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the excited molecular state of the substance. The action mecha-
References and notes
nisms accord to the following formulas:
1. Boyne, M.; Stratton, C.; Johnson, F.; Tonge, P. ACS Chem. Biol. 2006, 1, 43.
Stern-Volmer equation
2. Vicentini, C. B.; Guccione, S.; Giurato, L.; Ciaccio, R.; Mares, D.; Forlani, G.
J. Agric. Food. Chem. 2005, 53, 3848.
3. Waldrep, T. W.; Beck, J. R.; Lynch, M. P.; Wright, F. L. J. Agric. Food. Chem. 1990,
38, 541.
F0=F ¼ 1 þ Kqs0½Qꢂ ¼ 1 þ Ksv½Qꢂ
Lineweaver-Burk equation
4. Pevarello, P.; Brasca, M. G.; Amici, R.; Orsini, P.; Traquandi, G.; Corti, L.; Piutti,
C.; Sansonna, P.; Villa, M.; Pierce, B. S.; Pulici, M.; Giordano, P.; Martina, K.;
Fritzen, E. L.; Nugent, R. A.; Casale, E.; Cameron, A.; Ciomei, M.; Roletto, F.;
Isacchi, A.; Fogliatto, G.; Pesenti, E.; Pastori, W.; Marsiglio, A.; Leach, K. L.; Clare,
P. M.; Fiorentini, F.; Varasi, M.; Vulpetti, A.; Warpehoski, M. A. J. Med. Chem.
2004, 47, 3367.
5. Baraldi, P. G.; Balboni, G.; Pavani, M. G.; Spalluto, G.; Tabrizi, M. A.; Clercq, E. D.;
Balzarini, J.; Bando, T.; Sugiyama, H.; Romagnoli, R. J. Med. Chem. 2001, 44, 2536.
6. Fancelli, D.; Moll, J.; Varasi, M.; Bravo, R.; Artico, R.; Berta, D.; Bindi, S.;
Cameron, A.; Candiani, I.; Cappella, P.; Carpinelli, P.; Croci, W.; Forte, B.;
Giorgini, M. L.; Klapwijk, J.; Marsiglio, A.; Pesenti, E.; Rocchetti, M.; Roletto, F.;
Severino, D.; Soncini, C.; Storici, P.; Tonani, R.; Zugnoni, P.; Vianello, P. J. Med.
Chem. 2006, 49, 7247.
7. Ranatunge, R. R.; Augustyniak, M.; Bandarage, U. K.; Earl, R. A.; Ellis, J. L.;
Garvey, D. S.; Janero, D. R.; Letts, L. G.; Martino, A. M.; Murty, M. G.; Richardson,
S. K.; Schroeder, J. D.; Shumway, M. J.; Tam, S. W.; Trocha, A. M.; Young, D. V.
J. Med. Chem. 2004, 47, 2180.
8. Goel, A.; Madan, A. K. J. Chem. Inf. Comput. Sci. 1995, 35, 510.
9. Hansen, A. J. Crit. Rev. Plant Sci. 1989, 8, 45.
ðF0 ꢀ FÞꢀ1 ¼ Fꢀ0 1 þ KLBFꢀ1½Qꢂꢀ1
0
F0: the fluorescence intensity of substance as the quencher was not
added. F: the fluorescence intensity of substance as the quencher
was added. [Q]: the concentration of quencher. Ksv: the dynamic
quenching constants, or the constants of Stern-Volmer. Kq: the con-
stants of collisional quenching rates. KLB: the static quenching
constants.
6.11. The primary spectroscopic study of compound 4l for TMV
RNA
As RNA contained cyanine dye can emit more intensity of
fluorescence than RNA-treated only, some reports employ the
fluorescence method to study the interaction between RNA and
small drug molecules because quencher, small drug molecules,
can competitively bind with RNA, causing cyanine dye to depart
from RNA. TMV RNA was dissolved in 10 mM phosphate potas-
sium buffer, pH 7.1, 50 mM NaCl. At the concentration of 4l
10. Milosevic, N.; Slusarenko, A. J. Mol. Plant Pathol. 1996, 49, 143.
11. Wang, Y. C.; Hu, D. W.; Zhang, Z. G.; Ma, Z. G.; Zheng, X. B.; Li, D. B. Physiol. Mol.
Plant Pathol. 2003, 63, 223.
12. Sticher, L.; Mauch-Mani, B.; Me0traux, J. P. Annu. Rev. Phytopathol. 1997, 35, 235.
13. Malamy, J.; Carr, J.; Klessigm, D.; Raskin, I. Science 1990, 250, 1002.
14. Hahlbrock, K.; Scheel, D. Plant Mol. Biol. 1989, 40, 347.
15. Rusmussen, J. B.; Hammersschmidt, R.; Zook, M. N. Plant Physiol. 1991, 97,
1342.
varying from 19.952 l l
mol Lꢀ1 to 159.616 mol Lꢀ1, the interac-
tion between 4l and TMV RNA was found to disappear as de-
tected by fluorescence spectroscopy at the excitation and
emission wavelength of TMV RNA of 495 nm and 525 nm,
respectively.37
16. Van Loon, L. C. Plant Mol. Biol. 1985, 4, 111.
17. Tornero, P.; Gadea, J.; Conejero, V. Mol. Plant Microbe Interact. 1997, 10, 624.
18. Xi, Z.; Zhang, Y. R.; Yu, H. Z.; Ouyang, D. Bioorg. Med. Chem. Lett. 2005, 15, 2673.
19. Jin, G. Y.; Cao, C. Y.; Li, L. T.; Ren, J. J.; Zhao, G. F. Chin. J. Pestic. Sci. 1999, 1, 15 (in
Chinese).
20. Li, Z. G. Preparation of Organic Intermediates; Chemical Industry Press: Beijing,
2001. p 152, 445 (in Chinese).
6.12. Statistical analysis
21. Xu, K. X. Handbook of Materials and Intermediates of Fine Organic Chemical
Industry; Chemical Industry Press: Beijing, 1998. p 4, pp 4–39 (in Chinese).
22. (a) Xiao, H. Q.; Ouyang, G. P.; Sun, X. D.; Yao, X. D.; Bao, G. Q.; Qi, C. Z. Chin. J.
Syn. Chem. 2005, 13, 600; (b) Ouyang, G. P. Ph.D. Dissertation, Guizhou
University, Guiyang, China, 2008.
23. Wilson, A. J.. In International Table for X-ray Crystallography; Kluwer Academic
Publishers: Dordrecht, 1992; Vol. C,. pp 219–222, 500–502.
24. Sheldrick, G. M. In SHELXTL V5.1, Software Reference Manual; Bruker AXS, Inc:
Wisconsin, 1997.
All statistical analyses were performed with SPSS 10.0. Data
were analyzed by one-way analysis of variance (ANOVA). Mean
separations were performed using the least significant difference
method (LSD test). Each experiment had three replicates and all
experiments were run three times with similar results. Measure-
ments from all the replicates were combined and treatment effects
analyzed.
25. Sheldrick, G. M. In Program for Empirical Absorption Correction of Area Detector
Data; University of Gottingen: Germany, 1996.
26. Gooding, G. V., Jr.; Hebert, T. T. Phytopathology 1967, 10, 1285.
27. Li, S. Z.; Wang, D. M.; Jiao, S. M. In Pesticide Experiment Methods—Fungicide
Sector; Li, S. Z., Ed.; Agriculture Press of China: Beijing, 1991; pp 93–94.
28. He, Z. P. In A Guide to Experiments of Chemical Control for Crops; He, Z. P., Ed.;
Beijing Agricultural University Press: Beijing, 1933; pp 30–31.
29. Polle, A.; Otter, T.; Seifert, F. Plant Physiol. 1994, 106, 53.
30. Beauchamp, C.; Fridovich, J. Anal. Biochem. 1971, 444, 276.
31. Yamakawa, H.; Kamada, H.; Satoh, M.; Ohashi, Y. Plant Physiol. 1998, 118, 1213.
32. Anand, A.; Zhou, T.; Trick, H. N.; Gill, B. S.; Bockus, W. W. J. Exp. Bot. 2003, 54, 1101.
33. Mohamed, F.; Lydia, F.; Masumi, I.; Hideo, I. Physiol. Mol. Plant Pathol. 2004, 64,
319.
Acknowledgments
We are grateful for the financial support from the National Key
Project for Basic Research (2003CB114404), Key Technologies R&D
Program (2006BAE01A01-15) and the National Natural Science
Foundation of China (20562003).
34. Yuan, J. S.; Reed, A.; Chen, F.; Stewart, C. N. BMC Bioinform. 2006, 7, 85.
35. Chen, G. Z. Fluorescence Analytical Method; Science Press: Beijing, 1990 (in
Chinese).
36. The National Center for Biotechnology Information (NCBI). Protein AAD20291.
37. Fraenkel-Conrat, H.; Williams, R. C. Proc. Natl. Acad. Sci. U.S.A. 1955, 41, 690.
A. Supplementary data
Supplementary data associated with this article can be found, in