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2226-96-2, 4-Hydroxy-TEMPO

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Names

Name 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy
Synonym More Synonyms

 4-Hydroxy-TEMPO Biological Activity

Description Tempol is a general superoxide dismutase (SOD)-mimetic drug that efficiently neutralizes reactive oxygen species (ROS).
Related Catalog
Target

ROS[1]

In Vitro Tempol significantly attenuates H2O2-mediated decrease in mitochondrial respiration and increase in LDH release from rat PT cells, indicating a reduction in cell injury and death. The beneficial actions of Tempol are similar to those obtained using the Fe2+ chelator DEF. However, coadministration of DEF and Tempol does not produce any additional beneficial actions against renal ischemia/reperfusion injury or against oxidative stress-mediated PT cell injury/death[2].
In Vivo SOD-mimetic Tempol is able to mimic resveratrol’s effects on heart function. Tempol is administered daily by gavage. Mice treated with Met or Tmp had decreased PR and QTc intervals and increased heart rates compared to peroral vehicle (VEH). These results are similar to that obtained by treatment with RSV. Pre- and post-treatment profiles of individual mice are illustrated[1]. Tempol, a membrane-permeable radical scavenger, reduces oxidant stress-mediated renal dysfunction and injury in the rat. Tempol significantly reduces the increase in urea, creatinine, γGT, AST, NAG, and FENa produced by renal ischemia/reperfusion, suggesting an improvement in both renal function and injury. Tempol also significantly reduces kidney MPO activity and MDA levels, indicating a reduction in PMN infiltration and lipid peroxidation, respectively. Tempol reduces the histologic evidence of renal damage associated with ischemia/reperfusion and caused a substantial reduction in the staining for nitrotyrosine and PARS, suggesting reduced nitrosative and oxidative stress[2].
Cell Assay To investigate the effect of Tempol, DEF, and DEF coadministered with Tempol on H2O2-mediated cell injury and death, confluent cultures of PT cells are preincubated (10 min at 37°C) with Tempol (0.03 to 10 mM), DEF (0.03 to 10 mM), or DEF (3 mM) in combination with Tempol (3 mM). The ranges of concentrations of Tempol and DEF are based on those previously shown in this laboratory to reduce on H2O2-mediated cell injury and death in (1) cultured rat cardiac myoblasts (Tempol) and (2) primary cultures of rat PT cells (DEF ). PT cell cultures are then incubated with H2O2 (1 mM) for four hours, after which cellular injury and death are assessed. Upon completion of incubations, cellular injury and death are assessed using the spectrophotometric assays described later in this article[2].
Animal Admin Mice[1] Female or male BALB/c mice (5-7 weeks of age) are used. Mice are infected intraperitoneally (i.p.) with 102 blood trypomastigote forms of the type I Colombian strain of T. cruzi. Treatments are performed daily for 30 days from the establishment of CCC (60 dpi) by i.p. injection of 15 mg/kg trans-resveratrol (10% ethanol/PBS), vehicle (10% ethanol/PBS), 5 mg/Kg EX527 (0.1% DMSO), or peroral administration of 40 mg/Kg Resveratrol (10%ethanol-PBS), 500 mg/kg Metformin (dissolved in water), 100 mg/kg Tempol (dissolved in water), Benznidazole (25 mg/Kg, dissolved in water) and vehicle (water or 10%ethanol-PBS). Rats[2] 83 male Wistar rats weighing 230 to 320 g are used.Upon completion of surgical procedures, the animals are randomly allocated to the eight groups. At one minute before commencement of reperfusion, animals received a bolus injection of either vehicle (saline, 4 mL/kg, IV), Tempol (30 mg/kg in saline, IV), DEF (40 mg/kg in saline, IV), or DEF (40 mg/kg in saline, IV) in combination with Tempol (30 mg/kg in saline, IV). The corresponding groups then received a continuous infusion of one of the following throughout the reperfusion period: vehicle (saline, 4 mL/kg/h, IV), Tempol (30 mg/kg/h in saline, IV), DEF (40 mg/kg/h in saline, IV), or Tempol and DEF in combination (30 and 40 mg/kg/h, respectively, in saline, IV). To elucidate the effects of Tempol or DEF on cardiovascular hemodynamics and organ function in sham-operated rats, respective groups of animals received the treatments described previously in this article and as outlined. The concentration of Tempol administered in vivo is based on those previously demonstrated by us to provide significant protection against myocardial ischemia/reperfusion injury in an in vivo rat model. Similarly, the concentration of DEF used is identical to that which we have previously used to provide significant protection against hepatic ischemia/reperfusion injury in in vivo rat and rabbit models.
References

[1]. Vilar-Pereira G, et al. Resveratrol Reverses Functional Chagas Heart Disease in Mice. PLoS Pathog. 2016 Oct 27;12(10):e1005947.

[2]. Chatterjee PK, et al. Tempol, a membrane-permeable radical scavenger, reduces oxidant stress-mediated renal dysfunction and injury in the rat. Kidney Int. 2000 Aug;58(2):658-73.

 Chemical & Physical Properties

Density 1.187 g/cm3
Boiling Point 269ºC
Melting Point 69-71 °C(lit.)
Molecular Formula C9H18NO2*
Molecular Weight 172.24
PSA 23.47000
LogP 1.28370
Storage condition 2-8°C
Stability Stable. Incompatible with strong oxidizing agents.
Water Solubility soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TN8991000
CHEMICAL NAME :
Piperidinooxy, 4-hydroxy-2,2,6,6-tetramethyl-
CAS REGISTRY NUMBER :
2226-96-2
LAST UPDATED :
199710
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C9-H18-N-O2
MOLECULAR WEIGHT :
172.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
1053 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) – effect, not otherwise specified Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – dyspnea

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Bacteria – Salmonella typhimurium
DOSE/DURATION :
24 umol/plate
REFERENCE :
ABBIA4 Archives of Biochemistry and Biophysics. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.31- 1951- Volume(issue)/page/year: 251,393,1986

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22;R36/38
Safety Phrases S26-S36-S37/39
RIDADR NONH for all modes of transport
WGK Germany 1
RTECS TN8991000
HS Code 29333999

 Customs

HS Code 29333999

 Articles69

More Articles

NADPH oxidase 2-derived superoxide downregulates endothelial KCa3.1 in preeclampsia.

Free Radic. Biol. Med. 57 , 10-21, (2013)

Endothelial dysfunction is associated with KCa3.1 dysfunction and contributes to the development of hypertension in preeclampsia. However, evidence of endothelial KCa3.1 dysfunction in the vascular sy…

Gastrokine 1 inhibits the carcinogenic potentials of Helicobacter pylori CagA.

Carcinogenesis 35(11) , 2619-29, (2014)

Helicobacter pylori CagA directly injected by the bacterium into epithelial cells via a type IV secretion system, leads to cellular changes such as morphology, apoptosis, proliferation and cell motili…

Organic Radical Contrast Agents Based on Polyacetylenes Containing 2,2,6,6-Tetramethylpiperidine 1-Oxyl (TEMPO): Targeted Magnetic Resonance (MR)/Optical Bimodal Imaging of Folate Receptor Expressing HeLa Tumors in Vitro and in Vivo(a).

Macromol. Biosci. 15 , 788-98, (2015)

Nitroxides have great potential as magnetic resonance imaging (MRI) contrast agents for tumor detection. Polyacetylenes(PAs) containing 2,2,6,6-tetramethyl-piperidine oxyl (TEMPO) and poly(ethylene gl…

 Synonyms

4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl,TEMPOL
HYDROXY-TEMPO
(4-Hydroxy-2,2,6,6-tetramethyl-1-piperidinyl)oxidanyl
4-Hydroxy-TEMPO Free Radical
EINECS 218-761-4
Tempol
(4-Hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl
4-Oxypiperidol
Tetramethylpiperidino-N-oxyl
TMPN
4-Hydroxy-2,2,6,6-tetramethylpiperidine N-oxide
4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy, free radical
Tanol
4-Hydroxy-TEMPO
4-Hydroxy-2,2,6,6-tetramethylpiperidinoxyl
4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl free radical
4-Hydroxy-2,2,6,6-te
NR-I
4-hydroxy-2,2,6,6-tetramethyl piperidinyloxy,free radical
4-hydroxy-2,2,6,6-tetramethylpiperidinoxy radical
nr1
2,2,6,6-Tetramethyl-4-piperidinol 1-oxyl
2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy
4-Hydroxy-2,2,6,6-tetramethylpiperidinooxyl
nitroxyl2
OH-Tempo, 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical
2,2,6,6-Tetramethyl-4-hydroxy-1-piperidinyloxy radical
4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy,free radical
4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl
Tetramethylpiperidinol N-oxyl
2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy radical
4-OH-TEMPO
4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine
4-hydroxy-2,2,6,6-tetramethyl-piperidinyloxy
1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-
4-Hydroxy-2,2,6,6-tetramethylpiperidinooxy radical
4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxy
MFCD00006478

 

 

 

 

Names

Name 4-Hydroxy-2,2,6,6-tetramethyl-piperidinooxy
Synonym More Synonyms

 4-Hydroxy-TEMPO Biological Activity

Description Tempol is a general superoxide dismutase (SOD)-mimetic drug that efficiently neutralizes reactive oxygen species (ROS).
Related Catalog
Target

ROS[1]

In Vitro Tempol significantly attenuates H2O2-mediated decrease in mitochondrial respiration and increase in LDH release from rat PT cells, indicating a reduction in cell injury and death. The beneficial actions of Tempol are similar to those obtained using the Fe2+ chelator DEF. However, coadministration of DEF and Tempol does not produce any additional beneficial actions against renal ischemia/reperfusion injury or against oxidative stress-mediated PT cell injury/death[2].
In Vivo SOD-mimetic Tempol is able to mimic resveratrol’s effects on heart function. Tempol is administered daily by gavage. Mice treated with Met or Tmp had decreased PR and QTc intervals and increased heart rates compared to peroral vehicle (VEH). These results are similar to that obtained by treatment with RSV. Pre- and post-treatment profiles of individual mice are illustrated[1]. Tempol, a membrane-permeable radical scavenger, reduces oxidant stress-mediated renal dysfunction and injury in the rat. Tempol significantly reduces the increase in urea, creatinine, γGT, AST, NAG, and FENa produced by renal ischemia/reperfusion, suggesting an improvement in both renal function and injury. Tempol also significantly reduces kidney MPO activity and MDA levels, indicating a reduction in PMN infiltration and lipid peroxidation, respectively. Tempol reduces the histologic evidence of renal damage associated with ischemia/reperfusion and caused a substantial reduction in the staining for nitrotyrosine and PARS, suggesting reduced nitrosative and oxidative stress[2].
Cell Assay To investigate the effect of Tempol, DEF, and DEF coadministered with Tempol on H2O2-mediated cell injury and death, confluent cultures of PT cells are preincubated (10 min at 37°C) with Tempol (0.03 to 10 mM), DEF (0.03 to 10 mM), or DEF (3 mM) in combination with Tempol (3 mM). The ranges of concentrations of Tempol and DEF are based on those previously shown in this laboratory to reduce on H2O2-mediated cell injury and death in (1) cultured rat cardiac myoblasts (Tempol) and (2) primary cultures of rat PT cells (DEF ). PT cell cultures are then incubated with H2O2 (1 mM) for four hours, after which cellular injury and death are assessed. Upon completion of incubations, cellular injury and death are assessed using the spectrophotometric assays described later in this article[2].
Animal Admin Mice[1] Female or male BALB/c mice (5-7 weeks of age) are used. Mice are infected intraperitoneally (i.p.) with 102 blood trypomastigote forms of the type I Colombian strain of T. cruzi. Treatments are performed daily for 30 days from the establishment of CCC (60 dpi) by i.p. injection of 15 mg/kg trans-resveratrol (10% ethanol/PBS), vehicle (10% ethanol/PBS), 5 mg/Kg EX527 (0.1% DMSO), or peroral administration of 40 mg/Kg Resveratrol (10%ethanol-PBS), 500 mg/kg Metformin (dissolved in water), 100 mg/kg Tempol (dissolved in water), Benznidazole (25 mg/Kg, dissolved in water) and vehicle (water or 10%ethanol-PBS). Rats[2] 83 male Wistar rats weighing 230 to 320 g are used.Upon completion of surgical procedures, the animals are randomly allocated to the eight groups. At one minute before commencement of reperfusion, animals received a bolus injection of either vehicle (saline, 4 mL/kg, IV), Tempol (30 mg/kg in saline, IV), DEF (40 mg/kg in saline, IV), or DEF (40 mg/kg in saline, IV) in combination with Tempol (30 mg/kg in saline, IV). The corresponding groups then received a continuous infusion of one of the following throughout the reperfusion period: vehicle (saline, 4 mL/kg/h, IV), Tempol (30 mg/kg/h in saline, IV), DEF (40 mg/kg/h in saline, IV), or Tempol and DEF in combination (30 and 40 mg/kg/h, respectively, in saline, IV). To elucidate the effects of Tempol or DEF on cardiovascular hemodynamics and organ function in sham-operated rats, respective groups of animals received the treatments described previously in this article and as outlined. The concentration of Tempol administered in vivo is based on those previously demonstrated by us to provide significant protection against myocardial ischemia/reperfusion injury in an in vivo rat model. Similarly, the concentration of DEF used is identical to that which we have previously used to provide significant protection against hepatic ischemia/reperfusion injury in in vivo rat and rabbit models.
References

[1]. Vilar-Pereira G, et al. Resveratrol Reverses Functional Chagas Heart Disease in Mice. PLoS Pathog. 2016 Oct 27;12(10):e1005947.

[2]. Chatterjee PK, et al. Tempol, a membrane-permeable radical scavenger, reduces oxidant stress-mediated renal dysfunction and injury in the rat. Kidney Int. 2000 Aug;58(2):658-73.

 Chemical & Physical Properties

Density 1.187 g/cm3
Boiling Point 269ºC
Melting Point 69-71 °C(lit.)
Molecular Formula C9H18NO2*
Molecular Weight 172.24
PSA 23.47000
LogP 1.28370
Storage condition 2-8°C
Stability Stable. Incompatible with strong oxidizing agents.
Water Solubility soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TN8991000
CHEMICAL NAME :
Piperidinooxy, 4-hydroxy-2,2,6,6-tetramethyl-
CAS REGISTRY NUMBER :
2226-96-2
LAST UPDATED :
199710
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C9-H18-N-O2
MOLECULAR WEIGHT :
172.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 – Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent – rat
DOSE/DURATION :
1053 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) – effect, not otherwise specified Behavioral – convulsions or effect on seizure threshold Lungs, Thorax, or Respiration – dyspnea

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Bacteria – Salmonella typhimurium
DOSE/DURATION :
24 umol/plate
REFERENCE :
ABBIA4 Archives of Biochemistry and Biophysics. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.31- 1951- Volume(issue)/page/year: 251,393,1986

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22;R36/38
Safety Phrases S26-S36-S37/39
RIDADR NONH for all modes of transport
WGK Germany 1
RTECS TN8991000
HS Code 29333999

 Customs

HS Code 29333999

 Articles69

More Articles

NADPH oxidase 2-derived superoxide downregulates endothelial KCa3.1 in preeclampsia.

Free Radic. Biol. Med. 57 , 10-21, (2013)

Endothelial dysfunction is associated with KCa3.1 dysfunction and contributes to the development of hypertension in preeclampsia. However, evidence of endothelial KCa3.1 dysfunction in the vascular sy…

Gastrokine 1 inhibits the carcinogenic potentials of Helicobacter pylori CagA.

Carcinogenesis 35(11) , 2619-29, (2014)

Helicobacter pylori CagA directly injected by the bacterium into epithelial cells via a type IV secretion system, leads to cellular changes such as morphology, apoptosis, proliferation and cell motili…

Organic Radical Contrast Agents Based on Polyacetylenes Containing 2,2,6,6-Tetramethylpiperidine 1-Oxyl (TEMPO): Targeted Magnetic Resonance (MR)/Optical Bimodal Imaging of Folate Receptor Expressing HeLa Tumors in Vitro and in Vivo(a).

Macromol. Biosci. 15 , 788-98, (2015)

Nitroxides have great potential as magnetic resonance imaging (MRI) contrast agents for tumor detection. Polyacetylenes(PAs) containing 2,2,6,6-tetramethyl-piperidine oxyl (TEMPO) and poly(ethylene gl…

 Synonyms

4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl,TEMPOL
HYDROXY-TEMPO
(4-Hydroxy-2,2,6,6-tetramethyl-1-piperidinyl)oxidanyl
4-Hydroxy-TEMPO Free Radical
EINECS 218-761-4
Tempol
(4-Hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl
4-Oxypiperidol
Tetramethylpiperidino-N-oxyl
TMPN
4-Hydroxy-2,2,6,6-tetramethylpiperidine N-oxide
4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy, free radical
Tanol
4-Hydroxy-TEMPO
4-Hydroxy-2,2,6,6-tetramethylpiperidinoxyl
4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl free radical
4-Hydroxy-2,2,6,6-te
NR-I
4-hydroxy-2,2,6,6-tetramethyl piperidinyloxy,free radical
4-hydroxy-2,2,6,6-tetramethylpiperidinoxy radical
nr1
2,2,6,6-Tetramethyl-4-piperidinol 1-oxyl
2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy
4-Hydroxy-2,2,6,6-tetramethylpiperidinooxyl
nitroxyl2
OH-Tempo, 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-Oxyl Free Radical
2,2,6,6-Tetramethyl-4-hydroxy-1-piperidinyloxy radical
4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy,free radical
4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl
Tetramethylpiperidinol N-oxyl
2,2,6,6-Tetramethyl-4-hydroxypiperidinooxy radical
4-OH-TEMPO
4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine
4-hydroxy-2,2,6,6-tetramethyl-piperidinyloxy
1-Piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-
4-Hydroxy-2,2,6,6-tetramethylpiperidinooxy radical
4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxy
MFCD00006478

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