Retronecine N-oxideCAS# 6870-33-3 |
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| Cas No. | 6870-33-3 | SDF | Download SDF |
| PubChem ID | 5745210 | Appearance | Powder |
| Formula | C8H13NO3 | M.Wt | 171.2 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Synonyms | Isatinecine | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (1R,4S,8R)-7-(hydroxymethyl)-4-oxido-2,3,5,8-tetrahydro-1H-pyrrolizin-4-ium-1-ol | ||
| SMILES | C1C[N+]2(CC=C(C2C1O)CO)[O-] | ||
| Standard InChIKey | VUMAFSXBFDKENO-IWSPIJDZSA-N | ||
| Standard InChI | InChI=1S/C8H13NO3/c10-5-6-1-3-9(12)4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-,9-/m1/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
Retronecine N-oxide Dilution Calculator
Retronecine N-oxide Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 5.8411 mL | 29.2056 mL | 58.4112 mL | 116.8224 mL | 146.028 mL |
| 5 mM | 1.1682 mL | 5.8411 mL | 11.6822 mL | 23.3645 mL | 29.2056 mL |
| 10 mM | 0.5841 mL | 2.9206 mL | 5.8411 mL | 11.6822 mL | 14.6028 mL |
| 50 mM | 0.1168 mL | 0.5841 mL | 1.1682 mL | 2.3364 mL | 2.9206 mL |
| 100 mM | 0.0584 mL | 0.2921 mL | 0.5841 mL | 1.1682 mL | 1.4603 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Metabolic activation of retronecine and retronecine N-oxide - formation of DHP-derived DNA adducts.[Pubmed:18842697]
Toxicol Ind Health. 2008 Apr;24(3):181-8.
We have previously reported that metabolism of a series of pyrrolizidine alkaloids in vitro and in vivo generated a set of (+/-)6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP)-derived DNA adducts. It has also been shown that the levels of the DHP-derived DNA adduct formation correlated closely with the tumorigenic potencies of the mice fed with different doses of riddelliine. Retronecine is the necine base and the structurally smallest chemical of the retronecine-type pyrrolizidine alkaloids. Although it has been reported that microsomal metabolism of retronecine generated DHP as a metabolite, it was yet not known whether metabolism of retronecine in vivo could generate DHP-derived DNA adducts and if formed, whether or not the levels of DNA adducts were comparable with those formed from the other tumorigenic retronecine-type pyrrolizidine alkaloids, such as riddelliine, retrorsine, and monocrotaline. In this investigation, the in-vitro and in-vivo metabolic activation of retronecine was studied. Rat liver microsomal metabolism of retronecine in the presence of calf thymus DNA resulted in the formation of a set of DHP-DNA adducts. The metabolism of Retronecine N-oxide under similar conditions also formed the similar set of DHP-DNA adducts. The level of DNA adducts from retronecine was enhanced when metabolism by liver microsomes from phenobarbital (PB)-induced rats were used. The DHP-DNA adducts were also found in the liver DNA of female F344 rats treated with retronecine or Retronecine N-oxide. The highest level of the total DHP-DNA adducts was found in liver DNA from the rats treated with dehydroretronecine (DHR). The order of the levels of DNA adducts in the liver DNA samples from rats treated with various pyrrolizidine alkaloids was: DHR > riddelliine > riddelliine N-oxide >> retronecine > Retronecine N-oxide. The results indicate that 1) retronecine can be metabolized to form DHP by rat liver microsomal enzymes and interacts with DNA to produce DHP-DNA adducts and 2) Retronecine N-oxide undergoes the biotransformation to the parent compound, retronecine. The results from this and our previous findings strongly suggest that formation of DHP-DNA adducts may be a potential biomarker for pyrrolizidine alkaloid carcinogenesis.
