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C221

Sigma-Aldrich

Carboxy-PTIO potassium salt

Synonym(s):

2-(4-Carboxyphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide potassium salt, 2-(4-Carboxyphenyl)-4,5-dihydro-4,4,5,5-tetramethyl-1H-imidazol-1-yloxy-3-oxide potassium salt

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About This Item

Empirical Formula (Hill Notation):
C14H16KN2O4
CAS Number:
148819-94-7
Molecular Weight:
315.39
MDL number:
MFCD00216153
UNSPSC Code:
12352200
PubChem Substance ID:
24892474
NACRES:
NA.32

biological source

synthetic (organic)

Assay

≥98% (TLC)

form

powder

mp

>270 °C

solubility

H2O: 100 mg/mL
DMSO: soluble (lit.)(lit.)
methanol: soluble (lit.)(lit.)

storage temp.

2-8°C

SMILES string

[K+].CC1(C)N([O])C(c2ccc(cc2)C([O-])=O)=[N+]([O-])C1(C)C

InChI

1S/C14H17N2O4.K/c1-13(2)14(3,4)16(20)11(15(13)19)9-5-7-10(8-6-9)12(17)18;/h5-8H,1-4H3,(H,17,18);/q;+1/p-1

InChI key

VYEUQMVIGXFZQU-UHFFFAOYSA-M

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General description

2-(4-Carboxyphenyl)-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide (carboxy-PTIO) is mainly considered as a scavenger of nitric oxide (NO).

Application

Carboxy-PTIO potassium salt has been used to check the generation of hydroxyl radicals or nitric in reaction mixtures to examine the generation of nitric oxide in reaction mixture. It has also been added to neurons to analyse its effect on glucose/oxygen/serum deprivation (GOSD) condition(4)

Biochem/physiol Actions

Carboxy-PTIO can make a quick reaction with nitric oxide (NO) to produce nitrogen dioxide (NO2). It can be used to prevent hypotension and endotoxic shock, stimulated by lipopolysaccharide in- vivo. Carboxy-PTIO can also block in vitro vascular relaxation, stimulated by NO.
Reacts with nitric oxide to form carboxy-PTI derivatives which in turn inhibits nitric oxide synthase.

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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Raymond N Allan et al.
Nitric oxide : biology and chemistry, 65, 43-49 (2017-02-27)
Bacterial biofilms show high tolerance towards antibiotics and are a significant problem in clinical settings where they are a primary cause of chronic infections. Novel therapeutic strategies are needed to improve anti-biofilm efficacy and support reduction in antibiotic use. Treatment
Xinyi Zhu et al.
Applied and environmental microbiology, 85(3) (2018-11-28)
While both iron and nitric oxide (NO) are redox-active environmental signals shown to regulate biofilm development, their interaction and roles in regulating biofilms have not been fully elucidated. In this study, exposure of Pseudomonas aeruginosa biofilms to exogenous NO inhibited
Nitric oxide scavenger carboxy-PTIO potentiates the inhibition of dopamine uptake by nitric oxide donors
Cao B J and Reith M EA
European Journal of Pharmacology, 448(1), 27-30 (2002)
Interference of carboxy-PTIO with nitric oxide-and peroxynitrite-mediated reactions
Pfeiffer S, et al.
Free Radical Biology & Medicine, 22(5), 787-794 (1997)
M Yoshida et al.
Biochemical and biophysical research communications, 202(2), 923-930 (1994-07-29)
We recently found a new class of nitric oxide (NO) antidote, i.e., 2-phenyl-4,4,5,5,-tetramethylimidazoline-1-oxyl-3-oxide derivatives (PTIOs). It has a potent inhibitory action against endothelium-derived relaxing factor. Here, we report the effect of a water-soluble carboxy derivative of PTIO (carboxy-PTIO) on endotoxin
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