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Picropodophyllotoxin

$320

  • Brand : BIOFRON

  • Catalogue Number : BF-P2016

  • Specification : 98%

  • CAS number : 477-47-4

  • Formula : C22H22O8

  • Molecular Weight : 414.41

  • PUBCHEM ID : 72435

  • Volume : 20mg

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Catalogue Number

BF-P2016

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

414.41

Appearance

White crystalline powder

Botanical Source

Octagonal lotus

Structure Type

Lignanoids

Category

Standards;Natural Pytochemical;API

SMILES

COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O

Synonyms

(5R,5aS,8aR)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one/Picropodophyllinic Acid Lactone/(5R,5aS,8aR,9R)-9-Hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one/Picropodophyllin (8CI)/Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aS,8aR,9R)-/furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aS,8aR)-/[5R-(5a,5aa,8aa,9a)]-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one/Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aS,8aR,9R)-/Picropodophyllotoxin/(5R,5aS,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one/Picropodophyllin/PPP/IGF-1R Inhibitor/AXL1717

IUPAC Name

(5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Density

1.4±0.1 g/cm3

Solubility

Flash Point

210.2±23.6 °C

Boiling Point

597.9±50.0 °C at 760 mmHg

Melting Point

225-227ºC

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

3002900000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:477-47-4) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

31872595

Abstract

According to drug design flattening principle and using podophyllotoxin or 4′-demethylepipodophyllotoxin and aldehydes as starting material,a series of podophyllotoxin derivatives containing an imine structure with low toxicity were highly effective synthesized. Nine target compounds were successfully synthesized,and their structures were confirmed by ~1H-NMR,HR-ESI-MS and melting point data analysis. Using etoposide as positive control drug,nine target compounds were screened for cytotoxicity against He La cells in vitro by MTT method. The antitumor activity screening results showed that compound 6 b,6 d,6 e,6 f,6 g,6 i exhibited higher inhibitory rate against He La cells than those of control drug VP-16. It provides some practical reference value for the further development on the structure modification of podophyllotoxin and study on anti-tumor activity.

KEYWORDS

4'-demethylepipodophyllotoxin; antitumor activity; podophyllotoxin; structure-activity relationship

Title

[Synthesis and antitumor activity of podophyllotoxin derivatives].

Author

Tian DL1, Liang CP2, Luo G3, Chen H3.

Publish date

2019 Nov

PMID

31776519

Abstract

Micelle-forming amphiphilic drug conjugates were synthesized starting from a biologically active epipodophyllotoxin derivative which was covalently inserted in between a hydrophilic targeting spermine unit, and a hydrophobic stearyl chain. The amphiphilic drug conjugates were further assembled into the corresponding micelles and evaluated in vitro for the active targeting of tumor cells overexpressing the polyamine transport system.

Title

Polyamine transport system-targeted nanometric micelles assembled from epipodophyllotoxin-amphiphiles.

Author

Alliot J 1, Theodorou I , Duconge F , Gravel E , Doris E .

Publish date

2019 Dec 10;

PMID

31557166

Abstract

The progression of cancer through local expansion and metastasis is well recognized, but preventing these characteristic cancer processes is challenging. To this end, a new strategy is required. In this study, we presented a novel dual functional podophyllotoxin derivative, 2-pyridinealdehyde hydrazone dithiocarbamate S-propionate podophyllotoxin ester (PtoxPdp), which inhibited both matrix metalloproteinases and Topoisomerase II. This new podophyllotoxin derivative exhibited significant anti-proliferative, anti-metastatic that correlated with the downregulation of matrix metalloproteinase. In a xenograft animal local expansion model, PtoxPdp was superior to etoposide in tumor repression. A preliminary mechanistic study revealed that PtoxPdp induced apoptosis and autophagy via the PI3K/AKT/mTOR pathway. Furthermore, PtoxPdp could also inhibit epithelial-mesenchymal transition, which was achieved by downregulating both PI3K/AKT/mTOR and NF-κB/Snail pathways. Taken together, our results reveal that PtoxPdp is a promising antitumor drug candidate.

Title

Antitumor activity of a novel dual functional podophyllotoxin derivative involved PI3K/AKT/mTOR pathway.

Author

Li Y1, Huang T2, Fu Y2, Wang T2, Zhao T2, Guo S2, Sun Y3, Yang Y2, Li C2,3.

Publish date

2019 Sep 26


Description :

Picropodophyllin (AXL1717) is a selective insulin-like growth factor-1 receptor (IGF-1R) inhibitor with an IC50 of 1 nM.