(S)-Trolox, an analogue of vitamin E, substitutes the phytyl chain with a carboxyl group. This compound serves as a model substance in structural studies and as a standard for assessing antioxidant activity. Moreover, (S)-Trolox exhibits potent and specific neuroprotective and antioxidant properties.
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.
20-Ethyl Prostaglandin E2 (20-ethyl PGE2) is an analog of Prostaglandin E2 (PGE2) characterized by an extended ω-chain due to two additional methylene carbon atoms. Compared to unoprostone, a clinically approved glaucoma medication and the only extensively studied prostaglandin analog sharing this structural modification, 20-ethyl PGE2 maintains the natural 15(S) allylic hydroxyl in its lower side chain, potentially enhancing its effectiveness. Unoprostone, despite being an F-series prostaglandin, exhibits reduced affinity for FP receptors because of its lower side chain modifications (13,14-dihydro-15-keto), which diminishes its medicinal potency. Notably, 20-ethyl PGE2's efficacy relative to unoprostone and its interaction with EP or other prostanoid receptors remains unconfirmed due to the lack of published ligand binding assays. E-type prostaglandins, including 20-ethyl PGE2, are broadly acknowledged for their inflammatory, cytoprotective, and diverse biological activities.
Sphingosine-1-phosphate (S1P), a bioactive lipid crucial in numerous signaling pathways, undergoes irreversible degradation by membrane-bound S1P lyase, producing (E)-2-Hexadecenal, a derivative of sphingolipid breakdown. This compound can be oxidized to (2E)-hexadecenoic acid by long-chain fatty aldehyde dehydrogenase before being activated through linkage to coenzyme A. Notably, (E)-2-Hexadecenal induces cytoskeletal reorganization, leading to cell rounding, detachment, activation of JNK pathway targets, and ultimate apoptosis in a variety of cell types. Furthermore, it readily forms aldehyde-derived DNA adducts through reactions with deoxyguanosine and DNA.
Octanoic acid-13C is intended for use as an internal standard for the quantification of octanoic acid by GC- or LC-MS. Octanoic acid is a medium-chain saturated fatty acid. It has been found in Teleme cheeses made from goat, ovine, or bovine milk.1 Octanoic acid is active against the bacteria S. mutans, S. gordonii, F. nucleatum, and P. gingivalis (IC80s = <125, <125, 1,403, and 2,294 μM, respectively).2 Levels of octanoic acid are increased in the plasma of patients with medium-chain acyl-CoA dehydrogenase (MCAD) deficiency, an inborn error of fatty acid metabolism characterized by hypoketotic hypoglycemia, medium-chain dicarboxylic aciduria, and intolerance to fasting.3,4 |1. Mallatou, H., Pappa, E., and Massouras, T. Changes in free fatty acids during ripening of Teleme cheese made with ewes', goats', cows' or a mixture of ewes' and goats' milk. Int. Dairy J. 13(1-3), 211-219 (2003).|2. Hyang, C.B., Alimova, Y., Myers, T.M., et al. Short- and medium-chain fatty acids exhibit antimicrobial activity for oral microorganisms. Arch. Oral Biol. 56(7), 650-654 (2011).|3. Onkenhout, W., Venizelos, V., van der Poel, P.F.H., et al. Identification and quantification of intermediates of unsaturated fatty acid metabolism in plasma of patients with fatty acid oxidation disorders. Clin. Chem. 41(10), 1467-1474 (1995).|4. Rinaldo, P., O'Shea, J.J., Coates, P.M., et al. Medium-chain acyl-CoA dehydrogenase deficiency. Diagnosis by stable-isotope dilution measurement of urinary n-hexanoylglycine and 3-phenylpropionylglycine. N. Engl. J. Med. 319(20), 1308-1313 (1988).
Tunicamycin 17:1 is a mixture of tunicamycin structural isomers that contain a 17-carbon N-acyl chain with variable branching patterns. The N-acyl chain incorporated into tunicamycins, like tunicamycin 17:1, is derived from the same pool of cellular branched-chain fatty acids (BCFAs) inStreptomycesand directly impacts the biological activity of each individual tunicamycin variant.1,2,3Purified tunicamycin 17:1 withisooranteisobranching configurations inhibits bacterial phospho-MurNAc-pentapeptide transferase (MraY) with IC50values of 0.12 and 0.9 μM, respectively.2 1.Price, N.P.J., Jackson, M.A., Hartman, T.M., et al.Branched chain lipid metabolism as a determinant of the N-Acyl variation of Streptomyces natural productsACS Chem. Biol.16(1)116-124(2021) 2.Hering, J., Dunevall, E., Snijder, A., et al.Exploring the active site of the antibacterial target MraY by modified tunicamycinsACS Chem Biol.15(11)2885-2895(2020) 3.Duksin, D., and Mahoney, W.C.Relationship of the structure and biological activity of the natural homologues of tunicamycinJ. Biol. Chem.257(6)3105-3109(1982)
Enopeptin A, originally isolated from a culture broth of Streptomyces sp. RK-1051, is a depsipeptide antibiotic that contains two unusual amino acids (N-methylalanine and 4-methylproline) and features a pentaenone side chain. It is effective against Gram-positive bacteria, including methicillin-resistant S. aureus (MIC = 25 μg ml), and Gram-negative bacteria, including mutant forms of E. coli and P. aeruginosa (MICs = 200 μg ml); however, it is not inhibitory to fungi.
Tunicamycin 15:1 is a mixture of tunicamycin structural isomers that contain a 15-carbon N-acyl chain with variable branching patterns. The N-acyl chain incorporated into tunicamycins, like tunicamycin 15:1, is derived from the same pool of cellular branched-chain fatty acids (BCFAs) inStreptomycesand directly impacts the biological activity of each individual tunicamycin variant.1,2,3Purified tunicamycin 15:1 withiso,anteiso, or a mixture ofisoandanteisobranching configurations inhibit bacterial phospho-MurNAc-pentapeptide transferase (MraY) with IC50values of 0.05, 0.36, and 0.09 μM, respectively.2 1.Price, N.P.J., Jackson, M.A., Hartman, T.M., et al.Branched chain lipid metabolism as a determinant of the N-Acyl variation of Streptomyces natural productsACS Chem. Biol.16(1)116-124(2021) 2.Hering, J., Dunevall, E., Snijder, A., et al.Exploring the active site of the antibacterial target MraY by modified tunicamycinsACS Chem Biol.15(11)2885-2895(2020) 3.Duksin, D., and Mahoney, W.C.Relationship of the structure and biological activity of the natural homologues of tunicamycinJ. Biol. Chem.257(6)3105-3109(1982)
Acetyl-L-homoserine lactone belongs to the family of N-acylated homoserine lactones (HSLs) and has an acyl chain length of two carbons. HSLs perform a role in quorum sensing; however, unlike other HSLs, acetyl-L-homoserine lactone does not elicit a response in bacteria. In an assay of carbapenem antibiotic biosynthesis, acetyl-L-homoserine lactone does not induce a response in E. carotovora. In a fluorescence assay using E. coli containing a reporter plasmid of GFP expression in response to exogenous HSLs, acetyl-L-homoserine does not elicit GFP production.
Ribavirin-13C5is intended for use as an internal standard for the quantification of ribavirin by GC- or LC-MS. Ribavirin is an antiviral guanosine nucleoside analog.1,2Upon entry into cells, ribavirin is metabolized to an active triphosphate form that induces viral RNA chain termination and inhibits viral polymerases. It reduces replication in a panel of seven RNA and four DNA viruses in Vero cells (EC50s = 2-95 μg/ml).3Ribavirin also reduces replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells (EC50= 109.5 μM).4Aerosol administration of ribavirin (30 mg/kg) reduces mortality in a mouse model of influenza A infection.5Formulations containing ribavirin have been used in the treatment of respiratory syncytial virus (RSV), hepatitis C virus (HCV), and viral hemorrhagic fevers. 1.Gilbert, B.E., and Knight, V.Biochemistry and clinical applications of ribavirinAntimicrob. Agents Chemother.30(2)201-205(1986) 2.Gordon, C.J., Tchesnokov, E.P., Woolner, E., et al.Remdesivir is a direct-acting antiviral that inhibits RNA-dependent RNA polymerase from severe acute respiratory syndrome coronavirus 2 with high potencyJ. Biol. Chem.295(20)6785-6797(2020) 3.Kirsi, J.J., North, J.A., McKernan, P.A., et al.Broad-spectrum antiviral activity of 2-β-D-ribofuranosylselenazole-4-carboxamide, a new antiviral agentAntimicrob. Agents Chemother.24(3)353-361(1983) 4.Wang, M., Cao, R., Zhang, L., et al.Remdesivir and chloroquine effectively inhibit the recently emerged novel coronavirus (2019-nCoV) in vitroCell Res.30(3)269-271(2020) 5.Wilson, S.Z., Knight, V., Wyde, P.R., et al.Amantadine and ribavirin aerosol treatment of influenza A and B infection in miceAntimicrob. Agents Chemother.17(4)642-648(1980)
Menaquinone 9 (MK-9) is a vitamin K2 analog that has been found in various bacteria, including E. coli. MK-9 is UV-sensitive and binds to soluble nitrate reductase, a component of the bacterial electron transport chain. In vivo, MK-9 increases plasma prothrombin concentration in vitamin K-deficient rats.