Linagliptin

SKU: orb1310851

Description

Linagliptin (BI 1356) is a potent and orally bioavailable DPP-4 inhibitor of the dihydropurinedione class, used for its hypoglycemic effects. It is widely applied in diabetes research, including in vitro enzymatic assays and in vivo studies of glucose metabolism and pancreatic function.

Research Area

Cell Biology, Pharmacology & Drug Discovery, Protein Biochemistry

Key Properties

• CAS Number: 668270-12-0
• MW: 472.5422
• Purity: >99.99% (May vary between batches)
• Formula: C₂₅H₂₈N₈O₂
• SMILES: CC#CCN1C(=NC2=C1C(=O)N(CC1=NC3=CC=CC=C3C(C)=N1)C(=O)N2C)N1CCC[C@@H](N)C1
• Target: Ferroptosis,Autophagy,DPP-4
• Solubility: DMSO:26.67 mg/mL (56.44 mM);10% DMSO+40% PEG300+5% Tween 80+45% Saline:1 mg/mL (2.12 mM);Ethanol:1 mg/mL (2.12 mM);H2O:< 1 mg/mL (insoluble or slightly soluble)

Bioactivity

• Target IC50:
  DPP4:1 nM
• In Vivo:
  In male Wistar rats, Beagle dogs, and Rhesus monkeys, Linagliptin exhibits highly efficacious, long-lasting, and potent inhibitory activity against DPP-4 with over 70% inhibition for all three species after oral administration of 1 mg/kg. In db/db mice, oral administration of Linagliptin 45 min before an oral glucose tolerance test reduces plasma glucose excursion in a dose-dependent manner, achieving 15% inhibition at 0.1 mg/kg and 66% inhibition at 1 mg/kg. By inhibiting DPP-4 activity, Linagliptin also reduces the expression of the proinflammatory markers cyclooxygenase-2 and macrophage inflammatory protein-2, and enhances myofibroblast formation in healing wounds from ob/ob mice.
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• In Vitro:
  Linagliptin shows a potent inhibition effect against DPP-4 in vitro and a low affinity for hERG channel and M1 receptor (IC50 295 nM). Linagliptin acts as a competitive inhibitor with a Ki of 1 nM, and also shows 10,000-fold more selectivity for DPP-4 than DPP-8, DPP-9, amino-peptidases N and P, prolyloligopeptidase, trypsin, plasmin, and thrombin, and 90-fold more selectivity than fibroblast activation protein in vitro.
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• Cell Research:
  A total of 4.0×107 keratinocytes per well are seeded into 24-well plates. After reaching 50% confluence, cells are starved for 24 h with DMEM. Proliferation of cells is assessed by using 1 μCi/mL of [3H]methyl-thymidine in DMEM in the presence of 10% fetal bovine serum and increasing concentrations of linagliptin (3, 30, 300, or 600 nM) for 24 h. Cells are then washed twice with phosphate-buffered saline and incubated in 5% trichloroacetic acid at 4°C for 30 min, and the DNA is solubilized in 0.5mol/LNaOH for 30 min at 37°C. Finally, [3H]thymidine incorporation is determined.
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Storage & Handling

• Storage: -20°C
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

Dipeptidyl Peptidase, DPP, DPP4, DPP-4, Autophagy, BI 1356, BI1356, BI-1356, Inhibitor, Ferroptosis, inhibit, Linagliptin

Compound Identifiers

PubChem CID

10096344