ホーム>>Signaling Pathways>> Proteases>> Endogenous Metabolite>>4-Methyl-2-oxopentanoic acid

4-Methyl-2-oxopentanoic acid (Synonyms: 2-Ketoisocaproate, α-Ketoisocaproate, 2-Ketoisocapronic Acid, KIC, 4-MOP, 2-Oxoisocaproic Acid, 4-methyl-2-Oxopentanoate, 4-methyl-2-Oxovaleric Acid, 4-methyl-2-Oxovalerate)

カタログ番号GC31307

4-メチル-2-オキソペンタン酸 (α-ケトイソカプロン酸) は、異常な代謝産物であり、神経毒とメタボトキシンの両方です。

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4-Methyl-2-oxopentanoic acid 化学構造

Cas No.: 816-66-0

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100mg
$56.00
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Sample solution is provided at 25 µL, 10mM.

Description of 4-Methyl-2-oxopentanoic acid

4-Methyl-2-oxopentanoic acid is an abnormal metabolite, a neurotoxin and a metabolic toxin. 4-Methyl-2-oxopentanoic acid increases endoplasmic reticulum stress, promotes lipid accumulation in preadipocytes and insulin resistance by impairing mTOR and autophagy signaling pathways[1] [2].

4-Methyl-2-oxopentanoic acid (0-300μM; 2d) treatment concentration-dependently increased lipid accumulation and the expression of lipogenic proteins, such as processed SREBP1 and SCD1, in 3T3-L1 preadipocytes[1]. 4-Methyl-2-oxopentanoic acid (1-10mM) reduced the HT-22 cells’ metabolic ability to reduce cytotoxicity and increased RS production in hippocampal neurons[2].

Mitochondrial complexes activities were reduced, and the formation of reactive species (RS) was increased in the hippocampus of rats after 4-Methyl-2-oxopentanoic acid (4mol/L, 2μL; ICV) administration[2].4-Methyl-2-oxopentanoic acid(10mmol/l; ICV) stimulated insulin secretion and elevated the NADPH/NADP+ ratio of islets preincubated in the absence of fuel[3].4-Methyl-2-oxopentanoic acid (400μmol/kg/h; carotid arch injection; single dose injection 60 min) increases porcine skeletal muscle protein synthesis and plasma leucine levels[4].

References:
[1].Park T J, Park S Y, Lee H J, et al. α-ketoisocaproic acid promotes ER stress through impairment of autophagy, thereby provoking lipid accumulation and insulin resistance in murine preadipocytes[J]. Biochemical and Biophysical Research Communications, 2022, 603: 109-115.
[2]. Farias H R, Gabriel J R, Cecconi M L, et al. The metabolic effect of α-ketoisocaproic acid: in vivo and in vitro studies[J]. Metabolic Brain Disease, 2021, 36: 185-192.
[3]. Panten U, Rustenbeck I. Fuel-induced amplification of insulin secretion in mouse pancreatic islets exposed to a high sulfonylurea concentration: role of the NADPH/NADP+ ratio[J]. Diabetologia, 2008, 51: 101-109.
[4]. Escobar J, Frank J W, Suryawan A, et al. Leucine and α-ketoisocaproic acid, but not norleucine, stimulate skeletal muscle protein synthesis in neonatal pigs[J]. The Journal of nutrition, 2010, 140(8): 1418-1424.

Protocol of 4-Methyl-2-oxopentanoic acid

Cell experiment [1]:

Cell lines

Mouse preadipocyte 3T3-L1 cells

Preparation Method

Mouse preadipocyte 3T3-L1 cells were treated with 0–300μM 4-Methyl-2-oxopentanoic acid for 2 days.

Reaction Conditions

0-300μM; 2d

Applications

4-Methyl-2-oxopentanoic acid treatment concentration-dependently increased lipid accumulation and the expression of lipogenic proteins, such as processed SREBP1 and SCD1, in 3T3-L1 preadipocytes.
Animal experiment [2]:

Animal models

KIC exposure modle

Preparation Method

30-day-old male Wistar rats were anesthetized and placed in a stereotaxic apparatus, and two small holes were drilled in the skull (bilaterally) to inject 2µL of 4-Methyl-2-oxopentanoic acid or aCSF (control). The solution was slowly injected into the lateral ventricle over 4 minutes. The needle was left in place for 1 minute and then gently withdrawn. 4-Methyl-2-oxopentanoic acid solution (4µmol, pH 7.4) was dissolved in freshly prepared artificial cerebrospinal fluid (aCSF) (147mM NaCl; 2.9mM KCl; 1.6mM MgCl2; 1.7mM CaCl2 and 2.2mM glucose). One hour after administration, the animals were killed by decapitation, and the hippocampus was dissected.

Dosage form

4mol/L, 2μL; ICV

Applications

Mitochondrial complexes activities were reduced, and the formation of RS was increased in the hippocampus of rats after 4-Methyl-2-oxopentanoic acid administration.

References:
[1]. Park T J, Park S Y, Lee H J, et al. α-ketoisocaproic acid promotes ER stress through impairment of autophagy, thereby provoking lipid accumulation and insulin resistance in murine preadipocytes[J]. Biochemical and Biophysical Research Communications, 2022, 603: 109-115.
[2]. Farias H R, Gabriel J R, Cecconi M L, et al. The metabolic effect of α-ketoisocaproic acid: in vivo and in vitro studies[J]. Metabolic Brain Disease, 2021, 36: 185-192.

Chemical Properties of 4-Methyl-2-oxopentanoic acid

Cas No. 816-66-0 SDF
同義語 2-Ketoisocaproate, α-Ketoisocaproate, 2-Ketoisocapronic Acid, KIC, 4-MOP, 2-Oxoisocaproic Acid, 4-methyl-2-Oxopentanoate, 4-methyl-2-Oxovaleric Acid, 4-methyl-2-Oxovalerate
Canonical SMILES CC(C)CC(C(O)=O)=O
Formula C6H10O3 M.Wt 130.14
溶解度 DMSO: ≥ 100 mg/mL (768.40 mM); Water: 100 mg/mL (768.40 mM) Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 4-Methyl-2-oxopentanoic acid

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 7.684 mL 38.4202 mL 76.8403 mL
5 mM 1.5368 mL 7.684 mL 15.3681 mL
10 mM 0.7684 mL 3.842 mL 7.684 mL
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