N-乙酰基-S-烯丙基-L-半胱氨酸的合成及其抗辐射活性

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

Journal of Radiation Research and Radiation Proces ›› 2017, Vol. 35 ›› Issue (5): 50201-050201.doi: 10.11889/j.1000-3436.2017.rrj.35.050201

• RADIOBIOLOGY AND RADIOMEDICINE • Previous Articles Next Articles

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

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

Institute of Radiation Medicine, Chinese Academy of Medical Sciences & Peking Union Medical College, Tianjin 300192, China

Received:2017-05-22 Revised:2017-07-15 Online:2017-10-20 Published:2017-10-20
Supported by:
Supported by Tianjin Application Foundation and Research in Cutting-edge Technologies Program (15JCZDJC33400)

Abstract

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 ¹³⁷Csγ-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.

Key words: N-acetyl-S-allyl-L-cysteine (NAc-SAC), Radiation protection agent, Mice, Anti-radiation activity, ¹³⁷Cs γ-rays

CLC Number:

MU Gan'en, LONG Wei, LI Yuanyuan, YU Guangyun, SHEN Xiu, ZHOU Zewei. Synthesis and anti-irradiation activities of N-acetyl-S-allyl-L-cysteine[J].Journal of Radiation Research and Radiation Proces, 2017, 35(5): 50201-050201.

References

1 Patt H M, Tyree E B, Straube R L, et al. Cysteine protection against irradiation[J]. Science, 1949, 110(2852):213-214. DOI:10.1126/science.110.2852.213.
2 Citrin D, Cotrim A P, Hyodo F, et al. Otectors and mitigators of radiation-induced normal tissue injury[J]. Oncologist, 2010, 15(4):360-371. DOI:10.1634/theon-cologist.2009-S104.
3 Jang S S, Kim H G, Lee J S, et al. Melatonin reduces X-ray radiation-induced lung injury in mice by modulating oxidative stress and cytokine expression[J]. International Journal of Radiation Biology, 2013, 89(2):97-105. DOI:10.3109/09553002.2013.734943.
4 Ridnour L A, Thomas D D, Mancardi D, et al. The chemistry of nitrosative stress induced by nitric oxide and reactive nitrogen oxide species. Putting perspective on stressful biological situations[J]. Biology Chemistry, 2004, 385(1):1-10. DOI:10.1515/BC.2004.001.
5 Bai K, Xu W, Zhang J, et al. Assessment of free radical scavenging activity of dimethylalycine sodium salt and its role in providing protection against lipopoly-saccharide-induced oxidative stress in mice[J]. PLoS One, 2016, 11(5):e0155393. DOI:10.1371/journal.pone.0155393.
6 Sun Y E, Wang W D. Molecular detection and in vitro antioxidant activity of S-allyl-L-cysteine (SAC) extracted from Allium sativum[J]. Cellular and Molecular Biology, 2016, 62(7):85-90. DOI:10.1042/BA20080088.
7 Isabel D, Gerald M, Monika P, et al. S-allyl-L-cysteine and isoliquiritigenin mitochondrial function in cellular models of oxidative and nitrosativestress[J]. Food Chemistry, 2016, 194(1):843-848. DOI:10.1016/j. foodchem.2015.08.052.
8 Yang J, Wang T, Rao K, et al. S-allyl cysteine restores erectile function through inhibition of reactive oxygen species generation in diabetic rats[J]. Andrology, 2013, 1(3):487-94. DOI:10.1111/j.2047-2927.2012.00060.x.
9 Jia D, Koonce N A, Griffin R J, et al. Prevention and mitigation of acute death of mice after abdominal irradiation by the antioxidant N-acetyl-cysteine(NAC)[J]. Radiation Research, 2010, 173(5):579-589. DOI:10.1667/RR2030.1.
10 Xie Y, Zhang H, Hao J F, et al. Effect of N-acetylcysteine on ¹²C⁶⁺ ion irradiation-induced lymphocytes DNA damages and immunity changes in mice[J]. Radiation Research, 2009, 50(6):567-571. DOI:10.1269/jrr.09047.
11 Mansour H H, Hafez H F, Fahmy N M, et al. Protective effect of N-acetyl cysteine against radiation induced DNA damage and hepatic toxicity in rats[J]. Biochemical Pharmacology, 2008, 75(3):773-780. DOI:10.1016/j.bcp. 2007.09.018.
12 Goodson A G, Cotter M A, Cassidy P, et al. Use of oral N-acetylcysteine for protection of melanocytic nevi against UV-induced oxidative stress:towards a novel paradigm for melanoma Chemoprevention[J]. Clinical Cancer Research, 2009, 15(23):7434-7440. DOI:10.1158/1078-0432. CCR-09-1890.
13 Reliene R, Pollard J M, Sobol Z, et al. N-acetyl cysteine protects against ionizing radiation-induced DNA damage but not against cell killing in yeast and mammals[J]. Mutation Research/Fundamental and Molecular Mechanisms of Mutagenesis, 2009, 665(1-2):37-43. DOI:10.1016/j.mrfmmm.2009.02.016.
14 Chu Q, Lee D T, Tsao S W, et al. 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[J]. BJU International, 2007, 99(4):925-932.DOI:10.1111/j.1440-1673.2007. 01766.x.
15 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[J]. 辐射研究与辐射工艺学报. 2016, 34(2):020203(6). DOI:10.11889/j.1000-3436.2016. rrj.34.020203. ZHANG Guanghui, ZHOU Zewei, LIU Peixun, et al. Protective effects of the plant lectin PHA-L on acute radiation injuries in mice[J]. Radiation Research and Radiation Processing, 2016, 34(2):020203(6). DOI:10. 11889/j.1000-3436.2016. rrj.34.020203.
16 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[J]. 中国医学科学院学报, 2015, 37(5):496-500. DOI:10.3881/j.issn.1000-503X.2015.05.002. ZHENG Qisheng, YU Guangyun, HE Xin, et al. Protective effect of S-isopentenyl-L-cysteine against DNA damage in irradiated mice[J]. Acta Acadeniae Medicinae Sinicae, 2015, 37(5):496-500. DOI:10.3881/j.issn.1000-503X.2015.05.002.
17 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[J]. 福州总医学学报, 2010, 17(1):49-51. ZHANG Zaizhong, WANG Yu, WANG Lie. Advancement in protective effect of N-acetylcysteine on radiation inury[J]. Journal of Fuzhou General Hospital, 2010, 17(1):49-51.
18 Wambi C O, Sanzari J K, Sayers C M, et al. Protective effects of dietary anti-oxidants on proton total-body irradiation-mediated hematopoietic cell and animal survival[J]. Radiation Research, 2009, 172(2):175-186. DOI:10.1667/RR1708.1.
19 Brown S L, Kolozsvary A, Liu J, et al. Antioxidant diet supplementation starting 24 hours after exposure reduces radiation lethality[J]. Radiation Research, 2010, 173(4):462-468. DOI:10.1667/RR1716.1.
20 Demirel C, Kilçiksiz S, Ay O I, et al. Effect of N-acetyl cysteine on radiation-induced genotoxicity and cytotoxicity in rat bone marrow[J]. Radiation Research, 2009, 50(1):43-50. DOI:10.1269/jrr.08066.
21 Hirotaka A, Daichi K, Itoh K. Pharmacokinetics of S-Allyl-L-cysteine in rats is characterized by high oral absorption and extensive renal reabsorption[J]. The Journal of Nutrition, 2016, 13(1):456S-459S. DOI:10. 3945/jn.114.201749.

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

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