lipid y

Lipid Y is a monosaccharide precursor of E coli lipid A.

Tinoridine hydrochloride (Y-3642 hydrochloride) is a non-steroidal anti-inflammatory drug. Tinoridine hydrochloride (5-100 μM), produced a concentration-dependent inhibition on the simultaneous increases in lipid peroxide formation and renin release induced by 50 μM ascorbic acid in the renin granule fraction. On the other hand, indomethacin, hydrocortisone, and prednisolone, which had no ability to inhibit the lipid peroxidation in the renin granule fraction, did not influence the release of renin from the granules. These results suggest that tinoridine suppresses renin release by inhibiting the oxidative disintegration of membranes of renin granules.

1,2-Dioleoyl-rac-glycerol-13C3 is intended for use as an internal standard for the quantification of 1,2-dioleoyl-rac-glycerol by GC- or LC-MS. 1,2-dioleoyl-rac-glycerol is a diacylglycerol that contains oleic acid at the sn-1 and sn-2 positions. It effectively binds the C1 domain to activate conventional protein kinase C forms and serves as a substrate for diacylglycerol kinases and multisubstrate lipid kinase.1,2,3 |1. Yamaguchi, Y., Shirai, Y., Matsubara, T., et al. Phosphorylation and up-regulation of diacylglycerol kinase γ via its interaction with protein kinase Cγ. J. Biol. Chem. 281(42), 31627-31637 (2006).|2. Zhou, Q.Z., Raynor, R.L., Wood, M.G., Jr., et al. Structure-activity relationship of synthetic branched-chain distearoylglycerol (distearin) as protein kinase C activators. Biochemistry 27(19), 7361-7365 (1988).|3. Epand, R.M., Shulga, Y.V., Timmons, H.C., et al. Substrate chirality and specificity of diacylglycerol kinases and the multisubstrate lipid kinase. Biochemistry 46(49), 14225-14231 (2007).

DSPE-PEG(2000)-amine is a PEGylated derivative of 1,2-distearoyl-sn-glycero-3-PE . It has been used in the synthesis of solid lipid and thermosensitive liposomal nanoparticles for the delivery of anticancer agents.1,2,3DSPE-PEG(2000)-amine has also been used in the synthesis of fluorescein isothiocyanate-loaded mesoporous silica nanoparticles for imaging applications.4It can be conjugated to a variety of functional molecules for improved cellular targeting and uptake of DSPE-PEG(2000)-amine-containing nanoparticles.4,5 1.Sloat, B.R., Sandoval, M.A., Li, D., et al.In vitro and in vivo anti-tumor activities of a gemcitabine derivative carried by nanoparticlesInt. J. Pharm.409(1-2)278-288(2011) 2.Abd-Rabou, A.A., Bharali, D.J., and Mousa, S.A.Taribavirin and 5-fluorouracil-loaded pegylated-lipid nanoparticle synthesis, p38 docking, and antiproliferative effects on MCF-7 breast cancerPharm. Res.35(4)76(2018) 3.Affram, K., Udofot, O., Singh, M., et al.Smart thermosensitive liposomes for effective solid tumor therapy and in vivo imagingPLoS One12(9):e0815116(2017) 4.Wang, L.-S., Wu, L.-C., Lu, S.-Y., et al.Biofunctionalized phospholipid-capped mesoporous silica nanoshuttles for targeted drug delivery: Improved water suspensibility and decreased nonspecific protein bindingACS Nano4(8)4371-4379(2010) 5.Wen, X., Wang, K., Zhao, Z., et al.Brain-targeted delivery of trans-activating transcriptor-conjugated magnetic PLGA/lipid nanoparticlesPLoS One9(9):e106652(2014)

93-O17O is a chalcogen-containing cationic lipidoid used in the generation of lipid nanoparticles (LPNs). LPNs containing 93-O17O localize to the spleen after intravenous injection into mice and have been utilized for delivering Cre recombinase, ribonucleoproteins for genome editing, and intratumoral delivery of cGAMP to enhance cross-presentation of tumor antigens. [1,2,3]

14S(15R)-EET is an oxylipin and a cytochrome P450 metabolite of arachidonic acid .114S(15R)-EET binds to isolated guinea pig monocytes with a Kivalue of 612.5 nM in a competitive binding assay using [3H]14(15)-EET.2It induces dilation of precontracted isolated canine epicardial arterioles (EC50= 4 pM) and denuded porcine subepicardial arterioles (EC50= 3 pM).3Unlike 14R(15S)-EET, 14S(15R)-EET does not inhibit COX in enzyme assays or isolated platelets.4 1.Daikh, B.E., Lasker, J.M., Raucy, J.L., et al.Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C91J. Pharmacol. Exp. Ther.271(3)1427-1433(1994) 2.Wong, P.Y.-K., Lai, P.-S., and Falck, J.R.Mechanism and signal transduction of 14 (R), 15 (S)-epoxyeicosatrienoic acid (14,15-EET) binding in guinea pig monocytesProstaglandins Other Lipid Mediat.62(4)321-333(2000) 3.Zhang, Y., Oltman, C.L., Lu, T., et al.EET homologs potently dilate coronary microvessels and activate BKCa channelsAm. J. Physiol. Heart Circ. Physiol.280(6)H2430-H2440(2001) 4.Fitzpatrick, F.A., Ennis, M.D., Baze, M.E., et al.Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosatrienoic acidsJ. Biol. Chem.261(2)15334-15338(1986)

9(Z),11(E)-Conjugated linoleic acid is an isomer of linoleic acid that has been found in beef and milk fat.1It binds to peroxisome proliferator-activated receptor α (PPARα; IC50= 140 nM) and activates the receptor in a reporter assay using COS-1 cells expressing mouse PPARα when used at a concentration of 100 μM.29(Z),11(E)-Conjugated linoleic acid inhibits TNF-α-inducedGLUT4expression and increases insulin-stimulated glucose transport in 3T3-L1 adipocytes.3Dietary administration of 9(Z)11(E)-conjugated linoleic acid reduces serum fasting glucose, insulin, and triglyceride levels and decreases white adipose tissue macrophage infiltration inob/obmice. It also increases body weight gain and body fat in weanling mice.4[Matreya, LLC. Catalog No. 1278] 1.Shultz, T.D., Chew, B.P., Seaman, W.R., et al.Inhibitory effect of conjugated dienoic derivatives of linoleic acid and β-carotene on the in vitro growth of human cancer cellsCancer Lett.63(2)125-133(1992) 2.Moya-Camarena, S.Y., Heuvel, J.P.V., Blanchard, S.G., et al.Conjugated linoleic acid is a potent naturally occurring ligand and activator of PPARαJ. Lipid Res.40(8)1426-1433(1999) 3.Moloney, F., Toomey, S., Noone, E., et al.Antidiabetic effects of cis-9, trans-11-conjugated linoleic acid may be mediated via anti-inflammatory effects in white adipose tissueDiabetes56(3)574-582(2007) 4.Pariza, M.W., Park, Y., and Cook, M.E.The biologically active isomers of conjugated linoleic acidProg. Lipid Res.40(4)283-298(2001)

Palmitic acid-13C is intended for use as an internal standard for the quantification of palmitic acid by GC- or LC-MS. Palmitic acid-13C contains 13C at the C2 position and has been used in the study of free fatty acid incorporation into phospholipid fatty acids in soil microbes.1 Palmitic acid is a 16-carbon saturated fatty acid. It comprises approximately 25% of human total plasma lipids.2 It increases protein levels of COX-2 in RAW 264.7 cells when used at a concentration of 75 μM.3 Palmitic acid is involved in the acylation of proteins to anchor membrane-bound proteins to the lipid bilayer.3,4,5,6,7 |1. Dippold, M.A., and Kuzyakov, Y. Direct incorporation of fatty acids into microbial phospholipids in soils: Position-specific labeling tells the story. Geochim. Cosmochim. Acta 174(1), 211-221 (2016).|2. Santos, M.J., López-Jurado, M., Llopis, J., et al. Influence of dietary supplementation with fish oil on plasma fatty acid composition in coronary heart disease patients. Ann. Nutr. Metab. 39(1), 52-62 (1995).|3. Lee, J.Y., Sohn, K.H., Rhee, S.H., et al. Saturated fatty acids, but not unsaturated fatty acids, induced the expression of cyclooxygenase-2 mediated through toll-like receptor 4. J. Biol. Chem. 276(20), 16683-16689 (2001).|4. Dietzen, D.J., Hastings, W.R., and Lublin, D.M. Caveolin is palmitoylated on multiple cysteine residues. Palmitoylation is not necessary for localization of caveolin to caveolae. J. Biol. Chem. 270(12), 6838-6842 (1995).|5. Robinson, L.J., and Michel, T. Mutagenesis of palmitoylation sites in endothelial nitric oxide synthase identifies a novel motif for dual acylation and subcellular targeting. Proc. Nat. Acad. Sci. USA 92(25), 11776-11780 (1995).|6. Topinka, J.R., and Bredt, D.S. N-terminal palmitoylation of PSD-95 regulates association with cell membranes and interaction with K+ channel Kv1.4. Neuron 20(1), 125-134 (1998).|7. Miggin, S.M., Lawler, O.A., and Kinsella, B.T. Palmitoylation of the human prostacyclin receptor. Functional implications of palmitoylation and isoprenylation. J. Biol. Chem. 278(9), 6947-6958 (2003).

Cerebroside C is a fungal metabolite and glycosphingolipid that has been found in the rice pathogenic fungusM. grisea.1It induces production of the phytoalexin momilactone A when applied to wounded rice leaves, indicating that cerebroside C is an elicitor of the hypersensitive response in rice. Cerebroside C increases germination rate and reduces germination time in wheat seeds in a concentration-dependent manner at 4°C.2It also increases root length, fresh weight, and dry weight of wheat seedlings when used at a concentration of 20 μg/ml at 4°C, indicating increased chilling tolerance. 1.Koga, J., Yamuchi, T., Shimura, M., et al.Cerebrosides A and C, sphingolipid elicitors of hypersensitive cell death and phytoalexin accumulation in rice plantsJ. Biol. Chem.273(48)31985-31991(1998) 2.Li, H.-X., Xiao, Y., Cao, L.-L., et al.Cerebroside C increases tolerance to chilling injury and alters lipid composition in wheat rootsPLoS One8(9)e73380(2013)

OH-Chol is a cationic cholesterol derivative. OH-Chol, as a component of lipoplexes with [DOPE], has been used for siRNA delivery and gene silencing in MCF-7 cells and in mice via intravenous injection, resulting in lipoplex accumulation in the liver. Additionally, it has been employed in cationic nanoparticles with [Tween 80] to transfect pDNA and siRNA into PC3 mouse xenografts via intratumoral injection and with [Tween 80] and [folate-PEG2000-DSPE] in a KB mouse xenograft model for intratumoral gene delivery.

Geranylgeranoic acid (GGA) is an isoprenoid that has been found inS. chinensisand has anticancer activity.1It induces apoptosis in Huh7 and PLC/PRF/5 human hepatoma cells and MLE-10 transformed mouse hepatocytes, but not primary mouse hepatocytes, when used at concentrations ranging from 1 to 20 μM. GGA (10 μM) induces apoptosis in Huh7 cellsvialoss of the mitochondrial membrane potential and activation of interleukin-1β-converting enzyme (ICE) and cysteine protease precursor 32 (CPP32).2It also inhibits lysine-specific demethylase 1 (LSD1; IC50= 46.97 μM).3 1.Shidoji, Y., and Ogawa, H.Natural occurrence of cancer-preventive geranylgeranoic acid in medicinal herbsJ. Lipid Res.45(6)1092-1103(2004) 2.Shidoji, Y., Nakamura, N., Moriwaki, H., et al.Rapid loss in the mitochondrial membrane potential during geranylgeranoic acid-induced apoptosisBiochem. Biophys. Res. Commun.230(1)58-63(1997) 3.Sakane, C., Okitsu, T., Wada, A., et al.Inhibition of lysine-specific demethylase 1 by the acyclic diterpenoid geranylgeranoic acid and its derivativesBiochem. Biophys. Res. Commun.444(1)24-29(2014)

YW1128 is an inhibitor of Wnt/β-catenin signaling with an IC50 value of 4.1 nM in a reporter assay.1 It decreases protein levels of β-catenin in the presence of the GSK3β inhibitor lithium chloride and increases protein levels of Axin1 in HEK293 cells. YW1128 decreases lipid accumulation and the expression of gluconeogenic and lipogenic genes in Huh7 cells. It decreases the hepatic expression of Wnt target genes, improves glucose tolerance, and prevents body weight increases and hepatic lipid accumulation in mice fed a high-fat diet, but not mice fed normal chow, when administered at a dose of 40 mg/kg every other day for 11 weeks.References1. Obianom, O.N., Ai, Y., Li, Y., et al. Triazole-based inhibitors of the Wnt/β-catenin signaling pathway improve glucose and lipid metabolism in diet-induced obese mice. J. Med. Chem. 62(2), 727-741 (2019). YW1128 is an inhibitor of Wnt/β-catenin signaling with an IC50 value of 4.1 nM in a reporter assay.1 It decreases protein levels of β-catenin in the presence of the GSK3β inhibitor lithium chloride and increases protein levels of Axin1 in HEK293 cells. YW1128 decreases lipid accumulation and the expression of gluconeogenic and lipogenic genes in Huh7 cells. It decreases the hepatic expression of Wnt target genes, improves glucose tolerance, and prevents body weight increases and hepatic lipid accumulation in mice fed a high-fat diet, but not mice fed normal chow, when administered at a dose of 40 mg/kg every other day for 11 weeks. References1. Obianom, O.N., Ai, Y., Li, Y., et al. Triazole-based inhibitors of the Wnt/β-catenin signaling pathway improve glucose and lipid metabolism in diet-induced obese mice. J. Med. Chem. 62(2), 727-741 (2019).

93-O17S is a chalcogen-containing cationic lipidoid. It has been used in the synthesis of lipid nanoparticles (LPNs) for the delivery of Cre recombinase and ribonucleoproteins for genome editing in mice. LPNs containing 93-O17S have been utilized for the intratumoral delivery of cGAMP to enhance cross-presentation of tumor antigens and stimulation of interferon genes [STING] activation in a B16 F10 murine melanoma model.

MD001 is a dual agonist of peroxisome proliferator-activated receptor α (PPARα) and PPARγ.1 It binds to PPARα and PPARγ (Kds = 9.55 and 0.14 μM, respectively) but does not bind to PPARβ/δ at concentrations up to 500 μM. It increases transcriptional activity of PPARα and PPARγ in a cell-based luciferase reporter assay when used at a concentration of 10 μM. MD001 (10 μM) increases expression of PPARα, PPARγ, and retinoid X receptor (RXR), as well as PPARα and PPARγ target genes, in HepG2 cells. It increases glucose consumption as well as expression of GLUT2 and GLUT4 in HepG2 and 3T3-L1 cells, respectively, in a concentration-dependent manner. MD001 (20 mg/kg) decreases levels of glucose, insulin, free fatty acids, triglycerides, LDL, alanine aminotransferase (ALT), and aspartate aminotransferase (AST) in blood and reduces the size and number of hepatic lipid droplets in diabetic db/db mice.References1. Kim, S.-H., Hong, S.H., Park, Y.-J., et al. MD001, a novel peroxisome proliferator-activated receptor α/γ agonist, improves glucose and lipid metabolism. Sci. Rep. 9(1), 1656 (2019). MD001 is a dual agonist of peroxisome proliferator-activated receptor α (PPARα) and PPARγ.1 It binds to PPARα and PPARγ (Kds = 9.55 and 0.14 μM, respectively) but does not bind to PPARβ/δ at concentrations up to 500 μM. It increases transcriptional activity of PPARα and PPARγ in a cell-based luciferase reporter assay when used at a concentration of 10 μM. MD001 (10 μM) increases expression of PPARα, PPARγ, and retinoid X receptor (RXR), as well as PPARα and PPARγ target genes, in HepG2 cells. It increases glucose consumption as well as expression of GLUT2 and GLUT4 in HepG2 and 3T3-L1 cells, respectively, in a concentration-dependent manner. MD001 (20 mg/kg) decreases levels of glucose, insulin, free fatty acids, triglycerides, LDL, alanine aminotransferase (ALT), and aspartate aminotransferase (AST) in blood and reduces the size and number of hepatic lipid droplets in diabetic db/db mice. References1. Kim, S.-H., Hong, S.H., Park, Y.-J., et al. MD001, a novel peroxisome proliferator-activated receptor α/γ agonist, improves glucose and lipid metabolism. Sci. Rep. 9(1), 1656 (2019).

Palmitic acid-13C (C1, C2, C3, and C4 labeled) is intended for use as an internal standard for the quantification of palmitic acid by GC- or LC-MS. Palmitic acid is a common 16-carbon saturated fat that represents 10-20% of human dietary fat intake and comprises approximately 25 and 65% of human total plasma lipids and saturated fatty acids, respectively.1,2Acylation of palmitic acid to proteins facilitates anchoring of membrane-bound proteins to the lipid bilayer and trafficking of intracellular proteins, promotes protein-vesicle interactions, and regulates various G protein-coupled receptor functions.1Red blood cell palmitic acid levels are increased in patients with metabolic syndrome compared to patients without metabolic syndrome and are also increased in the plasma of patients with type 2 diabetes compared to individuals without diabetes.3,4 1.Fatima, S., Hu, X., Gong, R.-H., et al.Palmitic acid is an intracellular signaling molecule involved in disease developmentCell. Mol. Life Sci.76(13)2547-2557(2019) 2.Santos, M.J., López-Jurado, M., Llopis, J., et al.Influence of dietary supplementation with fish oil on plasma fatty acid composition in coronary heart disease patientsAnn. Nutr. Metab.39(1)52-62(1995) 3.Yi, L.-Z., He, J., Liang, Y.-Z., et al.Plasma fatty acid metabolic profiling and biomarkers of type 2 diabetes mellitus based on GC/MS and PLS-LDAFEBS Lett.580(30)6837-6845(2006) 4.Kabagambe, E.K., Tsai, M.Y., Hopkins, P.N., et al.Erythrocyte fatty acid composition and the metabolic syndrome: A National Heart, Lung, and Blood Institute GOLDN studyClin. Chem.54(1)154-162(2008)

Carotenoid mixture is a mixture of carotenoids that contains the antioxidative and anti-inflammatory carotenoid capsanthin and the antioxidative vitamin A precursor β-carotene , as well as additional carotenoids and carotenoid esters.1,2,3,4 1.Kim, J.S., Lee, W.M., Rhee, H.C., et al.Red paprika (Capsicum annuum L.) and its main carotenoids, capsanthin and β-carotene, prevent hydrogen peroxide-induced inhibition of gap-junction intercellular communicationChem. Biol. Interact.254146-155(2016) 2.Narisawa, T., Fukaura, Y., Hasebe, M., et al.Prevention of N-methylnitrosourea-induced colon carcinogenesis in rats by oxygenated carotenoid capsanthin and capsanthin-rich paprika juiceProc. Soc. Exp. Biol. Med.224(2)116-122(2000) 3.Horie, S., Okuda, C., T., Y., et al.Purified canola lutein selectively inhibits specific isoforms of mammalian DNA polymerases and reduces inflammatory responseLipids45(8)713-721(2010) 4.Negishi, H., Ueda, Y., and Azuma, M.Antioxidant fat-soluble vitamins and lipid peroxides in serumJ. Clin. Biochem. Nutr.26227-234(1999)