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D185

Sigma-Aldrich

Diethylenetriamine/nitric oxide adduct

≥97% (NMR), solid

Synonym(s):

2,2′-(Hydroxynitrosohydrazono)bis-ethanimine, DETA/NO

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About This Item

Empirical Formula (Hill Notation):
C4H13N5O2
CAS Number:
146724-94-9
Molecular Weight:
163.18
MDL number:
MFCD00210194
UNSPSC Code:
12352200
PubChem Substance ID:
24893279
NACRES:
NA.77

assay

≥97% (NMR)

form

solid

storage condition

desiccated
under inert gas

color

off-white

solubility

H2O: >20 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

NCCN(CC[NH3+])N([O-])N=O

InChI

1S/C4H12N5O2/c5-1-3-8(4-2-6)9(11)7-10/h1-6H2/q-1/p+1

InChI key

PAOXTYJXTPPVHU-UHFFFAOYSA-O

Application

Diethylenetriamine/nitric oxide adduct has been used as nitric oxide (NO) donor:
  • to evaluate the direct effects of NO on cell proliferation in ovine trophectoderm (oTr1) cells
  • to test its effects on recreating the growth inhibitory effect of NO without the presence of macrophages
  • to correlate the outflow function and outflow tract vessel diameter changes with other controls in porcine models

Biochem/physiol Actions

Diethylenetriamine/nitric oxide adduct (DETA/NO) is a NONOate, which has the longest NO?generating half?life in vitro. Inhaled DETA/NO acts as a pulmonary vasodilator in animals and humans. This NO donor releases nitric oxide in solution in a controlled manner. DETA/NO is associated with protein downregulation, upregulation of p53 expression. It enhances p53 post-translational modifications and also downregulates Nanog and Oct4 mRNA.

Caution

Air sensitive

pictograms

Flame
GHS02

signalword

Danger

hcodes

H242

Hazard Classifications

Self-react. C

Storage Class

5.2 - Organic peroxides and self-reacting hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Xiaoqiu Wang et al.
Biology of reproduction, 92(3), 75-75 (2015-02-06)
In mammal species, arginine is a multifunctional amino acid required for survival, growth, and development of conceptuses (embryo/fetus and associated extraembryonic membranes) during the peri-implantation period of pregnancy. However, functional roles of arginine with respect to it being a substrate
Susannah Waxman et al.
Investigative ophthalmology & visual science, 59(12), 4886-4895 (2018-10-23)
To correlate outflow function and outflow tract vessel diameter changes induced by nitric oxide (NO). In a porcine anterior segment perfusion model, the effects of a nitric oxide donor (100 μM DETA-NO) on outflow facility were compared with controls (n
Chen Fuh Lam et al.
Clinical and experimental pharmacology & physiology, 30(9), 709-711 (2003-08-28)
1. Inhaled diethylenetriamine nitric oxide adduct (DETA/NO) has been shown to be a selective pulmonary vasodilator in animal and human studies. The aims of the present study were to investigate the effect of DETA/NO on mouse precontracted isolated tracheal smooth
S Mora-Castilla et al.
Cell death and differentiation, 17(6), 1025-1033 (2010-01-16)
Exposure of mouse embryonic stem (mES) cells to high concentrations of chemical nitric oxide (NO) donors promotes differentiation, but the mechanisms involved in this process at the gene expression level are poorly defined. In this study we report that culture
Marcela Simontacchi et al.
Plant science : an international journal of experimental plant biology, 183, 159-166 (2011-12-27)
This work was aimed to investigate nitrosyl-Fe complexes formation by reaction of endogenous ligands and Fe, in sorghum embryonic axes exposed to NO-donors. Electron paramagnetic resonance (EPR) was employed to detect the presence of nitrosyl-Fe complexes in plant embryos, as
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