Ornithine-α-ketoglutarate | CAS# 5191-97-9 | Polyamine and NO Modulator

MedKoo Cat#: 564485 | Name: Ornithine-α-ketoglutarate

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ornithine-α-ketoglutarate is a modulator of the respiratory burst via nitric oxide and polyamine generation, thereby improving immune status during stress.

Chemical Structure

Ornithine-α-ketoglutarate

CAS#5191-97-9

Theoretical Analysis

MedKoo Cat#: 564485

Name: Ornithine-α-ketoglutarate

CAS#: 5191-97-9

Chemical Formula: C10H18N2O7

Exact Mass: 278.1114

Molecular Weight: 278.26

Elemental Analysis: C, 43.16; H, 6.52; N, 10.07; O, 40.25

Price and Availability

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100g	USD 215.00

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Synonym

OKG; L-Ornithine-α-ketoglutarate; L Ornithine α ketoglutarate; Ornithine-α-ketoglutarate; Ornithine α-ketoglutarate; Ornithine α ketoglutarate; Ornithine alpha ketoglutarate

IUPAC/Chemical Name

(S)-2,5-Diaminopentanoic acid compound with 2-oxopentanedioic acid

InChi Key

SLPUVFBNQHVEEU-WCCKRBBISA-N

InChi Code

InChI=1S/C5H12N2O2.C5H6O5/c6-3-1-2-4(7)5(8)9;6-3(5(9)10)1-2-4(7)8/h4H,1-3,6-7H2,(H,8,9);1-2H2,(H,7,8)(H,9,10)/t4-;/m0./s1

SMILES Code

O=C(O)[C@@H](N)CCCN.O=C(O)C(CCC(O)=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ornithine-α-ketoglutarate is a modulator of the respiratory burst via nitric oxide and polyamine generation.

In vitro activity:

In normoxia, AKG (alpha-ketoglutarate) inhibited proliferation of colon adenocarcinoma cell lines: Caco-2, HT-29, and LS-180, representing different stages of colon carcinogenesis. Furthermore, AKG influenced the cell cycle, enhancing the expression of the inhibitors of cyclin-dependent kinases p21 Waf1/Cip1 and p27 Kip1. Moreover, expression of cyclin D1, required in G1/S transmission, was decreased, which accompanied with the significant increase in cell number in G1 phase. AKG affected also one the key cell cycle regulator, Rb, and reduced its activation status. Reference: Scand J Gastroenterol. 2012 May;47(5):565-71. https://pubmed.ncbi.nlm.nih.gov/22486188/

In vivo activity:

This study was conducted to explore the impact of OKG (ornithine α-ketoglutarate) on growth performance, immunity, and ileal mucosa microbiota and its metabolites in piglets infected with ETEC. OKG inhibited serum IL-6, suppressed the phosphorylation of downstream signals of NF-κB/JNK in the ileum, and enhanced serum IL-10 and ileum SIgA in ETEC-challenged piglets. OKG supplementation enhanced the mRNA expression of IL-1β and IL-10 and reduced NF-κB and MyD88 in the ileum. Importantly, OKG reversed intestinal microbiota dysfunction, including the diversity of ileal microbiota, the relative abundances of Actinobacillus, Turicibacter, and [Acetivibrio]_ethanolgignens_group, which significantly affected arachidonic acid metabolism and primary bile acid biosynthesis. Reference: Front Nutr. 2022 Jun 7;9:862498. https://pubmed.ncbi.nlm.nih.gov/35747266/

Preparing Stock Solutions

The following data is based on the product molecular weight 278.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Rzeski W, Walczak K, Juszczak M, Langner E, Pożarowski P, Kandefer-Szerszeń M, Pierzynowski SG. Alpha-ketoglutarate (AKG) inhibits proliferation of colon adenocarcinoma cells in normoxic conditions. Scand J Gastroenterol. 2012 May;47(5):565-71. doi: 10.3109/00365521.2012.660539. PMID: 22486188. 2. Lescoat G, Desvergne B, Loreal O, Pasdeloup N, Deugnier Y, Bourel M, Brissot P. Modulation of albumin secretion by ornithine alpha-ketoglutarate in adult rat hepatocyte cultures and a human hepatoma cell line (HepG2). Ann Nutr Metab. 1989;33(5):252-60. doi: 10.1159/000177542. PMID: 2624435. 3. Li Y, Bao X, Yang F, Tian J, Su W, Yin J, Yao K, Li T, Yin Y. Ornithine α-Ketoglutarate Alleviates Inflammation via Regulating Ileal Mucosa Microbiota and Metabolites in Enterotoxigenic Escherichia coli-Infected Pigs. Front Nutr. 2022 Jun 7;9:862498. doi: 10.3389/fnut.2022.862498. PMID: 35747266; PMCID: PMC9211023. 4. Gonçalves ES, Rabelo CM, Prado Neto AX, Garcia JH, Guimarães SB, Vasconcelos PR. Effect of short-term ornithine alpha-ketoglutarate pretreatment on intestinal ischemia-reperfusion in rats. Acta Cir Bras. 2011;26 Suppl 1:2-7. doi: 10.1590/s0102-86502011000700002. PMID: 21971649.

In vitro protocol:

In vivo protocol:

1. Li Y, Bao X, Yang F, Tian J, Su W, Yin J, Yao K, Li T, Yin Y. Ornithine α-Ketoglutarate Alleviates Inflammation via Regulating Ileal Mucosa Microbiota and Metabolites in Enterotoxigenic Escherichia coli-Infected Pigs. Front Nutr. 2022 Jun 7;9:862498. doi: 10.3389/fnut.2022.862498. PMID: 35747266; PMCID: PMC9211023. 2. Gonçalves ES, Rabelo CM, Prado Neto AX, Garcia JH, Guimarães SB, Vasconcelos PR. Effect of short-term ornithine alpha-ketoglutarate pretreatment on intestinal ischemia-reperfusion in rats. Acta Cir Bras. 2011;26 Suppl 1:2-7. doi: 10.1590/s0102-86502011000700002. PMID: 21971649.

1: Roch-Arveiller M, Tissot M, Coudray-Lucas C, Fontagné J, Le Boucher J, Giroud JP, Cynober L. Immunomodulatory effects of ornithine alpha-ketoglutarate in rats with burn injuries. Arch Surg. 1996 Jul;131(7):718-23. PubMed PMID: 8678770. 2: Le Bricon T, Cynober L, Field CJ, Baracos VE. Supplemental nutrition with ornithine alpha-ketoglutarate in rats with cancer-associated cachexia: surgical treatment of the tumor improves efficacy of nutritional support. J Nutr. 1995 Dec;125(12):2999-3010. PubMed PMID: 7500178. 3: Cynober L. Ornithine alpha-ketoglutarate in nutritional support. Nutrition. 1991 Sep-Oct;7(5):313-22. Review. PubMed PMID: 1804465. 4: Guimarães Filho A, Cunha RM, Vasconcelos PR, Guimarães SB. Glutamine and ornithine alpha-ketoglutarate supplementation on malate dehydrogenases expression in hepatectomized rats. Acta Cir Bras. 2014 Jun;29(6):365-70. PubMed PMID: 24919044.