2-Propylpent-4-ynoic acid
2-Propylpent-4-ynoic acid (4-yn-VPA) is a HDAC inhibitor (with an IC50 of 0.5 mM against human HDAC). 2-Propylpent-4-ynoic acid also induces P-glycoprotein function, and exhibits teratogenicity, fetal growth inhibition and neurotoxicity. 2-Propylpent-4-ynoic acid shows significant stereospecific teratogenic effects, with the S-enantiomer being more teratogenic than the R-enantiomer and other analogs. The neurotoxicity of 2-Propylpent-4-ynoic acid is independent of its stereochemical structure. 2-Propylpent-4-ynoic acid has been used in studies related to the pathogenesis of colon cancer and neural tube defects such as exencephaly.
For research use only. We do not sell to patients.
- CAS No.: 24102-11-2
- Formula: C8H12O2
- Molecular Weight:140.18
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
2-Propylpent-4-ynoic acid (4-yn-VPA) (1 mM; 5 days) induces P-gp function in human colon adenocarcinoma SW620 cells, with an associated HDAC inhibition IC50 of 0.5 mM from HeLa nuclear extracts[1].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:human colon adenocarcinoma SW620 cells
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Concentration:1 mM
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Incubation Time:5 days
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Result:Induced P-gp function with IC50 of 0.5 mM.
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Han:NMRI (female, 29-36 g, neural tube defect induced by treatment on gestational day 8)[2]
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Dosage:0.40, 0.60, 0.73, 0.86, 1.05 mmol/kg (S(-)-4-yn-VPA);
3.00, 4.50, 6.00 mmol/kg (R(+)-4-yn-VPA) -
Administration:i.p.; single dose on gestational day 8
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Result:Induced exencephaly at rates of 3%, 23%, 38%, 51%, 65% for S(-)-4-yn-VPA at 0.40, 0.60, 0.73, 0.86, 1.05 mmol/kg, respectively.
Caused embryolethality at rates of 10%, 8%, 17%, 38%, 51% for S(-)-4-yn-VPA at 0.40, 0.60, 0.73, 0.86, 1.05 mmol/kg, respectively.
Reduced fetal weights significantly (vs control) to 1.05 g and 1.04 g for S(-)-4-yn-VPA at 0.86 mmol/kg and 1.05 mmol/kg, respectively.
Induced exencephaly at rates of 1%, 26%, 38% for R(+)-4-yn-VPA at 3.00, 4.50, 6.00 mmol/kg, respectively.
Caused embryolethality at rates of 10%, 16%, 45% for R(+)-4-yn-VPA at 3.00, 4.50, 6.00 mmol/kg, respectively.
Reduced fetal weight significantly (vs control) to 1.00 g ± 0.10 for R(+)-4-yn-VPA at 6.00 mmol/kg.
Achieved an ED50 of 0.83 mmol/kg for exencephaly induction with S(-)-4-yn-VPA, and 6.19 mmol/kg for R(+)-4-yn-VPA.
Chemical Information
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CAS No. 24102-11-2
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Molecular Weight 140.18
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Formula C8H12O2
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SMILES
O=C(O)C(CC#C)CCC
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Synonyms
4-yn-VPA
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Eyal S, et al. The antiepileptic and anticancer agent, valproic acid, induces P-glycoprotein in human tumour cell lines and in rat liver. Br J Pharmacol. 2006;149(3):250-260. [Content Brief]
[2]. Hauck RS, et al. The enantiomers of the valproic acid analogue 2-n-propyl-4-pentynoic acid (4-yn-VPA): asymmetric synthesis and highly stereoselective teratogenicity in mice. Pharm Res. 1992;9(7):850-855. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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