(-)PPP
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(-)PPP
structure -
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CAS No:
477-47-4
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Formula:
C22H22O8
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Chemical Name:
(-)PPP
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Synonyms:
PICROPODOPHYLLIN;(-)PPP;POLY(2,5-BIS(3-SULFONATOPROPOXY)-1,4-PHENYLENE, DISODIUM SALT-ALT-1,4-PHENYLENE);NSC 36407, Picropodophyllin, PPP, (5R,5aS,8aR,9R)-9-Hydroxy-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)furo[3μ,4μ:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;(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;IGF-1R Inhibitor, PPP;(5R,5aS,8aR,9R)-9-Hydroxy-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)fur[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;NSC 36407
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CAS No:
Description
Picropodophyllin (AXL1717) is a selective insulin-like growth factor-1 receptor (IGF-1R) inhibitor with an IC50 of 1 nM.
Picropodophyllotoxin is an organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents. It has a role as an antineoplastic agent, a tyrosine kinase inhibitor, an insulin-like growth factor receptor 1 antagonist and a plant metabolite. It is a lignan, a furonaphthodioxole and an organic heterotetracyclic compound.|Picropodophyllin has been investigated for the treatment of Non Small Cell Lung Cancer.|Picropodophyllin is a cyclolignan alkaloid found in the mayapple plant family (Podophyllum peltatum), and a small molecule inhibitor of the insulin-like growth factor 1 receptor (IGF1R) with potential antineoplastic activity. Picropodophyllin specifically inhibits the activity and downregulates the cellular expression of IGF1R without interfering with activities of other growth factor receptors, such as receptors for insulin, epidermal growth factor, platelet-derived growth factor, fibroblast growth factor and mast/stem cell growth factor (KIT). This agent shows potent activity in the suppression o f tumor cell proliferation and the induction of tumor cell apoptosis. IGF1R, a receptor tyrosine kinase overexpressed in a variety of human cancers, plays a critical role in the growth and survival of many types of cancer cells.
Picropodophyllotoxin (477-47-4) is a potent and selective inhibitor of insulin-like growth factor 1 receptor (IGF1R) which is non-competitive with ATP.1Displays no activity at IR, EGFR, FGFR or PDGFR. Inhibits IGF1R autophosphorylation IC50 ~ 1 nM.1Displays antiproliferative activity in numerous tumor cell lines, IC50 = 0.05 – 15 μM.2 Exhibits antiangiogenic activity.3Picropodophyllotoxin attenuates intimal hyperplasia after vascular injury.4Active in vivo.
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.
ChEBI: An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.
Characteristics
208 nm (in deoxygenated water)(lit.)
92.7
2
1.370
225-227℃
453.31°C (rough estimate)
210.2±23.6 °C
1.4480 (estimate)
H2O: soluble
2-8ºC
3.82E-15mmHg at 25°C
LD50 intraperitoneal in mouse: 280mg/kg
13.26±0.40(Predicted)
190.9 Ų [M+H-H2O]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Sealed in dry,2-8°C
Safety Information
Ⅱ
6.1
3462
3
Xi,T
26-36-45-36/37
LV2510000
Xi,T
Store at +4°C
P261-P280-P301 + P310-P305 + P351 + P338
36/37/38-68-25-21
UN 3462 6.1/PG 2
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
(-)PPP Use and Manufacturing
Insulin growth factor 1 receptor inhibitor, antineoplastic
Human drugs -> Rare disease (orphan)
Computed Properties
Molecular Weight:414.4
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:414.13146766
Monoisotopic Mass:414.13146766
Topological Polar Surface Area:92.7
Heavy Atom Count:30
Complexity:629
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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