Levomefolic acid
(Synonyms: 5-甲基四氢叶酸; 5-MTHF) 目录号 : GC36443
Levomefolic acid是一种具有口服活性且可通过血脑屏障的叶酸生物活性形式。
Cas No.:31690-09-2
Sample solution is provided at 25 µL, 10mM.
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Levomefolic acid is an orally available, bioactive form of folic acid that crosses the blood-brain barrier[1]. Levomefolic acid, a ligand with low binding energy, can form three hydrogen bonds with Arg169, Asp305 and Tyr276 of COVID-19 PLpro protein and form π-π stacking interaction with Tyr271[2]. Levomefolic acid has been widely used as a model compound and an internal reference to develop novel LC-MS/MS methods for the identification of related compounds[3].
In vitro, Levomefolic acid treatment at 10µg/ml for 24 hours significantly inhibited Caco-2 cell proliferation and induced cell cycle arrest[4]. Treatment of BEAS-2B cells with 0.012g/L Levomefolic acid for 24h protected BEAS-2B cells from oxidative stress and inflammatory injury induced by glucose (50mM) and restored cell viability[5]. Treatment with 50µM Levomefolic acid for 48h significantly induced DNA damage in MRC5 and IMR90 cells, resulting in decreased MTR gene expression and increased MTHFD1, EGFR, XRCC1, and DNA Polβ gene expression[6].
In vivo, intraperitoneal injection of Levomefolic acid (3µg/kg) at 30 minutes before ischemia and again 3 hours after reperfusion can improve renal function in Sprague-Dawley rats, alleviate oxidative stress, restore glutathione levels in the kidneys, and reduce lipid peroxidation[7]. Within 5 weeks after weaning, oral administration of 4ml of drinking water containing a dose of 47μg/ml of Levomefolic acid daily significantly increased the body weight of female mice and promoted the maturation of oocytes[8].
References:
[1] Lam N S K, Long X X, Li X, et al. The potential use of folate and its derivatives in treating psychiatric disorders: A systematic review[J]. Biomedicine & Pharmacotherapy, 2022, 146: 112541.
[2] Hosseini M, Chen W, Xiao D, et al. Computational molecular docking and virtual screening revealed promising SARS-CoV-2 drugs[J]. Precision clinical medicine, 2021, 4(1): 1-16.
[3] Golja M V, Trontelj J, Geršak K, et al. Simultaneous quantification of intracellular concentrations of clinically important metabolites of folate-homocysteine cycle by LC-MS/MS[J]. Analytical biochemistry, 2020, 605: 113830.
[4] Akoglu B, Milovic V, Caspary W F, et al. Hyperproliferation of homocysteinetreated colon cancer cells is reversed by folate and 5-methyltetrahydrofolate[J]. European journal of Nutrition, 2004, 43(2): 93-99.
[5] Pathikkal A, Puthusseri B, Divya P, et al. Folate derivatives, 5-methyltetrahydrofolate and 10-formyltetrahydrofolate, protect BEAS-2B cells from high glucose–induced oxidative stress and inflammation[J]. In Vitro Cellular & Developmental Biology-Animal, 2022, 58(5): 419-428.
[6] Karkera C, Senejani A G. Evaluating toxicity and level of DNA damage in human fetal lung cells upon exposure to 5-methyltetrahydrofolate (bioactive folate)[J]. Nutrition and Health, 2024: 02601060241302895.
[7] Wijerathne C U B, Au-Yeung K K W, Siow Y L, et al. 5-methyltetrahydrofolate attenuates oxidative stress and improves kidney function in acute kidney injury through activation of Nrf2 and antioxidant defense[J]. Antioxidants, 2022, 11(6): 1046.
[8] Nasr‐Esfahani F, Jafarpour F, Varnosfaderani S R, et al. Differential Effects of Folic Acid and 5‐Methyltetrahydrofolate on Mice Oocytes and Embryo Development In Vitro and In Vivo: Implications for Reproductive Health[J]. The FASEB Journal, 2025, 39(20): e71090.
Levomefolic acid是一种具有口服活性且可通过血脑屏障的叶酸生物活性形式[1]。Levomefolic acid能以低结合能作为配体，与COVID-19 PLpro蛋白的Arg169、Asp305和Tyr276形成三个氢键，并与Tyr271产生π-π堆叠相互作用[2]。Levomefolic acid已作为模型化合物和内参物广泛应用于开发鉴定相关化合物的新型LC-MS/MS方法[3]。
在体外，使用10µg/ml的Levomefolic acid处理Caco-2细胞24小时，可显著抑制Caco-2细胞增殖并诱导细胞周期阻滞[4]。用0.012g/L的Levomefolic acid处理BEAS-2B细胞24小时，能保护细胞免受葡萄糖(50mM)诱导的氧化应激和炎症损伤，并恢复细胞活力[5]。以50µM的Levomefolic acid处理MRC5和IMR90细胞48小时，可显著诱导DNA损伤，导致MTR基因表达下调，同时上调MTHFD1、EGFR、XRCC1和DNA Polβ基因表达[6]。
在体内，在缺血前30分钟及再灌注后3小时分别腹腔注射3µg/kg剂量的Levomefolic acid，可改善Sprague-Dawley大鼠的肾功能，减轻氧化应激，恢复肾脏谷胱甘肽水平并降低脂质过氧化[7]。在小鼠断奶后5周内每日口服4ml含47μg/ml的Levomefolic acid的饮用水，可显著增加雌鼠体重并促进卵母细胞成熟[8]。
| Cell experiment [1]: | |
Cell lines | BEAS-2B cells |
Preparation Method | BEAS-2B cells were cultured in DMEM medium supplemented with 10% fetal bovine serum (FBS), 100IU/ml penicillin and 100µg/ml streptomycin, and cultured at 37℃ in a humidified atmosphere with 5% CO2. Cells were seeded in 96-well microplate at a density of 2×104 cells/well, and 100µl culture medium was added to each well. After 24 hours of stable culture, cells were exposed to 50mM glucose and Levomefolic acid (0.012g/L) for 24 hours. At the end of the treatment, 40µl of MTT solution (2mg/ml) was added and incubated for 4h at 37°C. The medium was discarded, and the resulting purple formazan crystals were dissolved in 200µl dimethyl sulfoxide (DMSO), and the absorbance was measured at a wavelength of 540nm. |
Reaction Conditions | 0.012g/L; 24h |
Applications | Levomefolic acid treatment significantly restored the viability of BEAS-2B cells exposed to high glucose. |
| Animal experiment [2]: | |
Animal models | Male Sprague-Dawley rats |
Preparation Method | Male Sprague-Dawley rats (6 weeks old, 250-300 grams) were housed in a standard environment. The rats were randomly divided into three groups: (1) the renal ischemia-reperfusion group (IR group), (2) the renal ischemia-reperfusion combined with Levomefolic acid injection group (IR+5-MTHF group), and (3) the sham operation control group (Sham group) (n = 8 in each group). The left renal pedicle was clamped non-invasively with an intravascular clamp for 45 minutes to induce renal ischemia. After the ischemia ended, the vascular clamp was removed to restore the blood flow to the left kidney (reperfusion), and then the right kidney was removed. In IR+5-MTHF group of rats, Levomefolic acid (3µg/kg) was intraperitoneally injected 30 minutes before ischemia and 3 hours after reperfusion. The sham operation group was injected with normal saline. Kidney samples were collected from the rats 24 hours later for analysis. |
Dosage form | 3µg/kg for twice; i.p. |
Applications | Levomefolic acid treatment improved kidney morphology in rats with ischemia-reperfusion injury and attenuated kidney injury. |
References: | |
| Cas No. | 31690-09-2 | SDF | |
| 别名 | 5-甲基四氢叶酸; 5-MTHF | ||
| Canonical SMILES | O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(NC[C@@H]2N(C)C3=C(NC(N)=NC3=O)NC2)C=C1)=O | ||
| 分子式 | C20H25N7O6 | 分子量 | 459.46 |
| 溶解度 | 23 mg/mL DMSO（ultrasonic and warming and heat to 45°C) | 储存条件 | Store at -20°C |
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.1765 mL | 10.8823 mL | 21.7647 mL |
| 5 mM | 435.3 μL | 2.1765 mL | 4.3529 mL |
| 10 mM | 217.6 μL | 1.0882 mL | 2.1765 mL |
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动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
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| % DMSO % % Tween 80 % saline | ||||||||||
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