Picropodophyllotoxin

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

Picropodophyllotoxin Structure
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
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.

 Names

Name picropodophyllotoxin
Synonym More Synonyms

 Picropodophyllotoxin Biological Activity

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

 Chemical & Physical Properties

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

 Toxicological Information

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

 Safety Information

Symbol GHS06
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

 Synthetic Route

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 Synonyms

(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
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