(S)-Trolox
(Synonyms: (S)-(-)-6-羟基-2,5,7,8-四甲基色满-2-羧酸) 目录号 : GC38879
(S)-Trolox 是维生素 E 的水溶性类似物，其中的植酸基链被羧基取代。(S)-Trolox 经常用作研究结构特征的模型化合物，以及作为评估抗氧化剂活性的标准。(S)-Trolox 具有有效而特定的神经保护和抗氧化作用。
Cas No.:53174-06-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(S)-Trolox is a water-soluble analogue of vitamin E, in which the phytyl chain is replaced with a carboxyl group. (S)-Trolox is frequently used as a model compound for studies of structural features, as well as a standard for evaluation of antioxidant activity. (S)-Trolox has potent and specific neuroprotective and antioxidant effects[1][2].
The neuroprotective efficacy of antioxidant molecules against iodoacetate (IAA) neurotoxicity in rat cerebellar granule cell (CGC) cultures is investigated. In the absence of MK-801, (S)-Trolox displays marginal neuroprotective effects. In the presence of MK-801 (10 μM), the neuroprotective efficacy of (S)-Trolox is greatly enhanced, giving rise to a recovery in MTT-reductase activity equivalent to 80-100% of control cultures. (S)-Trolox displays EC50 value of 78 μM. The fluorescence increase in IAA-stimulated DCFH-DA-loaded cultures is inhibited in a dose-dependent manner by the antioxidants (S)-Trolox with an IC50 value of 97 μM. The antioxidant (S)-Trolox demonstrate apotent and specific neuroprotective action in an in vitro model of neurodegeneration induced by inhibition of the glycolytic enzyme GAPDH[1].
[1]. Malcolm CS, et al. Characterization of iodoacetate-mediated neurotoxicity in vitro using primary cultures of rat cerebellar granule cells. Free Radic Biol Med. 2000 Jan 1;28(1):102-7. [2]. GÓrecki M, et al. Chromane helicity rule--scope and challenges based on an ECD study of various trolox derivatives. Org Biomol Chem. 2014 Apr 14;12(14):2235-54.
| Cas No. | 53174-06-4 | SDF | |
| 别名 | (S)-(-)-6-羟基-2,5,7,8-四甲基色满-2-羧酸 | ||
| Canonical SMILES | O=C([C@]1(C)CCC2=C(C)C(O)=C(C)C(C)=C2O1)O | ||
| 分子式 | C14H18O4 | 分子量 | 250.29 |
| 溶解度 | DMSO : 100 mg/mL (399.54 mM; Need ultrasonic); H2O : < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.9954 mL | 19.9768 mL | 39.9537 mL |
| 5 mM | 0.7991 mL | 3.9954 mL | 7.9907 mL |
| 10 mM | 0.3995 mL | 1.9977 mL | 3.9954 mL |
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2.
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Carnosine and its (S)-Trolox™ derivative protect animals against oxidative stress
Amino Acids 2012 Jul;43(1):165-70.PMID:22389054DOI:10.1007/s00726-012-1256-4.
The novel synthetic derivative of carnosine, (S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carbonyl-β-alanyl-L-histidine (S-Trolox™-Carnosine, STC) increases the resistance of rats to experimental acute hypobaric hypoxia (AHH) thus protecting brain from the oxidative damage. This effect is accompanied by better preservation of the acquired skills in Morris water maze possibly by increasing efficiency of the brain antioxidant system. In addition, STC caused an increase in life span of both male and female fruit fly Drosophila melanogaster whereas carnosine increased life span only in male fruit flies. The results indicate that development of the drug based on STC could be beneficial in neurology and gerontology.
Effect of carnosine and its Trolox-modified derivatives on life span of Drosophila melanogaster
Rejuvenation Res 2010 Aug;13(4):453-7.PMID:20681748DOI:10.1089/rej.2009.1010.
This study investigated the effect of antioxidants, i.e., carnosine and its Trolox- (water-soluble analog of alpha-tocopherol) acylated derivatives (S,S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carbonyl-beta-alanyl-L-histidine (S,S-Trolox-carnosine, STC) and (R,S)-6-hydroxy-2,5,7,8-tetramethylchroman-2-carbonyl-beta-alanyl-L-histidine (R,S-Trolox-carnosine, RTC) on the life span of the fruit fly Drosophila melanogaster. Adding carnosine to foodstuff was accompanied and followed by a 20% increase in the average life span of males, but it did not influence the average life span of females. At the same time, adding STC to foodstuff prolonged average longevity both in males (by 16%) and females (by 36%), but the addition of RTC to foodstuff had no influence upon the average life span of insects of either gender. The compounds studied have previously been shown to protect neurons of the rat brain from oxidative stress in the descending order of efficiency: RTC > STC > carnosine. The finding obtained in the present study suggests another order of efficacy regarding the effect on life span in male insects: STC > carnosine > RTC (inefficient). No correlation between antioxidant protection of rat neurons and the effect on life span of the fruit fly makes it possible to suppose the presence of additional cellular targets to be acted upon by exposure of D. melanogaster to these compounds.
Chromane helicity rule--scope and challenges based on an ECD study of various trolox derivatives
Org Biomol Chem 2014 Apr 14;12(14):2235-54.PMID:24569389DOI:10.1039/c3ob42376j.
The validity of the chromane helicity rule correlating the sense of twist within the dihydropyran ring with the CD sign of the (1)Lb band observed at ca. 290 nm in their electronic circular dichroism (ECD) spectra is examined using a set of natural (S)-Trolox derivatives. To investigate both the scope and the limitations of the rule a combination of ECD spectroscopy, especially the temperature dependence of the ECD spectra, single crystal X-ray diffraction analyses, and density functional theory (DFT) calculations was used. A thorough conformational analysis supported by the X-ray data led to the identification of predominant conformers. Then, a comparison of the experimental ECD spectra with the spectra simulated by TDDFT calculations allowed for a reasonable interpretation of the accumulated data. The results clearly indicated that to avoid the possibility of erroneous conclusions the chromane helicity rule should be used with great caution. This is likely related to the conformational flexibility of tested compounds by which conformers of different helicities can be produced. Therefore, based on the results presented here, it is strongly recommended that the conclusions derived from analysis of experimental data are supported with the appropriate theoretical computations.
Biological activity of novel synthetic derivatives of carnosine
Cell Mol Neurobiol 2010 Apr;30(3):395-404.PMID:19798566DOI:10.1007/s10571-009-9462-7.
Two novel derivatives of carnosine--(S)-trolox-L-carnosine (STC) and (R)-trolox-L-carnosine (RTC) are characterized in terms of their antioxidant and membrane-stabilizing activities as well as their resistance to serum carnosinase. STC and RTC were synthesized by N-acylation of L-carnosine with (S)- and (R)-Trolox, respectively. STC and RTC were found to react more efficiently with 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and protect serum lipoproteins from Fe(2+)-induced oxidation more successfully than carnosine and trolox. At the same time, STC, RTC and trolox suppressed oxidative hemolysis of red blood cells (RBC) less efficiently than carnosine taken in the same concentration. When oxidative stress was induced in suspension of cerebellum granule cells by their incubation with N-methyl-D-aspartate (NMDA), or hydrogen peroxide (H(2)O(2)), both STC and RTC more efficiently decreased accumulation of reactive oxygen species (ROS) than carnosine and trolox. Both STC and RTC were resistant toward hydrolytic degradation by human serum carnosinase. STC and RTC were concluded to demonstrate higher antioxidant capacity and better ability to prevent cerebellar neurons from ROS accumulation than their precursors, carnosine and trolox.
Characterization of iodoacetate-mediated neurotoxicity in vitro using primary cultures of rat cerebellar granule cells
Free Radic Biol Med 2000 Jan 1;28(1):102-7.PMID:10656296DOI:10.1016/s0891-5849(99)00215-4.
The neuroprotective efficacy of antioxidant molecules against iodoacetate (IAA) neurotoxicity in rat cerebellar granule cell (CGC) cultures was investigated. Transient exposure to IAA caused a concentration-dependent decrease in cell viability (ED50 = 9.8 microM). Dizocilpine maleate (MK-801), and 1,2,3,4-tetrahydro-6-nitro-2,3-dioxobenzo[f]quinoxaline-7-sulfonamide (NBQX), failed to prevent IAA toxicity. Certain antioxidant molecules were shown to be neuroprotective against IAA when combined with MK-801 but were ineffective when administered alone. (S)-(-)-Trolox, butylated hydroxytoluene (BHT), and U-83836E exhibited EC50 values of 78, 5.9, and 0.25 microM, respectively, in the presence of 10 microM MK-801. IAA also induced an increase in intracellular oxidative stress, which was quenched by the antioxidants (in the presence of MK-801) in cultures loaded with the oxidant sensitive dye 2'7'-dichlorodihydrofluorescein diacetate (DCFH-DA).