Citation: SUN Ying, REN Ai-Min, MIN Chun-Gang, ZOU Lu-Yi, REN Xue-Feng. Theoretical Investigation of the Key Reaction for the Chemiluminescence of Cypridina Luciferin Analogues[J]. Acta Physico-Chimica Sinica, ;2010, 26(10): 2779-2786. doi: 10.3866/PKU.WHXB20101018 shu

Theoretical Investigation of the Key Reaction for the Chemiluminescence of Cypridina Luciferin Analogues

1.
State Key Laboratory of Theoretical and Computational Chemistry, Institute of Theoretical Chemistry, Jilin University,Changchun 130023, P. R. China

Received Date: 7 June 2010
Available Online: 27 September 2010
Fund Project: 国家自然科学基金(20673045, 20973078) (20673045, 20973078) 留学回国人员启动基金(外交司留(2008)890 号) (外交司留(2008)890 号)国家重点基础研究发展计划项目(973)(2002CBN613406) 资助 (973)(2002CBN613406)

A series of 6-aryl-2-methylimidazo[1,2-α]pyrazin-3-(7H)-ketone based derivatives MIPa-MIPd (cypridina luciferin analogues) were investigated using the B3LYP/6-311+G(d,p) method, and we modeled a 6-site replacement by different substituents. The effect of different substitutions on cypridina luciferin analogues in their transition from anions to free radicals was studied by electron extraction potentials (EEP) and natural charge population analysis (NPA) in gas phase, dimethyl sulfoxide (DMSO), and diglyme (DG). The calculated results indicated that MIPb (3-indolyl as the substituent) had a lower EEP and a larger natural charge population change occurred at the MIP moiety in DG when transitioning from the anion to its free radical than in the other solvents. We also showed that 3-indolyl, as a substituent, accelerated the luminescent reaction of MIP.
- Density functional theory,
- Cypridina luciferin,
- Chemiluminescence,
- Electron extraction potential,
- Natural charge population analysis
1. [1]
  
  1. Shimomura, O.; to, T.; Hirata, Y. Chem. Soc. Jpn., 1957, 30: 929
2. [2]
  2. Yang, Y. B.; Ji, S. M.; Zhou, F. K.; Zhao, J. Z. Biosensors and Bioelectronics, 2009, 24: 3442
3. [3]
  3. Wu, C.; Kawasaki, K. Anal. Chem., 2007, 79: 1634
4. [4]
  4. Tan, D. J.; Gu, R. X. Food and Machinery, 1994, 3: 25 [谭道经, 顾瑞霞.食品与机械, 1994, 3: 25]
5. [5]
  5. Hu, Z.; Yin, J. G.; Jiang, N.; Chen, Q. J. Chin. J. Vet. Sci., 2008,
6. [6]
  28: 732 [胡哲,尹继刚, 姜宁,陈启军.中国兽医学报, 2008, 28: 732]
7. [7]
  6. Lin, H. Envi. Sci., 1981, 6: 67 [林海.环境科学, 1981, 6: 67]
8. [8]
  7. Yang, X. L. Continuing Medical Education, 2007, 21: 56 [杨晓林. 继续医学教育, 2007, 21: 56]
9. [9]
  8. Zhang, J. C.; Wang, D. Y. Modern photochemistry. Beijing: Beijing Industry Press, 2006: 319-320 [张建成,王夺元.现代光化学.北京:北京工业出版社, 2006: 319-320]
10. [10]
  9. Katsunori, T. Bioorg. Chem., 2007, 35: 82
11. [11]
  10. Shimomura, O.; Johnson, F. H.; Masugi, T. Nature, 1969, 164: 1299
12. [12]
  11. Shimomura, O.; Johnson, F. H. Methods Enzymol., 1978, 57: 331
13. [13]
  12. Kishi, Y.; to, T.; Hirata, Y.; Shimomura, O.; Johnson, F. H. Tetrahedron Lett., 1966, 7: 3427
14. [14]
  13. Kishi, Y.; to, T.; Inoue, S.; Sugiura, S.; Kishimoto, H. Tetrahedron Lett., 1966, 7: 3445
15. [15]
  14. Takahashi, Y.; Kondo, H.; Maki, S.; Niwa, H.; Hiroshi, I.; Takashi, H. Tetrahedron Lett., 2006, 47: 6057
16. [16]
  15. Kondo, H.; Igarashi, T.; Maki, S.; Niwa, H.; Ikeda, H.; Hirano, T. Tetrahedron Lett., 2005, 46: 7701
17. [17]
  16. Hohenberg, P.; Kohn, W. Phys. Rev. B, 1964, 136: 864
18. [18]
  17. Kohn, W.; Sham, L. J. Phys. Rev. A, 1965, 140: 1133
19. [19]
  18. Becke, A. D. Phys. Rev. A, 1988, 38: 3098
20. [20]
  19. Becke, A. D. J. Chem. Phys., 1993, 98: 5648
21. [21]
  20. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B, 1988, 37: 785
22. [22]
  21 Navizet, I.; Liu, Y. J.; Ferre, N.; Xiao, H. Y.; Fang, W. H.; Lindh, R. J. Am. Chem. Soc., 2010, 132: 706
23. [23]
  22. Min, C. G.; Ren, A. M.; Guo, J. F.; Li, Z. W.; Zou, L. Y.; ddard, J. D.; Feng, J. K. ChemPhysChem, 2010, 11: 251
24. [24]
  23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; et al. Gaussian 03. Revision B.01. Pittsburgh, PA: Gaussian Inc., 2003
25. [25]
  24. Mennucci, B.; Tomasi, J. J. Chem. Phys., 1997, 106: 5151
26. [26]
  25. Hirano, T.; Takahashi, Y.; Kondo, H.; Maki, S.; Kojima, S.; Hiroshi, I.; Haruki, N. Photochem. Photobiol. Sci., 2008, 7: 197
27. [27]
  26. Okajima, T.; Tokuda, K.; Ohsaka, T. Bioelectrochem. Bioenerg., 1996, 41: 205
28. [28]
  27. to, T. Pure Appl. Chem., 1968, 17: 421
29. [29]
  28. Johnso, F. H.; Satchel, H. D.; Taylor, E. C.; Shimomura, O. Chemiluminescence and fluorescence of cypridina luciferin and of some newindole compounds in dimethylsufoxide//Bioluminescence in Progress. Princeton: Princeton University Press, 1966: 67
30. [30]
  29. to, T.; Inoue, S.; Sugiura, S.; Nishikawa, K.; Isobe, M.; Abe, Y. Tetrahedron Lett., 1968, 37: 4035
31. [31]
  30. Toya, Y.; Kayano, T.; Sato, K.; to, Y. Chem. Soc. Jpn., 1992, 65: 2475
32. [32]
  31. Nakamura, H.; Aizawa, M.; Takeuchi, D.; Murai, A.; Shimomura, O. Tetrahedron Lett., 2000, 41: 2185
1. [1]
  Borong Yu , Huijiao Zhang , Xinyu Zhang , Xiaoying Li , Shuming Chen , Zhangang Han . The Blue Elf in the Dark: Gradient Science Popularization Experiments on Chemiluminescence. University Chemistry, 2024, 39(9): 295-303. doi: 10.12461/PKU.DXHX202403107
2. [2]
  Hao XU , Ruopeng LI , Peixia YANG , Anmin LIU , Jie BAI . Regulation mechanism of halogen axial coordination atoms on the oxygen reduction activity of Fe-N₄ site: A density functional theory study. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 695-701. doi: 10.11862/CJIC.20240302
3. [3]
  Meifeng Zhu , Jin Cheng , Kai Huang , Cheng Lian , Shouhong Xu , Honglai Liu . Classical Density Functional Theory for Understanding Electrochemical Interface. University Chemistry, 2025, 40(3): 148-152. doi: 10.12461/PKU.DXHX202405166
4. [4]
  Kaifu Zhang , Shan Gao , Bin Yang . Application of Theoretical Calculation with Fun Practice in Raman Spectroscopy Experimental Teaching. University Chemistry, 2025, 40(3): 62-67. doi: 10.12461/PKU.DXHX202404045
5. [5]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
6. [6]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213
7. [7]
  Weina Wang , Lixia Feng , Fengyi Liu , Wenliang Wang . Computational Chemistry Experiments in Facilitating the Study of Organic Reaction Mechanism: A Case Study of Electrophilic Addition of HCl to Asymmetric Alkenes. University Chemistry, 2025, 40(3): 206-214. doi: 10.12461/PKU.DXHX202407022
8. [8]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
9. [9]
  Maitri Bhattacharjee , Rekha Boruah Smriti , R. N. Dutta Purkayastha , Waldemar Maniukiewicz , Shubhamoy Chowdhury , Debasish Maiti , Tamanna Akhtar . Synthesis, structural characterization, bio-activity, and density functional theory calculation on Cu(Ⅱ) complexes with hydrazone-based Schiff base ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1409-1422. doi: 10.11862/CJIC.20240007
10. [10]
  Xiaochen Zhang , Fei Yu , Jie Ma . 多角度数理模拟在电容去离子中的前沿应用. Acta Physico-Chimica Sinica, 2024, 40(11): 2311026-. doi: 10.3866/PKU.WHXB202311026
11. [11]
  Yaling Chen . Basic Theory and Competitive Exam Analysis of Dynamic Isotope Effect. University Chemistry, 2024, 39(8): 403-410. doi: 10.3866/PKU.DXHX202311093
12. [12]
  Xinyu Liu , Weiran Hu , Zhengkai Li , Wei Ji , Xiao Ni . Algin Lab: Surging Luminescent Sea. University Chemistry, 2024, 39(5): 396-404. doi: 10.3866/PKU.DXHX202312021
13. [13]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
14. [14]
  Simin Fang , Hong Wu , Wei Liu , Wei Wei , Hongyan Feng , Wan Li . Construction and Application of Teaching Resources for Inorganic and Analytical Chemistry Experimental Course in the Context of Digital Empowerment. University Chemistry, 2024, 39(10): 156-163. doi: 10.3866/PKU.DXHX202402053
15. [15]
  Qiqi Li , Su Zhang , Yuting Jiang , Linna Zhu , Nannan Guo , Jing Zhang , Yutong Li , Tong Wei , Zhuangjun Fan . 前驱体机械压实制备高密度活性炭及其致密电容储能性能. Acta Physico-Chimica Sinica, 2025, 41(3): 2406009-. doi: 10.3866/PKU.WHXB202406009
16. [16]
  Chongjing Liu , Yujian Xia , Pengjun Zhang , Shiqiang Wei , Dengfeng Cao , Beibei Sheng , Yongheng Chu , Shuangming Chen , Li Song , Xiaosong Liu . Understanding Solid-Gas and Solid-Liquid Interfaces through Near Ambient Pressure X-Ray Photoelectron Spectroscopy. Acta Physico-Chimica Sinica, 2025, 41(2): 100013-. doi: 10.3866/PKU.WHXB202309036
17. [17]
  Zishuo Yi , Peng Liu , Yan Xu . Fluorescent “Chameleon”: A Popular Science Experiment Based on Dynamic Luminescence. University Chemistry, 2024, 39(9): 304-310. doi: 10.12461/PKU.DXHX202311079
18. [18]
  Liwei Wang , Guangran Ma , Li Wang , Fugang Xu . A Comprehensive Analytical Chemistry Experiment: Colorimetric Detection of Vitamin C Using Nanozyme and Smartphone. University Chemistry, 2024, 39(8): 255-262. doi: 10.3866/PKU.DXHX202312094
19. [19]
  Qin Li , Kexin Yang , Qinglin Yang , Xiangjin Zhu , Xiaole Han , Tao Huang . Illuminating Chlorophyll: Innovative Chemistry Popularization Experiment. University Chemistry, 2024, 39(9): 359-368. doi: 10.3866/PKU.DXHX202309059
20. [20]
  Meng Lin , Heng Zhang , Shiling Yuan . Exploring a Combined Theory-Practice-Simulation Teaching Model in Physical Chemistry: A Case Study of Surface Tension. University Chemistry, 2025, 40(4): 189-194. doi: 10.12461/PKU.DXHX202407053

Get Citation

PDF

XML

Metrics

PDF Downloads(1222)
Abstract views(3779)
HTML views(196)

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