(-)PPP Chemical Properties

Melting point:

225-227℃

alpha 

D20 +9.4° (c = 0.7 in chloroform)

Boiling point:

453.31°C (rough estimate)

Density 

1.370

refractive index 

1.4480 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

H₂O: soluble

form 

powder

pka

13.26±0.40(Predicted)

color 

white

Water Solubility 

H2O: soluble

λmax

208 nm (in deoxygenated water)(lit.)

Sensitive 

Light Sensitive

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.

InChIKey

YJGVMLPVUAXIQN-HAEOHBJNSA-N

SMILES

O1C2=CC3=C(C=C2OC1)[C@@H](C1=CC(OC)=C(OC)C(OC)=C1)[C@]1([H])C(=O)OC[C@]1([H])[C@H]3O

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-68-25-21

Safety Statements 

26-36-45-36/37

RIDADR 

UN 3462 6.1/PG 2

WGK Germany 

3

RTECS 

LV2510000

HazardClass 

6.1

Toxicity

LD50 intraperitoneal in mouse: 280mg/kg

MSDS

• Language:English Provider:SigmaAldrich

(-)PPP Usage And Synthesis

Description

Picropodophyllotoxin (477-47-4) is a potent and selective inhibitor of insulin-like growth factor 1 receptor (IGF1R) which is non-competitive with ATP.1?Displays no activity at IR, EGFR, FGFR or PDGFR. Inhibits IGF1R autophosphorylation IC50 ~ 1 nM.1?Displays antiproliferative activity in numerous tumor cell lines, IC50 = 0.05 – 15 μM.2 Exhibits antiangiogenic activity.3?Picropodophyllotoxin attenuates intimal hyperplasia after vascular injury.4?Active in vivo.

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It comes from the rhizome of Dysosma versipellis (Hance.) M. Cheng, a plant of the Berberidaceae family.

Uses

Insulin growth factor 1 receptor inhibitor, antineoplastic

Uses

Picropodophyllotoxin is an insulin-like growth factor-I (IGF-I) receptor kinase inhibitor

Definition

ChEBI: An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.

General Description

Poly(2,5-bis(3-sulfonatopropoxy)-1,4-phenylene, disodium salt-alt-1,4-phenylene) (PPP-OPSO3) is a water soluble conjugating polymer that can be used as a donor molecule. It has a poly(p-phenylene) skeleton with each repeating unit having two phenylene groups. It can be used for a variety of optoelectronic applications.

Biological Activity

Orally active insulin-like growth factor 1 receptor (IGF1R) inhibitor that exhibits no activity at the insulin receptor, FGFR, PDGFR or EGFR. Inhibits IGF1R autophosphorylation (IC 50 ~ 1 nM), increases the fraction of cells in the G 2 /M phase and upregulates apoptosis. Exhibits antiproliferative effects in multiple cancer cell lines (IC 50 = 0.05 - 15 μ M), and has anticancer and antineovascularization activity in vivo .

Biochem/physiol Actions

Picropodophyllotoxin (PPP), an epimer of podophyllotoxin (PPT), has been reported to target insulin-like growth factor-I receptor (IGF-IR) and mediate anticancer functions. However, a study in 2007, has reported that PPP can induce G2-M cell cycle arrest even in IGF-IR deficient cells. Hence, the role of PPP in IGF-IR-mediated anticancer functions is debatable.

storage

Store at +4°C

References

[1] ADA GIRNITA. Cyclolignans as inhibitors of the insulin-like growth factor-1 receptor and malignant cell growth.[J]. Cancer research, 2004, 64 1: 236-242. DOI:10.1158/0008-5472.can-03-2522
[2] ADA GIRNITA. The insulin-like growth factor-I receptor inhibitor picropodophyllin causes tumor regression and attenuates mechanisms involved in invasion of uveal melanoma cells.[J]. Clinical Cancer Research, 2006, 12 4: 1383-1391. DOI:10.1158/1078-0432.ccr-05-1106
[3] ELINE MENU. Targeting the IGF-1R using picropodophyllin in the therapeutical 5T2MM mouse model of multiple myeloma: Beneficial effects on tumor growth, angiogenesis, bone disease and survival[J]. International Journal of Cancer, 2007, 121 8: 1857-1861. DOI:10.1002/ijc.22845
[4] ANTON RAZUVAEV MD  Leonard G M  Bimma Henderson MD, PHD  Olle L M, PHD  Magnus A M, et al. The cyclolignan picropodophyllin attenuates intimal hyperplasia after rat carotid balloon injury by blocking insulin-like growth factor-1 receptor signaling[J]. Journal of Vascular Surgery, 2007, 46 1: Pages 108-115. DOI:10.1016/j.jvs.2007.02.066

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