| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Targets |
7-BIA (7-butoxy illudalic acid analog) targets and inhibits the phosphatase activity of receptor-type protein tyrosine phosphatase D (PTPRD).
IC₅₀ for recombinant human PTPRD phosphatase: approximately 1–3 μM. IC₅₀ for recombinant human PTPRS phosphatase: approximately 40 μM. No significant activity at 77 other tested brain receptor/transporter sites (IC₅₀ > 10⁻⁵ M). [1] |
|---|---|
| ln Vitro |
7-BIA has an IC50 value of approximately 1-3 μM for recombinant human PTPRD and 40 μM for recombinant human PTPRS[1].
7-BIA inhibits recombinant human PTPRD and PTPRS phosphatase fusion proteins in a concentration-dependent manner, with greater potency against PTPRD. Precursor compounds (11–13) did not significantly inhibit PTPRD or PTPRS phosphatase activity. No significant binding or uptake inhibition at 77 known CNS drug targets at concentrations up to 10⁻⁵ M. [1] |
| ln Vivo |
7-BIA (10–20 mg/kg; i.p.; once only) decreases the amount of cocaine-independent medication administered to seasoned WT mice [1].
Pretreatment with 7-BIA (6 mg/kg i.p., 90 min before conditioning) significantly reduced cocaine-conditioned place preference in wild-type mice. Pretreatment with 7-BIA (10 or 20 mg/kg i.p., 90 min before session) reduced established cocaine self-administration in wild-type mice but not in PTPRD heterozygous KO mice. The effect persisted for 1–2 days after a single treatment. No rewarding or aversive properties were observed when environments were paired with 7-BIA alone. No significant changes in locomotor activity during cocaine sessions with 7-BIA vs. vehicle pretreatment. [1] |
| Enzyme Assay |
Recombinant human PTPRD and PTPRS D1 phosphatase domain fusion proteins were expressed in Escherichia coli BL21 cells and purified.
Phosphatase activity was measured spectrophotometrically by dephosphorylation of p-nitrophenyl phosphate to p-nitrophenolate at OD₆₀₀. For inhibition assays, enzyme and 7-BIA were preincubated for 16–18 min before substrate addition. IC₅₀ values were determined from concentration–response curves. Lineweaver–Burk analysis suggested a pseudoirreversible (non-competitive) mechanism of inhibition. [1] |
| Animal Protocol |
Animal/Disease Models: WT mice (cocaine available for 50 sessions, 1 mg/kg infusion) FR1 scheduled in ≥20 prior sessions) [1]
Doses: 10 mg/kg, 20 mg/kg Route of Administration: i.p. ; Experimental Results: diminished cocaine self-administration in experienced WT mice. For cocaine-conditioned place preference: Mice were pretreated with vehicle or 7-BIA (6 or 60 mg/kg i.p.) 90 min before each cocaine (10 mg/kg) conditioning session. Preference was tested 24 h after the last conditioning session. For cocaine self-administration: Mice with established cocaine self-administration history were pretreated with vehicle or 7-BIA (10 or 20 mg/kg i.p.) 90 min before a 3‑h self-administration session with 1 mg/kg/infusion cocaine. For acute and repeated toxicity: Mice received ascending i.p. doses of 7-BIA (6–60 mg/kg) or alternate-day dosing (60 mg/kg) for 2 weeks. Behavioral and histopathological analyses were performed. [1] |
| ADME/Pharmacokinetics |
7-BIA and its metabolites were detected in acetonitrile extracts of brain tissue 90 minutes after intraperitoneal injection using mass spectrometry.
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| Toxicity/Toxicokinetics |
No significant behavioral changes were observed after acute escalation of the dose (up to 60 mg/kg, intraperitoneal injection) or repeated administration (60 mg/kg every other day for 2 weeks). No drug-related gross or histopathological changes were found in the lungs, liver, kidneys, or intestines examined by veterinary pathologists. No significant effects on motor function, memory (Morris water maze), or pain sensitivity were observed. [1]
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| References | |
| Additional Infomation |
7-BIA is a small molecule inhibitor of PTPRD phosphatase and is considered a potential lead compound for the treatment of doping disorders. In vitro experiments have shown that it is more selective for PTPRD than for PTPRS, and its mechanism of action is pseudo-irreversible. Its action is PTPRD-dependent, and no therapeutic effect was observed in PTPRD heterozygous knockout mice. This compound is considered a framework for further optimization for clinical development in addiction and other diseases that may be associated with PTPRD variants. [1]
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| Molecular Formula |
C15H18O6
|
|---|---|
| Molecular Weight |
294.2998
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| Exact Mass |
294.11
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| CAS # |
1313403-49-4
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| PubChem CID |
137321149
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| Appearance |
Off-white to light yellow solid powder
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| LogP |
1.9
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
21
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| Complexity |
371
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O1C(C2=C([H])C(=C(C(C([H])=O)=C2C([H])([H])C1([H])O[H])OC([H])([H])[H])OC([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
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| InChi Key |
DAVCIYWSVYDJKW-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H18O6/c1-3-4-5-20-12-6-10-9(7-13(17)21-15(10)18)11(8-16)14(12)19-2/h6,8,13,17H,3-5,7H2,1-2H3
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| Chemical Name |
7-butoxy-3-hydroxy-6-methoxy-1-oxo-3,4-dihydroisochromene-5-carbaldehyde
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~125 mg/mL (~424.74 mM)
Ethanol : ~50 mg/mL (~169.89 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 6.25 mg/mL (21.24 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 6.25 mg/mL (21.24 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 62.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 6.25 mg/mL (21.24 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3979 mL | 16.9895 mL | 33.9789 mL | |
| 5 mM | 0.6796 mL | 3.3979 mL | 6.7958 mL | |
| 10 mM | 0.3398 mL | 1.6989 mL | 3.3979 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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