cis-isomer

Lomibuvir (VCH-222) 是丙型肝炎病毒 NS5B 聚合酶的一种非核苷变构抑制剂，Kd 值为 17 nM，已证明具有临床疗效。Lomibuvir 抑制 1b Con1 型 HCV 亚基因组复制子，EC50为 5.2 nM。Lomibuvir 优先抑制延长的 RNA 合成，而非从头合成的 RNA。

ACAT-IN-1 cis isomer是一种有效的 ACAT 抑制剂（IC50：100 nM），可用于研究免疫系统相关疾病。

trans-Urocanic Acid ((E)-Urocanic acid) 是一种主要分布于海马体和前额叶皮层的化合物，是顺式UCA的异构体，是表皮紫外线保护剂，可增强替诺福韦艾拉酚胺在长效HIV应用中的稳定性。trans-urocanic acid 可有效调节免疫功能，可在体外抑制人类自然杀伤细胞的活性，可用于研究阿尔茨海默病。

(Z)-Capsaicin (Zucapsaicin) 是天然辣椒素的合成顺式异构体，用于治疗膝骨关节炎。它是一种可口服的 TRPV1激动剂，可研究神经性疼痛。

Zuclomiphene citrate is a cis isomer of Clomiphene citrate, and has an antiestrogenic effect and can inhibit the secretion of luteinizing hormone (LH) more than the trans isomer.

BChE-IN-35 (Azo-9) 作为一种BChE抑制剂，主要通过其顺式异构体优先与BChE结合的动态顺式 反式构象变化发挥作用。该化合物在阿尔茨海默病 (AD) 的研究中具有应用潜力。

cis-KV1.3-IN-1（Compound cis-18）为KV1.3-IN-1的顺式异构体，具备KV1.3通道抑制功能。当在表达人hKV1.3的非洲爪蟾卵母细胞中应用10 μM浓度时，cis-KV1.3-IN-1的KV1.3通道抑制效率达25.53%。

PAD2-IN-2 (cis-isomer of 1) TFA 为蛋白质精氨酸脱亚胺酶 2 (PAD2) 的抑制剂，拥有偶氮苯光开关，可光学调控 PAD 活性。PAD2-IN-2 TFA 能抑制组蛋白 H3-瓜氨酸化。

Thalidomide-Photoswitch3-NH2 hydrochloride是合成PHOTACs的重要成分，这些PHOTACs是通过不同光波长调节可逆性激活的PROTACs，其在黑暗中会失去活性，而在390 nm波长的照射下被激活为顺式异构体。在450 nm以上的波长范围内，这些PHOTACs会被可逆失活。该共轭物由Cereblon (CRBN) 招募配体、偶氮苯光开关交联剂以及一个与目标弹头酸基反应的悬浮胺基组成，被用于PHOTAC-I-10和PHOTAC-II-6的制备。

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 is a stable analog of PGI2 and an isomer of carbaprostacyclin. It is a weak inhibitor of human platelet aggregation with an IC50 of 2.8 μM compared to 0.3 μM for carbaprostacyclin. 5-cis Carbaprostacyclin is a much weaker effector of rabbit mesenteric artery relaxation with an EC50 of 104 μM compared to 5.9 μM for carbaprostacyclin. It 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-4-Hydroxy-L-proline 是脯氨酸的一种类似物，抑制胶原蛋白的产生。它通过阻止三层螺旋胶原在细胞层上的沉积从而抑制成纤维细胞的生长。它还可抑制原发性N-亚硝基甲基脲诱导的大鼠乳腺肿瘤的生长。

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 resulting from the interaction of vitamin A palmitate in corn flakes. It exhibits a biological activity of 26% compared to all-trans-vitamin A palmitate, which is known to be the most biologically active form of vitamin A.

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 是 Germacrone 的异构体。Germacrone 具有广泛的抗肿瘤、抗氧化和抗炎作用。Germacrone 抑制肺癌细胞增殖并改变 Akt MDM2 p53。Germacrone 还能在 G1 S 期阻滞细胞周期。

cis-Lomibuvir (cis-VX-222) 是 Lomibuvir 的顺式异构体。Lomibuvir (VX-222) 是一种选择性的非核苷聚合酶抑制剂，靶向丙型肝炎病毒 NS5B 聚合酶 (RdRp) 的拇指口袋 2，Kd 为 17 nM。Lomibuvir 抑制 1b Con1 型 HCV 亚基因组复制子，EC50为 5.2 nM。Lomibuvir 优先抑制延长的 RNA 合成，而非从头合成的 RNA。