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Pyrroloquinoline quinone Sale

(Synonyms: 吡咯喹啉醌; PQQ; Methoxatin) 目录号 : GC44793

据报道,吡咯并喹啉醌是一种新的哺乳动物乳酸脱氢酶 (LDH) 辅酶。

Pyrroloquinoline quinone Chemical Structure

Cas No.:72909-34-3

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Sample solution is provided at 25 µL, 10mM.

Description

Pyrroloquinoline quinone was reported to be a new mammalian lactate dehydrogenase (LDH) coenzyme [1]. Pyrroloquinoline quinone has diverse effects including an antioxidant effect, a cell growth-promoting effect, and a stimulatory effect on mitochondriogensis [2,3,4,5,6,7]

Pyrroloquinoline quinone protected against oxidative damage caused by H2O2, because it has many reducing sites. It was suggested that HepG2 cells require more pyrroloquinoline quinone due to the greater damage caused by hydrogen peroxide than do SK-N-SH cells [8]. Pyrroloquinoline quinone showed protect effect on 6-OHDA using human neuroblastoma SH-SY5Y cells at 15 μM [9].

Pyrroloquinoline quinone can serve as a growth factor in BALB/c mice [10]. The lower values for RQ in PQQ-deficient mice compared with PQQ-supplemented mice, as a sign of compromised mitochondrial function and inefficient carbohydrate utilization [11].

References:
[1]. Akagawa M, Minematsu K, Shibata T, et al. Identification of lactate dehydrogenase as a mammalian pyrroloquinoline quinone (PQQ)-binding protein[J]. Scientific reports, 2016, 6(1): 1-19.
[2]. He K, Nukada H, Urakami T, et al. Antioxidant and pro-oxidant properties of pyrroloquinoline quinone (PQQ): implications for its function in biological systems[J]. Biochemical pharmacology, 2003, 65(1): 67-74.
[3]. Nunome K, Miyazaki S, Nakano M, et al. Pyrroloquinoline quinone prevents oxidative stress-induced neuronal death probably through changes in oxidative status of DJ-1[J]. Biological and Pharmaceutical Bulletin, 2008, 31(7): 1321-1326.
[4]. Zhang Y, Feustel P J, Kimelberg H K. Neuroprotection by pyrroloquinoline quinone (PQQ) in reversible middle cerebral artery occlusion in the adult rat[J]. Brain research, 2006, 1094(1): 200-206.
[5]. Yamaguchi K, Sasano A, Urakami T, et al. Stimulation of nerve growth factor production by pyrroloquinoline quinone and its derivatives in vitro and in vivo[J]. Bioscience, biotechnology, and biochemistry, 1993, 57(7): 1231-1233.
[6]. Stites T, Storms D, Bauerly K, et al. Pyrroloquinoline quinone modulates mitochondrial quantity and function in mice[J]. The Journal of nutrition, 2006, 136(2): 390-396.
[7]. Chowanadisai W, Bauerly K A, Tchaparian E, et al. Pyrroloquinoline quinone stimulates mitochondrial biogenesis through cAMP response element-binding protein phosphorylation and increased PGC-1α expression[J]. Journal of Biological Chemistry, 2010, 285(1): 142-152.
[8]. Yamada Y, Nishii K, Kuwata K, et al. Effects of pyrroloquinoline quinone and imidazole pyrroloquinoline on biological activities and neural functions[J]. Heliyon, 2020, 6(1): e03240.
[9]. Hara H, Hiramatsu H, Adachi T. Pyrroloquinoline quinone is a potent neuroprotective nutrient against 6-hydroxydopamine-induced neurotoxicity[J]. Neurochemical research, 2007, 32(3): 489-495.
[10]. Naito Y, Kumazawa T, Kino I, et al. Effects of pyrroloquinoline quinone (PQQ) and PQQ-oxazole on DNA synthesis of cultured human fibroblasts[J]. Life sciences, 1993, 52(24): 1909-1915.
[11]. Stites T, Storms D, Bauerly K, et al. Pyrroloquinoline quinone modulates mitochondrial quantity and function in mice[J]. The Journal of nutrition, 2006, 136(2): 390-396.

据报道,吡咯并喹啉醌是一种新的哺乳动物乳酸脱氢酶 (LDH) 辅酶[1]。吡咯并喹啉醌具有多种作用,包括抗氧化作用、细胞生长促进作用和对线粒体生成的刺激作用[2,3,4,5,6,7]

吡咯并喹啉醌可防止 H2O2 引起的氧化损伤,因为它具有许多还原位点。提示 HepG2 细胞由于过氧化氢引起的损伤比 SK-N-SH 细胞需要更多的吡咯并喹啉醌[8]。使用人神经母细胞瘤 SH-SY5Y 细胞,15 μM 吡咯并喹啉醌对 6-OHDA 具有保护作用 [9]

吡咯并喹啉醌可作为 BALB/c 小鼠的生长因子 [10]。与补充 PQQ 的小鼠相比,PQQ 缺陷小鼠的 RQ 值较低,表明线粒体功能受损和碳水化合物利用效率低下[11]

实验参考方法

Cell experiment [1]:

Cell lines

SK-N-SH cells and HepG2 cells

Preparation Method

SK-N-SH cells and HepG2 cells were incubated with various concentrations of pyrroloquinoline quinone (PQQ) for 24h.

Reaction Conditions

0-500 nM for 24,48, 72 hours

Applications

SK-N-SH and HepG2 cells were incubated with various concentrations of pyrroloquinoline quinone for 24 h. The IC50 values for pyrroloquinoline quinone in SK-N-SH and HepG2 cells were calculated to be 0.17 mM and 0.43 mM, respectively.

Animal experiment [2]:

Animal models

BALB/c and C57BL/6J

Preparation Method

Pyrroloquinoline quinone concentrations in the basal amino acid diet were determined to be <5 fmol/g diet using a glucose dehydrogenase (GDH) enzyme assay for pyrroloquinoline quinone quantitation. Pyrroloquinoline quinone was added to diets at 2 mg/kg (∼6 nmol/g) diet. In typical protocols, virgin females were adapted to the basal (devoid of Pyrroloquinoline quinone) diet for ≥2 wk. Half of the females were then switched to a diet supplemented with 2 mg PQQ/kg diet, and the other half were fed the basal diet. Both groups of females (F0 generation) were then bred; the resulting pups (F1 generation) were weaned at 28 d of age and fed the same diet as their dams until used in selected assays.

Dosage form

2 mg/kg (∼6 nmol/g) diet, more than 2 weeks

Applications

The amount of mitochondria in liver from pyrroloquinoline quinone -deprived mice was less than that from Pyrroloquinoline quinone -supplemented mice based on cross-sectional area estimates

References:

[1]: Yamada Y, Nishii K, Kuwata K, et al. Effects of pyrroloquinoline quinone and imidazole pyrroloquinoline on biological activities and neural functions[J]. Heliyon, 2020, 6(1): e03240.
[2]: Stites T, Storms D, Bauerly K, et al. Pyrroloquinoline quinone modulates mitochondrial quantity and function in mice[J]. The Journal of nutrition, 2006, 136(2): 390-396.

化学性质

Cas No. 72909-34-3 SDF
别名 吡咯喹啉醌; PQQ; Methoxatin
Canonical SMILES O=C(O)C1=C(C(NC(C(O)=O)=C2)=C2C(C3=O)=O)C3=NC(C(O)=O)=C1
分子式 C14H6N2O8 分子量 330.2
溶解度 DMF: 1 mg/ml,DMSO: 2 mg/ml,Ethanol: 0.1 mg/ml,PBS (pH 7.2): 0.1 mg/ml 储存条件 Store at -20°C
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1 mM 3.0285 mL 15.1423 mL 30.2847 mL
5 mM 0.6057 mL 3.0285 mL 6.0569 mL
10 mM 0.3028 mL 1.5142 mL 3.0285 mL
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