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N1165

Sigma-Aldrich

Pimonidazole

≥98% (HPLC)

Synonym(s):

NSC 380540, PD 126675;, Ro 03-8799;, alpha-((2-Nitroimidazol-1-yl)methyl)-1-piperidineethanol;, alpha-[(2-Nitro-1H-imidazol-1-yl)methyl]-1-piperidineethanol

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About This Item

Empirical Formula (Hill Notation):
C11H18N4O3
CAS Number:
70132-50-2
Molecular Weight:
254.29
MDL number:
MFCD00867974
UNSPSC Code:
12352200
PubChem Substance ID:
329818508
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

yellow

solubility

DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

OC(CN1CCCCC1)Cn2ccnc2[N+]([O-])=O

InChI

1S/C11H18N4O3/c16-10(8-13-5-2-1-3-6-13)9-14-7-4-12-11(14)15(17)18/h4,7,10,16H,1-3,5-6,8-9H2

InChI key

WVWOOAYQYLJEFD-UHFFFAOYSA-N

Biochem/physiol Actions

Pimonidazole is an effective and nontoxic exogenous 2-nitroimidazole hypoxia marker. Pimonidazole forms adducts with thiol groups in proteins, peptides and amino acids.
Pimonidazole possesses a nitro group at position 2 and an imidazole ring. Pimonidazole undergoes reduction and is activated in hypoxic cells.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Lena-Christin Conradi et al.
Angiogenesis, 20(4), 599-613 (2017-09-07)
Blockade of the glycolytic activator PFKFB3 in cancer cells (using a maximum tolerable dose of 70 mg/kg of the PFKFB3 blocker 3PO) inhibits tumor growth in preclinical models and is currently being tested as a novel anticancer treatment in phase I
Hypoxia Studies with Pimonidazole in vivo
Aguilera KY and Brekken RA
Bio-protocol, 4(19) (2014)
Yong Chen et al.
Disease models & mechanisms, 12(12) (2019-11-11)
Major risk factors for necrotizing enterocolitis (NEC) are formula feeding and prematurity; however, their pathogenic mechanisms are unknown. Here, we found that insufficient arginine/nitric oxide synthesis limits blood flow in the intestinal microvasculature, leading to hypoxia, mucosal damage and NEC
Loren P Thompson et al.
Biology of reproduction, 95(6), 128-128 (2016-11-04)
Chronic placental hypoxia is one of the root causes of placental insufficiencies that result in pre-eclampsia and maternal hypertension. Chronic hypoxia causes disruption of trophoblast (TB) development, invasion into maternal decidua, and remodeling of maternal spiral arteries. The pregnant guinea
Katarzyna B Leszczynska et al.
The Journal of clinical investigation, 125(6), 2385-2398 (2015-05-12)
Restoration of hypoxia-induced apoptosis in tumors harboring p53 mutations has been proposed as a potential therapeutic strategy; however, the transcriptional targets that mediate hypoxia-induced p53-dependent apoptosis remain elusive. Here, we demonstrated that hypoxia-induced p53-dependent apoptosis is reliant on the DNA-binding
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