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

531465
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Empirical FormulaCAS #
C₁₀H₂₃BN₂O₆S 150080-09-4

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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
      Quality LevelMQ100
      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.