Shipping to Germany We Offer Worldwide Shipping
Login Wishlist

Sempervirine nitrate

$3,600

  • Brand : BIOFRON

  • Catalogue Number : BN-O1860

  • Specification : 98%(HPLC)

  • CAS number : 549-92-8

  • Formula : C19H16N2

  • Molecular Weight : 272.3

  • PUBCHEM ID : 168919

  • Volume : 20mg

In stock

Quantity
Checkout Bulk Order?

Catalogue Number

BN-O1860

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

272.3

Appearance

Botanical Source

Structure Type

Category

SMILES

Synonyms

IUPAC Name

16,17,18,19-tetrahydroyohimban

Applications

Density

1.28g/cm3

Solubility

Flash Point

311.6ºC

Boiling Point

591.6ºC at 760mmHg

Melting Point

271ºC

InChl

InChl Key

UQVUEULZDJRMJR-UHFFFAOYSA-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#:549-92-8) 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

27259808

Abstract

The tumor suppressor p53 plays a critical role in suppressing cancer growth and progression and is an attractive target for the development of new targeted therapies. We synthesized several indolo-pyrido-isoquinolin based alkaloids to activate p53 function and examined their therapeutic efficacy using NCI-60 screening. Here, we provide molecular evidence that one of these compounds, 11-methoxy-2,3,4,13-tetrahydro-1H-indolo[2′,3′:3,4]pyrido[1,2-b]isoquinolin-6-ylium-bromide (termed P18 or NSC-768219) inhibits growth and clonogenic potential of cancer cells. P18 treatment results in downregulation of mesenchymal markers and concurrent upregulation of epithelial markers as well as inhibition of migration and invasion. Experimental epithelial-mesenchymal-transition (EMT) induced by exposure to TGFβ/TNFα is also completely reversed by P18. Importantly, P18 also inhibits mammosphere-formation along with a reduction in the expression of stemness factors, Oct4, Nanog and Sox2. We show that P18 induces expression, phosphorylation and accumulation of p53 in cancer cells. P18-mediated induction of p53 leads to increased nuclear localization and elevated expression of p53 target genes. Using isogenic cancer cells differing only in p53 status, we show that p53 plays an important role in P18-mediated alteration of mesenchymal and epithelial genes, inhibition of migration and invasion of cancer cells. Furthermore, P18 increases miR-34a expression in p53-dependent manner and miR-34a is integral for P18-mediated inhibition of growth, invasion and mammosphere-formation. miR-34a mimics potentiate P18 efficacy while miR-34a antagomirs antagonize P18. Collectively, these data provide evidence that P18 may represent a promising therapeutic strategy for the inhibition of growth and progression of breast cancer and p53-miR-34a axis is important for P18 function.

KEYWORDS

Breast cancer; EMT; Indolo-pyrido-isoquinolin based alkaloid; Invasion; miR34a; p53.

Title

Indolo-pyrido-isoquinolin based alkaloid inhibits growth, invasion and migration of breast cancer cells via activation of p53-miR34a axis

Author

Dimiter B Avtanski 1, Arumugam Nagalingam 1, Joseph E Tomaszewski 2, Prabhakar Risbood 2, Michael J Difillippantonio 2, Neeraj K Saxena 3, Sanjay V Malhotra 4, Dipali Sharma 5

Publish date

2016 Aug;

PMID

26828413

Abstract

Sempervirine and analogues were synthesized using a route featuring Sonogashira and Larock Pd-catalyzed reactions. Structure-activity relationships were investigated using three human cancer cell lines. 10-Fluorosempervirine is the most potently cytotoxic member of the family yet described.

Title

Synthesis and Cytoxicity of Sempervirine and Analogues

Author

Xiaohong Pan 1, Chunying Yang 2, John L Cleveland 2, Thomas D Bannister 1

Publish date

2016 Mar 4

PMID

19016214

Abstract

The 95 % ethanol extract of Gelsemium sempervirens showed inhibitory activity against human DNA topoisomerase I (Topo I). Phytochemical investigations of this active extract resulted in the isolation and identification of three new steroids ( 1 – 3), together with eight known compounds 12 beta-hydroxy-5 alpha-pregn-16-ene-3,20-dione ( 4), gelsemine ( 5), sempervirine ( 6), scopoletin ( 7), 7- O- beta- D-glucopyranosylscopoletin ( 8), 7- O- beta- D-apiofuranosyl-(1–>6)- beta- D-glucopyranosylscopoletin ( 9), uvaol ( 10), and 2-(4-hydroxyphenyl)ethyl heptadecanoate ( 11). The structures of the new steroids were determined by extensive NMR and HR-ESI-MS analyses as 21-hydroxy-5 alpha-pregn-16-ene-3,20-dione ( 1), 3-oxoandrosta-16-ene-17-carboxylic acid ( 2), and 3-oxoandrosta-4,16-diene-17-carboxylic acid ( 3). This study suggests that sempervirine ( 6) intercalates to DNA and also inhibits Topo I through modulating the enzyme activity with an IC (50) of 54.5 +/- 15.9 muM.

Title

Steroids, alkaloids, and coumarins from Gelsemium sempervirens

Author

Zhizhen Zhang 1, Ping Wang, Wei Yuan, Shiyou Li

Publish date

2008 Dec;