β-oxidation

Etomoxir sodium salt ((R)-Etomoxir sodium salt) is a carnitine palmitoyltransferase 1a (CPT-1a) inhibitor that inhibits fatty acid oxidation (FAO). Etomoxir sodium salt has antitumor activity.

NADH disodium salt (Disodium NADH) hydrate is the reduced form of nicotinamide adenine dinucleotide (NAD) that can donate electrons in a reducing reaction, becoming oxidized to produce NAD+. Various enzymes utilize NADH disodium salt hydrate plus H+ to reduce substrates, generating NAD+ and the reduced product.

Kinetin (N6-Furfuryladenine), a type of cytokinin, has plant growth regulation effects.

Oleuropeinic acid, initially present in olive tissues or produced through the thermal oxidation of oleuropein, is an antioxidant-soluble fiber.

7α-Hydroxycholesterol, a cholesterol oxide formed through both enzymatic and non-enzymatic oxidation, can serve as a biomarker for lipid peroxidation.

PF-6274484, a high affinity, irreversible covalent inhibitor of EGFR kinase with Ki of 0.14 nM, inhibits the autophosphorylation of wild-type EGFR in A549 cells and EGFRL858R T790M in H1975 cells with IC50 of 5.8 nM and 6.6 nM, respectively.

Tetradecylthioacetic acid is a synthetic fatty acid with a sulfur substitution in the β-position. This modification renders TTA unable to undergo complete β-oxidation and increases its biological activity, including activation of peroxisome proliferator activated receptors (PPARs) with preference for PPARα.

Notoginsenoside R1 (Sanchinoside R1) has been shown to exhibit antioxidant, antiapoptotic, anti-inflammatory, and immune-stimulatory properties.

Mildronate (Meldonium) is an inhibitor of biosynthesis of L-carnitine by gamma-butyrobetaine (GBB) hydroxylase and as a competitive inhibitor of renal carnitine reabsorption.

NAD+ (β-Nicotinamide Adenine Dinucleotide) is a coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH).

8-iso-13,14-dihydro-15-keto Prostaglandin F2α (8-iso-13,14-dihydro-15-keto PGF2α) is a metabolite of the isoprostane, 8-isoprostane (8-iso PGF2α), in rabbits, monkeys and humans. 8-iso PGF2α is a PG-like product of non-specific lipid peroxidation. In both humans and monkeys, exogenously infused 8-isoprostane is converted primarily to metabolites having 2 or 4 carbon atoms removed from the top side chain by β-oxidation. A similar pattern is observed when tritiated 8-isoprostane is infused into rabbits. Early in the infusion (within 10 minutes) 8-iso-13,14-dihydro-15-keto PGF2α was a significant component of the metabolite profile, which was comprised mostly of dinor 8-isoprostane metabolites. 8-iso-13,14-dihydro-15-keto PGF2α weakly inhibits the U-46619 or collagen-induced aggregation of human platelets, although a number of the E-series isoprostanes are much more potent in this assay.

Tianeptine metabolite MC5, an active derivative of the atypical antidepressant tianeptine produced through β-oxidation, exhibits selective G protein activation in bioluminescence resonance energy transfer (BRET) assays. Utilizing HEK293T cells expressing the human μ-opioid receptor (MOR) over the human δ-opioid receptor (DOR; EC50s = 0.454 and >100 µM, respectively), it demonstrates specificity. Moreover, this metabolite reduces immobility in wild-type mice during the forced swim test at a dose of 30 mg/kg, an effect not observed in MOR knockout mice, suggesting its antidepressant-like activity is MOR-dependent.

3-Aminoisobutyric acid, a non-protein amino acid resultant from thymine catabolism, plays a significant role in metabolic activities. At a 5 µM concentration, it triggers browning in primary adipocytes, notably elevating uncoupling protein 1 (UCP-1) and CIDEA expression. Additionally, it boosts PPARα expression in both primary adipocytes and mouse inguinal white adipose tissue (WAT) in vivo, alongside enhancing β-oxidation in hepatocytes. Its plasma levels surge post-exercise in mice, and its administration at 100 mg/kg daily curtails weight gain and body fat without diminishing food consumption or hiking energy output, whilst ameliorating glucose tolerance. Notably, 3-aminoisobutyric acid concentrations are heightened in individuals with β-ureidopropionase deficiency, a genetic flaw impairing pyrimidine degradation, affecting plasma, urine, and cerebrospinal fluid.

Roseoside ((6S,9R)-roseoside), a sesquiterpenoid isolated from Catharanthus roseus, has strong antioxidant and proinsulinic activity, inhibits lipid oxidation, enhances insulin release from the β-cell line INS-1, and can be used in cancer research.

20-hydroxy Prostaglandin E2 (20-hydroxy PGE2) is a product of cytochrome P450 metabolism of PGE2 . ω-Oxidation at C-20 followed by β-oxidation and the loss of up to four carbons from the lower side chain is a prominent metabolic pathway for PGE2. 20-hydroxy PGE2 is the putative first intermediate in this chain of chemical transformations.

GDP-β-L-fucose is a metabolite in plant and animal. It used for microbe agglutination assay and agglutination inhibition assay. GDP-β-L-fucose is formed by the oxidation-reduction and epimerization of GDP-R-D-mannose in most organisms.

L-Carnitine hydrochloride (Standard) is a small molecule water-soluble substance involved in fatty acid metabolism, helping long-chain fatty acids cross the inner mitochondrial membrane for beta-oxidation. L-Carnitine hydrochloride (Standard) can be used for the quantification in biological samples, to study fatty acid β-oxidation, mitochondrial function and energy metabolism.

Palmitoyl CoA lithium (Palmitoyl coenzyme A lithium) is a major component of fatty acids involved in the carnitine shuttle system, beta-oxidation, and the tricarboxylic acid cycle, and can be used to study metabolic disorders in the body.

Octanoyl coenzyme A (octanoyl-CoA) is a medium-chain acyl CoA and a metabolic intermediate in mitochondrial fatty acid β-oxidation. Levels of octanoyl-CoA are increased in the liver of patients with Reye's syndrome and β-oxidation of octanoyl-CoA by medium-chain acyl CoA dehydrogenase (MCADH) is decreased in patients with MCADH deficiency (MCD). Octanoyl-CoA inhibits citrate synthase and glutamate dehydrogenase.

Metabolism of 12(R)-HETE in corneal tissue produces predominantly the compound resulting from the loss of four carbon atoms through β-oxidation from C-1. This metabolite is 8(R)-hydroxy hexadecatrienoic acid (8(R)-HHxTrE) or 2,3,4,5-tetranor 12(R)-HETE.

Latanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. Oxidation of the C-15 hydroxyl group without isopropyl ester hydrolysis produces 15-keto latanoprost. 15-keto Latanoprost is a potential metabolite of latanoprost when administered to animals. 15-keto Latanoprost is also one of the common minor impurities found in commercial preparations of the bulk drug compound. Although much less potent that the parent compound latanoprost, 15-keto latanoprost still retains the ability to produce a small but measurable decrease (1 mm Hg) in the intraocular pressure of normal cynomolgus monkeys when administered at a dose of 1 μg/eye. 15-keto Latanoprost is also a miotic in the normal cat eye, causing an 8 mm reduction in pupillary diameter at 5 μg/eye. Again, this is not as potent as many other F-type PGs; for example, PGF2α will produce this degree of miosis at a dose of less than 1 μg/eye. Products of β-oxidation account for most of the metabolites of latanoprost recovered in plasma and urine. However, 15-keto latanoprost is a minor metabolite, and one which could be enhanced in situations where β-oxidation is reduced.

NADH disodium salt hydrate, also known as Disodium NADH hydrate, functions as an orally active reduced coenzyme. It serves as a donor of ADP-ribose units in ADP-ribosylation reactions and acts as a precursor to cyclic ADP-ribose. Additionally, it contributes to cellular energy metabolism by acting as a renewable electron donor in processes such as glycolysis, β-oxidation, and the tricarboxylic acid (TCA) cycle [1].

18-Carboxy dinor Leukotriene B4 (18-carboxy dinor LTB4) represents a β-oxidation metabolite of Leukotriene B4 (LTB4). Initially, LTB4 is metabolized in the liver to 20-carboxy LTB4, which subsequently undergoes β-oxidation to form 18-carboxy dinor LTB4.

9(S),12(S),13(S)-TriHOME is a linoleic acid-derived oxylipin that has diverse biological activities.1,2,3,4It has been found in various plants and is produced in human eosinophils in a 15-lipoxygenase-dependent, soluble epoxide hydrolase-independent manner.1,59(S),12(S)13(S)-TriHOME inhibits antigen-induced β-hexosaminidase release from RBL-2H3 mast cells (IC50= 28.7 μg ml).2It inhibits LPS-induced nitric oxide (NO) production in BV-2 microglia (IC50= 40.95 μM).3In vivo, 9(S),12(S),13(S)-TriHOME (1 g animal) enhances the antiviral IgA and IgG antibody responses induced by a nasal influenza hemagglutinin (HA) vaccine by 5.2- and 2-fold, respectively, in mice.4 1.Hamberg, M., and Hamberg, G.Peroxygenase-catalyzed fatty acid epoxidation in cereal seeds: Sequential oxidation of linoleic acid into 9(S),12(S),13(S)-trihydroxy-10(E)-octadecenoic acidPlant Physiol.110(3)807-815(1996) 2.Hong, S.S., and Oh, J.S.Inhibitors of antigen-induced degranulation of RBL-2H3 cells isolated from wheat branJ. Korean Soc. Appl. Biol. Chem.5569-74(2012) 3.Kim, C.S., Kwon, O.W., Kim, S.Y., et al.Five new oxylipins from Chaenomeles sinensisLipids49(11)1151-1159(2014) 4.Shirahata, T., Sunazuka, T., Yoshida, K., et al.Total synthesis, elucidation of absolute stereochemistry, and adjuvant activity of trihydroxy fatty acidsTetrahedron62(40)9483-9496(2006) 5.Fuchs, D., Tang, X., Johnsson, A.-K., et al.Eosinophils synthesize trihydroxyoctadecenoic acids (TriHOMEs) via a 15-lipoxygenase dependent processBiochim. Biophys. Acta Mol. Cell Biol. Lipids1865(4)158611(2020)