Pyrroloquinoline quinone
(Synonyms: 吡咯喹啉醌; PQQ; Methoxatin) 目录号 : GC44793
A quinone with diverse biological activities
Cas No.:72909-34-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
| Cell experiment [1]: | |
|
Cell lines |
SK-N-SH cells and HepG2 cells |
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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]: | |
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Animal models |
BALB/c and C57BL/6J |
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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. |
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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 |
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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. | |
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]。
| 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 |
| 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℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Pyrroloquinoline-Quinone Is More Than an Antioxidant: A Vitamin-like Accessory Factor Important in Health and Disease Prevention
Biomolecules 2021 Sep 30;11(10):1441.PMID:34680074DOI:10.3390/biom11101441.
Pyrroloquinoline quinone (PQQ) is associated with biological processes such as mitochondriogenesis, reproduction, growth, and aging. In addition, PQQ attenuates clinically relevant dysfunctions (e.g., those associated with ischemia, inflammation and lipotoxicity). PQQ is novel among biofactors that are not currently accepted as vitamins or conditional vitamins. For example, the absence of PQQ in diets produces a response like a vitamin-related deficiency with recovery upon PQQ repletion in a dose-dependent manner. Moreover, potential health benefits, such as improved metabolic flexibility and immuno-and neuroprotection, are associated with PQQ supplementation. Here, we address PQQ's role as an enzymatic cofactor or accessory factor and highlight mechanisms underlying PQQ's actions. We review both large scale and targeted datasets demonstrating that a neonatal or perinatal PQQ deficiency reduces mitochondria content and mitochondrial-related gene expression. Data are reviewed that suggest PQQ's modulation of lactate acid and perhaps other dehydrogenases enhance NAD+-dependent sirtuin activity, along with the sirtuin targets, such as PGC-1α, NRF-1, NRF-2 and TFAM; thus, mediating mitochondrial functions. Taken together, current observations suggest vitamin-like PQQ has strong potential as a potent therapeutic nutraceutical.
Pyrroloquinoline quinone Chemistry, Biology, and Biosynthesis
Chem Res Toxicol 2022 Mar 21;35(3):355-377.PMID:35166521DOI:10.1021/acs.chemrestox.1c00340.
The widely distributed, essential redox factor Pyrroloquinoline quinone (PQQ, methoxatin) (1) was discovered in the mid-1960s. The breadth and depth of its biological effects are steadily being revealed, and understanding its biosynthesis at the genomic level is a continuing process. In this review, aspects of the chemistry, biology, biosynthesis, and commercial production of 1 at the gene level, and some applications, are presented from discovery through to mid-2021.
Pyrroloquinoline quinone Prevents Estrogen Deficiency-Induced Osteoporosis by Inhibiting Oxidative Stress and Osteocyte Senescence
Int J Biol Sci 2019 Jan 1;15(1):58-68.PMID:30662347DOI:10.7150/ijbs.25783.
Accumulating studies have shown that oxidative stress increases with aging, which is related to the pathophysiology of postmenopausal osteoporosis. Pyrroloquinoline quinone (PQQ) is a natural anti-oxidant with anti-oxidative and anti-aging effects. However, it is unclear whether PQQ has a protective role against estrogen deficiency-induced osteoporosis. Here, we evaluated the efficacy of PQQ on bone mineral density, bone microarchitecture, bone turnover and biomechanical strength in ovariectomy (OVX)-induced osteoporosis mouse model. Although dietary PQQ supplement did not affect serum E2 levels and uterine weight in OVX mice, it could prevent OVX-induced bone loss and improve bone strength by inhibiting oxidative stress, osteocyte senescence and senescence-associated secretory phenotype (SASP), subsequently promoting osteoblastic bone formation and inhibiting osteoclastic bone resorption, which was comparable to treatment with exogenous estrogen. The results from our study provide experimental evidence for the clinical use of PQQ to prevent estrogen deficiency-induced osteoporosis.
Pyrroloquinoline quinone Inhibits Rotenone-Induced Microglia Inflammation by Enhancing Autophagy
Molecules 2020 Sep 23;25(19):4359.PMID:32977419DOI:10.3390/molecules25194359.
Neuroinflammation is a feature common to neurodegenerative diseases, such as Parkinson's disease (PD), which might be responsive to therapeutic intervention. Rotenone has been widely used to establish PD models by inducing mitochondrial dysfunction and inflammation. Our previous studies have reported that Pyrroloquinoline quinone (PQQ), a naturally occurring redox cofactor, could prevent mitochondrial dysfunction in rotenone induced PD models by regulating mitochondrial functions. In the present study, we aimed to investigate the effect of PQQ on neuroinflammation and the mechanism involved. BV2 microglia cells were pre-treated with PQQ followed by rotenone incubation. The data showed that PQQ did not affect the cell viability of BV2 cells treated with rotenone, while the conditioned medium (CM) of BV2 cells pre-treated with PQQ significantly increased cell viability of SH-SY5Y cells. In rotenone-treated BV2 cells, PQQ dose-dependently decreased lactate dehydrogenase (LDH) release and suppressed the up-regulation of pro-inflammation factors, such as interleukin-1β (IL-1β), IL-6 and tumor necrosis factor-α (TNF-α) in the cultured media, as well as nitric oxide (NO) release induced by rotenone. PQQ pretreatment also increased the ratio of LC3-II/LC3-I and expression of Atg5 in BV2 cells stimulated with rotenone. Additionally, the autophagosome observed by transmission electron microscopy (TEM) and co-localization of mitochondria with lysosomes indicated that mitophagy was induced by PQQ in rotenone-injured BV2 cells, and the PINK1/parkin mediated mitophagy pathway was regulated by PQQ. Further, autophagy inhibitor, 3-methyladenine (3-MA), partially abolished the neuroprotective effect of PQQ and attenuated the inhibition of inflammation with PQQ pretreatment. Taken together, our data extend our understanding of the neuroprotective effect of PQQ against rotenone-induced injury and provide evidence that autophagy enhancement might be a novel therapeutic strategy for PD treatment.
Pyrroloquinoline quinone promotes mitochondrial biogenesis in rotenone-induced Parkinson's disease model via AMPK activation
Acta Pharmacol Sin 2021 May;42(5):665-678.PMID:32860006DOI:10.1038/s41401-020-0487-2.
Mitochondrial dysfunction is considered to be one of the important pathogenesis in Parkinson's disease (PD). We previously showed that Pyrroloquinoline quinone (PQQ) could protect SH-SY5Y cells and dopaminergic neurons from cytotoxicity and prevent mitochondrial dysfunction in rotenone-induced PD models. In the present study we investigated the mechanisms underlying the protective effects of PQQ in a mouse PD model, which was established by intraperitoneal injection of rotenone (3 mg·kg-1·d-1, ip) for 3 weeks. Meanwhile the mice were treated with PQQ (0.8, 4, 20 mg·kg-1·d-1, ip) right after rotenone injection for 3 weeks. We showed that PQQ treatment dose-dependently alleviated the locomotor deficits and nigral dopaminergic neuron loss in PD mice. Furthermore, PQQ treatment significantly diminished the reduction of mitochondria number and their pathological change in the midbrain. PQQ dose-dependently blocked rotenone-caused reduction in the expression of PGC-1α and TFAM, two key activators of mitochondrial gene transcription, in the midbrain. In rotenone-injured human neuroblastoma SH-SY5Y cells, PTMScan Direct analysis revealed that treatment with PQQ (100 μM) differentially regulated protein phosphorylation; the differentially expressed phosphorylated proteins included the signaling pathways related with adenosine 5'-monophosphate (AMP)-activated protein kinase (AMPK) pathway. We conducted Western blot analysis and confirmed that AMPK was activated by PQQ both in PD mice and in rotenone-injured SH-SY5Y cells. Pretreatment with AMPK inhibitor dorsomorphin (4 μM) significantly attenuated the protective effect and mitochondrial biogenesis by PQQ treatment in rotenone-injured SH-SY5Y cells. Taken together, PQQ promotes mitochondrial biogenesis in rotenone-injured mice and SH-SY5Y cells via activation of AMPK signaling pathway.