X. Zhang et al.
15. Vennat B, Pourrat A, Pourrat H, Gross D, Bastide P, Bastide J.
Procyanidins from the roots of Fragaria vesca: characterization and
pharmacological approach. Chem Pharm Bull 1988;36:828–33.
16. Isik K, Özdemir-Kocak F. Antimicrobial activity screening of some
sulfonamide derivatives on some Nocardia species and isolates.
Microbiol Res 2009;164:49–58.
17. Lima LM, Ormelli CB, Brito FF, Miranda AL, Fraga CA, Barreiro EJ. Syn-
thesis and antiplatelet evaluation of novel aryl-sulfonamide deriva-
tives, from natural safrole. Pharm Acta Helv 1999;73:281–92.
18. Özdemir ÜÖ, Güvenç P, Şahin E, Hamurcu F. Synthesis, characteriza-
tion and antibacterial activity of new sulfonamide derivatives and
their nickel(II), cobalt(II) complexes. Inorg Chim Acta 2009;362:
2613–8.
19. Mandal G, Bardhan M, Ganguly T. Occurrence of Förster reso-
nance energy transfer between quantum dots and gold nanopar-
ticles in the presence of a biomolecule. J Phys Chem C 2011;115:
20840–8.
20. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, et al.
Automated docking using a Lamarckian genetic algorithm and an
empirical binding free energy function. J Comput Chem 1998;
19:1639–62.
to exclusion of solvent in docking simulations or rigidity of the
receptor other than tryptophan (42).
Conclusions
The interactions between BSA and SAD were investigated under
simulated physiological conditions using
a spectroscopic
method. SAD can quench the fluorescence of BSA via a static
quenching process, implying that BSA can bind with SAD and
form a BSA–SAD complex. The large association constants and
the shorter binding distances between BSA and SAD indicate
that SAD can bind with BSA with high possibility. The microenvi-
ronment and conformation of BSA were changed slightly in the
binding reaction based on analysis of the synchronous fluores-
cence and CD spectra. Molecular modeling results show that
SAD was situated in subdomain IIA of BSA. These results
will be helpful in understanding the pharmacodynamics and
pharmacokinetics of related drugs.
21. Bujacz A. Structures of bovine, equine and leporine serum albumin.
Acta Crystallogr D 2012;68:1278–89.
22. Sanner MF. Python: a programming language for software integra-
tion and development. J Mol Graph Model 1999;17:57–61.
23. Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy
of docking with a new scoring function, efficient optimization, and
multithreading. J Comput Chem 2010;31:455–61.
24. Laskowski RA, Swindells MB. LigPlot+: multiple ligand–protein
interaction diagrams for drug discovery. J Chem Inf Model 2011;51:
2778–86.
Acknowledgments
The research was financially supported by the Natural
Science Foundation of Guangxi Province (2011GXNSFA018051,
2013GXNSFDA019005).
25. Bardhan M, Misra T, Ganguly T. Quantization of bovine serum albu-
min by fluorescence enhancement effects and corresponding bind-
ing of macrocyclic host–protein assembly. J Photochem Photobiol B
2012;106:113–9.
26. Papadopoulou A, Green R J, Frazier RA. Interaction of flavonoids with
bovine serum albumin: a fluorescence quenching study. J Agric
Food Chem 2005;53:158–63.
27. Lakowicz JR, Weber G. Quenching of fluorescence by oxygen. Probe
for structural fluctuations in macromolecules. Biochemistry 1973;12:
4161–70.
28. Lakowicz JR. Principles of fluorescence spectroscopy. 3rd ed. New York:
Springer, 2006.
29. Zhang YP, Shi SY, Peng MJ. Investigation of proton pump inhibitors
binding with bovine serum albumin and their relationship to molec-
ular structure. J Lumin 2012;132:1921–8.
30. Wang J, Guo YW, Liu B, Cheng CP, Wang ZQ, Han GX, et al. Spectro-
scopic analyses on interaction of bovine serum albumin (BSA) with
toluidine blue (TB) and its sonodynamic damage under ultrasonic
irradiation. J Lumin 2011;131:231–7.
31. Zhao HW, Ge M, Zhang ZX, Wang WF, Wu GZ. Spectroscopic studies
on the interaction between riboflavin and albumins. Spectrochim
Acta A 2006;65:811–7.
References
1. Tan F, Guo M, Yu Q. Studies on interaction between gatifloxacin and
human serum albumin as well as effect of copper(II) on the reaction.
Spectrochim Acta A 2005;61:3006–12.
2. Figgie J, Rossing TH, Fencl V. The role of serum-proteins in acid–base
equilibria. J Lab Clin Med 1991;117:453–67.
3. Mathias U, Jung M. Determination of drug–serum protein interac-
tions via fluorescence polarization measurements. Anal Bioanal
Chem 2007;388:1147–56.
4. Yu ZL, Li DJ, Ji BM, Chen JJ. Characterization of the binding of
nevadensin to bovine serum albumin by optical spectroscopic tech-
nique. J Mol Struct 2008;889:422–8.
5. Rieutord A, Bourget P, Torché G, Zazzo JF. In vitro study of the pro-
tein binding of fusidic acid: a contribution to the comprehension of
its pharmacokinetic behaviour. Int J Pharm 1995;119:57–64.
6. Flarakos J, Morand KL, Vouros P. high-throughput solution-based
medicinal library screening against human serum albumin. Anal
Chem 2005;77:1345–53.
7. Dockal M, Carter DC, Rüker F. Conformational transitions of the three
recombinant domains of human serum albumin depending on pH. J
Biol Chem 2000;275:3042–50.
32. Yu XY, Lu SY, Yang Y, Li XF, Yi PG. Study on the interaction between
NCP-(4-hydroxycoumarins) and bovine serum albumin by spectro-
scopic techniques. Spectrochim Acta A 2012;91:113–7.
33. Machicote RG, Pacheco ME, Bruzzone L. Binding of several benzodi-
azepines to bovine serum albumin: fluorescence study. Spectrochim
Acta A 2010;77:466–72.
34. Ross PD, Subramanian S. Thermodynamics of protein association
reactions: forces contributing to stability. Biochemistry 1981;20:
3096–102.
8. Carter DC, Chang B, Ho JX, Keeling K, Krishnasami Z. Preliminary crys-
tallographic studies of four crystal forms of serum albumin. Eur J
Biochem 1994;226:1049–52.
9. El-Sayed NS, El-Bendary ER, El-Ashry SM, El-Kerdawy MM. Synthesis
and antitumor activity of new sulfonamide derivatives of
thiadiazolo[3,2-a]pyrimidines. Eur J Med Chem 2011;46:3714–20.
10. Nuria PN, Ester GI, Ángel M, Rosa P. Development of a group-specific
immunoassay for sulfonamides: application to bee honey analysis.
Talanta 2007;71:923–33.
35. Meng FY, Zhu JM, Zhao AR, Yu SR, Lin CW. Synthesis of
p-hydroxycinnamic acid sulfonamide derivatives and investigation
of fluorescence binding with bovine serum albumin. J Lumin
2012;132:1290–8.
36. He LL, Wang X, Liu B, Wang J, Sun YG. interaction between ranitidine
hydrochloride and bovine serum albumin in aqueous solution. J
Solution Chem 2010; 39:654–64.
37. Hua YJ, Liu Y, Wang JB, Xiao XH, Qua SS. Study of the interaction be-
tween monoammonium glycyrrhizinate and bovine serum albumin.
J Pharm Biomed Anal 2004;36:915–9.
38. Bi SY, Song DQ, Tian Y, Zhou X, Liu ZY, Zhang HQ. Molecular spectro-
scopic study on the interaction of tetracyclines with serum albumins.
Spectrochim Acta A 2005;61:629–36.
11. Silke MF, Peter E. Sulfonamides in dermatology. Clin Dermatol
2003;21:7–11.
12. Rice-Evans CA, Miller NJ, Pagana G. Structure–antioxidant activity re-
lationships of flavonoids and phenolic acids. Free Radical Biol Med
1996;20:933–56.
13. Huang MT, Smart RC, Wong CQ, Conney AH. Inhibitory effect of
curcumin, chlorogenic acid, caffeic acid, and ferulic acid on tumor
promotion in mouse skin by 12-o-tetradecanoylphorbol-13-acetate.
Cancer Res 1988;48:5941–6.
14. Arimoto S, Inada N, Rai H, Nakano H, Negishi T, Hayatsu H. Effect
of chlorophyllin sulfonamide derivatives on the mutagenicity of
3-hydroxyamino-1-methyl-5H-pyrido-[4,3-b]indole, Trp-P-2(NHOH).
Mutat Res 1991;253:242.
wileyonlinelibrary.com/journal/luminescence
Copyright © 2014 John Wiley & Sons, Ltd.
Luminescence 2014