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14-Deoxyandrographolide

$1,008

  • Brand : BIOFRON

  • Catalogue Number : BD-P0773

  • Specification : 98.0%(HPLC)

  • CAS number : 4176-97-0

  • Formula : C20H30O4

  • Molecular Weight : 334.45

  • PUBCHEM ID : 11624161

  • Volume : 25mg

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Catalogue Number

BD-P0773

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

334.45

Appearance

White powder

Botanical Source

Andrographis paniculata (Burm. f.) Nees/Andrographis paniculata

Structure Type

Diterpenoids

Category

Standards;Natural Pytochemical;API

SMILES

CC12CCC(C(C1CCC(=C)C2CCC3=CCOC3=O)(C)CO)O

Synonyms

20-ethyl-7,8-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)aconitan-14-one/14-Dehydro-browniin/14-Dehydrobrowniine/Aconitan-14-one,20-ethyl-7,8-dihydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-,(1alpha,6beta,16beta)/14-deoxy andrographolide/Dehydrobrowniin/10-Dehydro-browniin/3-(2-((1R,4aS,5R,6R,8aS)-6-hydroxyl-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethyl)furan-2(5H)-one/Deoxyandrographolide

IUPAC Name

4-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethyl]-2H-furan-5-one

Applications

14-Deoxyandrographolide, a bioactive compound of Andrographis paniculata, has hepatoprotective efficacy. 14-Deoxyandrographolide desensitizes hepatocytes to TNF-α-mediated apoptosis through the release of TNFRSF1A release[1].

Density

1.15g/cm3

Solubility

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

Flash Point

177.3ºC

Boiling Point

509.5ºC at 760 mmHg

Melting Point

176-178ºC

InChl

InChI=1S/C20H30O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h9,15-17,21-22H,1,4-8,10-12H2,2-3H3/t15-,16+,17-,19+,20+/m1/s1

InChl Key

GVRNTWSGBWPJGS-YSDSKTICSA-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#:4176-97-0) 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

24169353

Abstract

Background:
Prostate cancer remains dependent of androgen receptor (AR) signalling, even after emergence of castration resistance. EZN-4176 is a third-generation antisense oligonucleotide that binds to the hinge region (exon 4) of AR mRNA resulting in full-length AR mRNA degradation and decreased AR protein expression. This Phase I study aimed to evaluate EZN-4176 in men with castration-resistant prostate cancer (CRPC).

Methods:
Patients with progressing CRPC were eligible; prior abiraterone and enzalutamide treatment were allowed. EZN-4176 was administered as a weekly (QW) 1-h intravenous infusion. The starting dose was 0.5 mg kg−1 with a 4-week dose-limiting toxicity (DLT) period and a 3+3 modified Fibonacci dose escalation design. After determination of the DLT for weekly administration, an every 2 weeks schedule was initiated.

Results:
A total of 22 patients were treated with EZN-4176. At 10 mg kg−1 QW, two DLTs were observed due to grade 3-4 ALT or AST elevation. No confirmed biochemical or soft tissue responses were observed. Of eight patients with ⩾5 circulating tumour cells at baseline, a conversion to <5 was observed in three (38%) patients. The most common EZN-4176-related toxicities (all grades) were fatigue (59%), reversible abnormalities in liver function tests ALT (41%) and AST (41%) and infusion-related reactions including chills (36%) and pyrexia (14%). Conclusion: Activity of EZN-4176 at the doses and schedules explored was minimal. The highest dose of 10 mg kg−1 QW was associated with significant but reversible transaminase elevation.

KEYWORDS

castration-resistant prostate cancer, EZN-4176, antisense oligonucleotide, phase I clinical trial

Title

First-in-human Phase I study of EZN-4176, a locked nucleic acid antisense oligonucleotide to exon 4 of the androgen receptor mRNA in patients with castration-resistant prostate cancer

Author

D Bianchini,1,2 A Omlin,1,2 C Pezaro,1,2 D Lorente,1,2 R Ferraldeschi,1,2 D Mukherji,1,2 M Crespo,1,2 I Figueiredo,1,2 S Miranda,1,2 R Riisnaes,1,2 A Zivi,1,2 A Buchbinder,1,2 D E Rathkopf,1,2 G Attard,1,2 H I Scher,1,2 J de Bono,1,2,3,4,* and D C Danila1,2,3,4

Publish date

2013 Nov 12

PMID

2454464

Abstract

A poly-beta-hydroxybutyrate complex extracted from the plasma membranes of genetically competent Escherichia coli contained polyhydroxybutyrate:polyphosphate:calcium in molar ratios approximating 1:1:0.5. The chain length of the polyhydroxybutyrate was estimated as 120-200 subunits, and that of the polyphosphate was estimated as 130-170 subunits. The extracted complex, when incorporated into liposomes, exhibited a lipid phase transition in the same temperature range as that of the membrane complex in whole cells as well as the same properties of irreversibility, lability, and sensitivity to chelating buffers. Space-filling molecular models and molecular energy minimization methods (Charmm) were used to develop and evaluate a plausible structure for the complex. It is proposed that the polyhydroxybutyrate forms an exolipophilic-endopolarophilic helix around an inner framework helix of calcium polyphosphate. The calcium ions link the two polymers by forming ionic bonds with phosphoryl oxygens of the polyphosphate and ion-dipole bonds with the ester carbonyl oxygens of the polyhydroxybutyrate. This symmetrical structure forms a channel through the membrane and may play a role in the transport of calcium, phosphate, and DNA.

Title

Putative structure and functions of a poly-beta-hydroxybutyrate/calcium polyphosphate channel in bacterial plasma membranes.

Author

R N Reusch and H L Sadoff

Publish date

1988 Jun;

PMID

9094704

Abstract

Induction of immediate-early genes c-jun, junB, and c-fos was demonstrated during echovirus 1 infection in a human osteogenic sarcoma (HOS) cell line. Tenfold induction was seen at 10 h postinfection, corresponding approximately to the end of the first replication cycle of the virus. Echovirus 1 uses VLA-2 integrin as its cellular receptor, and ligand binding by integrin is known to trigger signal transduction pathways ultimately activating immediate-early genes. In the present study, however, VLA-2 binding alone was not sufficient to induce their expression; viral replication was needed. This conclusion was based on the observations that no stimulation of the immediate-early genes occurred in the MG-63 cell line where the virus attached only to VLA-2 but was not able to replicate and that induction of these genes was observed when the HOS cells were infected with echovirus type 7, known to use a different cellular receptor. Induction was not seen in the presence of the antiviral compound WIN 54954, which evidently inhibits the uncoating but not receptor binding of echovirus 1, suggesting that viral replication triggers the activation of the immediate-early genes. The induction of these genes may have a role in viral replication and in the pathogenesis of infection.

Title

Echovirus 1 replication, not only virus binding to its receptor, VLA-2, is required for the induction of cellular immediate-early genes.

Author

P Huttunen, J Heino, and T Hyypia

Publish date

1997 May;