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Marinobufagin

$608

  • Brand : BIOFRON

  • Catalogue Number : BD-R0073

  • Specification : 98%

  • CAS number : 470-42-8

  • Formula : C24H32O5

  • Molecular Weight : 400.52

  • PUBCHEM ID : 11969465

  • Volume : 5mg

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Catalogue Number

BD-R0073

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

400.52

Appearance

Powder

Botanical Source

Bufonis Venenum

Structure Type

Steroids

Category

Standards;Natural Pytochemical;API

SMILES

CC12CCC(CC1(CCC3C2CCC4(C35C(O5)CC4C6=COC(=O)C=C6)C)O)O

Synonyms

(3β,5β,15β)-3,5-Dihydroxy-14,15-epoxybufa-20,22-dienolide/5β-Bufa-20,22-dienolide, 14,15β-epoxy-3β,5-dihydroxy-/5beta-Bufa-20,22-dienolide,14,15beta-epoxy-3beta,5-dihydroxy/Bufa-20,22-dienolide,14,15-epoxy-3,5-dihydroxy-,(3beta,5beta,15beta)/Marinobufagenin/Marinobufogenin/Marinobufagin/Bufa-20,22-dienolide, 14,15-epoxy-3,5-dihydroxy-, (3β,5β,15β)-/MARCINOBUFAGIN/5-hydroxyl-resibufogenin

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

Density

1.3±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

203.0±23.6 °C

Boiling Point

589.0±50.0 °C at 760 mmHg

Melting Point

InChl

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

InChl Key

JMNQTHQLNRILMH-OBBGIPBRSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:470-42-8) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29287997

Abstract

Skin toad secretion present physiologically active molecules to protect them against microorganisms, predators and infections. This work detailed the antiproliferative action of marinobufagin on tumor and normal lines, investigate its mechanism on HL-60 leukemia cells and its toxic effects on Allium cepa meristematic cells. Initially, cytotoxic action was assessed by colorimetric assays. Next, HL-60 cells were analyzed by morphological and flow cytometry techniques and growing A. cepa roots were examined after 72 h exposure. Marinobufagin presented high antiproliferative action against all human tumor lines [IC50 values ranging from 0.15 (leukemia) to 7.35 (larynx) μM] and it failed against human erythrocytes and murine lines. Human normal peripheral blood mononuclear cells (PBMC) were up to 72.5-fold less sensitive [IC50: 10.88 μM] to marinobufagin than HL-60 line, but DNA strand breaks were no detected. Leukemia treaded cells exhibited cell viability reduction, DNA fragmentation, phosphatidylserine externalization, binucleation, nuclear condensation and cytoplasmic vacuoles. Marinobufagin also reduced the growth of A. cepa roots (EC50: 7.5 μM) and mitotic index, caused cell cycle arrest and chromosomal alterations (micronuclei, delays and C-metaphases) in meristematic cells. So, to find out partially targeted natural molecules on human leukemia cells, like marinobufagin, is an amazing and stimulating way to continue the battle against cancer.

KEYWORDS

Allium cepa; Anticancer action; Apoptosis; Chromosomal alterations; Murine lines.

Title

Marinobufagin, a Molecule From Poisonous Frogs, Causes Biochemical, Morphological and Cell Cycle Changes in Human Neoplasms and Vegetal Cells

Author

Katia da Conceicão Machado 1 , Livia Queiroz de Sousa 1 , Daisy Jereissati Barbosa Lima 2 , Bruno Marques Soares 2 , Bruno Coêlho Cavalcanti 2 , Sarah Sant'Anna Maranhão 2 , Janaina da Costa de Noronha 3 , Domingos de Jesus Rodrigues 3 , Gardenia Carmen Gadelha Militão 4 , Mariana Helena Chaves 5 , Gerardo Magela Vieira-Júnior 5 , Claudia Pessoa 2 , Manoel Odorico de Moraes 2 , João Marcelo de Castro E Sousa 6 , Ana Amelia de Carvalho Melo-Cavalcante 1 , Paulo Michel Pinheiro Ferreira 7

Publish date

2018 Mar 15

PMID

30223494

Abstract

Bufadienolides are cardiotonic steroids (CTS) identified in mammals. Besides Na⁺/K⁺-ATPase inhibition, they activate signal transduction via protein⁻protein interactions. Diversity of endogenous bufadienolides and mechanisms of action may indicate the presence of functional selectivity and unique cellular outcomes. We evaluated whether the bufadienolides telocinobufagin and marinobufagin induce changes in proliferation or viability of pig kidney (LLC-PK1) cells and the mechanisms involved in these changes. In some experiments, ouabain was used as a positive control. CTS exhibited an inhibitory IC50 of 0.20 (telocinobufagin), 0.14 (ouabain), and 3.40 μM (marinobufagin) for pig kidney Na⁺/K⁺-ATPase activity and concentrations that barely inhibited it were tested in LLC-PK1 cells. CTS induced rapid ERK1/2 phosphorylation, but corresponding proliferative response was observed for marinobufagin and ouabain instead of telocinobufagin. Telocinobufagin increased Bax:Bcl-2 expression ratio, sub-G0 cell cycle phase and pyknotic nuclei, indicating apoptosis. Src and MEK1/2 inhibitors blunted marinobufagin but not telocinobufagin effect, which was also not mediated by p38, JNK1/2, and PI3K. However, BIO, a GSK-3β inhibitor, reduced proliferation and, as telocinobufagin, phosphorylated GSK-3β at inhibitory Ser9. Combination of both drugs resulted in synergistic antiproliferative effect. Wnt reporter activity assay showed that telocinobufagin impaired Wnt/β-catenin pathway by acting upstream to β-catenin stabilization. Our findings support that mammalian endogenous bufadienolides may exhibit functional selectivity.

KEYWORDS

ERK1/2; GSK-3β; Na+/K+-ATPase; Wnt/β-catenin pathway; bufadienolides; cardiotonic steroids; functional selectivity.

Title

Telocinobufagin and Marinobufagin Produce Different Effects in LLC-PK1 Cells: A Case of Functional Selectivity of Bufadienolides

Author

Luciana S Amaral 1 , Jainne Martins Ferreira 2 , Danilo Predes 3 , Jose Garcia Abreu 4 , Francois Noël 5 , Luis Eduardo M Quintas 6

Publish date

2018 Sep 14

PMID

29853035

Abstract

Marinobufagenin (MBG) is a bufadienolide cardiac inotrope implicated in volume expansion-mediated hypertensive states including essential hypertension and preeclampsia (PE). Endogenous MBG is an inhibitor of the α1-isoform of Na+,K+-ATPase with vasoconstrictive and cardiotonic properties, causing hypertension and natriuresis. Elevated endogenous MBG-like material levels have been described by immunoassays in salt-sensitive pregnant and preeclamptic rats as well as in preeclamptic human patients. The rise of endogenous MBG-like material appears prior the development of the main symptoms of PE, leading us to consider MBG as one of the potential biomarkers for PE. The weak specificity and the high variability of the published immunoassays gives no certification about endogenous MBG existence. This led us to set-up a highly specific and sensitive analytical method to detect MBG in plasma at low levels relying on liquid chromatography combined to mass spectrometry (UHPLC-MS/MS) with recording of 7 highly specific MRM transitions for MBG. Pure MBG standard used in the method development was obtained by purification from the Bufo marinus toad venom. d3-25-hydroxyvitamin D3 was used as internal standard. An increasing organic gradient with mobile phase A and B composed of 97:3 (v/v) H2O: MeOH and 50:45:5 (v/v/v) MeOH:IPA:H2O at pH 4.5 respectively was used on a Pursuit 3 PFP column (100 mm × 3 mm; 3 µm) to allow elution and separation of the plasmatic compounds. Chromatographic analyses of plasma samples were preceded by a precipitation of proteins pretreatment. The developed UHPLC-MS/MS assay has been applied to early-pregnant women plasma samples allowing us to investigate MBG plasma levels. Thanks to the high specificity of the assay we were able to authenticate and certify the presence of endogenous MBG in early-pregnant women plasma with the use of the 7 selected specific mass transitions. These pioneering preliminary results are giving a promising perspective for early preeclampsia risk assessment in pregnant women.

KEYWORDS

Biomarker; Marinobufagenin; Pregnancy; Toad venom; UHPLC-MS/MS.

Title

Revealing of Endogenous Marinobufagin by an Ultra-Specific and Sensitive UHPLC-MS/MS Assay in Pregnant Women

Author

Charline Lenaerts 1 , Liz Bond 2 , Robin Tuytten 2 , Bertrand Blankert 3

Publish date

2018 Sep 1


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