477-47-4

Basic information

• Product Name: (-)PPP
• 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
• CAS NO: 477-47-4
• Molecular Formula: C₂₂H₂₂O₈
• Molecular Weight: 414.40528
• Product Categories: Insulin-like Growth Factor-1 Receptor Inhibitor;Picropodophyllin
• Mol File: 477-47-4.mol
• Article Data: 30

Chemical Properties

• Melting Point: 225-227℃
• Boiling Point: 453.31°C (rough estimate)
• Flash Point: 210.2°C
• Appearance: white/
• Density: 1.370
• Refractive Index: 1.4480 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble
• PKA: 13.26±0.40(Predicted)
• 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.
• CAS DataBase Reference: (-)PPP(CAS DataBase Reference)
• NIST Chemistry Reference: (-)PPP(477-47-4)
• EPA Substance Registry System: (-)PPP(477-47-4)

Safety Data

• Hazard Codes: Xi,T
• 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
• Hazardous Substances Data: 477-47-4(Hazardous Substances Data)

Usage

Description

(-)PPP, also known as Poly(2,5-bis(3-sulfonatopropoxy)-1,4-phenylene, disodium salt-alt-1,4-phenylene), is a water-soluble conjugating polymer with a poly(p-phenylene) skeleton and two phenylene groups in each repeating unit. It serves as a donor molecule and has potential applications in various optoelectronic fields.

Uses

Used in Optoelectronic Applications:
(-)PPP is used as a conjugating polymer for its water solubility and optoelectronic properties, making it suitable for a variety of applications in the optoelectronic industry.
Used in Insulin Growth Factor 1 Receptor Inhibition:
(-)PPP is used as an insulin growth factor 1 receptor inhibitor, specifically as an antineoplastic agent, to inhibit the growth of cancer cells by targeting the IGF1R.
Used in Picropodophyllotoxin Applications:
(-)PPP is used in conjunction with Picropodophyllotoxin, a potent and selective inhibitor of insulin-like growth factor 1 receptor (IGF1R), which is non-competitive with ATP. It displays antiproliferative activity in numerous tumor cell lines and exhibits antiangiogenic activity, making it useful in cancer treatment and prevention of intimal hyperplasia after vascular injury.

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.

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

Upstream product

• 477-48-5 (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 78216-05-4 picropodophyllic acid hydrazide 
• 1083302-72-0 6-{[(4R)-4-ethenyl-2-oxooxolan-3-yl](3,4,5-trimethoxyphenyl)methyl}-2H-1,3-benzodioxol-5-yl trifluoromethanesulfonate 
• 477-67-8 (+/-)-isopodophyllinic acid 
• 116097-18-8 6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 
• 79289-93-3 epipodophyllic acid 4,11-acetonide 
• 79305-58-1 methyl epipodophyllate 4,11-acetonide 
• 108763-85-5 ((4R,5S)-4-Benzo[1,3]dioxol-5-yl-2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-yl)-acetaldehyde 
• 86301-75-9 dimethyl 4-(3,4-trans)-hydroxy-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-cis-dicarboxylate 
• 13311-04-1 9r-(Tetrahydro-<2>pyranyloxy)-5c-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydro-8H-furo<3',4':6,7>naphtho<2,3-d>(1,3)-dioxol-6-on 
• 75-08-1 ethanethiol 
• 108448-52-8 (+)-4-O-(tert-butyldimethylsilyl)picropodophyllin 

Downstream Products

• 47789-93-5 O-(3-Carboxy-propionyl)-picropodophyllin 
• 38491-90-6 (5R,5aR,8aS,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl acetate 
• 78215-98-2 benzoylpicropodophyllin 
• 37158-54-6 (5aS)-5c-(2-bromo-3,4,5-trimethoxy-phenyl)-9c-hydroxy-(5ar,8ac)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 7470-99-7 2-(3,4,5-Trimethoxybenzoyl)-4,5-(methylenedioxy)benzoic Acid 
• 42123-13-7 7-(3,4,5-trimethoxy-phenyl)-7H-[1,3]dioxolo[4,5-f]isobenzofuran-5-one 
• 6258-41-9 5-(3,4,5-Trimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one 
• 4354-75-0 8-hydroxy-7-hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 
• 344585-17-7 α-apopicropodophyllotoxin 
• 477-48-5 (5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione 
• 245321-94-2 picropodophyllotoxin ethyl ether 
• 59123-24-9 (±)-β-apopicropodophyllin 
• 477-51-0 deoxypicropodophyllotoxin 
• 6559-91-7 (+/-)-4'-O-demethyl-1-epipodophyllotoxin 

Relevant articles and documents

Catalytic Enantioselective Synthesis of (-)-Podophyllotoxin

The first catalytic enantioselective total synthesis of (-)-podophyllotoxin is accomplished by a challenging organocatalytic cross-aldol Heck cyclization and distal stereocontrolled transfer hydrogenation in five steps from three aldehydes. Reversal of se

Insight into dihalogenation of E-ring of podophyllotoxins, and their acyloxyation derivatives at the C4 position as insecticidal agents

Unexpected sequential E-ring dihalogenation of podophyllotoxin analogues is reported. It demonstrated that a chlorine/bromine atom was prior introduced at the C2′ position of podophyllotoxin, and the corresponding free rotation of E-ring around the C1-C1′

NEW PROCESS FOR PREPARING CYCLOLIGNANS

The invention relates to a one-pot reaction for the preparation of a compound of Formula (I). The compound of Formula (I) may be further transformed into picropodophyllin and derivatives thereof.