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.
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- CAS. Nr.: 24102-11-2
- Formel: C8H12O2
- Molecular Weight:140.18
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Speicherung:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biologische Aktivität
Beschreibung
In Vitro
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.
In Vivo
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. Nr. 24102-11-2
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Molecular Weight 140.18
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Formel 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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Versand
Room temperature in continental US; may vary elsewhere.
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Speicherung
Please store the product under the recommended conditions in the Certificate of Analysis.
Reinheit & Dokumentation
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Data Sheet (272 KB)
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SDS (252 KB)
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Handling Instructions (2659 KB)
Verweise
[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
Konzentration (Stammlösung) × Volumen (Stammlösung) = Konzentration (Ziellösung) × Volumen (Ziellösung)
2-Propylpent-4-ynoic acid Related Classifications
HY-W787758 Related Classifications
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Keywords
- 2-Propylpent-4-ynoic acid
- 24102-11-2
- 4-yn-VPA
- HDAC
- P-glycoprotein
- Histone deacetylases
- P-gp
- Pgp
- Multidrug resistance protein 1
- MDR1
- ATP-binding cassette sub-family B member 1
- ABCB1
- Cluster of differentiation 243
- CD243
- histone deacetylase
- colon carcinoma
- HeLa nuclear extracts
- exencephaly
- mice
- human colon adenocarcinoma SW620 cells
- Inhibitor
- inhibitor
- inhibit