Synthesis and anti-irradiation activities of N-acetyl-S-allyl-L-cysteine

Gan'en MU; Wei LONG; Yuanyuan LI; Guangyun YU; Xiu SHEN; Zewei ZHOU

doi:10.11889/j.1000-3436.2017.rrj.35.050201

您当前的位置：

首页 >

文章列表页 >

Synthesis and anti-irradiation activities of N-acetyl-S-allyl-L-cysteine

RADIOBIOLOGY AND RADIOMEDICINE | 更新时间：2021-12-10

- Synthesis and anti-irradiation activities of N-acetyl-S-allyl-L-cysteine
- Journal of Radiation Research and Radiation Processing Vol. 35, Issue 5, (2017)
- 作者机构：
  
  1.中国医学科学院北京协和医学院放射医学研究所天津 300192
- 作者简介：
- 基金信息：
  
  Tianjin Application Foundation and Research in Cutting-edge Technologies Program(15JCZDJC33400)
- DOI：10.11889/j.1000-3436.2017.rrj.35.050201
  CLC：
扫描看全文
Gan'en MU, Wei LONG, Yuanyuan LI, et al. Synthesis and anti-irradiation activities of N-acetyl-S-allyl-L-cysteine. [J]. Journal of Radiation Research and Radiation Processing 35(5):050201-8(2017)
DOI：

Gan'en MU, Wei LONG, Yuanyuan LI, et al. Synthesis and anti-irradiation activities of N-acetyl-S-allyl-L-cysteine. [J]. Journal of Radiation Research and Radiation Processing 35(5):050201-8(2017) DOI： 10.11889/j.1000-3436.2017.rrj.35.050201.

摘要

以L-半胱氨酸为原料，经取代和酰化两步反应合成目标产物N-乙酰基-S-烯丙基-L-半胱氨酸（N-acetyl-S-allyl-L-cysteine，NAc-SAC）。以,137,Cs γ射线照射至不同剂量的ICR小鼠作为研究对象，通过30 d存活率实验、血相和免疫系统实验、各项脏器指数以及外周血淋巴细胞彗星实验，研究目标化合物分别在200、400、600 mg/kg给药剂量下的抗辐射活性。ICR小鼠经伽马射线照射至致死剂量7.5 Gy后，其存活率由单纯照射对照组的41.6%，分别提高到NAc-SAC给药组的58.3%、50.0%和66.7%，平均存活天数明显延长。,137,Cs γ射线照射至亚致死剂量6.0 Gy后，NAc-SAC在不同程度上增加了受照小鼠的脾指数、脾结节数（CFU-S）、骨髓DNA含量和白细胞数。彗星实验中7.0 Gy伽马射线照射联合NAc-SAC给药组小鼠外周血淋巴细胞的尾长、尾矩、Olive尾矩和尾部DNA百分含量明显低于7.0 Gy伽马射线单纯照射组（,p,<, 0.01），提示NAc-SAC可明显降低辐射导致的DNA损伤。本研究表明，目标化合物NAc-SAC具有一定的抗辐射损伤作用。

Abstract

The N-acetyl-S-allyl-L-cysteine (NAc-SAC) was synthesized by substitution and acylation reactions with L-cysteine as raw materials. Experiments on blood and immune-organs indexes, and survival rates of ICR mice within 30 d after ,137,Csγ-rays irradiation at different doses, as well as the comet assay were carried out to investigate the anti-irradiation effects of NAc-SAC. The survival rates of mice irradiated at 7.5 Gy with the dose of NAc-SAC at 200 mg/kg, 400 mg/kg, and 600 mg/kg increased to 58.3%, 50.0% and 66.7%, respectively, and the average survival time was significantly prolonged compared with that in the control group. The spleen indexes, colony forming cell-spleen (CFU-S), percentages of DNA, number of white blood cells of mice irradiated at 6.0 Gy increased under the action of NAc-SAC. The tail length, tail moment, olive tail moment, and tail DNA percentage of peripheral blood lymphocytes of mice irradiated at 7.0 Gy combined with NAc-SAC were higher than those for the control group (,p,<, 0.05). To conclude, NAc-SAC has a protective effect against damage induced by irradiation.

关键词

N-乙酰基-S-烯丙基-L-半胱氨酸辐射防护剂小鼠抗辐射活性137Cs γ射线

Keywords

N-acetyl-S-allyl-L-cysteine (NAc-SAC)Radiation protection agentMiceAnti-radiation activity137Cs γ-rays

references

H M Patt , E B Tyree , R L Straube , 等 . Cysteine protection against irradiation . Science , 1949 . 110 (2852 ):213 -214 . DOI:10.1126/science.110.2852.213http://doi.org/10.1126/science.110.2852.213 .

D Citrin , A P Cotrim , F Hyodo , 等 . Otectors and mitigators of radiation-induced normal tissue injury . Oncologist , 2010 . 15 (4 ):360 -371 . DOI:10.1634/theon-cologist.2009-S104http://doi.org/10.1634/theon-cologist.2009-S104 .

S S Jang , H G Kim , J S Lee , 等 . Melatonin reduces X-ray radiation-induced lung injury in mice by modulating oxidative stress and cytokine expression . International Journal of Radiation Biology , 2013 . 89 (2 ):97 -105 . DOI:10.3109/09553002.2013.734943http://doi.org/10.3109/09553002.2013.734943 .

L A Ridnour , D D Thomas , D Mancardi , 等 . The chemistry of nitrosative stress induced by nitric oxide and reactive nitrogen oxide species. Putting perspective on stressful biological situations . Biology Chemistry , 2004 . 385 (1 ):1 -10 . DOI:10.1515/BC.2004.001http://doi.org/10.1515/BC.2004.001 .

K Bai , W Xu , J Zhang , 等 . Assessment of free radical scavenging activity of dimethylalycine sodium salt and its role in providing protection against lipopoly-saccharide-induced oxidative stress in mice . PLoS One , 2016 . 11 (5 ):e0155393 DOI:10.1371/journal.pone.0155393http://doi.org/10.1371/journal.pone.0155393 .

Y E Sun , W D Wang . Molecular detection and in vitro antioxidant activity of S-allyl-L-cysteine (SAC) extracted from Allium sativum . Cellular and Molecular Biology , 2016 . 62 (7 ):85 -90 . DOI:10.1042/BA20080088http://doi.org/10.1042/BA20080088 .

D Isabel , M Gerald , P Monika , 等 . S-allyl-L-cysteine and isoliquiritigenin mitochondrial function in cellular models of oxidative and nitrosativestress . Food Chemistry , 2016 . 194 (1 ):843 -848 . DOI:10.1016/j.foodchem.2015.08.052http://doi.org/10.1016/j.foodchem.2015.08.052 .

J Yang , T Wang , K Rao , 等 . S-allyl cysteine restores erectile function through inhibition of reactive oxygen species generation in diabetic rats . Andrology , 2013 . 1 (3 ):487 -94 . DOI:10.1111/j.2047-2927.2012.00060.xhttp://doi.org/10.1111/j.2047-2927.2012.00060.x .

D Jia , N A Koonce , R J Griffin , 等 . Prevention and mitigation of acute death of mice after abdominal irradiation by the antioxidant N-acetyl-cysteine(NAC) . Radiation Research , 2010 . 173 (5 ):579 -589 . DOI:10.1667/RR2030.1http://doi.org/10.1667/RR2030.1 .

Y Xie , H Zhang , J F Hao , 等 . Effect of N-acetylcysteine on 12C6+ ion irradiation-induced lymphocytes DNA damages and immunity changes in mice . Radiation Research , 2009 . 50 (6 ):567 -571 . DOI:10.1269/jrr.09047http://doi.org/10.1269/jrr.09047 .

H H Mansour , H F Hafez , N M Fahmy , 等 . Protective effect of N-acetyl cysteine against radiation induced DNA damage and hepatic toxicity in rats . Biochemical Pharmacology , 2008 . 75 (3 ):773 -780 . DOI:10.1016/j.bcp.2007.09.018http://doi.org/10.1016/j.bcp.2007.09.018 .

A G Goodson , M A Cotter , P Cassidy , 等 . Use of oral N-acetylcysteine for protection of melanocytic nevi against UV-induced oxidative stress:towards a novel paradigm for melanoma Chemoprevention . Clinical Cancer Research , 2009 . 15 (23 ):7434 -7440 . DOI:10.1158/1078-0432.CCR-09-1890http://doi.org/10.1158/1078-0432.CCR-09-1890 .

R Reliene , J M Pollard , Z Sobol , 等 . N-acetyl cysteine protects against ionizing radiation-induced DNA damage but not against cell killing in yeast and mammals . Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis , 2009 . 665 (1-2 ):37 -43 . DOI:10.1016/j.mrfmmm.2009.02.016http://doi.org/10.1016/j.mrfmmm.2009.02.016 .

Q Chu , D T Lee , S W Tsao , 等 . S-allyl cysteine, a water soluble garlic derivative, suppresses the growth of a human androgen-independent prorate cancer xeno-graft, CWR22R, under in vivo conditions . BJU International , 2007 . 99 (4 ):925 -932 . DOI:10.1111/j.1440-1673.2007.01766.xhttp://doi.org/10.1111/j.1440-1673.2007.01766.x .

张广慧 , 周则卫 , 刘培勋 , 等 . 植物凝集素PHA-L对小鼠急性辐射防护作用 . 辐射研究与辐射工艺学报 , 2016 . 34 (2 ):020203(6) DOI:10.11889/j.1000-3436.2016.rrj.34.020203http://doi.org/10.11889/j.1000-3436.2016.rrj.34.020203 http://www.j.sinap.ac.cn/fushe/CN/abstract/abstract297.shtmlhttp://www.j.sinap.ac.cn/fushe/CN/abstract/abstract297.shtml, .

Guanghui ZHANG , Zewei ZHOU , Peixun LIU , 等 . Protective effects of the plant lectin PHA-L on acute radiation injuries in mice . Radiation Research and Radiation Processing , 2016 . 34 (2 ):020203 DOI:10.11889/j.1000-3436.2016.rrj.34.020203http://doi.org/10.11889/j.1000-3436.2016.rrj.34.020203 http://www.j.sinap.ac.cn/fushe/CN/abstract/abstract297.shtmlhttp://www.j.sinap.ac.cn/fushe/CN/abstract/abstract297.shtml, .

郑啓盛 , 于光允 , 贺欣 , 等 . S-异戊烯基-L-半胱氨酸对辐射诱导小鼠DNA损伤的保护作用 . 中国医学科学院学报 , 2015 . 37 (5 ):496 -500 . DOI:10.3881/j.issn.1000-503X.2015.05.002http://doi.org/10.3881/j.issn.1000-503X.2015.05.002 .

Qisheng ZHENG , Guangyun YU , Xin HE , 等 . Protective effect of S-isopentenyl-L-cysteine against DNA damage in irradiated mice . Acta Acadeniae Medicinae Sinicae , 2015 . 37 (5 ):496 -500 . DOI:10.3881/j.issn.1000-503X.2015.05.002http://doi.org/10.3881/j.issn.1000-503X.2015.05.002 .

张再重 , 王瑜 , 王烈 . N-乙酰半胱氨酸对辐射损伤防护作用的研究进展 . 福州总医学学报 , 2010 . 17 (1 ):49 -51 . http://cdmd.cnki.com.cn/Article/CDMD-10393-2008207857.htmhttp://cdmd.cnki.com.cn/Article/CDMD-10393-2008207857.htm, .

Zaizhong ZHANG , Yu WANG , Lie WANG . Advancement in protective effect of N-acetylcysteine on radiation inury . Journal of Fuzhou General Hospital , 2010 . 17 (1 ):49 -51 . http://cdmd.cnki.com.cn/Article/CDMD-10393-2008207857.htmhttp://cdmd.cnki.com.cn/Article/CDMD-10393-2008207857.htm, .

C O Wambi , J K Sanzari , C M Sayers , 等 . Protective effects of dietary anti-oxidants on proton total-body irradiation-mediated hematopoietic cell and animal survival . Radiation Research , 2009 . 172 (2 ):175 -186 . DOI:10.1667/RR1708.1http://doi.org/10.1667/RR1708.1 .

S L Brown , A Kolozsvary , J Liu , 等 . Antioxidant diet supplementation starting 24 hours after exposure reduces radiation lethality . Radiation Research , 2010 . 173 (4 ):462 -468 . DOI:10.1667/RR1716.1http://doi.org/10.1667/RR1716.1 .

C Demirel , S Kilçiksiz , O I Ay , 等 . Effect of N-acetyl cysteine on radiation-induced genotoxicity and cytotoxicity in rat bone marrow . Radiation Research , 2009 . 50 (1 ):43 -50 . DOI:10.1269/jrr.08066http://doi.org/10.1269/jrr.08066 .

A Hirotaka , K Daichi , K Itoh . Pharmacokinetics of S-Allyl-L-cysteine in rats is characterized by high oral absorption and extensive renal reabsorption . The Journal of Nutrition , 2016 . 13 (1 ):456S -459S . http://jn.nutrition.org/content/146/2/456S.full?related-urls=yes&legid=nutrition;146/2/456S&cited-by=yes&legid=nutrition;146/2/456Shttp://jn.nutrition.org/content/146/2/456S.full?related-urls=yes&legid=nutrition;146/2/456S&cited-by=yes&legid=nutrition;146/2/456S, .

Views

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Protective effects of a Chinese medicinal formula on the spleen of irradiated mice

Effects of 5G mobile phone radiation on sperm quality and sex hormone levels in mice

Protection against γ ray-induced damage using herbal formulas

Protective effect of Lanzhou lily polysaccharide fragment on X-ray-induced injury of bone marrow nucleated cells in mice

Relationship between cognitive impairment induced by local radiation and morphological changes of hippocampal microglia

Related Author

No data

Related Institution

Panzhihua Health Commission

Naval Medical Center of the PLA

Hubei University of Arts and Science, Xiangyang

Department of Radiation Protection Medicine, School of Military Preventive Medicine, Air Force Medical University

Shanghai Institute of Applied Physics, Chinese Academy of Sciences

⁰