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Merck

T9576

Picropodophyllotoxin

≥96% (HPLC), powder

Synonym(s):

(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, NSC 36407, PPP, Picropodophyllin

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About This Item

Empirical Formula (Hill Notation):
C22H22O8
CAS Number:
477-47-4
Molecular Weight:
414.41
NACRES:
NA.77
PubChem Substance ID:
329826907
UNSPSC Code:
12352200
MDL number:
MFCD01742647
Assay:
≥96% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Quality Level

100

assay

≥96% (HPLC)

form

powder

color

white

solubility

DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

COc1cc(cc(OC)c1OC)[C@H]2C3C(COC3=O)[C@@H](O)c4cc5OCOc5cc24

InChI

1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1

InChI key

YJGVMLPVUAXIQN-HAEOHBJNSA-N

Gene Information

human ... IGF1R(3480)

Related Categories

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.
Picropodophyllotoxin is an insulin-like growth factor-I (IGF-I) receptor kinase inhibitor.

Features and Benefits

This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the InsR page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

May contain 2-3% ethanol (w/w)
Picropodophyllotoxin is soluble in DMSO at a concentration that is greater than 5 mg/ml.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
067K47112
067K47111
067K4711

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Brenden Jongman et al.
Proceedings of the National Academy of Sciences of the United States of America, 112(18), E2271-E2280 (2015-04-23)
The global impacts of river floods are substantial and rising. Effective adaptation to the increasing risks requires an in-depth understanding of the physical and socioeconomic drivers of risk. Whereas the modeling of flood hazard and exposure has improved greatly, compelling
Thomas Strömberg et al.
Blood, 107(2), 669-678 (2005-09-17)
Emerging evidence suggests the insulin-like growth factor-1 receptor (IGF-1R) to be an important mediator of tumor-cell survival and resistance to cytotoxic therapy in multiple myeloma (MM). Recently, members of the cyclolignan family have been shown to selectively inhibit the receptor
Vladimir M Shkolnikov et al.
The Lancet. Public health, 4(4), e181-e188 (2019-04-08)
Since 2005, Russia has made substantial progress, experiencing an almost doubling of per-capita gross domestic product by purchasing power parity (GDP [PPP]) to US$24 800 and witnessing a 6-year increase in life expectancy, reaching 71·4 years by 2015. Even greater gains
Rigo Cintron-Colon et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(36), 9731-9736 (2017-08-23)
When food resources are scarce, endothermic animals can lower core body temperature (T
Ada Girnita et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 12(4), 1383-1391 (2006-02-21)
Uveal melanoma has a high mortality rate due to a high incidence of metastasis (up to 50%), which preferentially occurs in the liver. Conventional chemotherapy, being the only therapeutic option today against metastatic uveal melanoma, has not proved to be
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