Specific interaction of 4′-O-(a-l-Cladinosyl) daunorubicin with human serum albumin: The binding site II on HSA molecular using spectroscopy and modeling

Journal of Photochemistry and Photobiology B: Biology

Volumn 95, Issue 3, 2009, Pages 162-169

  Cui, Fengling ^a   Kong, Xiaoduo ^c   Qin, Lixia ^a   Zhang, Guisheng ^a   Liu, Qingfeng ^a   Lei, Beilei ^b   Yao, Xiaojun ^b  

^a HENAN NORMAL UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

^c Hebi College of Vocation and Technology   (China)

Author keywords

4 O (a l Cladinosyl) daunorubicin; Fluorescence quenching; Human serum albumin (HSA); Molecular modeling; Synchronous fluorescence

Indexed keywords

4' O (CLADINOSYL)DAUNORUBICIN; DAUNORUBICIN DERIVATIVE; HUMAN SERUM ALBUMIN; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING SITE; CANCER CELL CULTURE; CELL STRAIN K 562; COLON CANCER; CONTROLLED STUDY; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENTHALPY; ENTROPY; FLUORESCENCE ANALYSIS; FLUORESCENCE SPECTROSCOPY; HYDROPHOBICITY; LEUKEMIA CELL; MOLECULAR MODEL; PRIORITY JOURNAL; PROTEIN CONFORMATION; RADIATION ABSORPTION; ROOM TEMPERATURE; THERMODYNAMICS; ULTRAVIOLET RADIATION; ULTRAVIOLET SPECTROSCOPY;

ANTIBIOTICS, ANTINEOPLASTIC; BINDING SITES; COMPUTER SIMULATION; DAUNORUBICIN; ENERGY TRANSFER; HUMANS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; SERUM ALBUMIN; SPECTROMETRY, FLUORESCENCE; THERMODYNAMICS;

EID: 67349111287     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2009.03.001     Document Type: Article

References (54)

1. Arcamone F. Doxorubicin, anticancer antibiotics. Med. Chem. Ser. 17 (1981) 1-369
2. Zhang G., Fang L., Zhu L., Aimiuwu J.E., Shen J., H C., Muller M.T., Lee G.E., Sun D., and Wang P.G. Syntheses and biological activities of disaccharide daunorubicins. J. Med. Chem. 48 (2005) 5269-5278
3. Battisti R.F., Zhong Y., Fang L., Gibbs S., Shen J., Nadas J., Zhang G., and Sun D. Modifying the sugar moieties of daunorubicin overcomes p-gp-mediated multidrug resistance. Mol. Pharmacol. 4 (2007) 140-153
4. Carter D.C., and Ho J.X. Structure of serum albumin. Adv. Protein Chem. 45 (1994) 153-203
5. Olson R.E., and Christ D.D. Chapter 33 plasma protein binding of drugs. Annu. Rep. Med. Chem. 31 (1996) 327-337
6. Tang J.H., Qi S.D., and Chen X.G. Spectroscopic studies of the interaction of anti-coagulant rodenticide diphacinone with human serum albumin. J. Mol. Struct. 779 1-3 (2005) 87-95
7. Chadborn N., Bryant J., Bain A.J., and Shea P.O. Ligand-dependent conformational equilibria of serum albumin revealed by tryptophan fluorescence quenching. Biophys. J. 76 (1999) 2198-2207
8. Liu J.Q., Tian J.N., Zhang J.Y., Hu Z.D., and Chen X.G. Interaction of magnolol with bovine serum albumin: a fluorescence-quenching study. Anal. Bioanal. Chem. 376 (2003) 864-867
9. Tian J.N., Liu J.Q., Zhang J.Y., Hu Z.D., and Chen X.G. Fluorescence studies on the interactions of barbaloin with bovine serum albumin. Chem. Pharm. Bull. 51 (2003) 579-582
10. Royer R.E., David L., and Jagt V. Gossypol binds to a high-affinity binding site on human serum albumin. FEBS Lett. 157 (1983) 28-30
11. Thomas E.B., Bertil H., and Björn L. Internal motion at the chloride binding sites of human serum albumin by NMR relaxation studies. FEBS Lett. 86 (1978) 25-28
12. 25Mg NMR linewidth as a probe in protein binding studies: application to bovine serum albumin and nitrogenase Fe protein. FEBS Lett. 101 (1979) 31-34
13. Cui F.L., Fan J., Ma D.L., Liu M.C., Chen X.G., and Hu Z.D. A study of the interaction between a new reagent and serum albumin by fluorescence spectroscopy. Anal. Lett. 36 (2003) 2151-2166
14. Nahar S., Carpentier R., and Tajmir-Riahi H.A. Interaction of trivalent Al and Ga cations with proteins of PSII. Cations binding mode and protein conformation by FTIR spectroscopy. J. Inorg. Biochem. 65 (1997) 245-250
15. Filyasova A.I., Kudelina I.A., and Feofanov A.V. A spectroscopic study of the interaction of tetrasulfonated aluminum phthalocyanine with human serum albumin. J. Mol. Struct. 565-566 (2001) 173-176
16. 19F NMR investigation. J. Pharmaceut. Biomed. Anal. 13 (1995) 1087-1093
17. Zsila F., Bikádi Z., and Simonyi M. Probing the binding of the flavonoid, quercetin to human serum albumin by circular dichroism, electronic absorption spectroscopy and molecular modeling methods. Biochem. Pharmacol. 65 (2003) 447-456
18. Jiang C.Q., Gao M.X., and Meng X.Z. Study of the interaction between daunorubicin and human serum albumin, and the determination of daunorubicin in blood serum samples. Spectrochim. Acta, Part A 59 (2003) 1605-1610
19. Sułkowska A., Równicka J., Bojko B., and Sułkowski W. Interaction of anticancer drugs with human and bovine serum albumin. J. Mol. Struct. 651-653 (2003) 133-140
20. Kragh-Hansen U. Molecular aspect of ligand binding to serum albumin. J. Pharmacol. Rev. 33 (1981) 17-53
21. Lakowicz J.R. Principles of Fluorescence Spectroscopy (1983), Plenum Press, New York
22. Khan M.A., Muzammil S., and Musarrat J. Differential binding of tetracyclines with serum albumin and induced structural alterations in drug-bound protein. Int. J. Biol. Macromol. 30 (2002) 243-249
23. B Kandagal P., Ashoka S., Seetharamappa J., Shaikh S.M.T., Jadegoud Y., and Ijare O.B. Study of the interaction of an anticancer drug with human and bovine serum albumin: spectroscopic approach. J. Pharmacol. Biomed. Anal. 41 (2006) 393-399
24. Otagiri M., Masuda K., Imai T., Imamura Y., and Yamasaki M. Binding of pirprofen to human serum albumin studied by dialysis and spectroscopy techniques. Biochem. Pharmacol. 38 (1989) 1-7
25. Rahman M.H., Maruyama T., Okada T., and Yamasaki K. Study of interaction of carprofen and its enantiomers with human serum albumin-I: mechanism of binding studied by dialysis and spectroscopic methods. Biochem. Pharmacol. 46 (1993) 1721-1731
26. Shobini J., Mishra A.K., Sandhya K., and Chandra N. Interaction of coumarin derivatives with human serum albumin: investigation by fluorescence spectroscopic technique and modeling studies. Spectrochim. Acta, Part A 57 (2001) 1133-1147
27. He W.Y., Li Y., Tian J.N., Liu H.X., Hu Z.D., and Chen X.G. Spectroscopic studies on binding of shikonin to human serum albumin. J. Photochem. Photobiol. A 174 (2005) 53-61
28. Seedher N., and Bhatia S. Reversible binding of celecoxib and valdecoxib with human serum albumin using fluorescence spectroscopic technique. Pharmacol. Res. 54 (2006) 77-84
29. Rubio S., Gomez-Hens A., and Ualcarcel M. Analytical applications of synchronous fluorescence spectroscopy. Talanta 33 (1986) 633-640
30. Cui F.L., Fan J., Li J.P., and Hu Z.D. Interactions between 1-benzoyl-4-p-chlorophenyl thiosemicarbazide and serum albumin: investigation by fluorescence spectroscopy. Bioorg. Med. Chem. 12 (2004) 151-157
31. Hua Y.J., Liu Y., Wang J.B., Xiao X.H., and Qu S.S. Study of the interaction between monoammonium glycyrrhizinate and bovine serum albumin. J. Pharm. Biomed. Anal. 36 (2004) 915-919
32. Cui F.L., Fan J., Fan Y.C., Li W., and Hu Z.D. Fluorescence spectroscopy studies on 5-aminosalicylic acid and zinc 5-aminosalylicylate interaction with human serum albumin. J. Pharm. Biomed. Anal. 34 (2004) 189-197
33. SYBYL Software, Version 6.9, Tripos Associates Inc., St. Louis, 2002, 584.
34. Sułkowska A. Interaction of drugs with bovine and human serum albumin. J. Mol. Struct. 614 (2002) 227-232
35. Trynda-Lemiesz L., Keppler B.K., and Koztowski H. Studies on the interactions between human serum albumin and imidazolium [trans-tetrachlorobis(imidazol)ruthenate(III)]. J. Inorg. Biochem. 73 (1999) 123-128
36. Chen G.Z., Huang X.Z., Xu J.G., Zheng Z.Z., and Wang Z.B. Methods of Florescence Analysis. second ed. (1990), Science, Beijing
37. Lakowica J.R., and Weber G. Quenching of fluorescence by oxygen, probe for structural fluctuations in macromolecules. Biochemistry 12 (1973) 4161-4170
38. Ware W.R. Oxygen quenching of fluorescence in solution - an experimental study of diffusion process. J. Phys. Chem. 66 (1962) 455-458
39. Hu Y.J., Liu Y., and Zhang L.X. Studies of interaction between colchicine and bovine serum albumin by fluorescence quenching method. J. Mol. Struct. 750 (2005) 174-178
40. Bi S.Y., Song D.Q., Tian Y., Zhou X., Liu X., and Zhang H.Q. Molecular spectroscopic study on the interaction of tetracyclines with serum albumins. Spectrochim. Acta, Part A 61 (2005) 629-636
41. Neméthy G., and Scheraga H.A. The structure of water and hydrophobic bonding in protein. III The thermodynamic properties of hydrophobic bonds in proteins. J. Phys. Chem. 66 (1962) 1773-1789
42. Timasheff S.N. Thermodynamic of protein interactions. In: Peeters H. (Ed). Proteins of Biological Fluids (1972), Pergamon Press, Oxford 511-519
43. Ross P.D., and Subramanian S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry 20 (1981) 3096-3102
44. Förster T. In: Sinanoglu O. (Ed). Modern Quantum Chemistry vol. 3 (1996), Academic Press, New York
45. Yang P. The Guide Bioinorganic Chemistry (1991), Xi'an Jiaotong Press
46. Lakowicz J.R. Principle of Fluorescence Spectroscopy (1983), Plenum Press, New York
47. Yang M.M., Yang P., and Zhang L.W. Study on interaction of caffeic acid series medicine and albumin by fluorescence method. Chin. Sci. Bull. 39 (1994) 734-739
48. Tian J.N., Liu J.Q., He W.Y., Hu D., and Chen X.G. Probing the binding of scutellarin to human serum albumin by circular dichroism, fluorescence spectroscopy, FTIR, and molecular modeling method. Biomacromolecules 5 (2004) 1956-1961
49. 19F NMR investigation. J. Pharm. Biomed. Anal. 13 (1995) 1087-1093
50. He J.X., and Carter D.C. Atomic structure and chemistry of human serum albumin. Nature 258 (1992) 209-215
51. Curry S., Mandelkow H., Brick P., and Franks N. Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nat. Struct. Biol. 5 (1998) 827-835
52. Brockhinke A., Plessow R., Kohse-Höinghaus K., and Herrmann C. Structural changes in the Ras protein revealed by fluorescence spectroscopy. Phys. Chem. Chem. Phys. 5 (2003) 3498-3506
53. Miller J.N. Recent advances in molecular luminescence analysis. Anal. Proc. 16 (1979) 203-208
54. Sklar L.A., Hudson B.S., and Simoni R.D. Conjugated polyene fatty acids as fluorescent probes: binding to bovine serum albumin. Biochemistry 16 (1977) 5100-5108