marinobufagenin

• CAT Number: R000002
• CAS Number: 470-42-8
• Molecular Formula: C24H32O5
• Molecular Weight: 400.515
• Purity: ≥95%
• Synonyms: Marinobufagin;Marinobufogenin;marinobufagenin;3β,5β-Dihydroxy-14β,15β-epoxybufa-20,22-dienolide;3β,5-Dihydroxy-14,15β-epoxy-5β-bufa-20,22-dienolide;14,15β-Epoxy-3β,5-dihydroxy-5β-bufa-20,22-dienolide
• Solubility: Insoluble in water
• Storage: -20oC
• 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
• InChIKey: JMNQTHQLNRILMH-OBBGIPBRSA-N
• SMILES: CC12CCC(CC1(CCC3C2CCC4(C35C(O5)CC4C6=COC(=O)C=C6)C)O)O

Marinobufagenin (CAS 470-42-8) is a cardiotonic bufadienolide steroid secreted by the toad Bufo rubescens and other related species such as Bufo marinus. It is a vasoconstrictor with effects similar to digitalis.

Reference

1: Haller ST, Yan Y, Drummond CA, Xie J, Tian J, Kennedy DJ, Shilova VY, Xie Z, Liu J, Cooper CJ, Malhotra D, Shapiro JI, Fedorova OV, Bagrov AY. Rapamycin Attenuates Cardiac Fibrosis in Experimental Uremic Cardiomyopathy by Reducing Marinobufagenin Levels and Inhibiting Downstream Pro-Fibrotic Signaling. J Am Heart Assoc. 2016 Sep 30;5(10). pii: e004106. PubMed PMID: 27694325; PubMed Central PMCID: PMC5121507.
2: Lenaerts C, Bond L, Tuytten R, Delporte C, Van Antwerpen P, Blankert B. D3. Early prediction of preeclampsia risk assessment: analytical determination for marinobufagenin in pregnant women. J Matern Fetal Neonatal Med. 2016 Aug;29(sup2):18. PubMed PMID: 27680799.
3: Fedorova OV, Zernetkina VI, Shilova VY, Grigorova YN, Juhasz O, Wei W, Marshall CA, Lakatta EG, Bagrov AY. Synthesis of an Endogenous Steroidal Na Pump Inhibitor Marinobufagenin, Implicated in Human Cardiovascular Diseases, Is Initiated by CYP27A1 via Bile Acid Pathway. Circ Cardiovasc Genet. 2015 Oct;8(5):736-45. doi: 10.1161/CIRCGENETICS.115.001217. Epub 2015 Sep 15. PubMed PMID: 26374826; PubMed Central PMCID: PMC4618091.
4: Oliver J, Abbas K, Lightfoot JT, Baskin K, Collins B, Wier D, Bramhall JP, Huang J, Puschett JB. Comparison of Neurocognitive Testing and the Measurement of Marinobufagenin in Mild Traumatic Brain Injury: A Preliminary Report. J Exp Neurosci. 2015 Jul 27;9:67-72. doi: 10.4137/JEN.S27921. eCollection 2015. PubMed PMID: 26351409; PubMed Central PMCID: PMC4517832.
5: Grigorova YN, Juhasz O, Zernetkina V, Fishbein KW, Lakatta EG, Fedorova OV, Bagrov AY. Aortic Fibrosis, Induced by High Salt Intake in the Absence of Hypertensive Response, is Reduced by a Monoclonal Antibody to Marinobufagenin. Am J Hypertens. 2016 May;29(5):641-6. doi: 10.1093/ajh/hpv155. Epub 2015 Sep 7. PubMed PMID: 26350300; PubMed Central PMCID: PMC5014083.
6: Klimanova EA, Petrushanko IY, Mitkevich VA, Anashkina AA, Orlov SN, Makarov AA, Lopina OD. Binding of ouabain and marinobufagenin leads to different structural changes in Na,K-ATPase and depends on the enzyme conformation. FEBS Lett. 2015 Sep 14;589(19 Pt B):2668-74. doi: 10.1016/j.febslet.2015.08.011. Epub 2015 Aug 20. PubMed PMID: 26297827.