((2S)-2-amino-3-methyl-1-oxobutyl)-2-pyrrolidinyl)-, monomethanesulfonate Unii-V8zg4Y1B51 Methanesulfonic acid ((R)-1-((S)-2-amino-3-methyl-butanoyl)pyrrolidin-2-yl)boronic acid (1:1) Talabostat mesylate Talabostat Mesilate [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Talabostat mesilate Talabostat mesylate [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate [(2R)-1-(L-Valyl)-2-pyrrolidinyl]boronic acid methanesulfonate (1:1) [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate ISO 9001：2015 REACH (2R)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronicacid,methanesulfonicaci PT100 mesylate B-[(2R)-1-[(2S)-2-Amino-3-methyl-1-oxobutyl]-2-pyrrolidinyl]boronic acid methanesulfonate Talabostat-mesylate, PT-100 CS-1219 Val-boroPro mesylate [(2R)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid,methanesulfonic acid (R)-1-[(S)-2-Amino-3-methylbutanoyl]pyrrolidine-2-boronic Acid Methanesulfonate Adrafinil Impurity 6 methanesulfonic acid compound with ((R)-1-((S)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)boronic acid (1:1) 150080-09-4 C10H23BN2O6S C9H19BN2O3CH4O3S