Resibufogenin

CAS# 465-39-4

Resibufogenin

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Quality Control of Resibufogenin

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Chemical structure

Resibufogenin

3D structure

Chemical Properties of Resibufogenin

Cas No. 465-39-4 SDF Download SDF
PubChem ID 10063 Appearance White powder
Formula C24H32O4 M.Wt 384.51
Type of Compound Steroids Storage Desiccate at -20°C
Synonyms Bufogenin; Recibufogenin
Solubility DMSO : 100 mg/mL (260.07 mM; Need ultrasonic)
SMILES CC12CCC(CC1CCC3C2CCC4(C35C(O5)CC4C6=COC(=O)C=C6)C)O
Standard InChIKey ATLJNLYIJOCWJE-NEKURZDCSA-N
Standard InChI InChI=1S/C24H32O4/c1-22-9-7-16(25)11-15(22)4-5-18-17(22)8-10-23(2)19(12-20-24(18,23)28-20)14-3-6-21(26)27-13-14/h3,6,13,15-20,25H,4-5,7-12H2,1-2H3/t15-,16+,17?,18?,19-,20-,22+,23-,24-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Resibufogenin

The glandular body of Bufo bufo gargarizans Cantor

Biological Activity of Resibufogenin

DescriptionResibufogenin is a cytotoxic steroid isolated from the Chinese drug ChanSu, which exhibits the anti-proliferative effect against cancer cells through the degradation of cyclin D1 caused by the activation of GSK-3β. Resibufogenin can inhibit rectifier potassium current ( I K ) and transient potassium current ( I A ), it has pathological effects on central nervous system. Resibufogenin corrects hypertension in a rat model of human preeclampsia, it not only prevents the advent of hypertension and proteinuria, but also the development of intrauterine growth restriction.
TargetsCalcium Channel | Sodium Channel | ATPase | P450 (e.g. CYP17) | GSK-3β
In vivo

Isolation and identification of phase I metabolites of resibufogenin in rats.[Pubmed: 23153055]

Xenobiotica. 2013 May;43(5):479-85.

1. Resibufogenin (1), a major bufadienolide of Chinese medicine Chan Su, had a wide range of pharmacological activities. In present work, the metabolism of 1 in male Sprague-Dawley rats was investigated by identifying the metabolites of Resibufogenin excreted in rat bile.
METHODS AND RESULTS:
2. Following an oral dose of 60 mg/kg resibufagenin, nine metabolites were isolated from bile of rats, and their structures were identified as 3-keto- Resibufogenin (2), 3-epi-Resibufogenin (3), 5β-hydroxy-3-epi-Resibufogenin (4), 1α, 5β-dihydroxy-3-epi-Resibufogenin (5), 3α, 5β, 14α, 15β-tetrahydroxyl-bufa- 20, 22-dienolide (6), 3α, 14α, 15β-trihydroxy-bufa-20, 22-dienolide (7), 3-epi- 5β-hydroxy-bufalin (8), 12α, 16β-dihydroxy-3-epi-Resibufogenin (9), and 5β, 16β-dihydroxy-3-epi-Resibufogenin (10), respectively, on the basis of widely spectroscopic methods including 2D-NMR technology. It is first time to describe the metabolites of 1 in vivo, and metabolites 5-7 and 9-10 are novel.
CONCLUSIONS:
3. On the basis of these identified metabolites, a possible metabolism pathway for 1 in rats has been proposed. This is the first systematic study on the phase I metabolites of Resibufogenin.

Resibufogenin prevents the manifestations of preeclampsia in an animal model of the syndrome.[Pubmed: 19277924 ]

Hypertens Pregnancy. 2010 Jan;29(1):1-9.

We have developed a rat model of preeclampsia which is based upon excessive volume expansion and includes hypertension, proteinuria and intrauterine growth restriction. In this model, the urinary excretion of the circulating steroid inhibitor of Na +/ K+ ATPase, marinobufagenin, is increased prior to the development of hypertension and proteinuria. An analogue of marinobufagenin, Resibufogenin, successfully treats the hypertension and proteinuria.
METHODS AND RESULTS:
We administered Resibufogenin early in pregnancy in this model, prior to the development of the syndrome. We found that Resibufogenin not only prevented the advent of hypertension and proteinuria, but also the development of intrauterine growth restriction.
CONCLUSIONS:
These results may have relevance to the human condition.

Protocol of Resibufogenin

Kinase Assay

Effects of Resibufogenin and Cinobufagin on voltage-gated potassium channels in primary cultures of rat hippocampal neurons.[Pubmed: 21798339]

Characterization of phase I metabolism of resibufogenin and evaluation of the metabolic effects on its antitumor activity and toxicity.[Pubmed: 25504504]

Drug Metab Dispos. 2015 Mar;43(3):299-308.

Resibufogenin (RB), one of the major active compounds of the traditional Chinese medicine Chansu, has displayed great potential as a chemotherapeutic agent in oncology. However, it is a digoxin-like compound that also exhibits extremely cardiotoxic effects. The present study aimed to characterize the metabolic behaviors of RB in humans as well as to evaluate the metabolic effects on its bioactivity and toxicity. The phase I metabolic profile in human liver microsomes was characterized systemically, and the major metabolite was identified as marinobufagenin (5β-hydroxylResibufogenin, 5-HRB) by liquid chromatography-mass spectrometry and nuclear magnetic imaging techniques.
METHODS AND RESULTS:
Both cytochrome P450 (P450) reaction phenotyping and inhibition assays using P450-selective chemical inhibitors demonstrated that CYP3A4 was mainly involved in RB 5β-hydroxylation with much higher selectivity than CYP3A5. Kinetic characterization demonstrated that RB 5β-hydroxylation in both human liver microsomes and human recombinant CYP3A4 obeyed biphasic kinetics and displayed similar apparent kinetic parameters. Furthermore, 5-HRB could significantly induce cell growth inhibition and apoptosis in A549 and H1299 by facilitating apoptosome assembly and caspase activation. Meanwhile, 5-HRB displayed very weak cytotoxicity of human embryonic lung fibroblasts, and in mice there was a greater tolerance to acute toxicity.
CONCLUSIONS:
In summary, CYP3A4 dominantly mediated 5β-hydroxylation and was found to be a major metabolic pathway of RB in the human liver, whereas its major metabolite (5-HRB) displayed better druglikeness than its parent compound RB. Our findings lay a solid foundation for RB metabolism studies in humans and encourage further research on the bioactive metabolite of RB.

Toxicol In Vitro. 2011 Dec;25(8):1644-53.

Outward delayed rectifier potassium channel and outward transient potassium channel have multiple important roles in maintaining the excitability of hippocampal neurons. The present study investigated the effects of two bufadienolides, Resibufogenin (RBG) and Cinobufagin (CBG), on the outward delayed rectifier potassium current (IK) and outward transient potassium current (IA) in rat hippocampal neurons.
METHODS AND RESULTS:
RBG and CBG have similar structures and both were isolated from the venom gland of toad skin. RBG inhibited both IK and IA, whereas CBG inhibited IK without noticeable effect on IA. Moreover, at 1 μM concentration both RBG and CBG could alter some channel kinetics and gating properties of IK, such as steady-state activation and inactivation curves, open probability and time constants.
CONCLUSIONS:
These findings suggested that IK is probably a target of bufadienolides, which may explain the mechanisms of bufadienolides' pathological effects on central nervous system.

Animal Research

Resibufogenin corrects hypertension in a rat model of human preeclampsia.[Pubmed: 16446498]

Exp Biol Med (Maywood). 2006 Feb;231(2):215-20.

The study of the pathogenesis of preeclampsia has been hampered by a relative dearth of animal models.
METHODS AND RESULTS:
We developed a rat model of preeclampsia in which the excretion of a circulating inhibitor of Na/K ATPase, marinobufagenin (MBG), is elevated. These animals develop hypertension, proteinuria, and intrauterine growth restriction. The administration of a congener of MBG, Resibufogenin (RBG), reduces blood pressure to normal in these animals, as is the case when given to pregnant animals rendered hypertensive by the administration of MBG. Studies of Na/K ATPase inhibition by MBG and RBG reveal that these agents are equally effective as inhibitors of the enzyme.

Resibufogenin Dilution Calculator

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Preparing Stock Solutions of Resibufogenin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6007 mL 13.0036 mL 26.0071 mL 52.0143 mL 65.0178 mL
5 mM 0.5201 mL 2.6007 mL 5.2014 mL 10.4029 mL 13.0036 mL
10 mM 0.2601 mL 1.3004 mL 2.6007 mL 5.2014 mL 6.5018 mL
50 mM 0.052 mL 0.2601 mL 0.5201 mL 1.0403 mL 1.3004 mL
100 mM 0.026 mL 0.13 mL 0.2601 mL 0.5201 mL 0.6502 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Resibufogenin

Resibufogenin, a component of huachansu, has been shown to exhibit the anti-proliferative effect against cancer cells, and this may be attributed to the degradation of cyclin D1 caused by the activation of GSK-3β. IC50 Value: Target: In vitro: The effects of Resibufogenin on the outward delayed rectifier potassium current (IK) and outward transient potassium current (IA) in rat hippocampal neurons was investigated, and it inhibited both IK and IA, at 1 μM concentration RBG could alter some channel kinetics and gating properties of IK, such as steady-state activation and inactivation curves, open probability and time constants [1]. In vivo: Resibufogenin prevented evidence of oxidative stress in preeclamptic rats [2].

References:
[1]. Hao S, et al. Effects of Resibufogenin and Cinobufagin on voltage-gated potassium channels in primary cultures of rat hippocampal neurons. Toxicol In Vitro. 2011 Dec 25(8):1644-53. [2]. Uddin MN, et al. Resibufogenin administration prevents oxidative stress in a rat model of human preeclampsia. Hypertens Pregnancy. 2012 31(1):70-8. [3]. Ichikawa M, et al. Resibufogenin Induces G1-Phase Arrest through the Proteasomal Degradation of Cyclin D1 in Human Malignant Tumor Cells. PLoS One. 2015 Jun 29 10(6):e0129851. [4]. Hao S, et al. Effects of resibufogenin on voltage-gated sodium channels in cultured rat hippocampal neurons. Neurosci Lett. 2011 Aug 26 501(2):112-6. [5]. Zheng J, et al. Novel microbial transformation of resibufogenin by Absidia coerules. Nat Prod Commun. 2011 Nov 6(11):1581-4. [6]. Xin XL, et al. Novel microbial transformation of resibufogenin by Fusarium solani. J Asian Nat Prod Res. 2011 Sep 13(9):831-7.

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References on Resibufogenin

Isolation and identification of phase I metabolites of resibufogenin in rats.[Pubmed:23153055]

Xenobiotica. 2013 May;43(5):479-85.

1. Resibufogenin (1), a major bufadienolide of Chinese medicine Chan Su, had a wide range of pharmacological activities. In present work, the metabolism of 1 in male Sprague-Dawley rats was investigated by identifying the metabolites of Resibufogenin excreted in rat bile. 2. Following an oral dose of 60 mg/kg resibufagenin, nine metabolites were isolated from bile of rats, and their structures were identified as 3-keto- Resibufogenin (2), 3-epi-Resibufogenin (3), 5beta-hydroxy-3-epi-Resibufogenin (4), 1alpha, 5beta-dihydroxy-3-epi-Resibufogenin (5), 3alpha, 5beta, 14alpha, 15beta-tetrahydroxyl-bufa- 20, 22-dienolide (6), 3alpha, 14alpha, 15beta-trihydroxy-bufa-20, 22-dienolide (7), 3-epi- 5beta-hydroxy-bufalin (8), 12alpha, 16beta-dihydroxy-3-epi-Resibufogenin (9), and 5beta, 16beta-dihydroxy-3-epi-Resibufogenin (10), respectively, on the basis of widely spectroscopic methods including 2D-NMR technology. It is first time to describe the metabolites of 1 in vivo, and metabolites 5-7 and 9-10 are novel. 3. On the basis of these identified metabolites, a possible metabolism pathway for 1 in rats has been proposed. This is the first systematic study on the phase I metabolites of Resibufogenin.

Effects of Resibufogenin and Cinobufagin on voltage-gated potassium channels in primary cultures of rat hippocampal neurons.[Pubmed:21798339]

Toxicol In Vitro. 2011 Dec;25(8):1644-53.

Outward delayed rectifier potassium channel and outward transient potassium channel have multiple important roles in maintaining the excitability of hippocampal neurons. The present study investigated the effects of two bufadienolides, Resibufogenin (RBG) and Cinobufagin (CBG), on the outward delayed rectifier potassium current (IK) and outward transient potassium current (IA) in rat hippocampal neurons. RBG and CBG have similar structures and both were isolated from the venom gland of toad skin. RBG inhibited both IK and IA, whereas CBG inhibited IK without noticeable effect on IA. Moreover, at 1 muM concentration both RBG and CBG could alter some channel kinetics and gating properties of IK, such as steady-state activation and inactivation curves, open probability and time constants. These findings suggested that IK is probably a target of bufadienolides, which may explain the mechanisms of bufadienolides' pathological effects on central nervous system.

Characterization of phase I metabolism of resibufogenin and evaluation of the metabolic effects on its antitumor activity and toxicity.[Pubmed:25504504]

Drug Metab Dispos. 2015 Mar;43(3):299-308.

Resibufogenin (RB), one of the major active compounds of the traditional Chinese medicine Chansu, has displayed great potential as a chemotherapeutic agent in oncology. However, it is a digoxin-like compound that also exhibits extremely cardiotoxic effects. The present study aimed to characterize the metabolic behaviors of RB in humans as well as to evaluate the metabolic effects on its bioactivity and toxicity. The phase I metabolic profile in human liver microsomes was characterized systemically, and the major metabolite was identified as marinobufagenin (5beta-hydroxylResibufogenin, 5-HRB) by liquid chromatography-mass spectrometry and nuclear magnetic imaging techniques. Both cytochrome P450 (P450) reaction phenotyping and inhibition assays using P450-selective chemical inhibitors demonstrated that CYP3A4 was mainly involved in RB 5beta-hydroxylation with much higher selectivity than CYP3A5. Kinetic characterization demonstrated that RB 5beta-hydroxylation in both human liver microsomes and human recombinant CYP3A4 obeyed biphasic kinetics and displayed similar apparent kinetic parameters. Furthermore, 5-HRB could significantly induce cell growth inhibition and apoptosis in A549 and H1299 by facilitating apoptosome assembly and caspase activation. Meanwhile, 5-HRB displayed very weak cytotoxicity of human embryonic lung fibroblasts, and in mice there was a greater tolerance to acute toxicity. In summary, CYP3A4 dominantly mediated 5beta-hydroxylation and was found to be a major metabolic pathway of RB in the human liver, whereas its major metabolite (5-HRB) displayed better druglikeness than its parent compound RB. Our findings lay a solid foundation for RB metabolism studies in humans and encourage further research on the bioactive metabolite of RB.

Resibufogenin corrects hypertension in a rat model of human preeclampsia.[Pubmed:16446498]

Exp Biol Med (Maywood). 2006 Feb;231(2):215-20.

The study of the pathogenesis of preeclampsia has been hampered by a relative dearth of animal models. We developed a rat model of preeclampsia in which the excretion of a circulating inhibitor of Na/K ATPase, marinobufagenin (MBG), is elevated. These animals develop hypertension, proteinuria, and intrauterine growth restriction. The administration of a congener of MBG, Resibufogenin (RBG), reduces blood pressure to normal in these animals, as is the case when given to pregnant animals rendered hypertensive by the administration of MBG. Studies of Na/K ATPase inhibition by MBG and RBG reveal that these agents are equally effective as inhibitors of the enzyme.

Resibufogenin prevents the manifestations of preeclampsia in an animal model of the syndrome.[Pubmed:19277924]

Hypertens Pregnancy. 2010 Jan;29(1):1-9.

BACKGROUND AND OBJECTIVES: We have developed a rat model of preeclampsia which is based upon excessive volume expansion and includes hypertension, proteinuria and intrauterine growth restriction. In this model, the urinary excretion of the circulating steroid inhibitor of Na +/ K+ ATPase, marinobufagenin, is increased prior to the development of hypertension and proteinuria. An analogue of marinobufagenin, Resibufogenin, successfully treats the hypertension and proteinuria. METHODS: We administered Resibufogenin early in pregnancy in this model, prior to the development of the syndrome. RESULTS: We found that Resibufogenin not only prevented the advent of hypertension and proteinuria, but also the development of intrauterine growth restriction. DISCUSSION: These results may have relevance to the human condition.

Description

Resibufogenin, a component of huachansu, has been shown to exhibit the anti-proliferative effect against cancer cells, and this may be attributed to the degradation of cyclin D1 caused by the activation of GSK-3β.

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