meso-Zeaxanthin
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meso-Zeaxanthin ((3R,3′S)-Zeaxanthin) is an orally active xanthophyll carotenoid. meso-Zeaxanthin inhibits CYP1A1, CYP1A2, CYP2B1/2, COX-2, TNF-α and iNOS, and enhances the activities of Uridine diphosphate glucuronosyltransferase and Glutathione-S-transferase. meso-Zeaxanthin quenches oxygen free radicals. meso-Zeaxanthin filters short-wavelength blue light, alleviates oxidative damage and visual abnormalities. meso-Zeaxanthin reduces tumor incidence, prolongs tumor latency and survival rate of tumor-bearing mice, and inhibits paw edema. meso-Zeaxanthin can be used in research related to sarcoma and age-related macular degeneration.
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- Pureza: 93.09%
- No. CAS: 31272-50-1
- Fòrmula: C40H56O2
- Peso molecular:568.87
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Almacenamiento:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Actividad biológica
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Chemical Information
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Solvente y solubilidad
- Pureza y Documentación
- Referencias
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Help & FAQs
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Actividad biológica
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COX-2 |
CYP1A1 |
CYP1A2 |
CYP2B1 |
CYP2B2 |
iNOS |
meso-Zeaxanthin (5-25 μg/mL; 24 h) potently inhibits LPS-induced inflammatory responses in mouse peritoneal macrophages, reducing pro-inflammatory cytokine, C-reactive protein, and nitric oxide production (with maximum inhibition at 25 μg/mL) and down-regulating mRNA expression of TNF-α, iNOS, and COX-2[2].
meso-Zeaxanthin acts as a potent singlet oxygen-quenching antioxidant when bound to a zeaxanthin-binding protein, and a 1:1:1 mixture of meso-Zeaxanthin, lutein, and zeaxanthin has greater singlet oxygen-quenching activity than any of the individual carotenoids in vitro[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Meso-Zeaxanthin (50-250 mg/kg; p.o.; once daily; for 15 consecutive days) dose-dependently inhibits Phenobarbitone-induced cytochrome P450 isoenzyme activity, and the 250 mg/kg dose restores this activity to baseline levels[1].
Meso-Zeaxanthin (50-250 mg/kg; p.o.; once daily; for 15 consecutive days) dose-dependently increases the activity of hepatic phase II detoxifying enzymes. Specifically, in the 250 mg/kg dose group, UDP-glucuronosyltransferase activity doubles compared to the baseline level, and glutathione-S-transferase activity increases to 3-fold of the baseline level[1].
meso-Zeaxanthin (50-250 mg/kg; p.o.; once daily; for 5 consecutive days) dose-dependently inhibits carrageenan (HY-125474)-induced acute paw edema in male Balb/c mice[2].
meso-Zeaxanthin (50-250 mg/kg; p.o.; once daily; for 5 consecutive days) dose-dependently inhibits dextran-induced acute paw edema in male Balb/c mice[2].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Swiss albino (male, 6-8 wk old, 25 g body weight, 3-methylcholanthrene-induced sarcoma)[1]
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Dosage:50 mg/kg; 250 mg/kg
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Administration:p.o.; 6 days/week; 20 weeks
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Result:Delayed sarcoma onset to week 15 (vs week 6 in controls).
Kept all animals alive through week 16.
Delayed sarcoma onset to week 18, with only 1 animal developing sarcoma by week 18.
Kept all animals alive through week 20.
Achieved 9 of 15 (60%) animals alive with no tumors at 30-week endpoint.
Reduced tumor size compared to controls.
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Animal Model:Wistar (male, 5-6 wk old, 180 g body weight, phenobarbitone-induced microsomal enzyme activation)[1]
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Dosage:50 mg/kg; 250 mg/kg
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Administration:p.o.; once daily; 15 days
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Result:Reduced CYP1A1 (PROD) activity to 7 nmol resorufin formed/min/mg protein.
Reduced CYP1A2 (MROD) activity to 6.9 nmol resorufin formed/min/mg protein.
Reduced CYP2B1/2 (EROD) activity to 10 nmol resorufin formed/min/mg protein.
Reduced CYP1A1 (PROD) activity to 3.9 nmol resorufin formed/min/mg protein.
Reduced CYP1A2 (MROD) activity to 5.4 nmol resorufin formed/min/mg protein.
Reduced CYP2B1/2 (EROD) activity to 6.8 nmol resorufin formed/min/mg protein, levels near those of untreated normal rats.
Produced statistically significant reductions (P = 0.003 for EROD; P = 0.004 for MROD and PROD) compared to phenobarbitone-only controls.
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Animal Model:Wistar (male, 5-6 wk old, 180 g body weight)[1]
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Dosage:50 mg/kg; 250 mg/kg
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Administration:p.o.; once daily; 15 days
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Result:Increased UDP-glucuronyl transferase activity to 34.93 nmol/min/mg protein.
Increased glutathione-S-transferase activity to 75.1 nmol/min/mg protein.
Increased UDP-glucuronyl transferase activity to 55.6 nmol/min/mg protein.
Increased glutathione-S-transferase activity to 130.8 nmol/min/mg protein.
Produced statistically significant increases (P = 0.004) compared to untreated normal rats.
| NCT Number | Sponsor | Condition | Start Date |
Phase
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|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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No. CAS 31272-50-1
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Appearance Solid
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Peso molecular 568.87
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Fòrmula C40H56O2
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Color Orange to red
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SMILES
CC1(C)C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C[C@@H](O)CC2(C)C)=C(C)C[C@H](O)C1
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Synonyms
(3R,3′S)-Zeaxanthin
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Envío
Room temperature in continental US; may vary elsewhere.
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Almacenamiento
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvente y solubilidad
DMSO : 0.29 mg/mL (0.51 mM; ultrasonic and warming and heat to 60°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Pureza y Documentación
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Ficha de datos (272 KB)
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SDS (254 KB)
- English - EN (254 KB)
- Français - FR (254 KB)
- Deutsch - DE (254 KB)
- Norwegian - NO (254 KB)
- Español - ES (254 KB)
- Swedish - SV (254 KB)
- Italian - IT (254 KB)
- Korean - KR (254 KB)
- Portuguese - PT (254 KB)
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Instrucciones de manejo (2659 KB)
Referencias
[1]. Firdous AP, et al. Anticarcinogenic activity of meso-zeaxanthin in rodents and its possible mechanism of action. Nutrition and cancer. 2013;65(6):850-6. [Content Brief]
[2]. Firdous AP, et al. Anti-inflammatory potential of carotenoid meso-zeaxanthin and its mode of action. Pharmaceutical biology. 2015 Jul;53(7):961-7. [Content Brief]
[3]. Nolan JM, et al. What is meso-zeaxanthin, and where does it come from?. Eye (London, England). 2013 Aug;27(8):899-905. [Content Brief]
[4]. Bernstein PS, et al. Lutein, zeaxanthin, and meso-zeaxanthin: The basic and clinical science underlying carotenoid-based nutritional interventions against ocular disease. Progress in retinal and eye research. 2016 Jan;50:34-66. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
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