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T9576

Picropodophyllotoxin

Name: Picropodophyllotoxin
Brand: SIGMA

≥96% (HPLC), powder

Sinónimos:

(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

Fórmula empírica (notación de Hill):

C₂₂H₂₂O₈

Número de CAS:

477-47-4

Peso molecular:

414.41

MDL number:

MFCD01742647

UNSPSC Code:

12352200

PubChem Substance ID:

329826907

NACRES:

NA.77

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)

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.

Quality

May contain 2-3% ethanol (w/w)

Preparation Note

Picropodophyllotoxin is soluble in DMSO at a concentration that is greater than 5 mg/ml.

pictograms

GHS06

signalword

Danger

hcodes

H301,H312,H315,H319,H335

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P305 + P351 + P338

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Declining vulnerability to river floods and the global benefits of adaptation.

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

IGF-1 receptor tyrosine kinase inhibition by the cyclolignan PPP induces G2/M-phase accumulation and apoptosis in multiple myeloma cells.

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

Patterns in the relationship between life expectancy and gross domestic product in Russia in 2005-15: a cross-sectional analysis.

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

Insulin-like growth factor 1 receptor regulates hypothermia during calorie restriction.

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

The insulin-like growth factor-I receptor inhibitor picropodophyllin causes tumor regression and attenuates mechanisms involved in invasion of uveal melanoma cells.

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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