Purity: ≥98%
| ln Vitro |
Addition of Anserine (10 mM) to the physiological solution surrounding fatigued frog skeletal muscle (m. sartorius) caused resumption of contraction, with the experimental muscle contracting more vigorously than control despite lower levels of energy-rich compounds (ATP, creatine phosphate, glycogen) [1].
In isolated pigeon breast muscle mitochondria, Anserine added to the suspension maintained a sufficiently high level of coupling between substrate oxidation and phosphorylation; this effect was not observed in freshly isolated mitochondria with a high P/O ratio or in heart mitochondria even under uncoupling conditions [1]. Anserine (along with carnosine and D-carnosine) decreased the rate of membrane lipid peroxidation (LPO) in frog sarcoplasmic reticulum (SR) membrane fragments induced by Fe²⁺ + ascorbate system, as judged by reduced levels of TBA-active products (expressed as malondialdehyde, MDA); the intensity of LPO inhibition was directly proportional to the dipeptide concentration [1]. Anserine (25 mM) also maintained long-term coupling of the Ca²⁺-pump in SR membranes during LPO, preserving the ability of membrane vesicles to accumulate Ca²⁺ and hydrolyze ATP [1]. |
|---|---|
| ln Vivo |
In AβPPswe/ PSEN1dE9 Alzheimer's disease (AD) model mice older than 18 months, anserine (dranking water at a concentration of 2.0 g/L, or 10 mg/mouse); for 8 weeks) totally recovers the memory deficits, enhances pericyte coverage on endothelial cells in the brain, and reduces chronic glial neuroinflammatory reactions[2].
|
| Enzyme Assay |
For the study of oxidative phosphorylation, isolated pigeon breast muscle mitochondria were incubated with Anserine (concentration not specified), and the ability to couple substrate oxidation with phosphorylation was assessed; anserine maintained coupling at a sufficiently high level, whereas no such effect was seen in heart mitochondria or in freshly isolated mitochondria with high P/O ratios [1].
In experiments with transport ATPases (Na,K-ATPase and Ca-ATPase), Anserine (as part of the dipeptide family) decreased the activation energy and increased coupling between the hydrolytic and transport reactions catalyzed by these enzymes, thereby providing optimal operation of the Na/K- and Ca-pumps; these effects were observed only in injured membranes where uncoupling had been induced by exogenous factors [1]. To assess lipid peroxidation (LPO) inhibition, frog sarcoplasmic reticulum (SR) membrane fragments (1 mg membrane protein) were incubated in 1 ml of 25 mM buffer containing Anserine (concentration not specified, but carnosine was used at 25 mM in related experiments), along with 10 μM FeSO₄ and 200 μM ascorbate to induce LPO; at defined intervals, aliquots were withdrawn to measure LPO intensity by the colorimetric reaction between LPO products and 2-thiobarbituric acid (TBA), with results expressed as malondialdehyde (MDA) concentration; anserine decreased the rate of LPO and the steady-state level of TBA-active products [1]. |
| References |
|
| Additional Infomation |
Anserine is a dipeptide composed of β-alanine and 3-methyl-L-histidine units. It is an animal metabolite, specifically a mouse metabolite. It is a derivative of β-alanine and also a dipeptide. It is a zwitterionic tautomer of anserine. Anserine is present in or produced by Escherichia coli (strains K12 and MG1655). Anserine has also been reported in C. elegans, with relevant data. Anserine is a dipeptide composed of β-alanine and methylhistidine, found in dietary red meat, and possesses antioxidant activity. It is a dipeptide containing β-alanine.
Anserine is a methylated derivative of carnosine, with methylation occurring on the 1-nitrogen of the imidazole ring [1]. In ontogenetic development, anserine appears in muscle tissues at later periods than carnosine, and in birds it is the predominant histidine-containing dipeptide [1]. The dipeptide exhibits a remarkable buffering capacity at physiological pH (pKa 7.04), which has been suggested as a possible biological role, but the authors argue that its function should not be restricted to this property [1]. Anserine is not digested by dipeptide hydrolases and is broken down within the organism by specific carnosinase and homocarnosinase, which are present in kidney, liver, and blood plasma but are absent in skeletal muscle [1]. Acetylated derivative (acetylanserine) has been detected in myocardium, though its biological function remains obscure [1]. |
| Molecular Formula |
C10H16N4O3
|
|---|---|
| Molecular Weight |
240.2590
|
| Exact Mass |
240.122
|
| CAS # |
584-85-0
|
| Related CAS # |
10030-52-1 (nitrate);584-85-0;
|
| PubChem CID |
112072
|
| Appearance |
White to off-white solid powder
|
| Density |
1.38±0.1 g/cm3
|
| Boiling Point |
526.0±60.0 °C at 760 mmHg
|
| Melting Point |
268 ºC
|
| Flash Point |
271.9±32.9 °C
|
| Vapour Pressure |
0.0±1.5 mmHg at 25°C
|
| Index of Refraction |
1.615
|
| LogP |
-1.24
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
6
|
| Heavy Atom Count |
17
|
| Complexity |
285
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
CN1C=NC=C1C[C@@H](C(=O)O)NC(=O)CCN
|
| InChi Key |
MYYIAHXIVFADCU-QMMMGPOBSA-N
|
| InChi Code |
InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1
|
| Chemical Name |
(2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
H2O : ~100 mg/mL (~416.22 mM)
DMSO :< 1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (416.22 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1622 mL | 20.8108 mL | 41.6216 mL | |
| 5 mM | 0.8324 mL | 4.1622 mL | 8.3243 mL | |
| 10 mM | 0.4162 mL | 2.0811 mL | 4.1622 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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