Citation: JIANG Xiao-Xiao, WANG Jiang, GUAN Qi-Yuan, HU Jun, XU Jing-Juan, CHEN Hong-Yuan. Identification of C＝C Location of Unsaturated Phosphatidylcholines in Cell by Photochemical Reaction-Tandem Mass Spectrometry[J]. Chinese Journal of Analytical Chemistry, ;2017, 45(12): 1988-1995. doi: 10.11895/j.issn.0253-3820.170350 shu

Identification of C＝C Location of Unsaturated Phosphatidylcholines in Cell by Photochemical Reaction-Tandem Mass Spectrometry

State Key Laboratory of Analytical Chemistry for Life Science in Nanjing University, Nanjing 210023, China

Corresponding author: XU Jing-Juan, xujj@nju.edu.cn
Received Date: 3 June 2017
Accepted Date: 28 September 2017

Fund Project: the National Natural Science Foundation of China 21327902This work was supported by the National Natural Science Foundation of China (No. 21327902)

Figures(4)

A method of identification of C＝C location and relative quantitation of unsaturated phosphatidylcholine (PC) isomers in breast cells by online photochemical reaction-pulsed directed current electrospray-tandem mass spectrometry (PB-pulsed-dc-ESI-MS/MS) was established with benzophenone (BP) as a photochemical reactant. The three-phase extraction method was used to extract the lipids in the cells, and then the C＝C in the unsaturated PC and the carbonyl in BP were specifically cycled under the irradiation of 254 nm ultraviolet light (Paternò-Büchi, PB reaction). The PB products were ionized and mass-isolated for low-energy collision dissociation through the non-contact pulsed-dc-ESI ionization method. The double bond position and the relative content of the location isomers were obtained from the resulting ions in the MS/MS spectrum. The C＝C location of 8 kinds of unsaturated PCs in MCF-7 and MCF-10A was detected, and the relative contents of 4 kinds of C＝C location isoforms were analyzed. It was found that the relative abundance of Δ9 isomer in PC 16:0_18:1 was not significantly different between the two cells. The relative abundance of Δ9 isomers in PC 18:0_18:1 and PC 18:1_18:1 was slightly different. However, there is a big difference of Δ9 in LPC 18:1 between the cancer cell and normal cell (56.0% ±1.3% vs. 71.7% ±6.8%). The establishment of such a rapid and easy mass spectrometry method can analyze the C＝C location and the relative content of location isomers, and it is expected to be a powerful tool to identify different cell states and different disease states.
- Online photochemical reaction,
- Unsaturated phosphatidylcholines,
- C C location,
- Tandem mass spectrometry
1. [1]
  Griffin J L, Shockcor J P. Nat. Rev. Cancer, 2004, 4(7):551-561 doi: 10.1038/nrc1390
2. [2]
  Corda D, de Matteis M A. FEBS J., 2013, 280(24):6280 doi: 10.1111/febs.12604
3. [3]
  Wymann M P, Schneiter R. Nat. Rev. Mol. Cell Biol., 2008, 9(2):162-176 doi: 10.1038/nrm2335
4. [4]
  Pastural É, Ritchie S, Lu Y, Jin W, Kavianpour A, Khine Su-Myat K, Heath D, Wood P L, Fisk M, Goodenowe D B. Prostaglandins Leukot. Essent. Fatty Acids, 2009, 81(4):253-264 doi: 10.1016/j.plefa.2009.06.003
5. [5]
  Lagarde M, Bernoud-Hubac N, Guichardant M. Mol. Membr. Biol., 2012, 29(7):222-228 doi: 10.3109/09687688.2012.689378
6. [6]
  Eberlin L S, Dill A L, Golby A J, Ligon K L, Wiseman J M, Cooks R G, Agar N Y R. Angew. Chem. Int. Ed., 2010, 49(34):5953-5956 doi: 10.1002/anie.201001452
7. [7]
  Ejsing C S, Sampaio J L, Surendranath V, Duchoslav E, Ekroos K, Klemm R W, Simons K, Shevchenko A. Proc. Natl. Acad. Sci. USA, 2009, 106(7):2136-2141 doi: 10.1073/pnas.0811700106
8. [8]
  Zhang Y M, Rock C O. Nat. Rev. Microbiol., 2008, 6(3):222-233 doi: 10.1038/nrmicro1839
9. [9]
  Martinez-Seara H, Rog T, Pasenkiewicz-Gierula M, Vattulainen I, Karttunen M, Reigada R. Biophys. J., 2008, 95(7):3295-3305 doi: 10.1529/biophysj.108.138123
10. [10]
  Shinzawa-Itoh K, Aoyama H, Muramoto K, Terada H, Kurauchi T, Tadehara Y, Yamasaki A, Sugimura T, Kurono S, Tsujimoto K, Mizushima T, Yamashita E, Tsukihara T, Yoshikawa S. EMBO J., 2007, 26(6):1713-1725 doi: 10.1038/sj.emboj.7601618
11. [11]
  Odegaard A O, Pereira M A. Nutr. Rev., 2006, 64(8):364-372 doi: 10.1111/nure.2006.64.issue-8
12. [12]
  Kelley N S, Hubbard N E, Erickson K L. J. Nutr., 2007, 137(12):2599-2607
13. [13]
  Bordoni A, Lopez-Jimenez J A, Spanò C, Biagi P, Horrobin D F, Hrelia S. Mol. Cell. Biochem., 1996, 157(1):217-222
14. [14]
  Hsu F F, Turk J. J. Chromatogr. B, 2009, 877(26):2673-2695 doi: 10.1016/j.jchromb.2009.02.033
15. [15]
  Pulfer M, Murphy R C. Mass Spectrom. Rev., 2003, 22(5):332-364 doi: 10.1002/(ISSN)1098-2787
16. [16]
  Harrison K A, Murphy R C. Anal. Chem., 1996, 68(18):3224-3230 doi: 10.1021/ac960302c
17. [17]
  Francis G W. Chem. Phys. Lipids, 1981, 29(4):369-374 doi: 10.1016/0009-3084(81)90070-0
18. [18]
  Blomquist G J, Howard R W, McDaniel C A, Remaley S, Dwyer L A, Nelson D R. J. Chem. Ecol., 1980, 6(1):257-269 doi: 10.1007/BF00987544
19. [19]
  Tomer K B, Crow F W, Gross M L. J. Am. Chem. Soc., 1983, 105(16):5487-5488 doi: 10.1021/ja00354a055
20. [20]
  Thomas M C, Mitchell T W, Harman D G, Deeley J M, Nealon J R, Blanksby S J. Anal. Chem., 2008, 80(1):303-311 doi: 10.1021/ac7017684
21. [21]
  Pham H T, Ly T, Trevitt A J, Mitchell T W, Blanksby S J. Anal. Chem., 2012, 84(17):7525-7532 doi: 10.1021/ac301652a
22. [22]
  Poad B L J, Green M R, Kirk J M, Tomczyk N, Mitchell T W, Blanksby S J. Anal. Chem., 2017, 89(7):4223-4229 doi: 10.1021/acs.analchem.7b00268
23. [23]
  Ma X, Xia Y. Angew. Chem. Int. Ed., 2014, 53(10):2592-2596 doi: 10.1002/anie.201310699
24. [24]
  Wei Z, Xiong X, Guo C, Si X, Zhao Y, He M, Yang C, Xu W, Tang F, Fang X, Zhang S, Zhang X.Anal. Chem., 2015, 87(22):11242-11248 doi: 10.1021/acs.analchem.5b02115
25. [25]
  Sapcariu S C, Kanashova T, Weindl D, Ghelfi J, Dittmar G, Hiller K. METHODSX, 2014, 1(1):74-80
26. [26]
  Kind T, Liu K H, Lee D Y, DeFelice B, Meissen J K, Fiehn O. Nat. Methods, 2013, 10(8):755-758 doi: 10.1038/nmeth.2551
27. [27]
  Liebisch G, Vizcaíno J A, Köfeler H, Trötzmüller M, Griffiths W J, Schmitz G, Spener F, Wakelam M J O. J. Lipid Res., 2013, 54(6):1523-1530 doi: 10.1194/jlr.M033506
28. [28]
  Simopoulos A P. Exp. Biol. Med. (Maywood), 2008, 233(6):674-688 doi: 10.3181/0711-MR-311
1. [1]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
2. [2]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
3. [3]
  Lijuan Liu , Xionglei Wang . Preparation of Hydrogels from Waste Thermosetting Unsaturated Polyester Resin by Controllable Catalytic Degradation: A Comprehensive Chemical Experiment. University Chemistry, 2024, 39(11): 313-318. doi: 10.12461/PKU.DXHX202403060
4. [4]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
5. [5]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
6. [6]
  Yang Lv , Yingping Jia , Yanhua Li , Hexiang Zhong , Xinping Wang . Integrating the Ideological Elements with the “Chemical Reaction Heat” Teaching. University Chemistry, 2024, 39(11): 44-51. doi: 10.12461/PKU.DXHX202402059
7. [7]
  Dexin Tan , Limin Liang , Baoyi Lv , Huiwen Guan , Haicheng Chen , Yanli Wang . Exploring Reverse Teaching Practices in Physical Chemistry Experiment Courses: A Case Study on Chemical Reaction Kinetics. University Chemistry, 2024, 39(11): 79-86. doi: 10.12461/PKU.DXHX202403048
8. [8]
  Ruming Yuan , Pingping Wu , Laiying Zhang , Xiaoming Xu , Gang Fu . Patriotic Devotion, Upholding Integrity and Innovation, Wholeheartedly Nurturing the New: The Ideological and Political Design of the Experiment on Determining the Thermodynamic Functions of Chemical Reactions by Electromotive Force Method. University Chemistry, 2024, 39(4): 125-132. doi: 10.3866/PKU.DXHX202311057
9. [9]
  Xuzhen Wang , Xinkui Wang , Dongxu Tian , Wei Liu . Enhancing the Comprehensive Quality and Innovation Abilities of Graduate Students through a “Student-Centered, Dual Integration and Dual Drive” Teaching Model: A Case Study in the Course of Chemical Reaction Kinetics. University Chemistry, 2024, 39(6): 160-165. doi: 10.3866/PKU.DXHX202401074
10. [10]
  Yiying Yang , Dongju Zhang . Elucidating the Concepts of Thermodynamic Control and Kinetic Control in Chemical Reactions through Theoretical Chemistry Calculations: A Computational Chemistry Experiment on the Diels-Alder Reaction. University Chemistry, 2024, 39(3): 327-335. doi: 10.3866/PKU.DXHX202309074
11. [11]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
12. [12]
  Shuyu Liu , Xiaomin Sun , Bohan Song , Gaofeng Zeng , Bingbing Du , Chongshen Guo , Cong Wang , Lei Wang . Design and Fabrication of Phospholipid-Vesicle-based Artificial Cells towards Biomedical Applications. University Chemistry, 2024, 39(11): 182-188. doi: 10.12461/PKU.DXHX202404113
13. [13]
  Zian Lin , Yingxue Jin . Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) for Disease Marker Screening and Identification: A Comprehensive Experiment Teaching Reform in Instrumental Analysis. University Chemistry, 2024, 39(11): 327-334. doi: 10.12461/PKU.DXHX202403066
14. [14]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
15. [15]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
16. [16]
  Mei Yan , Rida Feng , Yerdos·Tohtarkhan , Biao Long , Li Zhou , Chongshen Guo . Expansion and Extension of Liquid Saturated Vapor Measurement Experiment. University Chemistry, 2024, 39(3): 294-301. doi: 10.3866/PKU.DXHX202308103
17. [17]
  Tao Jiang , Yuting Wang , Lüjin Gao , Yi Zou , Bowen Zhu , Li Chen , Xianzeng Li . Experimental Design for the Preparation of Composite Solid Electrolytes for Application in All-Solid-State Batteries: Exploration of Comprehensive Chemistry Laboratory Teaching. University Chemistry, 2024, 39(2): 371-378. doi: 10.3866/PKU.DXHX202308057
18. [18]
  Yongmei Chen , Lidan Zhang , Shunlai Li , Chunting Zhang , Meng Cui , Qinghong Xu , Lan Jin , Chunchuang Li , Zhi Lv . Development of a National First-Class Course of “University Chemistry Experiment” Based on MOOCs. University Chemistry, 2024, 39(7): 8-12. doi: 10.3866/PKU.DXHX202404017
19. [19]
  Nuo Zhang , Xiaojun Sun , Hongmin Ma , Yan Li , Xiang Ren , Dan Wu , Chuannan Luo , Qin Wei . Construction and Practice of National Experimental Teaching Demonstration Center of Applied Chemistry. University Chemistry, 2024, 39(7): 116-120. doi: 10.12461/PKU.DXHX202405031
20. [20]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(547)
HTML views(116)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142