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Crotonoside

$105

  • Brand : BIOFRON

  • Catalogue Number : AV-P10308

  • Specification : 98%

  • CAS number : 1818-71-9

  • Formula : C10H13N5O5

  • Molecular Weight : 283.24

  • PUBCHEM ID : 65085

  • Volume : 25mg

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Catalogue Number

AV-P10308

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

283.24

Appearance

White crystal

Botanical Source

Occurs in the seeds of Croton tiglium. Also the nudibranch Diaulula sandiegensis/Croton tiglium L.

Structure Type

Nucleosides/Nucleotide

Category

Standards;Natural Pytochemical;API

SMILES

C1=NC2=C(NC(=O)N=C2N1C3C(C(C(O3)CO)O)O)N

Synonyms

3-Hydroadenosine, 2-oxo-/iso-Gr/Isoguanosine/2(1H)-Oxoadenosine/adenosine, 2-oxo-/2-Oxo-1,2-dihydro-adenosin/ISOGUANOSINE RIBOSIDE/2-Oxoadenosine/2-Oxo-3-hydroadenosine/2-Hydroxyadenosine/CROTONOSID/isoguanineriboside/CROTONOSIDE/ISOGUANOSINE(P)

IUPAC Name

6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-2-one

Density

2.3±0.1 g/cm3

Solubility

Methanol; Water

Flash Point

456.4ºC

Boiling Point

831ºC at 760 mmHg

Melting Point

InChl

InChI=1S/C10H13N5O5/c11-7-4-8(14-10(19)13-7)15(2-12-4)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1

InChl Key

MIKUYHXYGGJMLM-UUOKFMHZSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:1818-71-9) 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

28100102

Abstract

1. Crotonoside is a bioactive ingredient from Croton Herba with a strong antitumour activity. This study aimed to develop a highly sensitive and selective high-performance liquid chromatography (HPLC) method to quantify crotonoside in biological samples for pharmacokinetics and distribution studies. 2. Protein precipitation by perchloric acid was used to separate crotonoside from the biological samples, and the recovery rates for crotonoside and the internal standard (luteoloside) were >80%. All calibration curves examining the crotonoside levels in plasma and tissues were linear (all correlation coefficients > 0.99). 3. The response to crotonoside appeared to be dose disproportional to the maximum plasma concentration and the area under the time-concentration curve in plasma over the range of 12.5-50.0 mg/kg, and crotonoside was highly distributed in tissues after intravenous administration. The highest crotonoside level was detected in the liver (28.79 ± 14.96 μg/g), whereas crotonoside was undetected in the brain.

KEYWORDS

Crotonoside; HPLC; pharmacokinetics; tissue distribution.

Title

Pharmacokinetics and Tissue Distribution of Crotonoside

Author

Peiao Yan 1 2 3 , Lan Zhang 1 2 3 , Cheng Peng 1 2 3 , Ruoqi Zhang 1 2 3

Publish date

2018 Jan

PMID

29262547

Abstract

Targeted therapies for the treatment of acute myeloid leukemia (AML), specifically the FLT3 inhibitors, have shown promising results. Nevertheless, it is very unlikely that inhibitors which target a single pathway will provide long-term disease control. Here, we report the characterization of crotonoside, a natural product extracted from Chinese medicinal herb, Croton, for the treatment of AML via inhibition of FLT3 and HDAC3/6. In vitro, crotonoside exhibited selective inhibition in AML cells. In vivo, crotonoside treatment at 70 and 35 mg/kg/d produced significant AML tumor inhibition rates of 93.5% and 73.6%, respectively. Studies on the anti-AML mechanism of crotonoside demonstrated a significant inhibition of FLT3 signaling, cell cycle arrest in G0/G1 phase, and apoptosis. In contrast to classic FLT3 inhibitor; sunitinib, crotonoside was able to selectively suppress the expression of HDAC3 and HDAC6 without altering the expression of other HDAC isoforms. Inhibitors of HDAC3 and HDAC6; RGFP966 and HPOB, respectively, also exhibited selective inhibition in AML cells. Furthermore, we established novel signaling pathways including HDAC3/NF-κB-p65 and HDAC6/c-Myc besides FLT3/c-Myc which are aberrantly regulated in the progression of AML. In addition, crotonoside alone or the combination of sunitinib/RFP966/HPOB exhibited a significant post-inhibition effect in AML cells by the inhibition of FLT3 and HDAC3/6. Inhibitors targeting the FLT3 and HDAC3/6 might provide a more effective treatment strategy for AML. Taken together, the present study suggests that crotonoside could be a promising candidate for the treatment of AML, and deserves further investigations.

KEYWORDS

Crotonoside; HPLC; pharmacokinetics; tissue distribution.

Title

Crotonoside Exhibits Selective Post-Inhibition Effect in AML Cells via Inhibition of FLT3 and HDAC3/6

Author

Yu-Zhi Li 1 , Si Yu 1 , Pei-Ao Yan 1 , Dao-Yin Gong 1 , Fang-Li Wu 2 , Zhi He 2 , Yu-Yao Yuan 2 , An-Yan Zhao 2 , Xue Tang 1 , Ruo-Qi Zhang 1 , Cheng Peng 1 , Zhi-Xing Cao 1

Publish date

2017 Sep 8

PMID

25684598

Abstract

The synthesis, base-pairing properties and in vitro and in vivo characteristics of 5-methyl-isocytosine (isoC(Me) ) and isoguanine (isoG) nucleosides, incorporated in an HNA(h) (hexitol nucleic acid)-DNA(d) mosaic backbone, are described. The required h-isoG phosphoramidite was prepared by a selective deamination as a key step. As demonstrated by Tm measurements the hexitol sugar showed slightly better mismatch discrimination against dT. The d-isoG base mispairing follows the order T>G>C while the h-isoG base mispairing follows the order G>C>T. The h- and d-isoC(Me) bases mainly mispair with G. Enzymatic incorporation experiments show that the hexitol backbone has a variable effect on selectivity. In the enzymatic assays, isoG misincorporates mainly with T, and isoC(Me) misincorporates mainly with A. Further analysis in vivo confirmed the patterns of base-pair interpretation for the deoxyribose and hexitol isoC(Me) /isoG bases in a cellular context, through incorporation of the bases into plasmidic DNA. Results in vivo demonstrated that mispairing and misincorporation was dependent on the backbone scaffold of the base, which indicates rational advances towards orthogonality.

KEYWORDS

HNA; XNA plasmid; isoG; nucleosides; polymerase.

Title

Isoguanine and 5-methyl-isocytosine Bases, in Vitro and in Vivo

Author

Omprakash Bande 1 , Rania Abu El Asrar, Darren Braddick, Shrinivas Dumbre, Valerie Pezo, Guy Schepers, Vitor B Pinheiro, Eveline Lescrinier, Philipp Holliger, Philippe Marliere, Piet Herdewijn

Publish date

2015 Mar 23


Description :

Crotonoside is isolated from Chinese medicinal herb, Croton. Crotonoside inhibits FLT3 and HDAC3/6, exhibits selective inhibition in acute myeloid leukemia (AML) cells. Crotonoside could be a promising new lead compound for the treatment of AML[1]