Picropodophyllotoxin

Modify Date: 2024-01-02 16:27:11

Picropodophyllotoxin structure	Common Name	Picropodophyllotoxin
	CAS Number	477-47-4	Molecular Weight	414.405
	Density	1.4±0.1 g/cm3	Boiling Point	597.9±50.0 °C at 760 mmHg
	Molecular Formula	C₂₂H₂₂O₈	Melting Point	225-227ºC
	MSDS	Chinese USA	Flash Point	210.2±23.6 °C
	Symbol	GHS06	Signal Word	Danger

Use of Picropodophyllotoxin

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

Name	picropodophyllotoxin
Synonym	More Synonyms

Description	Picropodophyllin (AXL1717) is a selective insulin-like growth factor-1 receptor (IGF-1R) inhibitor with an IC50 of 1 nM.
Related Catalog	Signaling Pathways >> Protein Tyrosine Kinase/RTK >> IGF-1R Research Areas >> Cancer
Target	IC50: 1 nM (IGF-1R)
In Vitro	Picropodophyllin (AXL1717) (0.5, 2.5, 10 μM) potently inhibits IGF-1-stimulated IGF-1R, Akt (Ser 473) and Erk1/2 phosphorylation in intact cells. Picropodophyllin (AXL1717) also inhibits cell growth, and induces apoptosis in cultured IGF-1R-positive tumor cells[1]. Picropodophyllin (AXL1717) synergistically sensitizes HMCL, primary human MM and murine 5T33MM cells to ABT-737 and ABT-199 via further decreasing cell viability and enhancing apoptosis[3]. Picropodophyllin and sorafenib synergistically suppress the proliferation and motility of hepatocellular carcinoma cells[4].
In Vivo	Picropodophyllin (AXL1717) (20 mg/kg/12 h, i.p.) causes complete tumor regression in SCID mice xenografted with human ES-1, BE, and PC3[1]. Picropodophyllin (AXL1717) shows a potent antitumor activity, increases survival in the 5T33MM mouse model[2].
Animal Admin	Four to 5-week-old pathogen-free SCID mice are used and housed within plastic isolators in a sterile facility. ES-1, BE, and PC3 cells (all proved to express IGF-1R), or R-v-src (IGF-1R negative) and P12 (overexpressing IGF-1 and IGF-1R), are injected s.c. at 107 cells/mice in a 0.2 mL volume of sterile saline solution. Immunocompetent Balb-c mice are injected with 107JC murine breast cancer cells per mouse in 0.15 mL volume of sterile saline solution. Experimental treatments with Picropodophyllin (AXL1717) (20 mg/kg/12 h) are performed by daily i.p. injections of the compound in 10 μL volume of DMSO: vegetable oil, 10:1 (v/v). Control mice are treated with the vehicle only. Three animals are treated in each group. Tumor growth is measured every second day using vernier calipers, and the tumor volumes are calculated. The mice are carefully observed for the presence of side effects and are sacrificed at the end of the experiments for histological analysis of the lesions. A separate experiment on Picropodophyllin (AXL1717)-treated (systemically and locally) tumor-free mice, including histological analyses of various organs, confirms previous observations that Picropodophyllin (AXL1717) appears to be nontoxic.
References	[1]. Girnita A, et al. Cyclolignans as inhibitors of the insulin-like growth factor-1 receptor and malignant cell growth. Cancer Res. 2004 Jan 1;64(1):236-42. [2]. Menu E, et al. Inhibiting the IGF-1 receptor tyrosine kinase with the cyclolignan PPP: an in vitro and in vivo study in the 5T33MM mouse model. Blood. 2006 Jan 15;107(2):655-60. Epub 2005 Jul 26. [3]. Bieghs L, et al. The IGF-1 receptor inhibitor picropodophyllin potentiates the anti-myeloma activity of a BH3-mimetic. Oncotarget. 2014 Nov 30;5(22):11193-208. [4]. Tomizawa M, et al. Picropodophyllin and sorafenib synergistically suppress the proliferation and motility of hepatocellular carcinoma cells. Oncol Lett. 2014 Nov;8(5):2023-2026. Epub 2014 Aug 27. [5]. Stromberg T, et al. IGF-1 receptor tyrosine kinase inhibition by the cyclolignan PPP induces G2/M-phase accumulation and apoptosis in multiple myeloma cells. Blood. 2006 Jan 15;107(2):669-78. Epub 2005 Sep 15. [6]. Kong YL, et al. Insulin deficiency induces rat renal mesangial cell dysfunction via activation of IGF-1/IGF-1R pathway. Acta Pharmacol Sin. 2016 Feb;37(2):217-27.

Density	1.4±0.1 g/cm3
Boiling Point	597.9±50.0 °C at 760 mmHg
Melting Point	225-227ºC
Molecular Formula	C₂₂H₂₂O₈
Molecular Weight	414.405
Flash Point	210.2±23.6 °C
Exact Mass	414.131470
PSA	92.68000
LogP	1.60
Vapour Pressure	0.0±1.8 mmHg at 25°C
Index of Refraction	1.606
Storage condition	2-8°C

Picropodophyllotoxin MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LV2510000

CAS REGISTRY NUMBER :: 477-47-4

BEILSTEIN REFERENCE NO. :: 0099161

LAST UPDATED :: 199801

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C22-H22-O8

MOLECULAR WEIGHT :: 414.44

WISWESSER LINE NOTATION :: T E5 C665 FVO NO PO OHTT&&J DR CO1 DO1 EO1& JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 280 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - tremor Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 77,269,1951 *** U.S. STANDARDS AND REGULATIONS *** MSHA STANDARD-air:TWA 0.1 mg/m3 DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: 3,212,1971

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301-H312-H315-H319-H335
Precautionary Statements	P261-P280-P301 + P310-P305 + P351 + P338
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	Xi,T
Risk Phrases	36/37/38-68-25-21
Safety Phrases	26-36-45-36/37
RIDADR	UN 3462 6.1/PG 2
WGK Germany	3.0
RTECS	LV2510000
Hazard Class	6.1

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DownStream 5
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(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

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Picropodophyllotoxin
Price: ￥998.0/20mg
Purity: 98.0%
Stocking Period: 1 Day
Contact: Liu jia

DC Chemicals Limited
China
Product Name: Picropodophyllin (PPP)
Price: $400.0/100mg $800.0/250mg $1700.0/1g
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: 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)-
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Stocking Period: Inquiry
Contact: Ms Wang

Zhejiang Hangyu API Co., Ltd
China
Product Name: (-)PPP
Price: ￥Inquiry/1kg
Purity: 99.5%
Stocking Period: Inquiry
Contact: Vinnie

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Picropodophyllotoxin

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