GlpBio

N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid

目录号: GC44298纯度: >98.00%同义词: N-乙酰-2,3-二脱氢-2-脱氧神经氨酸,Neu5Ac2en; DANA
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid是一种高效的哺乳动物唾液酸酶（神经氨酸酶）抑制剂。
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid
Cas No.: 24967-27-9
规格价格库存数量操作
1mg¥508.00现货
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10mg¥2,998.00现货
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产品描述 Description

N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid is an effective mammal sialidase (neuraminidase) inhibitor[1]. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid can also inhibite Clostridium Perfringens sialidase, which has the IC50 value of 4μM[2]. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid is sialidase transition state analog, and has been used as an important probe for structural and mechanistic studies of sialidases[3].

N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (50μM; 3 days) decreased the growing number of myotube induced by lactate (15mM; 3-5 days) treatment in C2C12 cells[4]. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (1mM; 180min) increased glutamate release from rat hippocampus neurons[5].

N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (70-2100μmol/kg; intravenous injection; 30min) attenuated the mice blood glucose level after injection with glucose (2g/kg; i.p. ;120min) in a concentration-dependent manner[6]. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (10mg/kg; i.p. ; 20 days) and Tamiflu (10mg/kg; i.p. ; 20 days) treatments decreased the bleomycin (3U/kg; oropharyngeal aspiration; 1 day) induced lung fibrosis in mice[7].

References:
[1] MAGESH S, MORIYA S, SUZUKI T, et al. Design, synthesis, and biological evaluation of human sialidase inhibitors. Part 1: selective inhibitors of lysosomal sialidase (NEU1) [J]. Bioorg Med Chem Lett, 2008, 18(2): 532-7.
[2] HUNT M E, BROWN D R. Role of sialidase in Mycoplasma alligatoris-induced pulmonary fibroblast apoptosis [J]. Vet Microbiol, 2007, 121(1-2): 73-82.
[3] XIAO A, LI Y, LI X, et al. Sialidase-catalyzed one-pot multienzyme (OPME) synthesis of sialidase transition-state analogue inhibitors [J]. ACS Catal, 2018, 8(1): 43-7.
[4] DAI W, WU G, LIU K, et al. Lactate promotes myogenesis via activating H3K9 lactylation-dependent up-regulation of Neu2 expression [J]. J Cachexia Sarcopenia Muscle, 2023, 14(6): 2851-65.
[5] MINAMI A, ISHII A, SHIMBA S, et al. Down-regulation of glutamate release from hippocampal neurons by sialidase [J]. J Biochem, 2018, 163(4): 273-80.
[6] MINAMI A, FUJITA Y, SHIMBA S, et al. The sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid is a glucose-dependent potentiator of insulin secretion [J]. Sci Rep, 2020, 10(1): 5198.
[7] KARHADKAR T R, PILLING D, COX N, et al. Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model [J]. Sci Rep, 2017, 7(1): 15069.

N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid是一种高效的哺乳动物唾液酸酶（神经氨酸酶）抑制剂[1]。N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid对产气荚膜梭菌唾液酸酶也有抑制作用，IC50值为4μM[2]。N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid是唾液酸酶过渡态类似物，已被用作研究唾液酸酶结构和机理的重要探针[3]。

N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid（50μM; 3 days）减少由乳酸（15mM; 3-5 days）诱导的C2C12细胞中过量的肌管的合成[4]。N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid（1mM; 180min）增加大鼠海马神经元细胞的谷氨酸释放[5]。

使用N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid（70-2100μmol/kg; intravenous injection; 30min）处理腹腔注射葡萄糖（2g/kg; i.p. ;120min）的小鼠，N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid以浓度依赖的方式降低小鼠的血葡萄糖水平[6]。N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid bleomycin减少由bleomycin（3U/kg; ; 1 day）诱导的小鼠肺纤维化。N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid（10mg/kg; i.p. ; 20 days）和Tamiflu（10mg/kg; i.p. ; 20 days）联合治疗降低了由Bleomycin（3U/kg；oropharyngeal aspiration；1day）诱导的小鼠肺纤维化程度[7]。

实验参考方法 Experimental Reference Method

Cell experiment [1]:

Cell lines

 Mouse myoblast C2C12 cells

Preparation Method

Mouse myoblast C2C12 cells were grown in incubators at 37℃, 5% CO2. Proliferating cells were cultured in high-glucose Dulbecco’s modified Eagle’s medium added with 1% penicillin-streptomycin and 10% fetal bovine serum. After C2C12 cells grown to 80-90% confluence, cells were cultured in Dulbecco’s modified Eagle’s medium with 1% penicillin-streptomycin and 2% horse serum for myogenic differentiation.
C2C12 were treated with the addition of either 15mM L-lactate or sodium lactate with differentiation medium changes every 24h for 3–5 days. To inhibit activity of lactate dehydrogenase A (LDHA), C2C12 cells were cultured with (R)-GNE-140 (10μM) or dimethyl sulfoxide for 3 days. To block lactate uptake, myoblasts were treated with AZD3965 (0, 25, 50 and 100nM) for 3 days. In order to inhibit function of Neu2, C2C12 cells were treated with N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (50μM) and cultured in differentiation medium for 3 days.

Reaction Conditions

50μM; 3 days

Applications

N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid decreased the growing number of myotube induced by lactate treatment in C2C12 cells.
Animal experiment [2]:

Animal models

Male C57BL/6J mice

Preparation Method

The mice were housed under standard laboratory conditions (23±1℃, 55±5% humidity) and had access to tap water and diet ad libitum. The lights were automatically turned on at 8:00 and turned off at 20:00. To investigate the effect of N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid on insulin secretion under the fasting condition, N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (70μmol-2100μmol/kg; intravenous injection; 30min) and glucose (2g/kg; i.p. ;120min) were administered by intravenous injection and intraperitoneal injection, respectively, after 24 hour fasting. Blood was sampled before (0min) and at 30min after administration.

Dosage form

70-2100μmol/kg; intravenous injection; 30min

Applications

 N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid attenuated the mice blood glucose level after injection with glucose in a concentration-dependent manner.

References:
[1] DAI W, WU G, LIU K, et al. Lactate promotes myogenesis via activating H3K9 lactylation-dependent up-regulation of Neu2 expression [J]. J Cachexia Sarcopenia Muscle, 2023, 14(6): 2851-65.
[2] MINAMI A, FUJITA Y, SHIMBA S, et al. The sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid is a glucose-dependent potentiator of insulin secretion [J]. Sci Rep, 2020, 10(1): 5198.

产品文档 Product Documents

Purity:>98.00%

化学性质Chemical Properties

CAS 号
24967-27-9
同义词
N-乙酰-2,3-二脱氢-2-脱氧神经氨酸,Neu5Ac2en; DANA
SMILES
OC(C1=C[C@H](O)[C@@H](NC(C)=O)[C@@]([C@H](O)[C@H](O)CO)([H])O1)=O
分子式
C11H17NO8
分子量
291.3 g/mol
溶解性
DMF: 0.1 mg/ml,DMSO: 1 mg/ml,PBS (pH 7.2): 10 mg/ml
保存条件
Store at -20°C
General tips
请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。
储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。
为了提高溶解度，请将管子加热至 37°C，然后在超声波浴中震荡一段时间。
Shipping Condition
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