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Merck

T9576

Sigma-Aldrich

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
MDL number:
MFCD01742647
UNSPSC Code:
12352200
PubChem Substance ID:
329826907
NACRES:
NA.77

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

Signal Word

Danger

Hazard Statements

H301,H312,H315,H319,H335

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 Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
081M4720V
067K47114
067K47113
067K47112
067K47111

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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)
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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)
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Proceedings of the National Academy of Sciences of the United States of America, 114(36), 9731-9736 (2017-08-23)
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Clinical cancer research : an official journal of the American Association for Cancer Research, 12(4), 1383-1391 (2006-02-21)
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