3-hydroxy-DL-Kynurenine
(Synonyms: DL-3-羟基犬尿氨酸,DL-3-Hydroxykynurenine) 目录号 : GC45336An active metabolite of tryptophan
Cas No.:484-78-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
3-hydroxy-DL-Kynurenine is an active metabolite of tryptophan.1,2,3 It inhibits yeast and rat liver aldehyde dehydrogenase by 97 and 69%, respectively, when used at a concentration of 100 μM.1 3-hydroxy-DL-Kynurenine is active against methicillin-resistant S. aureus (MRSA), S. epidermidis, vancomycin-resistant E. faecalis (VRE), E. coli, multidrug-resistant P. aeruginosa (MDRP), and C. albicans (IC50s = 31.2, 39.2, 57.6, 24, 25.6, and 137.6 μg/ml, respectively).2 It increases intracellular NAD+ levels and extracellular lactate dehydrogenase (LDH) activity in human neurons and astrocytes in a concentration-dependent manner.3
References
1. Badawy, A.A.-B., and Morgan, C.J. Tryptophan metabolites as potent inhibitors of aldehyde dehydrogenase activity and potential alcoholism-aversion therapeutic agents. Int. Congr. Ser. 1304, 344-351 (2007).
2. Narui, K., Noguchi, N., Saito, A., et al. Anti-infectious activity of tryptophan metabolites in the L-tryptophan-L-kynurenine pathway. Biol. Pharm. Bull. 32(1), 41-44 (2009).
3. Braidy, N., Grant, R., Brew, B.J., et al. Effects of kynurenine pathway metabolites on intracellular NAD+ synthesis and cell death in human primary astrocytes and neurons. Int. J. Tryptophan Res. 2, 61-69 (2009).
| Cas No. | 484-78-6 | SDF | |
| 别名 | DL-3-羟基犬尿氨酸,DL-3-Hydroxykynurenine | ||
| 化学名 | α,2-diamino-3-hydroxy-γ-oxo-benzenebutanoic acid | ||
| Canonical SMILES | OC1=CC=CC(C(CC(N)C(O)=O)=O)=C1N | ||
| 分子式 | C10H12N2O4 | 分子量 | 224.2 |
| 溶解度 | DMF: 0.5 mg/ml,DMSO: 1 mg/ml,Ethanol: 2 mg/ml,PBS (pH 7.2): 0.5 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 | 4.4603 mL | 22.3015 mL | 44.603 mL |
| 5 mM | 0.8921 mL | 4.4603 mL | 8.9206 mL |
| 10 mM | 0.446 mL | 2.2302 mL | 4.4603 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。
The influence of tryptophan and its metabolites upon rabbit lens electrolyte balance
Curr Eye Res 1982;2(5):309-15.PMID:6219861DOI:10.3109/02713688209000775.
The effect of tryptophan and three major metabolites of tryptophan on the rabbit lens electrolyte balance was examined. Even at 3 x 10(-3) M tryptophan, tryptamine and xanthurenic acid had no effect on lens sodium, potassium and calcium content after a 20 hr incubation. Small but significant changes in lens sodium and potassium content were induced by 20 hr incubation in 2 x 10(-3) M 3-hydroxy-DL-Kynurenine and 10(-3) M hydroxyanthranilic acid. Lens Na, K-ATPase activity was unaffected by 3 x 10(-3) M tryptophan. Tryptamine reduced, to a small extent, Na,K-ATPase activity at 3 x 10(-3) M, but was without effect at 10(-3) M. 3-hydroxy-DL-Kynurenine (2 x 10(-3) M) and 3-hydroxyanthranilic acid (10(-3) M) inhibited Na,K-ATPase activity by 27% and 30% respectively. Only 3-hydroxy-DL-Kynurenine had a demonstrable effect on 86Rb uptake. It is concluded that, in contrast to findings in the amphibian lens, metabolites of tryptophan have minimal or no detrimental effects upon rabbit lens electrolyte balance under the in vitro conditions of these experiments. However, this does not rule out a long term effect of these compounds should they accumulate in the lens.
Crystal structure of Homo sapiens kynureninase
Biochemistry 2007 Mar 13;46(10):2735-44.PMID:17300176DOI:10.1021/bi0616697.
Kynureninase is a member of a large family of catalytically diverse but structurally homologous pyridoxal 5'-phosphate (PLP) dependent enzymes known as the aspartate aminotransferase superfamily or alpha-family. The Homo sapiens and other eukaryotic constitutive kynureninases preferentially catalyze the hydrolytic cleavage of 3-hydroxy-l-kynurenine to produce 3-hydroxyanthranilate and l-alanine, while l-kynurenine is the substrate of many prokaryotic inducible kynureninases. The human enzyme was cloned with an N-terminal hexahistidine tag, expressed, and purified from a bacterial expression system using Ni metal ion affinity chromatography. Kinetic characterization of the recombinant enzyme reveals classic Michaelis-Menten behavior, with a Km of 28.3 +/- 1.9 microM and a specific activity of 1.75 micromol min-1 mg-1 for 3-hydroxy-DL-Kynurenine. Crystals of recombinant kynureninase that diffracted to 2.0 A were obtained, and the atomic structure of the PLP-bound holoenzyme was determined by molecular replacement using the Pseudomonas fluorescens kynureninase structure (PDB entry 1qz9) as the phasing model. A structural superposition with the P. fluorescens kynureninase revealed that these two structures resemble the "open" and "closed" conformations of aspartate aminotransferase. The comparison illustrates the dynamic nature of these proteins' small domains and reveals a role for Arg-434 similar to its role in other AAT alpha-family members. Docking of 3-hydroxy-l-kynurenine into the human kynureninase active site suggests that Asn-333 and His-102 are involved in substrate binding and molecular discrimination between inducible and constitutive kynureninase substrates.
Effects of kynurenine metabolites on mesangial cell proliferation and gene expression
Exp Mol Pathol 2009 Aug;87(1):70-5.PMID:19268458DOI:10.1016/j.yexmp.2009.02.002.
In the present study, we examined the effects of kynurenine metabolites on cultured mesangial cells (MCs) and demonstrated for the first time that they affect MC proliferation and gene expression. Anthranilic acid and 3-hydroxy-DL-Kynurenine suppressed MC proliferation by 32% and 43%, respectively at 10(-6) M compared to the control. In contrast, quinolinic acid and l-kynurenine promoted MC proliferation by 49% and 35% at 10(-8) M respectively, although promoting activities declined at higher concentrations. In addition, quinolinic acid upregulated the gene expression of platelet-derived growth factor-B, collagen type-Ialpha1, and collagen type-IValpha1. However, the gene expression of hepatocyte growth factor (HGF) was downregulated. We further examined the gene expressions in the glomeruli of high serum IgA (HIGA) mice with IgA nephropathy using microarray technology and found that the gene expression of insulin-like growth factor-1 was higher, but that of HGF was lower at 40 weeks of age compared to 8 weeks of age. In Balb/c mice, the gene expression of three kynurenine pathway enzymes (kynurenine aminotransferase I, kynurenine aminotransferase II, and quinolinate phospho-ribosyltransferase) increased 2- to 3.5-fold, whereas those in HIGA mice did not change significantly. These results suggest that abnormalities in the kynurenine pathway are associated with the dysfunction of MCs and progression of chronic kidney diseases.
HPLC Gradient Retention of Tryptophan and its Metabolites on Three Stationary Phases in Context of Lipophilicity Assessment
J Chromatogr Sci 2021 Jan 1;59(1):40-46.PMID:33107556DOI:10.1093/chromsci/bmaa074.
This paper is a continuation of lipophilicity research on 14 compounds (tryptophan, kynurenine pathway products, auxin pathway products, serotonin pathway products, tryptamine, as well as two synthetic auxin analogs): indole-2-acetic acid sodium salt (IAA), serotonin, 5-hydroxy-L-tryptophan, tryptamine, L-tryptophan, L-kynurenine (KYN), kynurenic acid (KYA), 3-hydroxy-DL-Kynurenine, naphtyl-1-acetamide, indole-3-propionic acid (IPA), naphthalene-1-acetic acid (NAA), indole-3-butyric acid (IBA), indole-3-pyruvic acid (IPV), as well as melatonin. They were chromatographed in high performance liquid chromatography gradient conditions on tree stationary phases (C18, CN, DIOL) using three modifiers on each phase (methanol, acetonitrile and acetone). The resulting retention data was correlated with computational lipophilicity indices. Six compounds were proven to be ionized in neutral pH physiological conditions (IAA, KYA, IPA, NAA, IBA and IPV) and they were rechromatographed with acidic mobile phase to enhance the resulting dataset. It can be concluded that the retention times are highly correlated with lipophilicity regardless of used modifier and column and the main differentiating trend can be only connected to presence of naphthalene or indole ring. The principal component analysis, additive linear modeling, as well as multiplicative trilinear parallel factor analysis (PARAFAC) modeling helped to understand the internal structure of the obtained results.
Ultraviolet and yellow reflectance but not fluorescence is important for visual discrimination of conspecifics by Heliconius erato
J Exp Biol 2017 Apr 1;220(Pt 7):1267-1276.PMID:28108668DOI:10.1242/jeb.153593.
Toxic Heliconius butterflies have yellow hindwing bars that - unlike those of their closest relatives - reflect ultraviolet (UV) and long wavelength light, and also fluoresce. The pigment in the yellow scales is 3-hydroxy-DL-Kynurenine (3-OHK), which is found in the hair and scales of a variety of animals. In other butterflies like pierids with color schemes characterized by independent sources of variation in UV and human-visible yellow/orange, behavioral experiments have generally implicated the UV component as most relevant to mate choice. This has not been addressed in Heliconius butterflies, where variation exists in analogous color components, but moreover where fluorescence due to 3-OHK could also contribute to yellow wing coloration. In addition, the potential cost due to predator visibility is largely unknown for the analogous well-studied pierid butterfly species. In field studies with butterfly paper models, we show that both UV and 3-OHK yellow act as signals for H. erato when compared with models lacking UV or resembling ancestral Eueides yellow, respectively, but attack rates by birds do not differ significantly between the models. Furthermore, measurement of the quantum yield and reflectance spectra of 3-OHK indicates that fluorescence does not contribute to the visual signal under broad-spectrum illumination. Our results suggest that the use of 3-OHK pigmentation instead of ancestral yellow was driven by sexual selection rather than predation.