5α-Cyprinol sulfate
5α-Cyprinol sulfate is an orally active bile salt and heterospecific pheromone. 5α-Cyprinol sulfate promotes lipid digestion in fish. 5α-Cyprinol sulfate inhibits taurocholic acid uptake mediated by apical bile salt transporters in rat ileum. 5α-Cyprinol sulfate can be used in studies of fish toxic acute renal failure.
For research use only. We do not sell to patients.
- CAS No.: 53939-19-8
- Formula: C27H48O8S
- Molecular Weight:532.73
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biological Activity
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Chemical Information
- Purity & Documentation
- References
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Help & FAQs
Biological Activity
5α-Cyprinol sulfate (100 μM; 15 min at 37°C) completely inhibits sodium-dependent taurocholate uptake in COS-7 cells transiently transfected with the ileal apical bile salt transporter (asbt) after 15 minutes of incubation at 37°C[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
5α-Cyprinol sulfate (1-4 μmol/min/kg; i.v. into perfused liver; 20-minute infusion) administered to isolated perfused rat livers shows a maximum biliary secretion rate (Tmax) of 0.5 μmol/kg/min, reduces bile flow at the higher dose, and competitively inhibits taurocholate hepatic uptake and secretion[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:unspecified strain (isolated perfused liver model)[2]
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Dosage:1 μmol/min/kg; 4 μmol/min/kg
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Administration:i.v. into perfused liver; 20-minute infusion
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Result:Achieved hepatic uptake exceeding 90% during infusion and recovery of 65.3 (n=6) at 1 μmol/min/kg.
Reached biliary secretion peak of unchanged reagent and minor disulfate metabolite at 30 minutes, with maximal secretion rate of 0.5 μmol/kg/min at 1 μmol/min/kg.
Showed no significant increase in bile flow at 1 μmol/min/kg.
Resulted in extremely low recovery of 17.0% at 4 μmol/min/kg.
Reduced bile flow immediately upon infusion, with gradual recovery over the experiment at 4 μmol/min/kg.
Caused dose-dependent reduction in taurocholate uptake and biliary recovery in competition experiments; effect reversed immediately when infusion stopped.
Chemical Information
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CAS No. 53939-19-8
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Molecular Weight 532.73
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Formula C27H48O8S
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SMILES
O[C@H]1[C@@]2([H])[C@@]3([H])[C@@]([C@@](CC3)([H])[C@H](C)CCCC(CO)COS(=O)(O)=O)([C@H](C[C@]2([H])[C@@]4([C@](C[C@@H](CC4)O)([H])C1)C)O)C
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Structure Classification
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Initial Source
carp
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Hahn MA, et al. 5α-cyprinol sulfate, a bile salt from fish, induces diel vertical migration in Daphnia. Elife. 2019;8:e44791. Published 2019 May 2. [Content Brief]
[2]. Goto T, et al. Physicochemical and physiological properties of 5alpha-cyprinol sulfate, the toxic bile salt of cyprinid fish. J Lipid Res. 2003;44(9):1643-1651. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
5α-Cyprinol sulfate Related Classifications
HY-N18490 Related Classifications
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