8(9)-ee-14e

TLR7/8/9 antagonist 2 is an orally active and highly bioavailable vTLR7/8/9 antagonist. TLR7/8/9 antagonist 2 inhibits HEK/hTLR7, HEK/hTLR8 and HEK/hTLR9 with IC50s of 0.011 μM, 0.029 μM and 0,052 μM, respectively. TLR7/8/9 antagonist 2 can be used to study auto-inflammatory diseases such as systemic lupus erythematosus or lupus nephritis.

(3ξ,4ξ,5ξ,6ξ,7ξ,11ξ)-3,6-Dihydroxy-8-oxo-9-eremophilene-12-oic acid, a phytotoxin recently identified in Alternaria alternata ssp. tenuissima isolates, is associated with fruit spots on apples.

7,10-dihydroxy-8(E)-Octadecenoic acid is a hydroxy fatty acid and metabolite of oleic acid that is produced byP. aeruginosafrom vegetable oils.1It is active against the food-borne pathogenic bacteriaS. aureus,S. typhimurium,L. monocytogenes,B. subtilis, andE. coli(MIC50s = 31.3, 125, 125, 62.5, and 250 μg/ml, respectively), as well as the plant pathogenic bacteriaErwinia,R. solanacearum,C. glutamicum, andP. syringae(MIC90s = 125, 125, 250, and 500 μg/ml, respectively).2,1 1.Sohn, H.-R., Bae, J.-H., Hou, C.T., et al.Antibacterial activity of a 7,10-dihydroxy-8(E)-octadecenoic acid against plant pathogenic bacteriaEnzyme Microb. Technol.53(3)152-153(2013) 2.Chen, K.Y., Kim, I.H., Hou, C.T., et al.Monoacylglycerol of 7,10-dihydroxy-8(E)-octadecenoic acid enhances antibacterial activities against food-borne bacteriaJ. Agric. Food Chem.67(29)8191-8196(2019)

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)

Compound 4, 14-Benzoylmesaconine-8-palmitate, is a lipo-alkaloid that can be isolated from A. toxicum [1].

15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene is a natural product for research related to life sciences. The catalog number is TN2631 and the CAS number is 61597-55-5.

Eicosapentaenoic acid is converted to epoxyeicosatetraenoic acids (EpETEs) by several cytochrome P450 isoforms. The major product of this epoxygenase pathway, (±)17(18)-EpETE , relaxes vascular and airway smooth muscle by activating large conductance Ca2+-activated K+ (BKCa) channels by directly interacting with BKα channel subunits. (±)8(9)-EpETE is an epoxygenase pathway product produced from EPA by CYP450 both in vitro and in vivo. The biological actions and physiological effects of this epoxide remain to be determined.

8-Epidiosbulbin E acetate exhibits broad-spectrum plasmid-curing activity against multidrug-resistant (MDR) bacteria, including vancomycin-resistant enterococci.

8-Epicrepiside E is a natural product of Saussurea, Asteraceae. The catalog number is TN3275 and the CAS number is 93395-30-3. 8-Epicrepiside E can be used as a reference standard.

Epoxide hydrolases convert the EETs into vicinal diols, with the concurrent loss of much of their biological activity. The 8(S),9(R)-EET isomer is metabolized by platelet COX to form 8(S),9(R),11(R)-THETA, a trihydroxy fatty acid which may act as a renal vasoconstrictor.

9(E),11(E),13(E)-Octadecatrienoic acid (β-ESA) is a conjugated polyunsaturated fatty acid that is found in plant seed oils and in mixtures of conjugated linolenic acids synthesized by the alkaline isomerization of linolenic acid. It reduces growth of Caco-2 colon cancer cells in a dose-dependent and time-dependent manner. In vitro, β-ESA induces DNA fragmentation and upregulation of pro-apoptotic Bax mRNA. β-ESA decreases protein expression of the apoptosis suppression factor Bcl-2 and induces apoptosis in T24 bladder cancer cells via production of reactive oxygen species. It also inhibits bacterial fatty acid dioxygenase with a Ki value of 49 nM in vitro.

MMP-9-IN-8 (Compound 3), an MMP-9 inhibitor, exhibits inhibitory activities of 42.16% at 10 μM and 58.28% at 50 μM. Additionally, MMP-9-IN-8 demonstrates anti-cancer properties, inducing apoptosis in MCF-7 cells with an IC50 value of 23.42 μM [1].

Compound 9, 15-Nor-14-oxolabda-8(17),12E-diene-18-oic acid, is an isolated compound derived from the roots of Chloranthus spicatus [1].

8-Acetoxy-15,16-epoxy-8,9-secolabda-13(16),14-diene-7,9-dione is a natural product for research related to life sciences. The catalog number is TN5610 and the CAS number is 76497-89-7.

9(Z),11(E),13(E)-Octadecatrienoic Acid (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil. α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats. It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ. In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 μM. It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 μM for different isoforms of the enzymes.

10-Isobutyryloxy-8,9-epoxythymol isobutyrate is a major constituent of Inula helenium and Inula royleana root cultures.

9,13β-Epidioxy-8(14)-abieten-18-oic acid has anti-inflammatory activities, it exhibits moderate activities on NO levels in LPS-stimulated murine microglia BV2 cells, with IC50 values of 57.3 ± 0.2 uM. It is also a potential antitumor-promoting diterpenoid, it shows potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol 13-acetate. 9 α ,13 β -Epidioxyabeit-8(14)en-18-oic acid may contribute to the growth inhibitory effect of the pine needles and may play an important role in the allelopathy of red pine.

8-Hydroxy-9,10-diisobutyryloxy-thymol, a potent terpenoid found in Inula sericophylla [1], exhibits significant bioactivity.

17(13→14)-Abeo-ent-3S*,13S*,16-trihydroxystrob-8(15)-ene is a sesquiterpene lactone of natural origin that exhibits anti-inflammatory properties [1].

9(E),11(E)-12-nitro Conjugated linoleic acid (9(E),11(E)-12-nitro CLA) is a nitrated fatty acid. It is formed from 9(Z),11(E)-CLA upon exposure to acidified nitrite, peroxynitrite, gaseous nitrogen dioxide, or a combination of myeloperoxidase, hydrogen peroxide, and nitrite.1It is also formed in LPS-stimulated RAW 264.7 macrophages, an effect that can be reduced by the nitric oxide synthase (NOS) inhibitor L-NAME .29(E),11(E)-12-nitro CLA has been found in human plasma. 1.Woodcock, S.R., Salvatore, S.R., Bonacci, G., et al.Biomimetic nitration of conjugated linoleic acid: Formation and characterization of naturally occurring conjugated nitrodienesJ. Org. Chem.79(1)25-33(2014) 2.Bonacci, G., Baker, P.R.S., Salvatore, S.R., et al.Conjugated linoleic acid is a preferential substrate for fatty acid nitrationJ. Biol. Chem.287(53)44071-44082(2012)

5(Z),8(Z),14(Z)-Eicosatrienoic acid is a polyunsaturated fatty acid that can be a substrate for 5-lipoxygenase (5-LO). 5-LO from RBL-1 cells converts this fatty acid to 5-hydroxy-6,8,14-eicosatrienoic acid and 5-hydroperoxy-6,8,14-eicosatrienoic acid. Due to the lack of a double bond at C-11, this particular fatty acid cannot be used in leukotriene A formation.

9-Deacetyltaxinine E is a natural product from Taxus mairei.

ent-11alpha-Hydroxyabieta-8(14),13(15)-dien-16,12alpha-olide shows significant cytotoxic activity against ANA-1 and Jurkat cells with IC50 values 7.12 x 10(-3) and 1.79 x 10(-2) microM.

(±)14(15)-EE-8(Z)-E is a potent vasodilator in bovine coronary arteries. The synthesis of this analog involves the formation of the epoxide at the 14,15-double bond, however, epoxidation can also occur at the 8,9-double bond. (±)8(9)-EE-14(Z)-E is a minor product from the synthesis of (±)14(15)-EE-8(Z)-E. This compound has not been reported in the literature, and its biological activity is not known. It may serve as a tool to verify that the parent compound, (±)14(15)-EE-8(Z)-E, is pure and does not contain the 8,9-epoxy regioisomer.

Nucleoside Derivatives - Xylo-nucleosides; 8-Modified purine nucleosides; Amino nucleosides; N-Methylated alkylated nucleosides

3-Cyanovinyl-9-(5’-O-(4,4’-dimethoxytrityl)-2’-deoxyribofuranosyl)carbazole (trans: CAS#1044273-26-8) is a useful organic compound for research related to life sciences and the catalog number is TNU0955.

TLR7/8 agonist 9 (Compound 25a), exhibiting EC50 values of 40 nM and 23 nM for hTLR7 and hTLR8 respectively, demonstrates anti-tumor properties and enhances the efficacy of PD-1/PD-L1 blockade treatments. This compound is utilized in cancer immunotherapy research [1].

13-Oxopodocarp-8(14)-en-18-oic acid is a natural product for research related to life sciences. The catalog number is TN2619 and the CAS number is 63976-69-2.

1-Amino-8-benzyloxy-9-(b-D-xylofuranosyl)guanine is a Nucleoside Derivative - Xylo-nucleoside; 8-Modified purine nucleoside; Amino nucleoside.

2-Methoxyfuranoguaia-9-ene-8-one is a natural product for research related to life sciences. The catalog number is TN6585 and the CAS number is 88010-62-2.

3,5,7,15-Tetraacetoxy-9-nicotinoyloxy-6(17),11-jatrophadien-14-one is a natural product of Euphorbia, Euphorbiaceae. The catalog number is TN2890 and the CAS number is 244277-75-6. 3,5,7,15-Tetraacetoxy-9-nicotinoyloxy-6(17),11-jatrophadien-14-one can be used as a reference standard.

Epoxyeicosatrienoic acids (EETs), such as 11(12)-EET and 14(15)-EET, are cytochrome P450 metabolites of arachidonic acid that have been identified as endothelium-derived hyperpolarizing factors with vasodilator activity. 14,15-EE-5(Z)-E is a structural analog of 14,15-epoxyeicosatrienoic acids (14,15-EET) that antagonizes EET-induced relaxation of vascular smooth muscle. Relaxation of U46619-constricted bovine arteries by 14,15-EET could be inhibited approximately 80% by 14,15-EE-5(Z)-E at a concentration of 10 μM. 14,15-EE-5(Z)-E does not appear to antagonize nitric oxide- or iloprost-mediated vascular relaxation.

Novel oxylipins, referred to as docosanoids, have been derived from C22polyunsaturated fatty acids 7(S),17(S)-dihydroxy-8(E),10(Z),13(Z),15(E),19(Z)-Docosapentaenoic acid (7(S),17(S)-hydroxy DPA) is a DPA-derived analog of the 17(S)-dihydroxy series of docosanoids known as protectins. Protectin D1, a DHA-derived dihydroxy fatty acid, exhibits potent anti-inflammatory activities.1,2,3Potentially, 7(S),17(S)-hydroxy DPA demonstrates similar properties; however, its biological activity has yet to be determined. 1.Serhan, C.N., Gotlinger, K., Hong, S., et al.Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: Assignments of dihydroxy-containing docosatrienesJ. Immunol.176(3)1848-1859(2006) 2.Ariel, A., and Serhan, C.N.Resolvins and protectins in the termination program of acute inflammationTRENDS in Immunology28(4)176-183(2007) 3.Schwab, J.M., Chiang, N., Arita, M., et al.Resolvin E1 and protectin D1 activate inflammation-resolution programmesNature447(7146)869-874(2007)

Heptadecan-9-yl 8-((6-(decyloxy)-6-oxohexyl)(2-hydroxyethyl)amino)octanoate is utilized in lipid nanoparticle (LNP) delivery systems for the delivery of mRNA vaccines [1].

Heptadecan-9-yl 8-bromooctanoate is a chemical compound that can be utilized in the construction or modification of lipid nanoparticles.

2-Amino -7-propargyl-7,8-dihydro-8-oxo-9-(beta-D-2,3,5-tri-O-actyl-xylofuranosyl)purine is a useful organic compound for research related to life sciences. The catalog number is TNU1331 and the CAS number is 2389988-52-5.

(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylnon-8-enoic acid is a useful organic compound for research related to life sciences. The catalog number is T66542 and the CAS number is 1311933-83-1.

7α-Methoxy-5α,6α-epoxyergosta-8(14),22-dien-3β-ol is a natural product for research related to life sciences. The catalog number is TN5314 and the CAS number is 1207441-49-3.

[(2R,3S,4R,5R)-3,4-diacetyloxy-5-[2-amino-7-(cyclopropylmethyl)-8-oxopurin-9-yl]oxolan-2-yl]methyl acetate is a useful organic compound for research related to life sciences and the catalog number is TNU1306.

TLR7/8/9-IN-1 is a potent inhibitor of Toll-like receptors 7/8/9 (TLR7/8/9) with an IC50 of 43 nM.

9(Z),11(E),13(E)-Octadecatrienoic Acid ethyl ester (α-ESA) is a conjugated polyunsaturated fatty acid commonly found in plant seed oil. This fatty acid accounts for about 60% of the total fatty acid composition of bitter gourd seed oil and about 70% in tung oil. α-ESA is metabolized and converted to conjugated linoleic acid (9Z,11E-CLA) in rats. It has shown potential as a tumor growth suppressor. In colon cancer Caco-2 cells, α-ESA induced apoptosis through up-regulation of GADD45, p53, and PPARγ. In DLD-1 cells supplemented with α-ESA, apoptosis was induced via lipid peroxidation with an EC50 of 20 μM. It also inhibits DNA polymerases and topoisomerases with IC50s ranging from ~5-20 μM for different isoforms of the enzymes. α-ESA ethyl ester is a neutral, more lipid soluble form of the free acid.

Des(8-14)brevinin-1PMa is a host-defense peptide known for its potent antimicrobial properties, particularly against Staphylococcus aureus and Echerichia coli. Additionally, this compound demonstrates hemolytic activity [1].

9(E),11(E)-9-nitro Conjugated Linoleic Acid (9E,11E-9-nitro CLA) is a nitrated fatty acid produced from 9Z,11E-CLA through exposure to acidified nitrite, peroxynitrite, gaseous nitrogen dioxide, or the combined action of myeloperoxidase, hydrogen peroxide, and nitrite. Additionally, it forms in LPS-stimulated RAW 264.7 macrophages, a process that can be inhibited by the nitric oxide synthase (NOS) inhibitor L-NAME. This compound has also been detected in human plasma.

2-Amino-7-cyclopropyl methyl-7,8-dihydro-8-oxo-9-(beta-D-xylo furanosyl)purine is a useful organic compound for research related to life sciences. The catalog number is TNU0169 and the CAS number is 2389988-30-9.

8(E),10(E),12(Z)-Octadecatrienoic acid is a conjugated polyunsaturated fatty acid (PUFA) that has been found inC. officinalisseed oil and has anticancer activity.1,2,3It inhibits the growth of Caco-2 cells when used at concentrations ranging from 10 to 50 μM.28(E),10(E),12(Z)-Octadecatrienoic acid (10 μM) induces formation of thiobarbituric acid reactive substances (TBARS) and apoptosis in DLD-1 colorectal adenocarcinoma cells.3It also inhibits prostaglandin biosynthesis in sheep vesicular gland microsomes (IC50= 31 μM).4 1.Crombie, L., and Holloway, S.J.The biosynthesis of calendic acid, octadeca-(8E,10E, 12Z)-trienoic, acid, by developing marigold seeds: origins of (E,E,Z) and (Z,E,Z) conjugated triene acids in higher plantsJ. Chem. Soc. Perk. T. 12425-2434(1985) 2.Yasui, Y., Hosokawa, M., Kohno, H., et al.Growth inhibition and apoptosis induction by all-trans-conjugated linolenic acids on human colon cancer cellsAnticancer Res.26(3A)1855-1860(2006) 3.Shinohara, N., Ito, J., Tsuduki, T., et al.Jacaric acid, a linolenic acid isomer with a conjugated triene system, reduces stearoyl-CoA desaturase expression in liver of miceJ. Oleo Sci.61(8)433-441(2012) 4.Nugteren, D.H., and Christ-Hazelhof, E.Naturally occurring conjugated octadecatrienoic acids are strong inhibitors of prostaglandin biosynthesisProstaglandins33(3)403-417(1987)

8(14)-Abietenic acid, a racemic abietane diterpenoid, functions as a dual activator of PPARα/γ.

8,9-Epoxy-3-isobutyryloxy-10-(2-methylbutanoyl)thymol is a chemical composition of essential oils from Telekia speciosa. It also shows marked antipro-liferative activity against human cancer cell lines in vitro.

ent-8(14),15-pimaradien-3beta-ol (8(14),15-Isopimaradien-3-ol) can induce vascular relaxation. It displays high antibacterial activities (MIC values lower than 10 microg /mL for most pathogens).

(9E)-Erythromycin A oxime is a metabolite of the semisynthetic antibiotic roxithromycin .

8-Bromo-9-(b-D-xylofuranosyl)guanine is a Nucleoside Derivative - Xylo-nucleoside; 8-Modified purine nucleoside.