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H9415

Sigma-Aldrich

5HPP-33

≥98% (HPLC), solid

Synonym(s):

2-[2,6-bis(1-Methylethyl)phenyl]-5-hydroxy-1H-isoindole-1,3(2H)-dione, 5-Hydroxy-2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione

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About This Item

Empirical Formula (Hill Notation):
C20H21NO3
CAS Number:
105624-86-0
Molecular Weight:
323.39
MDL number:
MFCD03085294
UNSPSC Code:
12352200
PubChem Substance ID:
329815265
NACRES:
NA.77

Assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

CC(C)c1cccc(C(C)C)c1N2C(=O)c3ccc(O)cc3C2=O

InChI

1S/C20H21NO3/c1-11(2)14-6-5-7-15(12(3)4)18(14)21-19(23)16-9-8-13(22)10-17(16)20(21)24/h5-12,22H,1-4H3

InChI key

LAKWINYVWJPHQW-UHFFFAOYSA-N

Biochem/physiol Actions

5HPP-33 is a thalidomide derivative which was reported to be active as anticancer agent through stabilization of the microtubules. 5HPP-33 has shown inhibition of cell proliferation of both estrogen-dependent (MCF-7) and estrogen-independent (MDA-MB-231) breast cancer cells as well as other cell lines. A study in tubulin forming assay reported that 5HPP-33 acts as a microtubule formation inhibitor (IC50=810 nM).

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Nicole C Kleinstreuer et al.
Environmental health perspectives, 119(11), 1596-1603 (2011-07-27)
Understanding health risks to embryonic development from exposure to environmental chemicals is a significant challenge given the diverse chemical landscape and paucity of data for most of these compounds. High-throughput screening (HTS) in the U.S. Environmental Protection Agency (EPA) ToxCast™
Robert G Ellis-Hutchings et al.
Reproductive toxicology (Elmsford, N.Y.), 70, 82-96 (2017-05-22)
Embryonic vascular disruption is an important adverse outcome pathway (AOP) as chemical disruption of cardiovascular development induces broad prenatal defects. High throughput screening (HTS) assays aid AOP development although linking in vitro data to in vivo apical endpoints remains challenging.
Nicole Kleinstreuer et al.
PLoS computational biology, 9(4), e1002996-e1002996 (2013-04-18)
Vascular development is a complex process regulated by dynamic biological networks that vary in topology and state across different tissues and developmental stages. Signals regulating de novo blood vessel formation (vasculogenesis) and remodeling (angiogenesis) come from a variety of biological
Takahiro Hamoya et al.
Journal of clinical biochemistry and nutrition, 60(3), 199-207 (2017-06-07)
It is important to establish effective methods for preventing colorectal cancer because the number of colorectal cancer deaths is increasing. Erythromycin one of the macrolide antibiotics, has been shown to exert pleiotropic effects, such as anti-inflammatory and anti-oxidative effects, on
Maria Ivshina et al.
Molecular and cellular biology, 35(3), 610-618 (2014-12-03)
The cytoplasmic-element-binding (CPEB) protein is a sequence-specific RNA-binding protein that regulates cytoplasmic polyadenylation-induced translation. In mouse embryo fibroblasts (MEFs) lacking CPEB, many mRNAs encoding proteins involved in inflammation are misregulated. Correlated with this aberrant translation in MEFs, a macrophage cell

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