Allocholic acid
(Synonyms: 别胆酸) 目录号 : GC60044
Allocholic acid( 3α， 7α， 12α-三羟基-5α-胆酸(ACA))，Allocholic acid是异胆酸的共轭体及胆酸的同分异构体。Allocholic acid存在于脊椎动物，某些哺乳动物和人类中, 在肝脏再生和癌变过程中出现。
Cas No.:2464-18-8
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
| Animal experiment [1]: | |
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Animal models |
Male C57BL/six mice (8 weeks old) |
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Preparation Method |
α-naphthylisothiocyanate (ANIT) modeling achieved cholestasis in mice, and Allocholic acid was administered to mice at different doses for 14 days. |
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Dosage form |
25-100mg/kg; i.g; 14days |
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Applications |
Allocholic acid treatment alleviates liver damage in ANIT-induced cholestatic mice. |
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References: |
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Allocholic acid(3α, 7α, 12α-trihydroxy-5α-cholic acid(ACA)), Allocholic acid is a conjugated and isomer of isocholic acid. Allocholic acid is found in vertebrates, some mammals, and humans and occurs during liver regeneration and carcinogenesis. It has been suggested to function as a migratory pheromone in some migratory fish species, such as the sea lamprey [1-4]. Allocholic acid concentrations are typically low or undetectable in healthy adults but elevated in fetuses, infants, pregnant women, certain malignancies, and during liver regeneration [5-7]. Compared to its 5β differential isome-Major bile acids (BAs), allocholic acid induces a more pronounced cholestatic effect, leading to enhanced bile flow [8].
Allocholic acid(100mg/kg; i.g; 14days) treated normal mice at high doses without causing liver damage for 14 days. Allocholic acid(25-100mg/kg; i.g; 14days) pretreatments substantially alleviated the necrosis of hepatocytes and significantly reduced the elevated aspartate aminotransferase (AST), alkaline phosphatase (ALP), and direct bilirubin (DBIL) levels brought on by ANIT. Allocholic acid may protect mice from ANIT-induced cholestasis with liver injury[9].
References:
[1]. Elliott, W. H. (1971). Allo bile acids. In P. P. Nair & D. Kritchevsky (Eds.), The bile acids chemistry, physiology, and metabolism (pp. 47–93). Springer, Boston, MA.
[2]. Yamasaki K, Ayaki Y, et,al. Allocholic acid, a metabolite of 7 -hydroxycholesterol in the rat and rabbit. J Biochem. 1972 May;71(5):927-9. doi: 10.1093/oxfordjournals.jbchem.a129848. PMID: 5073332.
[3]. Li W, Sorensen PW, et,al. The olfactory system of migratory adult sea lamprey (Petromyzon marinus) is specifically and acutely sensitive to unique bile acids released by conspecific larvae. J Gen Physiol. 1995 May;105(5):569-87. doi: 10.1085/jgp.105.5.569. PMID: 7658193; PMCID: PMC2216950.
[4]. Briggs T, Bussjaeger C. Allocholic acid, the major component in bile from the river carpsucker, Carpiodes carpio (Rafinesque) (Catostomidae). Comp Biochem Physiol B. 1972 Jul 15;42(3):493-6. doi: 10.1016/0305-0491(72)90264-7. PMID: 4644219.
[5]. Mendoza ME, Monte MJ, et,al. Physiological characteristics of allo-cholic acid. J Lipid Res. 2003 Jan;44(1):84-92. doi: 10.1194/jlr.m200220-jlr200. PMID: 12518026.
[6]. Kimura A, Mahara R, et,al. Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. doi: 10.1203/00006450-199904010-00022. PMID: 10203155.
[7]. Mendoza, M. E., et,al. Changes in the pattern of bile acids in the nuclei of rat liver cells during hepatocarcinogenesis. Clinical Science, 102(2), 143–150. https://doi.org/10.1042/cs1020143
[8]. Mendoza ME, Monte MJ, et,al. Physiological characteristics of allo-cholic acid. J Lipid Res. 2003 Jan;44(1):84-92. doi: 10.1194/jlr.m200220-jlr200. PMID: 12518026.
[9]. Han X, Lin C, et,al. Allocholic acid protects against α-naphthylisothiocyanate-induced cholestasis in mice by ameliorating disordered bile acid homeostasis. J Appl Toxicol. 2024 Apr;44(4):582-594. doi: 10.1002/jat.4562. Epub 2023 Nov 15. PMID: 37968239.
Allocholic acid( 3α， 7α， 12α-三羟基-5α-胆酸(ACA))，Allocholic acid是异胆酸的共轭体及胆酸的同分异构体。Allocholic acid存在于脊椎动物，某些哺乳动物和人类中, 在肝脏再生和癌变过程中出现。它被认为是一些洄游鱼类的洄游信息素，如海七鳃鳗[1-4]。Allocholic acid浓度在健康成人中通常较低或检测不到，但在胎儿、婴儿、孕妇、某些恶性肿瘤和肝脏再生过程中升高[5-7]。与其5β差异异构体Major bile acids (BAs) 相比，Allocholic acid诱导更明显的胆汁淤积作用，导致胆汁流量增强[8]。
高剂量Allocholic acid(100mg/kg; i.g; 14days)处理正常小鼠14天不会造成肝损伤。Allocholic acid(25-100mg/kg; i.g; 14days)预处理可显著缓解肝细胞坏死，降低ANIT引起的天冬氨酸转氨酶(AST)、碱性磷酸酶(ALP)和直接胆红素(DBIL)水平升高。Allocholic acid可以保护小鼠免受抗氧化酶诱导的胆汁淤积肝损伤[9]。
| Cas No. | 2464-18-8 | SDF | |
| 别名 | 别胆酸 | ||
| Canonical SMILES | C[C@H](CCC(O)=O)[C@H]1CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C | ||
| 分子式 | C24H40O5 | 分子量 | 408.57 |
| 溶解度 | DMSO: 125 mg/mL (305.95 mM) | 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 | 2.4476 mL | 12.2378 mL | 24.4756 mL |
| 5 mM | 0.4895 mL | 2.4476 mL | 4.8951 mL |
| 10 mM | 0.2448 mL | 1.2238 mL | 2.4476 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。
Bacterial 7-dehydroxylation of cholic acid and Allocholic acid
J Lipid Res 1969 Jul;10(4):421-6.PMID:5797529doi
An obligate anaerobic organism capable of dehydroxylating cholic acid to deoxycholic acid and Allocholic acid to allodeoxycholic acid was isolated from feces of the rabbit. It was a member of the bacteroides group (Gram-variable, nonsporulating anaerobes). The growth of the organism was inhibited by neomycin, 10-20 micro g/ml. The existence of this organism affords a satisfactory explanation for the development of gallstones in the cholestanol-fed rabbit and for their absence in rabbits simultaneously treated with neomycin.
Bile acids. XLIX. Allocholic acid, the major bile acid of Uromastix hardwickii
J Lipid Res 1976 Jan;17(1):21-4.PMID:1255017doi
Tauroallocholate is the major bile salt of the lizard, Uromastix hardwickii. Alkaline hydrolysis of bile from 25 gallbladders provided 1.21 g of acidic material, about 90% of which was Allocholic acid. Analyses by gas-liquid chromatography, and mass spectrometry verified the presence of almost 10% of deoxycholic acid and smaller amounts of other 5alpha and 5beta-bile acids.
Pheromones of the male sea lamprey, Petromyzon marinus L.: structural studies on a new compound, 3-keto Allocholic acid, and 3-keto petromyzonol sulfate
Steroids 2003 Mar;68(3):297-304.PMID:12628693DOI:10.1016/s0039-128x(02)00178-2.
This study reports the results of chemical and chromatographic studies which establish the presence of 3-keto Allocholic acid (3kACA) in water extracts from spermiating male sea lamprey, Petromyzon marinus. This is the second compound to be isolated and identified from these extracts. The first was 3-keto petromyzonol sulfate (3kPZS), which was shown to act as strong pheromonal attractant for ovulated females. Some new characterization data on 3kPZS (utilizing an only recently available synthetic preparation of the compound) is also included. The possibility that a mixture of 3kACA and 3kPZS might be a more potent pheromonal attractant than either compound alone is discussed.
Bile acid profiles in bile, urine, and feces of a patient with cerebrotendinous xanthomatosis
Steroids 1986 Jul-Aug;48(1-2):109-19.PMID:3660436DOI:10.1016/0039-128x(86)90045-0.
Bile acid profiles of bile, urine, and feces obtained from a patient with cerebrotendinous xanthomatosis on the same day have been analyzed by gas-liquid chromatography-mass spectrometry after fractionation into groups by mode of conjugation by an ion-exchange chromatography. The predominant biliary bile acid was cholic acid conjugated with glycine and taurine. Lesser amounts of the amino acid conjugates of chenodeoxycholic acid, ursodeoxycholic acid, 7-ketodeoxycholic acid, Allocholic acid, and deoxycholic acid, and of unconjugated norcholic acid and allonorcholic acid were also present in the bile. The major fecal bile acid was 7-epicholic acid. Relatively large amounts of bile acids were excreted in the urine. Unconjugated 7-epicholic acid, norcholic acid, allonorcholic acid, and cholic acid predominated. The bile acid profiles of the patient were different from those of normal subjects and should be useful for the diagnosis.
Bile acid production is life-stage and sex-dependent and affected by primer pheromones in the sea lamprey
J Exp Biol 2021 Mar 23;224(9):jeb229476.PMID:33758020DOI:10.1242/jeb.229476.
Pheromonal bile salts are important for sea lampreys (Petromyzon marinus Linnaeus) to complete their life cycle. The synthesis and release of a releaser/primer pheromone 3-keto petromyzonol sulfate (3kPZS) by spermiating males have been well characterized. 3kPZS evokes sexual behaviors in ovulatory females, induces immediate 3kPZS release in spermiating males, and elicits neuroendocrine responses in prespawning adults. Another primer pheromone released by spermiating males, 3-keto Allocholic acid (3kACA), antagonizes the neuroendocrine effects of 3kPZS in prespermiating males. However, the effects of 3kACA and 3kPZS on pheromone production in prespawning adults is unclear. To understand the foundation of pheromone production, we examined sea lamprey bile salt levels at different life stages. To investigate the priming effects of 3kACA and 3kPZS, we exposed prespawning adults with vehicle or synthetic 3kACA or 3kPZS. We hypothesized that endogenous bile salt levels were life-stage and sex-dependent, and differentially affected by 3kACA and 3kPZS in prespawning adults. Using ultra-performance liquid chromatography tandem mass spectrometry, we found that sea lampreys contained distinct mixtures of bile salts in the liver and plasma at different life stages. Males usually contained higher amounts of bile salts than females. Petromyzonamine disulfate was the most abundant C27 bile salt and petromyzonol sulfate was the most abundant C24 bile salt. Waterborne 3kACA and 3kPZS exerted differential effects on bile salt production in the liver and gill, their circulation and clearance in the plasma, and their release into water. We conclude that bile salt levels are life-stage and sex-dependent and differentially affected by primer pheromones.