epimer

Negative control for LC 2.

Tacrolimus anhydrous 8-epimer is a new l-pipecolic acid macrolide lactone, an important immunosuppressive drug that blocks T cell proliferation in vitro by inhibiting the generation of several lymphokines, especially IL-2.

3 Hydroxy Midostaurin Epimer 1-d5 is a deuterated compound of 3 Hydroxy Midostaurin Epimer 1. 3 Hydroxy Midostaurin Epimer 1 has a CAS number of 945260-14-0.

3 Hydroxy Midostaurin Epimer 2-d5 is a deuterated compound of 3 Hydroxy Midostaurin Epimer 2.3 Hydroxy Midostaurin Epimer 2 has a CAS number of 155848-20-7.

WIN 5063-3 is the enantiomeric analog of the antimicrobial Thiamphenicol.

Aldose 1-epimerase (mutarotases), an essential enzyme for carbohydrate metabolism, facilitates the interconversion between α- and β-anomers of hexose sugars, including glucose and galactose. This enzyme plays a vital role in normal carbohydrate metabolism and the synthesis of complex oligosaccharides [1].

(-)-Gallocatechin ((−)-GC) has free radical scavenging ability and moderate affinity to the human cannabinoid receptor.

Chlortetracycline is an analog of tetracycline , a broad spectrum antibiotic. In addition to its actions against microorganisms, chlortetracycline suppresses inflammation by inhibiting neutrophil action and other aspects of the innate immune response. 4-epi-Chlortetracycline is an epimer of chlortetracycline.

Epiprogoitrin (epi-Progoitrin) is a epimer that can be deglycosylated to epigoitrin.

Ganorbiformin B, a lanostane triterpenoid, belongs to the same structural class as ganoderic acids, sharing the lanostane skeleton. It is the C-3 epimer of ganoderic acid T, known for its potent antimycobacterial activity against Mycobacterium tuberculosis H37Ra [1].

(R)-Butaprost (free acid) is a prostaglandin E2 (PGE2) analog exhibiting high EP2 receptor subtype selectivity, commonly used to delineate EP receptor expression in human and animal tissues and cells. In 1986, Gardiner induced significant confusion regarding its structure by incorrectly identifying the selective C-16 epimer as (R)-butaprost (refer to the British Journal of Pharmacology, page 46, as TR 4979, and notes). By removing the methyl ester and restoring the native carboxylic acid at C-1, the binding affinity for prostaglandin receptors was enhanced, given such free acids typically display 10 to 100 times greater affinity than their ester counterparts. Although not extensively studied pharmacologically, (R)-butaprost is generally viewed as the less active C-16 epimer, with careful studies conducted later in the United States and Japan ultimately establishing the correct active structure as the 16(S) epimer.

5(S),12(S)-DiHETE is a natural bioactive lipid derived from arachidonic acid . It is synthesized by glycogen-induced rabbit peritoneal polymorphonuclear leukocytes (PMNLs) incubated with AA. 5(S),12(S)-DiHETE can be produced by successive oxygenation of AA by 5-lipoxygenase (5-LO) in platelets and 12-LO in leukocytes. It can also be synthesized from 12(S)-HETE by 5-LO, in the presence of 5-LO activating protein (FLAP), activated with calcium ionophore. 5(S),12(S)-DiHETE is an epimer of leukotriene B4 that is weakly chemotactic for PMNL.

3-epi-25-hydroxy Vitamin D3is the C-3 epimer of 25-hydroxy vitamin D3.1Dietary administration of 3-epi-25-hydroxy vitamin D3(0.5 and 1 IU/g) decreases levels of serum parathyroid hormone (PTH) in male, but not female, weanling rats. 1.Djekic-Ivankovic, M., Lavery, P., Agellon, S., et al.The C-3α epimer of 25-hydroxycholecalciferol from endogenous and exogenous sources supports normal growth and bone mineral density in weanling ratsJ. Nutr.147(2)141-151(2017)

Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid and docosahexaenoic acid.[1] In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state.[2] Resolvin D1 is produced physiologically from the sequential oxygenation of DHA by 15- and 5-lipoxygenase.[1] 17(R)-RvD1 is an aspirin-triggered epimer of RvD1 that reduces human polymorphonuclear leukocyte (PMN) transendothelial migration, the earliest event in acute inflammation, with equipotency to RvD1 (EC50 = ~30 nM).[3] 17(R)-RvD1 exhibits a dose-dependent reduction in leukocyte infiltration in a mouse model of peritonitis with maximal inhibition of ~35% at a 100 ng dose.[3] In contrast to RvD1, the aspirin-triggered form resists rapid inactivation by eicosanoid oxidoreductases. Analytical and biological comparisons of synthetic 17(R)-RvD1 with endogenously derived 17(R)-RvD1 have confirmed its identity as matching the natural product.[4]

S-30-Hydroxygambogic acid, a polyprenylated xanthone epimer isolated from the gamboges of Garcinia hanburyi, exhibits cytotoxicity against Human Leukemia K562 cell lines with IC50 values of 4.49 μM for K562/R and 3.61 μM for K562/S. This compound is utilized in cancer research [1].

R-30-Hydroxygambogic acid, a polyprenylated xanthone epimer isolated from the gamboge of Garcinia hanburyi, exhibits cytotoxicity against human leukemia K562 cell lines, with IC50 values of 2.89 μM for the resistant strain (K562/R) and 1.27 μM for the sensitive strain (K562/S). This compound is utilized in cancer research [1].

16α-Hydroxyprednisolone is a stereoselective metabolite of the 22(R) epimer of the glucocorticoid budesonide

15(S)-Fluprostenol, an isomer of the FP receptor agonist fluprostenol, serves as a potential active metabolite of 15(S)-fluprostenol isopropyl ester. It can function as an agonist at FP receptors, though with lower potency compared to its 15(R) epimer, fluprostenol.

19(R)-Hydroxylated prostaglandins (PGs) are present at µg/ml concentrations in the semen of some mammalian species, notably primates, with the majority being from the PGE series and featuring a 15(S),19(R) hydroxyl stereochemistry. These compounds are also observed in marsupials' seminal plasma, where F-type 1 and 2-series compounds are predominant. The 15(R)-hydroxy epimer represents the inverse or unnatural isomer at C-15 for these 19-hydroxylated PGs. Although the biological function of 19(R)-hydroxylated PGs remains unclear, 19(R)-hydroxylation in the F-series leads to a notable reduction in receptor-mediated biological activity in certain assays.

8-iso-15(R)-Prostaglandin F2α (8-iso-15(R) PGF2α) is a chemically distinct member within a broad group of prostaglandin-like eicosanoids, produced through the free radical peroxidation of arachidonic acid contained in membrane phospholipids. It represents the C-15 epimer of 8-isoPGF2α, distinguished as the sole isoprostane isomer extensively examined across numerous biological systems.

(3S,5S)-Pitavastatin calcium is the 3-epimer of Pitavastatin which is a potent HMG-CoA reductase inhibitor.

7-epi Maresin 1 is the inactive 7(S) epimer of Maresin 1 , which contains a 7(R) hydroxyl group. It can be used as an experimental negative control.

Epitetracycline is an epimer of the antibiotic tetracycline . Epimers of tetracycline form without catalysis and are considered degradation products. Epitetracycline has decreased activity as an antibiotic or a Tet repressor effector but may have stronger toxic effects in animals.

15(R)-Pinane thromboxane A2 is the (R)-epimer of pinane thromboxane A2 . 15(R)-PTA2 does not inhibit collagen-induced platelet aggregation (IC50s = 120-130 μM). It does not affect gastric tone in isolated rat gastric fundus when used at concentrations of 0.5 or 1.5 μg/ml and is less effective than PTA2 at inhibiting prostaglandin-induced contraction of isolated rat stomach muscle.

17(R)-Protectin D1 is an aspirin-triggered epimer of the specialized pro-resolving mediator protectin D1 .1It decreases leukotriene B4-induced transendothelial migration of human polymorphonuclear (PMN) neutrophils when used at concentrations ranging from 0.1 to 10 nM. 17(R)-Protectin D1 (0.01-10 ng) reduces the recruitment of neutrophils in a mouse model of TNF-α-induced peritonitis. 1.Serhan, C.N., Fredman, G., Yang, R., et al.Novel proresolving aspirin-triggered DHA pathwayChem. Biol.18(18)976-987(2011)

D-chiro-Inositol (D-(+)-CHIRO-INOSITOL) is an epimer of myo-inositol that is found in certain mammalian glycosylphosphatidylinositol protein anchors and inositol phosphoglycans possessing insulin-like bioactivity.

15(S)-Fluprostenol isopropyl ester, an isomer of the prostaglandin F2α analog, fluprostenol isopropyl ester, serves as a possible prodrug to 15(S)-fluprostenol. It has the potential to act as an agonist at FP receptors, albeit with lower potency compared to the 15(R) epimer and the FP receptor agonist, fluprostenol. Additionally, it may be present as a potential impurity in commercial formulations of fluprostenol isopropyl ester.

17(R)-Resolvin D1 (17(R)-RvD1) is an aspirin-triggered epimer of RvD1 that equivalently inhibits human polymorphonuclear leukocyte migration across the endothelium (EC50= ~30 nM), a precursor to acute inflammation. Unlike RvD1, it resists rapid degradation by eicosanoid oxidoreductases. In a mouse peritonitis model, 17(R)-RvD1 dose-dependently reduces leukocyte infiltration, achieving up to a 35% decrease with a 100 ng dose. Additionally, its methyl ester derivative, designed to enhance its pharmacokinetic and distribution properties as a more lipophilic prodrug, can be converted back into the active acid form by intracellular esterases.

15(R)-Prostaglandin E2, the C-15 epimer of the more physiologically abundant 15(S)-PGE2 (sc-201225) isomer, is produced mainly from arachidonic acid (sc-200770) via the action of COX and PGES enzymes. Present in nearly all cell types, PGE2 interacts with four distinct receptors, EP1 to EP4, leading to a wide range of biological effects. However, 15(R)-Prostaglandin E2 exhibits significantly lower efficacy in most biological assays compared to its 15(S) counterpart. Notably, acid catalyzed epimerization can transform 15(R)-Prostaglandin E2 into the more active 15(S)-Prostaglandin E2 form.

17(R)-Resolvin D4 (17(R)-RvD4) is an epimer of RvD4, generated through the aspirin-induced modification process.

3-Epideoxycholic acid (EDCA), a secondary bile acid and an epimer of deoxycholic acid, serves as a steroidal host compound in the enantioselective purification of (2R,3S)-3-methyl-2-pentanol from its racemates via enclathration. Additionally, decreased fecal levels of EDCA have been observed in pediatric patients with non-alcoholic fatty liver disease (NAFLD).

11β-PGE2 is the C-11 epimer of PGE2. It is a moderate inhibitor of PGE2 binding to rat hypothalamic membranes with a Ki value of 53 nM.[1] 11β-PGE2 also stimulates bone resorption in rats at concentrations of 10-8 to 10-6 M which is similar to PGE2.2 11β-PGE2 inhibits PGE2 binding to the prostaglandin transporter protein with a Ki of 56 nM.[3] .

Dithioerythritol (DTE), a sulfur-containing sugar derivative of the 4-carbon monosaccharide erythrose, is an epimer of dithiothreitol (DTT).

10-Deacetylcephalomannin exhibits activity against PS leukemia in vivo; however, its instability leads to an equilibrium mixture with its cytotoxic C-7 epimer. Additionally, 10-Deacetylcephalomannine demonstrates growth inhibitory effects on human cancer cell lines, including cervical HeLa adenocarcinoma.

17(R)-Resolvin D3 (17(R)-RvD3) is an aspirin-triggered epimer of resolvin D3, produced from docosahexaenoic acid (DHA) through the action of COX-2 in the presence of aspirin, via a 17(R)-hydroperoxy DHA (17(R)-HDHA) intermediary. Identified in mouse inflammatory exudates, 17(R)-RvD3 notably inhibits the transmigration of isolated human polymorphonuclear cells (PMNs) and fosters the efferocytosis of apoptotic PMNs by macrophages. Furthermore, in a mouse model of zymosan-induced peritonitis, 17(R)-RvD3 administration (10 ng/animal) significantly curtails neutrophil infiltration into the peritoneal cavity and modulates cytokine levels by reducing IL-6 and increasing IL-10 in the inflammatory exudate. It engages GPR32, evidenced by activation in a β-arrestin reporter assay and augments phagocytosis more effectively in CHO cells overexpressing GPR32 compared to controls. Additionally, 17(R)-RvD3 enhances the clearance of etoposide-induced tumor cell debris by monocyte-derived macrophages in H460 human lung carcinoma.