5α-Cyprinol sulfate

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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.

5α-Cyprinol sulfate Chemical Structure

CAS No. : 53939-19-8

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Description

In Vitro

5α-Cyprinol sulfate (100-10700 pM; day 3 or 4 of incubation) induces diel vertical migration (increased daytime residence depth) in Daphnia magna at concentrations ≥100 pM, with a threshold activity concentration of 100 pM^[1].
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.

In Vivo

5α-Cyprinol sulfate (1 μmol/min/kg; i.v.; single infusion) administered intravenously to anesthetized rats induces hemolysis, hemobilia, and death^[2].
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 (T_max) 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.

Animal Model:	unspecified strain (isolated perfused liver model)^[2]
Dosage:	1 μmol/min/kg; 4 μmol/min/kg
Administration:	i.v. into perfused liver; 20-minute infusion
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.

Molecular Weight

532.73

Formula

C₂₇H₄₈O₈S

CAS No.

53939-19-8

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

Structure Classification

Steroids

Initial Source

Animals

carp

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

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]