150080-09-4

Basic information

• Product Name: [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate
• Synonyms: [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate;Talabostat 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 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
• CAS NO: 150080-09-4
• Molecular Formula: C10H23BN2O6S
• Molecular Weight: 310.17
• Mol File: 150080-09-4.mol
• Article Data: 0

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Soluble in DMSO (up to at least 25 mg/ml)
• 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.
• CAS DataBase Reference: [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate(CAS DataBase Reference)
• NIST Chemistry Reference: [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate(150080-09-4)
• EPA Substance Registry System: [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate(150080-09-4)

Safety Data

• Hazardous Substances Data: 150080-09-4(Hazardous Substances Data)

Usage

Description

[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate, also known as Talabostat, is a prolineboronic acid-based broad-spectrum dipeptidyl peptidase (DPP) IV activity inhibitor. It belongs to the DPP (DASH) family and can convert between the protonated active form and a cyclized inactive form due to a reversible intramolecular B-N dative bond formation. Talabostat exhibits high affinity binding to CD26 and is reported to inhibit various DPPs, including DPP7/DPPII/QPP, CD26/DPPIV, fibroblast activation protein/FAP, DPP8, and DDP9, with little potency against other proteases. It also demonstrates hematopoietic stimulatory effects and has been shown to promote the propagation of human bone marrow CD34+ cells.

Uses

1. Used in Cancer Treatment:
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate is used as an anticancer agent for the treatment of various types of cancer, including fibrosarcoma, lymphoma, melanoma, and mastocytoma. It inhibits the proliferation of superantigen-stimulated human peripheral blood mononuclear cells (PBMCs) and increases the expression of cytokines and chemokines in tumors and tumor-draining lymph nodes, reducing tumor growth.
2. Used in Hematopoietic Stimulation:
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate is used as a hematopoietic stimulant, promoting the propagation of human bone marrow CD34+ cells by stimulating stromal cells' cytokine production in vitro and displaying hematopoietic stimulatory effects in mice in vivo.
3. Used in Enhancing Antitumor Antibody Efficacy:
In the field of cancer treatment, [(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate is used to increase the efficacy of antitumor antibodies such as rituximab and trastuzumab in B cell lymphoma and colon carcinoma mouse xenograft models, respectively.
4. Used in Biological and Pharmacological Studies:
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate is used in biological and pharmacological research for the study and development of treatments for cancer using immunomodulation.
5. Used in Drug Development:
[(2R)-1-[(2S)-2-Amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid mesylate is used in the development of novel drug delivery systems to enhance its applications and efficacy against cancer cells, employing various organic and metallic nanoparticles as carriers for improved delivery, bioavailability, and therapeutic outcomes.

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

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

InChI:InChI=1/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