[(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 (PT-100) ，S8455;Talabostat-mesylate, PT-100;methanesulfonic acid - [A83080]
- CBNumber
- CB52128758
- Molecular Formula
- C10H23BN2O6S
- Formula Weight
- 310.17
- MOL File
- 150080-09-4.mol
[(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.
- InChI
- 1S/C9H19BN2O3.CH4O3S/c1-6(2)8(11)9(13)12-5-3-4-7(12)10(14)15;1-5(2,3)4/h6-8,14-15H,3-5,11H2,1-2H3;1H3,(H,2,3,4)/t7-,8-;/m0./s1
- InChIKey
- OXYYOEIGQRXGPI-WSZWBAFRSA-N
- SMILES
- B(O)(O)[C@H]1N(CCC1)C(=O)[C@@H]([N+H3])C(C)C.[S](=O)(=O)([O-])C
Safety
- WGK Germany
- WGK 3
- Storage Class
- 11 - Combustible Solids
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
P362Take off contaminated clothing and wash before reuse.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 5.31465
- Product name
- Val-boroPro - CAS 150080-09-4 - Calbiochem
- Packaging
- 10mg
- Price
- $267
- Updated
- 2025/07/31
- Product number
- 29007
- Product name
- Talabostat (mesylate)
- Packaging
- 5mg
- Price
- $49
- Updated
- 2024/03/01
- Product number
- 29007
- Product name
- Talabostat (mesylate)
- Packaging
- 10mg
- Price
- $82
- Updated
- 2024/03/01
- Product number
- 29007
- Product name
- Talabostat (mesylate)
- Packaging
- 25mg
- Price
- $190
- Updated
- 2024/03/01
- Product number
- 29007
- Product name
- Talabostat (mesylate)
- Packaging
- 50mg
- Price
- $333
- Updated
- 2024/03/01
[(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] PETERS J, MATTEI P. Dipeptidyl Peptidase IV Inhibitors for the Treatment of Type 2 Diabetes[C]. 2010: 0. DOI:10.1002/9783527630035.ch5
[2] SHARLENE ADAMS. PT-100, a small molecule dipeptidyl peptidase inhibitor, has potent antitumor effects and augments antibody-mediated cytotoxicity via a novel immune mechanism.[J]. Cancer research, 2004, 64 15: 5471-5480. DOI:10.1158/0008-5472.can-04-0447
[3] MEGHAAN P WALSH. Val-boroPro accelerates T cell priming via modulation of dendritic cell trafficking resulting in complete regression of established murine tumors.[J]. PLoS ONE, 2013: e58860. DOI:10.1371/journal.pone.0058860
[4] MARIAN C OKONDO. DPP8 and DPP9 inhibition induces pro-caspase-1-dependent monocyte and macrophage pyroptosis[J]. Nature chemical biology, 2016, 13 1: 46-53. DOI:10.1038/nchembio.2229
[5] MARIAN C. OKONDO . Inhibition of Dpp8/9 Activates the Nlrp1b Inflammasome[J]. Cell Chemical Biology, 2018, 25 3: Pages 262-267.e5. DOI:10.1016/j.chembiol.2017.12.013
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate Preparation Products And Raw materials
Raw materials
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View Lastest Price from [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate manufacturers
- 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
- 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
- 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