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Derivatization Enhanced Raman Characteristic Vibration Spectrum of PAEs Based on Pharmacophore Model |
QIU You-li1,2, XIN Mei-ling1,2, LI Yu1,2* |
1. Resources and Environmental Science and Engineering, North China Electric Power University, Beijing 102206, China
2. MOE Key Laboratory of Resources Environmental Systems Optimization, North China Electric Power University, Beijing 102206, China |
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Abstract In this paper, 3D QSAR pharmacophore models of PAEs Raman characteristic vibration spectrum were established by Discovery Studio software for 17 phthalic acid esters were used as training set and 5phthalic acid esters used as test set. The substitution reaction of PAEs (take environmental priority controlled pollutants DMP, DBP and DNOP for example) used the optimal pharmacophore model built by Hypo 1 and 9 kinds of common hydrophobic groups. At the same time, the Raman characteristic vibration spectrum of PAEs and derivatives in gaseous environment were calculated by using density functional theory at B3LYP/6-31g(d) level, which was to screen derivative reaction of PAEs Raman characteristic vibration spectrum enhanced significantly. The results showed that the pharmacophore model (Hypo 1) was significant and had good predictive abilities with the greatest correlation coefficient (R2) of 0.83, the smallest value of root mean square (RMS) of 0.182 and the total cost of 71.865, the configuration value of 12.68 (<17). There were 23PAEs derivatives based on Hypo 1, including 9 DMP derivatives, 9 DBP derivatives, 5 DNOP derivatives, and the positive frequencies of derivative molecules were greater than 0, which illustrate the structure of PAEs derivatives were stable. The Raman characteristic vibration spectrum intensity of DMP-CH2CH3, DBP-Cl, DNOP-C6H5 increased comparing with DMP, DBP, DNOP by 6.25 times, 2.05 times and 1.56 times respectively, which indicated that PAEs derivatization had significantly enhanced effect on Raman characteristic vibration spectrum intensity. In addition, the substitution reaction energy barriers of PAEs derivatives were calculated by using density functional theory at B3LYP/6-31g(d) level, (take DNOP for example), and the substitution reaction order of the substituent —C6H5, —CH2CH2CH3, —SH, —Cl, —NO2 and DNOP molecule was —CH2CH2CH3>—C6H5>—NO2>—SH>—Cl, which can be uesd as the basis of screening PAEs molecular derivatization enhanced Raman spectrum reaction and provide theoretical support for the enhanced Raman spectrum detection technology.
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Received: 2017-02-15
Accepted: 2017-07-21
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Corresponding Authors:
LI Yu
E-mail: liyuxx@jlu.edu.cn
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[1] LIU Xiu-feng, CHEN Dong-wan, Lü Jin-chang, et al(刘秀峰, 陈东宛, 吕金昌, 等). Chinese Journal of Health Laboratory Technology(中国卫生检验杂志), 2016, 26(3): 347.
[2] Yang J, Li Y, Wang Y, et al. Trends in Analytical Chemistry, 2015, 72: 10.
[3] Magdouli S, Daghrir R, Brar S K, et al. Journal of Environmental Management,2013, 127: 36.
[4] QIU Zhi-qun, SHU Wei-qun, CAO Jia(邱志群, 舒为群, 曹 佳). Carcinogenesis, Teratogenesis & Mutagenesis(癌变·畸变·突变), 2007, 19(3): 188.
[5] YANG Ying-zhou(杨影州). China High-Tech Enterprises(中国高新技术企业), 2010, 30: 39.
[6] WU Ming-hong, WANG Fu-lin, YANG Xue-xia, et al(吴明红, 王扶琳, 杨雪霞, 等). Journal of Shanghai University·Natural Science Edition(上海大学学报·自然科学版), 2016, 22(2): 105.
[7] Kumar N, Sharan S, Srivastava S, et al. Reproductive Toxicology, 2014, 49: 12.
[8] Mahmoud M A, José R U, Raúl O P, et al. Journal of Environmental Management, 2012, 109: 164.
[9] DENG Bin(邓 彬). Science & Technology Vision(科技视界), 2016, 4: 256.
[10] FAN Shi-liang, HE Li-zhi, LU Kou-ping, et al(樊诗亮, 何丽芝, 陆扣萍, 等). Environmental Pollution & Control(环境污染与防治), 2016, 38(6): 81.
[11] LIU Yan-de, JIN Tan-tan(刘燕德, 靳昙昙). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2015, 35(9): 2567.
[12] ZENG Ya-ling, JIANG Long, CAI Xiao-yu, et al(曾娅玲, 姜 龙, 蔡啸宇, 等). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2014, 34(11): 2999.
[13] QIU You-li, ZENG Ya-ling, JIANG Long, et al(邱尤丽, 曾娅玲, 姜 龙, 等). Chinese Journal of Luminescence(发光学报), 2015, 36(8): 976.
[14] WU Ya-dong(吴亚东). Rapid Detection of Phthalic Acid Ester (PAEs) Using Surface-Enhanced Raman Spectroscopy (SERS). Anhui: Anhui University of Chinese Medicine(安徽: 安徽中医药大学), 2015.
[15] Luo X, Zhang F, Ji S, et al. Talanta, 2014, 120: 71.
[16] Alicia J A, àlex L G, Suzanne G R, et al. Bioorganic & Medicinal Chemistry Letters, 2016, 26(23): 5792.
[17] Long J, Yu L. Journal of Hazardous Materials, 2016, 307: 202.
[18] LIU Ming-ming(刘明明). Study on the Design, Synthesis and Anti-HCV Activity of Small Molecular Compounds Based on Diketoacid Structure. Shanghai: Fudan University (上海: 复旦大学), 2012.
[19] TAN Yong, HAN Xue-jie, LIU Da-sheng, et al(谭 勇, 韩学杰, 刘大胜, 等). Chinese Journal of Experimental Traditional Medical Formulae(中国实验方剂学杂志), 2016, 22(5): 199.
[20] LIN Ke-jiang, HUANG Zhen-gui, LI Ting, et al(林克江, 黄振桂, 李 婷, 等). Chemical Journal of Chinese Universities(高等学校化学学报), 2013, 34(5): 1240.
[21] BAO Hong-juan, TANG Ya-lin, XU Xiao-jie, et al(鲍红娟, 唐亚林, 徐筱杰, 等). Chemical Journal of Chinese Universities(高等学校化学学报), 2010, 31(5): 938.
[22] Arooj M, Thangapandian S, John S, et al. International Journal of Molecular Sciences, 2011, 12: 9236.
[23] YANG Ye(杨 晔). The Research of Constructing Antivirus Related Pharmacophore and Evaluating Method. Beijing: Beijing University of Chinese Medicine(北京中医药大学), 2010.
[24] SHAO Xin, YI Qian-ying, YANG Chun-lei, et al(邵 鑫, 衣倩颖, 杨春蕾, 等). Journal of China Pharmaceutical University(中国药科大学学报), 2016, 47(1): 38.
[25] LIU Jian-hua(刘建华). Study on the Synthesis and Bioactivities of Novel Compounds Containing Amide Bond. Zhejiang: Zhejiang University of Technology(浙江: 浙江工业大学), 2014.
[26] ZHANG Yi-liang, ZHANG Gang(张贻亮, 张 钢). Chinese Journal of Organic Chemistry(有机化学), 2014, 34(1): 178.
[27] HUANG Jin-bao, WU Shu-bin, LEI Ming, et al(黄金保, 武书彬, 雷 鸣, 等). Journal of Fuel Chemistry and Technology(燃料化学学报), 2015, 43(11): 1334.
[28] Hajipour A R, Ghorbani S, Karimzadeh M, et al. Computational & Theoretical Chemistry, 2016, 1084: 67. |
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