| Identification | Back Directory | [Name]
(-)PPP | [CAS]
477-47-4 | [Synonyms]
(-)PPP
AXL1717
AXL-1717
AXL 1717
Metacavir
NSC 36407
PICROPODOPHYLLIN
(-)PPP USP/EP/BP
Pictopodophyllotoxin
IGF-1R Inhibitor, PPP
Podophyllotoxin 5a-Epimer
Picropodophyllin (AXL1717)
Picropodophyllotoxin, >=98%
AXL1717 (Picropodophyllotoxin)
IGF-1R Inhibitor, PPP - CAS 477-47-4 - Calbiochem
POLY(2,5-BIS(3-SULFONATOPROPOXY)-1,4-PHENYLENE, DISODIUM SALT-ALT-1,4-PHENYLENE)
(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
(5R,5aS,8aR,9R)-9-Hydroxy-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)furo[3′,4′: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
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)-
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 | [Molecular Formula]
C22H22O8 | [MDL Number]
MFCD07785535 | [MOL File]
477-47-4.mol | [Molecular Weight]
414.41 |
| Chemical Properties | Back Directory | [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 | [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. |
| Hazard Information | Back Directory | [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. | [Uses]
Insulin growth factor 1 receptor inhibitor, antineoplastic | [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) Girnita et al. (2004), Cyclolignans as inhibitors of the insulin-like growth factor-1 receptor and malignant cell growth; Cancer Res., 64 236
2) Girnita et al. (2006), The insulin-like growth factor-I receptor inhibitor picropodophyllin causes tumor regression and attenuates mechanisms involved in invasion of iveal melanoma cells; Clin. Cancer Res., 12 1383
3) Menu et al. (2007), Targeting the IGF-1R using picropodophyllin in therapeutical 5T2MM mouse model of multiple myeloma: beneficial effects on tumor growth, angiogenesis, bone disease and survival; Int. J. Cancer, 121 1857
4) Razuvaev et al. (2007), The cyclolignan picropodophyllin attenuates intimal hyperplasia after rat carotid balloon injury by blocking insulin-like growth factor-1 receptor signaling; J. Vasc. Surg., 46 108 |
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