cis-isomer

ACAT-IN-1 cis isomer is a potent ACAT inhibitor (IC50: 100 nM) used for the study of immune system-related diseases.

trans-Urocanic Acid ((E)-Urocanic acid), a compound predominantly distributed in the hippocampus and prefrontal cortex, is an isomer of cis-UCA, an epidermal UV-protectant, which enhances the stability of tenofovir eplerenomide in long-acting HIV applications. trans-Urocanic acid potently modulates immune trans-urocanic acid effectively modulates immune function, inhibits human natural killer cell activity in vitro, and can be used in Alzheimer's disease research.

(Z)-Capsaicin (Zucapsaicin) is a medication used to treat osteoarthritis of the knee and Others neuropathic pain.(Z)-Capsaicin is a synthetic cis isomer of natural capsaicin that has shown therapeutic efficacy in pain accompanying osteoarthritis of the knee.

Zuclomiphene citrate, a cis isomer of Clomiphene citrate, exhibits an antiestrogenic effect and inhibits the secretion of luteinizing hormone (LH) more effectively than its trans isomer.

BChE-IN-35 (Azo-9) is an inhibitor of BChE. This compound exhibits dynamic cis trans conformational changes, with the cis isomer preferentially binding to BChE. Additionally, BChE-IN-35 can be utilized in research on Alzheimer's disease (AD).

cis-KV1.3-IN-1, also known as Compound cis-18, is the cis-isomer of KV1.3-IN-1 and functions as an inhibitor of the KV1.3 channel. In Xenopus laevis oocytes expressing human hKV1.3, cis-KV1.3-IN-1 (10 μM) achieves an inhibition rate of 25.53% against KV1.3.

PAD2-IN-2 (cis-isomer of 1) TFA is an inhibitor of protein arginine deiminase 2 (PAD2). This molecule features an azobenzene photoswitch, enabling the optical regulation of PAD activity. Additionally, PAD2-IN-2 TFA inhibits the citrullination of histone H3.

Thalidomide-Photoswitch3-NH2 hydrochloride is essential in creating PHOTACs, which are PROTACs activated by specific light wavelengths. These compounds become inactive in darkness and switch to an active cis isomer state under 390 nm irradiation, while wavelengths above 450 nm reverse this activation. This compound comprises a CRBN-recruiting ligand, an azobenzene photoswitchable crosslinker, and a pendant amine that interacts with an acid on the target warhead, and is used to synthesize PHOTAC-I-10 and PHOTAC-II-6.

Photoswitchable PAD inhibitor is a photoactivated protein arginine deiminase (PAD) inhibitor and a derivative of BB-Cl-amidine that contains an azobenzene photoswitch allowing optical control of PAD activity.1 Without photoactivation, it is a weak inhibitor of PAD2 (IC50 = >100 μM) and is less potent than BB-Cl-amidine in inhibiting citrulline production in vitro (kinact/KIs = 2,300, 600, 1,000, and 10,510 M-1min-1 for PAD1-4, respectively) and does not inhibit histone H3 citrullination in HEK293T cells overexpressing PAD2 when used at concentrations up to 100 μM. However, it can rapidly be photoactivated with UV-A radiation to the more active cis-isomer, which is an irreversible, competitive inhibitor of histone H3 citrullination with an IC50 value of 9.1 μM.References1. Mondal, S., Parelkar, S.S., Nagar, M., et al. Photochemical control of protein arginine deiminase (PAD) activity. ACS Chem. Biol. 13(4), 1057-1065 (2018). Photoswitchable PAD inhibitor is a photoactivated protein arginine deiminase (PAD) inhibitor and a derivative of BB-Cl-amidine that contains an azobenzene photoswitch allowing optical control of PAD activity.1 Without photoactivation, it is a weak inhibitor of PAD2 (IC50 = >100 μM) and is less potent than BB-Cl-amidine in inhibiting citrulline production in vitro (kinact/KIs = 2,300, 600, 1,000, and 10,510 M-1min-1 for PAD1-4, respectively) and does not inhibit histone H3 citrullination in HEK293T cells overexpressing PAD2 when used at concentrations up to 100 μM. However, it can rapidly be photoactivated with UV-A radiation to the more active cis-isomer, which is an irreversible, competitive inhibitor of histone H3 citrullination with an IC50 value of 9.1 μM. References1. Mondal, S., Parelkar, S.S., Nagar, M., et al. Photochemical control of protein arginine deiminase (PAD) activity. ACS Chem. Biol. 13(4), 1057-1065 (2018).

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)

5-cis Carbaprostacyclin, a stable analog of PGI2 and an isomer of carbaprostacyclin, is a weak inhibitor of human platelet aggregation with an IC50 of 2.8 μM compared to 0.3 μM for carbaprostacyclin. It is a much weaker effector of rabbit mesenteric artery relaxation with an EC50 of 104 μM compared to 5.9 μM for carbaprostacyclin and even antagonizes the adenylate cyclase activation induced by carbaprostacyclin.

Latanoprost is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug. 5-trans Latanoprost is an isomer of latanoprost wherein the double bond between carbons 5 and 6 has been changed from cis (Z) to trans (E). The trans isomer of latanoprost occurs as an impurity of between 2-5% in most commercial preparations of the bulk drug product. The present compound was prepared primarily as an analytical standard for detection and quantitation of this impurity. From what can be inferred from the study of other trans isomers of F-type prostaglandins, 5-trans latanoprost's biological activity is likely to be similar to that of the cis isomer. However, there are no specific published reports on the biological activity, and on the intraocular hypotensive activity in particular, of 5-trans latanoprost.

Latanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug. Latanoprost is an isopropyl ester, a prodrug form which is converted to latanoprost (free acid) by endogenous esterase enzymes. The free acid form is 200 times more potent than latanoprost as a ligand for the human recombinant FP receptor. 5-trans Latanoprost (free acid) is an isomer of latanoprost (free acid) wherein the double bond between carbons 5 and 6 has been changed from cis (Z) to trans (E). The trans isomer of latanoprost occurs as an impurity in commercial preparations of the bulk drug product. The present compound was prepared primarily as an analytical standard for detection and quantitation of this impurity. From what can be inferred from the study of other trans isomers of F-type prostaglandins, the biological activity of this isomer is likely to be similar to that of the cis isomer. However, there are no specific published reports on the biological activity, and on reducing intraocular pressure in particular, of 5-trans latanoprost.

Cloprostenol is a synthetic derivative of prostaglandin F2α that is used in veterinary medicine as a luteolytic agent for the induction of estrus and in the treatment of reproductive disorders in cattle, swine, and horses. (+)-5-trans Cloprostenol is a minor impurity produced in the synthesis of (+)-cloprostenol. The (+)-5-trans isomer is 20-fold less active than the 5-cis form in terminating pregnancy in the hamster.

The lipoxins are trihydroxy fatty acids containing a 7,9,11,13-conjugated tetraene. Lipoxin A4 (LXA4) was first described as a metabolite of 15-HpETE and/or 15-HETE when added in vitro to isolated human leukocytes. The material obtained in this manner consists of at least four distinct isomers: 5(S), 6(S); 5(S), 6(R); and the 11-trans and 11-cis isomers of each of these. 6(S)-LXA4 is one of the original four metabolites first identified by Serhan, Nicolaou, and Samuelsson. It was considered to be an artifact by these authors because it lacked the potency of the 5(S),6(R) isomer with respect to contraction of isolated guinea pig lung parenchymal strips. It has not been possible to isolate natural LXA4 from humans or other mammals in amounts sufficient for determination of absolute stereochemistry. Most authors refer to LXA4 as the 5(S)

13-epi-12-oxo Phytodienoic acid (13-epi-12-oxo PDA) is a lipoxygenase metabolite of α-linolenic acid in the leaves of green plants such as corn. ω-3 and ω-6 polyunsaturated fatty acids in plants are substrates for plant lipoxygenases. 12-oxo PDA is one of the best studied end metabolites of this enzymatic pathway. While the initial enzymatic product and major isomer of 12-oxo PDA contains side chains in the cis position, both being β to the ring, the upper side chain attached at C-13, can and frequently does, isomerize when 12-oxo PDA is extracted, isolated, or stored. 13-epi-12-oxo PDA is the product of this isomerization.

cis-L-Hydroxyproline inhibits the synthesis and extracellular deposition of collagen. The growth inhibition of pancreatic cancer cells induced by the Hyp isomer could be due to endoplasmatic reticulum stress.

11-cisRetinol is an isomer of vitamin A . It is formed from vitamin A,viaatrans-retinyl ester intermediate, by the enzyme RPE65 in the retinal pigment epithelium and then converted to 11-cis retinal as part of the visual cycle.1,211-cisRetinol is an agonist of salamander and human red rod opsins expressed in COS cells and an inverse agonist of salamander red cone opsin, as well as human red and green cone opsins expressed in COS cells.3It promotes pigment formation in cone, but not rod, photoreceptors. 1.Rando, R.R.The biochemistry of the visual cycleChem. Rev.101(7)1881-1896(2001) 2.Guignard, T.J.P., Jin, M., Pequignot, M.O., et al.FATP1 inhibits 11-cis retinol formation via interaction with the visual cycle retinoid isomerase RPE65 and lecithin: Retinol acyltransferaseJ. Biol. Chem.285(24)18759-18768(2010) 3.Ala-Laurila, P., Cornwall, M.C., Crouch, R.K., et al.The action of 11-cis-retinol on cone opsins and intact cone photoreceptorsJ. Biol. Chem.284(24)16492-16500(2009)

9-cis-Vitamin A palmitate (9-cis-Retinyl palmitate) is a 9-cis isomer derived from the interaction of vitamin A palmitate in corn flakes, exhibiting 26% of the biological activity of the all-trans-vitamin A palmitate, the most biologically active form of vitamin A.

Lomibuvir (VCH-222) is a selective, non-nucleoside allosteric inhibitor of HCV NS5B polymerase (RdRp) with a Kd of 17 nM. Lomibuvir inhibits the 1b Con1 HCV subgenomic replicon with an EC 50 of 5.2 nM. Lomibuvir preferentially inhibits elongative RNA synthesis rather than de novo -initiated RNA synthesis [1].

AEW541, also known as NVP-AEW541, is a novel, potent IGF-IR kinase inhibitor. NVP-AEW541 is capable of distinguishing between the IGF-IR (IC50 = 0.086 microM) and the closely related InsR (IC50 = 2.3 microM) in cells. NVP- AEW541 abrogates IGF-I-mediated survival and colony formation in soft agar at concentrations that are consistent with inhibition of IGF-IR autophosphorylation. Note: AEW541 has a Cis-configuration on the cyclobutane ring. Its CAS# is 475489-16-8. Many vendors and Sc-finder scholar made mistake - AEW541 was mistakenly listed as CAS#475488-34-7, the trans-isomer of AEW541. The correct structure of AEW541 can be confirmed from Joel Slade, et al (from Novartis), Org. Process Res. Dev. 2007, 11, 5, 825–835.

RK-20448 is an ATP-competitive inhibitor of Lck, Src, KDR VEGF2R, and Tie-2. It also inhibits BLK, Csk, Fyn, and Lyn. RK-20448 is the cis isomer of A-419259

Cis,trans-Germacrone, an isomer of Germacrone, demonstrates extensive antitumor, antioxidant, and anti-inflammatory properties. It hinders lung cancer cell proliferation and impacts the Akt MDM2 p53 pathway. Additionally, Germacrone induces cell cycle arrest at the G1 S phase [1].

Cis-Lomibuvir (cis-VX-222), a cis-isomer of Lomibuvir, is a selective non-nucleoside inhibitor of the hepatitis C virus (HCV) NS5B polymerase (RdRp), targeting thumb pocket 2 with a dissociation constant (Kd) of 17 nM. It exhibits an EC50 of 5.2 nM against the 1b Con1 HCV subgenomic replicon, demonstrating a preference for inhibiting elongative RNA synthesis over de novo-initiated RNA synthesis.