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

  • 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.

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    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


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