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

Product Name
[(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 mesylate;Talabostat Mesilate;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
Formula Weight
310.17
MOL File
150080-09-4.mol
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[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Property

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.
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
5.31465
Product name
Val-boroPro - CAS 150080-09-4 - Calbiochem
Packaging
10mg
Price
$260
Updated
2024/03/01
Cayman Chemical
Product number
29007
Product name
Talabostat (mesylate)
Packaging
5mg
Price
$49
Updated
2024/03/01
Cayman Chemical
Product number
29007
Product name
Talabostat (mesylate)
Packaging
10mg
Price
$82
Updated
2024/03/01
Cayman Chemical
Product number
29007
Product name
Talabostat (mesylate)
Packaging
25mg
Price
$190
Updated
2024/03/01
Cayman Chemical
Product number
29007
Product name
Talabostat (mesylate)
Packaging
50mg
Price
$333
Updated
2024/03/01
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[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Chemical Properties,Usage,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

Treatment of cancer; hematopoetic stimulant.

Uses

Talabostat Mesylate can be used in biological study and pharmacological activity of treatment of cancer using immunomodulation.

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

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

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View Lastest Price from [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate manufacturers

Zhuozhou Wenxi import and Export Co., Ltd
Product
Talabostat mesylate 150080-09-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Talabostat mesylate 150080-09-4
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09
Shaanxi Dideu Medichem Co. Ltd
Product
(2R)-1-(2S)-2-Amino-3-methylbutanoylpyrrolidin-2-ylboronic acid mesylate 150080-09-4
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%+
Supply Ability
100 tons
Release date
2019-12-31

150080-09-4, [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylateRelated Search:

6-Aminocaproic acid Pefloxacin mesylate Imatinib Trifluoromethanesulfonic acid ALTRENOGEST Pazufloxacin mesilate Tris(hydroxymethyl)aminomethane Phentolamine mesilate Levofloxacin Methylate Glycine Methanesulfonic acid AMPRENAVIR Masitinib Tamsulosin hydrochloride Orlistat Bendamustine hydrochloride [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate AMINO ACIDS

  • [(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
  • Val-boroPro mesylate
  • CS-1219
  • Talabostat-mesylate, PT-100
  • 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)
  • B-[(2R)-1-[(2S)-2-Amino-3-methyl-1-oxobutyl]-2-pyrrolidinyl]boronic acid methanesulfonate
  • PT100 mesylate
  • (2R)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronicacid,methanesulfonicaci
  • [(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]boronic acid,methanesulfonic acid
  • (R)-1-[(S)-2-Amino-3-methylbutanoyl]pyrrolidine-2-boronic Acid Methanesulfonate
  • methanesulfonic acid compound with ((R)-1-((S)-2-amino-3-methylbutanoyl)pyrrolidin-2-yl)boronic acid (1:1)
  • Adrafinil Impurity 6
  • 150080-09-4
  • C10H23BN2O6S
  • C9H19BN2O3CH4O3S