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marinobufagenin

CAS No.:
470-42-8
Catalog Number:
AG00DHNE
Molecular Formula:
C24H32O5
Molecular Weight:
400.5079
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$176
- +
5mg
≥98%
1 week
United States
$589
- +
Product Description
Catalog Number:
AG00DHNE
Chemical Name:
marinobufagenin
CAS Number:
470-42-8
Molecular Formula:
C24H32O5
Molecular Weight:
400.5079
MDL Number:
MFCD01740864
IUPAC Name:
5-[(1R,2S,4R,6R,7R,10S,11R,14S,16S)-14,16-dihydroxy-7,11-dimethyl-3-oxapentacyclo[8.8.0.02,4.02,7.011,16]octadecan-6-yl]pyran-2-one
InChI:
InChI=1S/C24H32O5/c1-21-8-5-15(25)12-23(21,27)10-7-17-16(21)6-9-22(2)18(11-19-24(17,22)29-19)14-3-4-20(26)28-13-14/h3-4,13,15-19,25,27H,5-12H2,1-2H3/t15-,16-,17+,18+,19+,21+,22+,23-,24+/m0/s1
InChI Key:
JMNQTHQLNRILMH-OBBGIPBRSA-N
SMILES:
O[C@H]1CC[C@]2([C@](C1)(O)CC[C@@H]1[C@@H]2CC[C@]2([C@]31O[C@@H]3C[C@@H]2c1ccc(=O)oc1)C)C
UNII:
3KBT25GV2B
NSC Number:
234205
Properties
Complexity:
833  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
400.225g/mol
Formal Charge:
0
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
400.515g/mol
Monoisotopic Mass:
400.225g/mol
Rotatable Bond Count:
1  
Topological Polar Surface Area:
79.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.5  
Literature
Title Journal
Na/K-ATPase signaling regulates collagen synthesis through microRNA-29b-3p in cardiac fibroblasts. Physiological genomics 20160301
Marinobufagenin predicts and resibufogenin prevents preeclampsia: a review of the evidence. American journal of perinatology 20121101
Age-associated increase in salt sensitivity is accompanied by a shift in the atrial natriuretic peptide modulation of the effect of marinobufagenin on renal and vascular sodium pump. Journal of hypertension 20120901
Pathogenesis of pre-eclampsia: marinobufagenin and angiogenic imbalance as biomarkers of the syndrome. Translational research : the journal of laboratory and clinical medicine 20120801
Monoclonal antibody against marinobufagenin reverses cardiac fibrosis in rats with chronic renal failure. American journal of hypertension 20120601
Reduction of Na/K-ATPase potentiates marinobufagenin-induced cardiac dysfunction and myocyte apoptosis. The Journal of biological chemistry 20120511
DOCA-salt hypertension does not require the ouabain-sensitive binding site of the α2 Na,K-ATPase. American journal of hypertension 20120401
Marinobufagenin and cyclic strain may activate endothelial NADPH oxidase, contributing to the adverse impact of salty diets on vascular and cerebral health. Medical hypotheses 20120201
Resibufogenin administration prevents oxidative stress in a rat model of human preeclampsia. Hypertension in pregnancy 20120101
Systemic hypertension: the roles of salt, vascular Na+/K+ ATPase and the endogenous glycosides, ouabain and marinobufagenin. Cardiology in review 20120101
Endogenous cardiotonic steroids in chronic renal failure. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20110901
Marinobufagenin levels in preeclamptic patients: a preliminary report. American journal of perinatology 20110801
Both high and low maternal salt intake in pregnancy alter kidney development in the offspring. American journal of physiology. Renal physiology 20110801
Inhibitory effect of combinations of digoxin and endogenous cardiotonic steroids on Na+/K+-ATPase activity in human kidney membrane preparation. Life sciences 20110103
Marinobufagenin is an upstream modulator of Gadd45a stress signaling in preeclampsia. Biochimica et biophysica acta 20110101
A chemifluorescent immunoassay for the determination of marinobufagenin in body fluids. Journal of immunoassay & immunochemistry 20110101
The sodium pump and cardiotonic steroids-induced signal transduction protein kinases and calcium-signaling microdomain in regulation of transporter trafficking. Biochimica et biophysica acta 20101201
Marinobufagenin, resibufogenin and preeclampsia. Biochimica et biophysica acta 20101201
Renal ischemia regulates marinobufagenin release in humans. Hypertension (Dallas, Tex. : 1979) 20101101
Emerging role of the bufadienolides in cardiovascular and kidney diseases. American journal of kidney diseases : the official journal of the National Kidney Foundation 20100801
Low-dose cardiotonic steroids increase sodium-potassium ATPase activity that protects hippocampal slice cultures from experimental ischemia. Neuroscience letters 20100405
The treatment of preeclampsia in a rat model employing Digibind. American journal of perinatology 20100401
Interaction of Digibind with endogenous cardiotonic steroids from preeclamptic placentae. Journal of hypertension 20100201
Contribution of angiogenic factors in a rat model of pre-eclampsia. American journal of nephrology 20100101
Spironolactone attenuates experimental uremic cardiomyopathy by antagonizing marinobufagenin. Hypertension (Dallas, Tex. : 1979) 20091201
Vascular leak in a rat model of preeclampsia. American journal of nephrology 20090701
Marinobufagenin enhances cardiac contractility in mice with ouabain-sensitive alpha1 Na+-K+-ATPase. American journal of physiology. Heart and circulatory physiology 20090601
Marinobufagenin causes endothelial cell monolayer hyperpermeability by altering apoptotic signaling. American journal of physiology. Regulatory, integrative and comparative physiology 20090601
Endogenous cardiotonic steroids and differential patterns of sodium pump inhibition in NaCl-loaded salt-sensitive and normotensive rats. American journal of hypertension 20090501
Marinobufagenin induces increases in procollagen expression in a process involving protein kinase C and Fli-1: implications for uremic cardiomyopathy. American journal of physiology. Renal physiology 20090501
Acute sodium loading in Dahl-s rats: alterations in renal and vascular sodium pump inhibition amidst unaltered cardiotonic steroid levels? American journal of hypertension 20090501
The cardiotonic steroid hormone marinobufagenin induces renal fibrosis: implication of epithelial-to-mesenchymal transition. American journal of physiology. Renal physiology 20090401
Monoclonal antibody to an endogenous bufadienolide, marinobufagenin, reverses preeclampsia-induced Na/K-ATPase inhibition and lowers blood pressure in NaCl-sensitive hypertension. Journal of hypertension 20081201
[Effect of nicotine on electrogenic contribution of the Na,K-ATPase isoforms and contractile characteristics of the rat skeletal muscle]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20081001
Role of endogenous cardiotonic steroids in sodium homeostasis. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20080901
Comparison of non-digitalis binding properties of digoxin-specific Fabs using direct binding methods. Journal of immunological methods 20080731
Effects of cardiotonic steroids on dermal collagen synthesis and wound healing. Journal of applied physiology (Bethesda, Md. : 1985) 20080701
Examination of the cellular mechanisms by which marinobufagenin inhibits cytotrophoblast function. The Journal of biological chemistry 20080627
The death of ouabain-treated renal epithelial cells: evidence against anoikis occurrence. Apoptosis : an international journal on programmed cell death 20080501
Endogenous sodium pump inhibitors and age-associated increases in salt sensitivity of blood pressure in normotensives. American journal of physiology. Regulatory, integrative and comparative physiology 20080401
Marinobufagenin inhibits proliferation and migration of cytotrophoblast and CHO cells. Placenta 20080301
Partial nephrectomy as a model for uremic cardiomyopathy in the mouse. American journal of physiology. Renal physiology 20080201
Endogenous bufadienolide mediates pressor response to ethanol withdrawal in rats. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20080101
Effects of resibufogenin in experimental hypertension. American journal of nephrology 20080101
Vascular effects of the bufodienolides. Transactions of the American Clinical and Climatological Association 20080101
Endogenous and exogenous cardiac glycosides: their roles in hypertension, salt metabolism, and cell growth. American journal of physiology. Cell physiology 20070801
Marinobufagenin interferes with the function of the mineralocorticoid receptor. Biochemical and biophysical research communications 20070518
Novel digitalis-like factor, marinobufotoxin, isolated from cultured Y-1 cells, and its hypertensive effect in rats. Hypertension (Dallas, Tex. : 1979) 20070101
Marinobufagenin stimulates fibroblast collagen production and causes fibrosis in experimental uremic cardiomyopathy. Hypertension (Dallas, Tex. : 1979) 20070101
Endogenous Na/K-ATPase inhibitors in patients with preeclampsia. Cellular and molecular biology (Noisy-le-Grand, France) 20061230
Marinobufagenin in hypertensive patients with obstructive sleep apnea. Cellular and molecular biology (Noisy-le-Grand, France) 20061230
Atrial peptides modify the effect of marinobufagenin on sodium pumps: implications for blood pressure control. Hypertension (Dallas, Tex. : 1979) 20061201
ANP differentially modulates marinobufagenin-induced sodium pump inhibition in kidney and aorta. Hypertension (Dallas, Tex. : 1979) 20061201
[Effects of marinobufagenin on electrophysiological and contractile characteristics of the rat diaphragm]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20061201
The central role of the brain in salt-sensitive hypertension. Current opinion in cardiology 20060701
[Endogenous digitalis-like factor]. Nihon rinsho. Japanese journal of clinical medicine 20060701
Central role for the cardiotonic steroid marinobufagenin in the pathogenesis of experimental uremic cardiomyopathy. Hypertension (Dallas, Tex. : 1979) 20060301
Cardiac glycosides and cardiomyopathy. Hypertension (Dallas, Tex. : 1979) 20060301
Resibufogenin corrects hypertension in a rat model of human preeclampsia. Experimental biology and medicine (Maywood, N.J.) 20060201
[Analysis of the interaction between nicotinic acetylcholine receptor and Na+,K(+)-ATPase in the rat skeletal muscle and the Torpedo electric organ membrane preparation]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20060201
Marinobufagenin impairs first trimester cytotrophoblast differentiation. Placenta 20060101
[Role of the alpha2-isoform of Na+, K(+)-ATPase in the positive inotropic effect of ouabain and marinobufagenin in the rat diaphragm]. Biofizika 20060101
Regulation of adrenocortical cardiotonic steroid production by dopamine and PKA signaling. Frontiers in bioscience : a journal and virtual library 20050901
Endogenous cardiac glycosides: hormones using the sodium pump as signal transducer. Seminars in nephrology 20050901
Brain ouabain stimulates peripheral marinobufagenin via angiotensin II signalling in NaCl-loaded Dahl-S rats. Journal of hypertension 20050801
Antimicrobial activity of the bufadienolides marinobufagin and telocinobufagin isolated as major components from skin secretion of the toad Bufo rubescens. Toxicon : official journal of the International Society on Toxinology 20050501
Salt loading induces redistribution of the plasmalemmal Na/K-ATPase in proximal tubule cells. Kidney international 20050501
Antibody to marinobufagenin lowers blood pressure in pregnant rats on a high NaCl intake. Journal of hypertension 20050401
A novel endogenous digitalis, telocinobufagin, exhibits elevated plasma levels in patients with terminal renal failure. Clinical biochemistry 20050101
Marinobufagenin may mediate the impact of salty diets on left ventricular hypertrophy by disrupting the protective function of coronary microvascular endothelium. Medical hypotheses 20050101
Marinobufagenin may mediate the adverse impact of salty diets on renal calcium retention by impairing the efficiency of renal tubular sodium-calcium exchange. Medical hypotheses 20050101
Involvement of marinobufagenin in a rat model of human preeclampsia. American journal of nephrology 20050101
Marinobufagenin, an endogenous inhibitor of alpha-1 Na/K-ATPase, is a novel factor in pathogenesis of diabetes mellitus. Doklady biological sciences : proceedings of the Academy of Sciences of the USSR, Biological sciences sections 20050101
[Involvement of ouabain (digitalis-like factor) in the pathogenesis of hypertension and hypertensive target-organ damage]. Nihon rinsho. Japanese journal of clinical medicine 20040301
Different effects of marinobufagenin and endogenous ouabain. Journal of hypertension 20040201
Coordinated shifts in Na/K-ATPase isoforms and their endogenous ligands during cardiac hypertrophy and failure in NaCl-sensitive hypertension. Journal of hypertension 20040201
Marinobufagenin may mediate the impact of salty diets on left ventricular hypertrophy by disrupting the protective function of coronary microvascular endothelium. Medical hypotheses 20040101
Ouabain- and marinobufagenin-induced proliferation of human umbilical vein smooth muscle cells and a rat vascular smooth muscle cell line, A7r5. Circulation 20031216
Effect of green tea extract on cardiac hypertrophy following 5/6 nephrectomy in the rat. Kidney international 20030501
Myocardial PKC beta2 and the sensitivity of Na/K-ATPase to marinobufagenin are reduced by cicletanine in Dahl hypertension. Hypertension (Dallas, Tex. : 1979) 20030301
Effects of cardiac glycosides on sodium pump expression and function in LLC-PK1 and MDCK cells. Kidney international 20021201
Marinobufagenin (MBG) suppression of ethanol-seeking behavior is associated with inhibition of brain cortex Na/K-ATPase in mice. European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 20020601
Marinobufagenin, an endogenous ligand of alpha-1 sodium pump, is a marker of congestive heart failure severity. Journal of hypertension 20020601
Endogenous ligand of alpha(1) sodium pump, marinobufagenin, is a novel mediator of sodium chloride--dependent hypertension. Circulation 20020305
Phorbol diacetate potentiates na(+)-k(+) ATPase inhibition by a putative endogenous ligand, marinobufagenin. Hypertension (Dallas, Tex. : 1979) 20020201
Racial differences in resting end-tidal CO2 and circulating sodium pump inhibitor. American journal of hypertension 20010801
Interaction of NaCl and behavioral stress on endogenous sodium pump ligands in rats. American journal of physiology. Regulatory, integrative and comparative physiology 20010701
[Effect of marinobufagenin on the primary reinforcing effect of ethanol]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20010501
Abnormalities of sodium pump function in hypertension and the role of endogenous cardiotonic steroids. Cellular and molecular biology (Noisy-le-Grand, France) 20010301
Marinobufagenin, an endogenous alpha-1 sodium pump ligand, in hypertensive Dahl salt-sensitive rats. Hypertension (Dallas, Tex. : 1979) 20010201
Properties