531465 Val-boroPro - CAS 150080-09-4 - Calbiochem

531465
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₁₀H₂₃BN₂O₆S 150080-09-4

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          Glass bottle 10 mg
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          Description
          OverviewAn orally available amino boronic acid dipeptide with antihyperglycemic and anticancer properties. Acts as a highly potent, reversible, and transition state analog inhibitor of dipeptidyl peptidase IV (DPP-IV; IC50 = 26 nM; Ki = 180 pM). Also inhibits the activity of other prolyl peptidases (IC50 = 15 nM for DPP-II; and Ki = 1.5 nM and 760 pM for DPP8 and DPP9, respectively) and at much higher concentrations affects the activities of quiescent cell proline dipeptidase (QPP, DPP7; IC50 = 310 nM), PEP (IC50 = 390 nM) and fibroblast activation protein (FAP; IC50 = 560 nM). However, it does not inhibit the activity of trypsin, chymoptrypsin, thrombin, plasmin, tryptase, leukocyte elastase, and plasma kallikrein even at high levels (~100 µM). Promotes hematopoiesis and the growth of primitive hematopoietic progenitor cells by increasing the production of G-CSF, IL-6, and IL-11 by bone marrow stromal cells in mice. Although it has no direct cytotoxic effect on tumors in vitro, but oral administration in mice is shown to reduce the growth of syngeneic tumors derived from fibrosarcoma (WEHI164), lymphoma (EL4 and A20/2J), melanoma (B16-F10), and mastocytoma (P815) cell lines and augments antibody-dependent cell-mediated cytotoxicity. Note: In aqueous physiological solutions, it can cyclize in a time-dependent manner causing a 100-fold diminution in its inhibitory potency. However, at lower pH range it remains in an active open chain form. Maximum tolerated dose in mice or rats is ~ 25 µg/kg.

          Please note that the molecular weight for this compound is batch-specific due to variable water content.
          Catalogue Number531465
          Brand Family Calbiochem®
          SynonymsPT-100, Talabostat, H₂N-(S)-Val-(R)-boroPro-OH, CH₃SO₃H, H-(S)-Val-(R)-boroPro-OH, CH₃SO₃H, Valinyl-L-boroproline, CH₃SO₃H, DPP Inhibitor
          References
          ReferencesPoplawski, S.E., et al. 2011, J. Med. Chem. 54, 2022.
          Connolly, B.A., et al. 2008. J. Med. Chem. 51, 6005.
          Lankas, G.R., et al. 2005. Diabetes 54, 2988.
          Cheng, J.D., et al. 2005. Mol. Cancer Ther. 4, 351.
          Adams, S., et al. 2004. Cancer Res. 64, 5471.
          Jones, B., et al. 2003. Blood 102, 1641.
          Coutts, S.J., et al. 1996. J. Med. Chem. 39, 2087.
          Snow, R.J., et al. 1994. J. Am. Chem. Soc. 116, 10860.
          Kelly, T.A., et al. 1993. J. Am. Chem. Soc. 115, 12637.
          Product Information
          CAS number150080-09-4
          FormLight beige solid
          Hill FormulaC₁₀H₂₃BN₂O₆S
          Chemical formulaC₁₀H₂₃BN₂O₆S
          Hygroscopic Hygroscopic
          ReversibleY
          Applications
          Biological Information
          Primary TargetDPP-IV, DPP8 and DPP9
          Primary Target IC<sub>50</sub>15 nM for DPP-II
          Primary Target K<sub>i</sub>180 pM
          Secondary targetQPP, PEP and FAP
          Purity≥98% by HPLC
          Physicochemical Information
          Cell permeableY
          Dimensions
          Materials Information
          Toxicological Information
          Safety Information according to GHS
          Safety Information
          Product Usage Statements
          Storage and Shipping Information
          Ship Code Ambient Temperature Only
          Toxicity Standard Handling
          Storage +2°C to +8°C
          Protect from Light Protect from light
          Hygroscopic Hygroscopic
          Do not freeze Ok to freeze
          Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
          Packaging Information
          Packaged under inert gas Packaged under inert gas
          Transport Information
          Supplemental Information
          Specifications

          Documentation

          Val-boroPro - CAS 150080-09-4 - Calbiochem SDS

          Title

          Safety Data Sheet (SDS) 

          References

          Reference overview
          Poplawski, S.E., et al. 2011, J. Med. Chem. 54, 2022.
          Connolly, B.A., et al. 2008. J. Med. Chem. 51, 6005.
          Lankas, G.R., et al. 2005. Diabetes 54, 2988.
          Cheng, J.D., et al. 2005. Mol. Cancer Ther. 4, 351.
          Adams, S., et al. 2004. Cancer Res. 64, 5471.
          Jones, B., et al. 2003. Blood 102, 1641.
          Coutts, S.J., et al. 1996. J. Med. Chem. 39, 2087.
          Snow, R.J., et al. 1994. J. Am. Chem. Soc. 116, 10860.
          Kelly, T.A., et al. 1993. J. Am. Chem. Soc. 115, 12637.
          Data Sheet

          Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

          Revision15-August-2014 JSW
          SynonymsPT-100, Talabostat, H₂N-(S)-Val-(R)-boroPro-OH, CH₃SO₃H, H-(S)-Val-(R)-boroPro-OH, CH₃SO₃H, Valinyl-L-boroproline, CH₃SO₃H, DPP Inhibitor
          DescriptionA 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.
          FormLight beige solid
          Intert gas (Yes/No) Packaged under inert gas
          CAS number150080-09-4
          Chemical formulaC₁₀H₂₃BN₂O₆S
          Purity≥98% by HPLC
          SolubilityDMSO (100 mg/ml). Use only fresh DMSO for reconstitution.
          Storage +2°C to +8°C
          Hygroscopic
          Protect from light
          Do Not Freeze Ok to freeze
          Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.
          Toxicity Standard Handling
          ReferencesPoplawski, S.E., et al. 2011, J. Med. Chem. 54, 2022.
          Connolly, B.A., et al. 2008. J. Med. Chem. 51, 6005.
          Lankas, G.R., et al. 2005. Diabetes 54, 2988.
          Cheng, J.D., et al. 2005. Mol. Cancer Ther. 4, 351.
          Adams, S., et al. 2004. Cancer Res. 64, 5471.
          Jones, B., et al. 2003. Blood 102, 1641.
          Coutts, S.J., et al. 1996. J. Med. Chem. 39, 2087.
          Snow, R.J., et al. 1994. J. Am. Chem. Soc. 116, 10860.
          Kelly, T.A., et al. 1993. J. Am. Chem. Soc. 115, 12637.