DL-Penicillamine
(Synonyms: (±)-Penicillamine) 目录号 : GC68045DL-Penicillamine [(±)-Penicillamine] 是一种铜螯合剂。DL-Penicillamine 与 Prussian blue 联合使用时对铊中毒大鼠有解毒作用。DL-Penicillamine 可引起吡哆辛缺乏，进而诱发视神经炎。DL-Penicillamin 还会抑制初级免疫反应。
Cas No.:52-66-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
DL-Penicillamine [(±)-Penicillamine] is a copper chelating agent. DL-Penicillamine has antidotal effects in thallotoxicosis rats when co-treated with Prussian blue . DL-Penicillamine can cause pyridoxine deficiency and then induce optic axial neuritis. DL-Penicillamine can also depress primary immune response[1][2][3].
DL-Penicillamine (25 mg/kg; i.p.; twice daily, for 5 days) has antidotal effects in thallotoxicosis rats when co-treated with Prussian blue [2].
| Animal Model: | Male Wistar rats, NIH strain (intoxicated by i.p. injection of 32 mg/kg thallium (I) acetate)[2] |
| Dosage: | 25 mg/kg |
| Administration: | i.p.; twice daily, for 5 days |
| Result: | Decreased slightly the thallium content in blood, organs and brain. Increased the probability survival when co-treated with Prussian blue (50 mg/kg; p.o.). |
[1]. TU J, BLACKWELL RQ, LEE PF. DL-penicillamine as a cause of optic axial neuritis. JAMA. 1963 Jul 13;185:83-6.
[2]. Montes S, et al. Additive effect of DL-penicillamine plus Prussian blue for the antidotal treatment of thallotoxicosis in rats. Environ Toxicol Pharmacol. 2011 Nov;32(3):349-55.
[3]. Huebner Kf, Gengozian N. Depression Of The Primary Immune Response By Dl-Penicillamine. Proc Soc Exp Biol Med. 1965 Feb;118:561-5.
| Cas No. | 52-66-4 | SDF | Download SDF |
| 别名 | (±)-Penicillamine | ||
| 分子式 | C5H11NO2S | 分子量 | 149.21 |
| 溶解度 | H2O : 33.33 mg/mL (223.38 mM; Need ultrasonic) | 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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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.702 mL | 33.5098 mL | 67.0196 mL |
| 5 mM | 1.3404 mL | 6.702 mL | 13.4039 mL |
| 10 mM | 0.6702 mL | 3.351 mL | 6.702 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Enantioresolution of DL-Penicillamine
Biomed Chromatogr 2010 Jan;24(1):66-82.PMID:19904729DOI:10.1002/bmc.1355.
Penicillamine (PenA) is a nonproteinogenic amino acid containing a thiol group. The three functional groups in penicillamine undergo characteristic chemical reactions and differ in their ability to participate in various chemical and biochemical reactions. d-penicillamine is more active pharmacologically, while the l-isomer occurs 'naturally'. This review deals with the enantioresolution of PenA both by direct and indirect methods using liquid chromatography. HPLC separation of its diastereomers prepared with different chiral derivatizing reagents (on reversed-phase columns) and separation of the derivatives prepared with achiral reagents (on chiral columns or via ligand exchange mode) has been discussed. Separation of enantiomers tagged with achiral reagent (to add a chromophore for ehanced detection) when there is no diastereomer formation has been considered separately. In addition, application of PenA and its derivatives as chiral selector for enentioresolution of certain other compounds has also been discussed.
Additive effect of DL-Penicillamine plus Prussian blue for the antidotal treatment of thallotoxicosis in rats
Environ Toxicol Pharmacol 2011 Nov;32(3):349-55.PMID:22004953DOI:10.1016/j.etap.2011.07.002.
DL-Penicillamine (DL-P) and Prussian blue (PB) given alone or in combination were tested as possible treatments against acute thallium toxicity. Rats were intoxicated by i.p. injection of thallium (I) acetate at LD(50) (32 mg/kg). A day later, pharmacological treatment was administered until day 4 as follows: (1) vehicles, (2) PB 50mg/kg, by oral route, twice a day, (3) DL-P 25mg/kg i.p. route, twice daily and (4) PB+DL-P. The Estimated Probability Survival (EPS) was recorded during the experiment for each treatment. DL-P alone did not show a significant effect on survival. However, when it was used in combination with PB, it increased the survival significantly (EPS=0.8, P<0.05) as compared to the control group (EPS=0.4). In a different experiment, using 16 mg/kg of Thallium I acetate, the metal levels were analyzed in blood, body organs and brain regions after treatments. DL-P given alone decreased slightly the thallium content in blood, organs and brain. Meanwhile, its administration in combination with PB diminished the thallium levels significantly (P<0.05) in the majority of tissues, at levels lower than those achieved in the PB group. Those results indicate that DL-P administered alone did not prevent the mortality nor accumulation of the metal in body tissues. Its combination with PB could be considered an alternative antidotal treatment in thallium toxicity, because this chelating agent given alone did not cause thallium redistribution to the brain. When given in combination with PB it has an additive effect in the treatment of acute thallotoxicosis.
Analytical and preparative enantioseparation of DL-Penicillamine and DL-cysteine by high-performance liquid chromatography on alpha-acid glycoprotein and beta-cyclodextrin columns using ninhydrin as a reversible tagging reagent
J Chromatogr A 2009 Apr 10;1216(15):3413-7.PMID:19246042DOI:10.1016/j.chroma.2009.02.015.
Two sulfur-containing amino acids, DL-cysteine (Cys) and DL-Penicillamine (PenA), were condensed with ninhydrin to form their spirothiazolidine derivatives. These were separated by HPLC using alpha-acid glycoprotein (AGP) and beta-cyclodextrin (beta-CD) columns. The resolution conditions were optimized and the results were compared. Since the method provided resolution greater than 2 it was also applied to preparative separation. After separation, each of them was detagged using Zn dust and 10% aqueous trifluoroacetic acid. For analytical purposes dinitrophenyl (DNP) derivatives of DL-Cys and DL-PenA were also prepared and were resolved on both the columns. The detection was carried out using photodiode array detection system at 231 nm. The limits of detection were found to be 0.01% and 0.004% for spirothiazolidine carboxylic acid and DNP derivatives, respectively.
DL-Penicillamine induced alteration of elastic fibers of periosteum-perichondrium and associated growth inhibition: an experimental study
J Orthop Res 2001 May;19(3):398-404.PMID:11398852DOI:10.1016/S0736-0266(00)90033-0.
Perichondrium-periosteum, being of collagen and elastic fiber, is regarded as a bone growth regulating factor. The aim of the present study was to investigate the role of collagen and elastic fibers on bone growth, by interfering with the fiber assembly in growing chicks upon administration of DL-Penicillamine (DL-PNA). Our findings demonstrated that DL-PNA determined relevant modifications in the perichondrium-periosteum, as shown by histochemical, histomorphometrical,biochemical and ultrastructural analysis. This chemical has been shown to inhibit the formation of desmosine cross-links in elastin and to induce an increase of elastin associated microfibrils. On the contrary, the collagen network and the biochemical collagen markers were not affected. These changes resulted in a dramatically reduced growth of long bones in comparison with control. Perichondrial-periosteal regulation of bone growth may be mediated by mechanical and biological factors. This study demonstrates a microstructural change in the perichondrium-periosteum with decreased elastin and increased elastic microfibrils content in penicillamine treated chicks. The mechanism linking changes in the perichondrium-periosteum with altered growth still needs to be elucidated.
Effect of DL-Penicillamine on the aorta of growing chickens. Ultrastructural and biochemical studies
Am J Pathol 1986 Sep;124(3):436-47.PMID:2876639doi
The effect of DL-Penicillamine on the architecture of the aortic wall of growing chickens was studied, with particular attention to elastin and collagen. Penicillamine was added to the diet (0.2% and 0.4%, in the presence or not of 10 mg/kg CuSO4 and 100 mg/kg vitamin B6) from hatching, for periods from 7 days up to 2 months. The same regions of the thoracic aortas were examined and compared in all the different experimental conditions. The results showed that penicillamine induced relevant modifications in the process of elastin fibrogenesis. The alterations consisted of an increase of elastin in the extracellular space, associated with an increase in the number of elastin fibers per unit area, and a decrease of the mean profile area of the fibers. Interestingly, penicillamine induced the formation of numerous bundles of microfibrils associated or not with elastin fibers. After prolonged treatment, elastin tended to diminish and the fibers tended to fuse into polymorphic syncytia. Collagen fibrils were larger, showed more heterogeneous cross diameters, were less numerous, and were more spread out within the tissue. All the other components of the aortic wall appeared not to be altered by the chemical. Penicillamine did not modify the copper content of chick aortas, whereas it induced a 40-50% reduction of the activity of both salt and 4 M urea-soluble peptidyl lysyl oxidases in the same tissue. These data may help in understanding some of the pathologic manifestations in human beings during D-penicillamine treatment.