Characterization of thymoquinone binding to human α1-acid glycoprotein

Journal of Pharmaceutical Sciences

Volumn 101, Issue 7, 2012, Pages 2564-2573

  Lupidi, Giulio ^a   Camaioni, Emidio ^b   Khalifé, Hamal ^a   Avenali, Luca ^a   Damiani, Elisabetta ^c   Tanfani, Fabio ^c   Scirè, Andrea ^c  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

^c UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

Alpha 1 acid glycoprotein; Drug interactions; Fluorescence spectroscopy; FTIR; Molecular modeling; Thymoquinone

Indexed keywords

OROSOMUCOID; THYMOQUINONE; BENZOQUINONE DERIVATIVE; CARAWAY OIL; VEGETABLE OIL;

ARTICLE; BINDING AFFINITY; BINDING SITE; CONTROLLED STUDY; DRUG BINDING; DRUG DISTRIBUTION; DRUG METABOLISM; DRUG STRUCTURE; FLUORESCENCE SPECTROSCOPY; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; HIGH TEMPERATURE; HYDROGEN BOND; MOLECULAR DOCKING; THERMODYNAMICS; THERMOSTABILITY; BLACK CUMIN; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; INFRARED SPECTROSCOPY; METABOLISM; PROTEIN BINDING; SPECTROFLUOROMETRY;

BENZOQUINONES; BINDING SITES; HUMANS; HYDROGEN BONDING; MODELS, MOLECULAR; NIGELLA SATIVA; OROSOMUCOID; PLANT OILS; PROTEIN BINDING; SPECTROMETRY, FLUORESCENCE; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS;

EID: 84866272308     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23138     Document Type: Article

References (55)

1. Aguirre C, Troconiz IF, Valdivieso A, Jimenez RM, Gonzalez JP, Calvo R, Rodriguez-Sasiain JM. 1996. Pharmacokinetics and pharmacodynamics of penbutolol in healthy and cancer subjects: Role of altered protein binding. Res Commun Mol Pathol Pharmacol 92(1):53-72.
2. 1-acid glycoprotein. Biochem Biophys Res Commun 372(3):503-507.
3. 1-acid glycoprotein variants. Biol Pharm Bull 33(1):95-99.
4. Saldova R, Wormald MR, Dwek RA, Rudd PM. 2008. Glycosylation changes on serum glycoproteins in ovarian cancer may contribute to disease pathogenesis. Dis Markers 25(4-5):219-232.
5. 1-acid glycoprotein and albumin binding of various marketed and preclinical kinase inhibitors. Curr Med Chem 16(16):1964-1977.
6. Flaherty JF Jr, Gatti G, White J, Bubp J, Borin M, Gambertoglio JG. 1996. Protein binding of clindamycin in sera of patients with AIDS. Antimicrob Agents Chemother 40(5):1134-1138.
7. Holladay JW, Dewey MJ, Michniak BB, Wiltshire H, Halberg DL, Weigl P, Liang Z, Halifax K, Lindup WE, Back DJ. 2001. Elevated alpha-1-acid glycoprotein reduces the volume of distribution and systemic clearance of saquinavir. Drug Metab Dispos 29(3):299-303.
8. Johnson JA. 2000. Predictability of the effects of race or ethnicity on pharmacokinetics of drugs. Int J Clin Pharmacol Ther 38(2):53-60.
9. El Gazzar M, El Mezayen R, Marecki JC, Nicolls MR, Canastar A, Dreskin SC. 2006. Anti-inflammatory effect of thymoquinone in a mouse model of allergic lung inflammation. Int Immunopharmacol 6(7):1135-1142.
10. Padhye S, Banerjee S, Ahmad A, Mohammad R, Sarkar FH. 2008. From here to eternity-The secret of Pharaohs: Therapeutic potential of black cumin seeds and beyond. Cancer Ther 6(b):495-510.
11. Banerjee S, Padhye S, Azmi A, Wang Z, Philip PA, Kucuk O, Sarkar FH, Mohammad RM. 2010. Review on molecular and therapeutic potential of thymoquinone in cancer. Nutr Cancer 62(7):938-946.
12. Gali-Muhtasib H, Roessner A, Schneider-Stock R. 2006. Thymoquinone: A promising anti-cancer drug from natural sources. Int J Biochem Cell Biol 38(8):1249-1253.
13. Houghton PJ, Zarka R, de las Heras B, Hoult JR. 1995. Fixed oil of Nigella sativa and derived thymoquinone inhibit eicosanoid generation in leukocytes and membrane lipid peroxidation. Planta Med 61(1):33-36.
14. Hosseinzadeh H, Parvardeh S, Asl MN, Sadeghnia HR, Ziaee T. 2007. Effect of thymoquinone and Nigella sativa seeds oil on lipid peroxidation level during global cerebral ischemia-reperfusion injury in rat hippocampus. Phytomedicine 14(9):621-627.
15. Mansour MA, Nagi MN, El-Khatib AS, Al-Bekairi AM. 2002. Effects of thymoquinone on antioxidant enzyme activities, lipid peroxidation and DT-diaphorase in different tissues of mice: A possible mechanism of action. Cell Biochem Funct 20(2):143-151.
16. Gali-Muhtasib H, Diab-Assaf M, Boltze C, Al-Hmaira J, Hartig R, Roessner A, Schneider-Stock R. 2004. Thymoquinone extracted from black seed triggers apoptotic cell death in human colorectal cancer cells via a p53-dependent mechanism. Int J Oncol 25(4):857-866.
17. Gali-Muhtasib HU, Abou Kheir WG, Kheir LA, Darwiche N, Crooks PA. 2004. Molecular pathway for thymoquinone-induced cell-cycle arrest and apoptosis in neoplastic keratinocytes. Anticancer Drugs 15(4):389-399.
18. Worthen DR, Ghosheh OA, Crooks PA. 1998. The in vitro anti-tumor activity of some crude and purified components of blackseed, Nigella sativa L. Anticancer Res 18(3A):1527-1532.
19. Sethi G, Ahn KS, Aggarwal BB. 2008. Targeting nuclear factor-kappa B activation pathway by thymoquinone: Role in suppression of antiapoptotic gene products and enhancement of apoptosis. Mol Cancer Res 6(6):1059-1070.
20. Yi T, Cho SG, Yi Z, Pang X, Rodriguez M, Wang Y, Sethi G, Aggarwal BB, Liu M. 2008. Thymoquinone inhibits tumor angiogenesis and tumor growth through suppressing AKT and extracellular signal-regulated kinase signaling pathways. Mol Cancer Ther 7(7):1789-1796.
21. Lupidi G, Scire A, Camaioni E, Khalife KH, De Sanctis G, Tanfani F, Damiani E. 2010. Thymoquinone, a potential therapeutic agent of Nigella sativa, binds to site I of human serum albumin. Phytomedicine 17(10):714-720.
22. 1-acid glycoprotein (Orosomucoid) solved by UV RIP reveals the broad drug-binding activity of this human plasma lipocalin. J Mol Biol 384(2):393-405.
23. Salomaa P, Schaleger LL, Long FA. 1964. Solvent deuterium isotope effects on acid-base equilibria. J Am Chem Soc 86:1-7.
24. Tanfani F, Galeazzi T, Curatola G, Bertoli E, Ferretti G. 1997. Reduced beta-strand content in apoprotein B-100 in smaller and denser low-density lipoprotein subclasses as probed by Fourier-transform infrared spectroscopy. Biochem J 322(Pt 3):765-769.
25. Osborne HB, Nabedryk-Viala E. 1982. Infrared measurement of peptide hydrogen exchange in rhodopsin. Methods Enzymol 88:676-680.
26. Griessler R, D'Auria S, Tanfani F, Nidetzky B. 2000. Thermal denaturation pathway of starch phosphorylase from Corynebacterium callunae: Oxyanion binding provides the glue that efficiently stabilizes the dimer structure of the protein. Protein Sci 9(6):1149-1161.
27. Sobiecka-Szkatula A, Polit A, Scire A, Gieldon A, Tanfani F, Szkarlat Z, Ciarkowski J, Zurawa-Janicka D, Skorko-Glonek J, Lipinska B. 2009. Temperature-induced conformational changes within the regulatory loops L1-L2-LA of the HtrA heat-shock protease from Escherichia coli. Biochim Biophys Acta 1794(11):1573-1582.
28. Meersman F, Smeller L, Heremans K. 2002. Comparative Fourier transform infrared spectroscopy study of cold-, pressure-, and heat-induced unfolding and aggregation of myoglobin. Biophys J 82(5):2635-2644.
29. Lakowicz JR. 1999. Principles of fluorescence spectroscopy. 2nd ed.New York: Kluwer, Academic/Plenum Publishers.
30. Goodsell DS, Morris GM, Olson AJ. 1996. Automated docking of flexible ligands: Applications of AutoDock. J Mol Recognit 9(1):1-5.
31. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE. 2000. The protein data bank. Nucleic Acids Res 28(1):235-242.
32. Vriend G. 1990. WHAT IF: A molecular modeling and drug design program. J Mol Graph 8(1):52-56, 29.
33. Sanner MF, Olson AJ, Spehner JC. 1996. Reduced surface: An efficient way to compute molecular surfaces. Biopolymers 38(3):305-320.
34. Bolton E, Wang Y, Thiessen PA, Bryant SH. 2008. Chapter 12 Pubchem: Integrated platform of small molecules and biological activities. Annu Rep Comput Chem 4:217-241.
35. Schuttelkopf AW, van Aalten DM. 2004. PRODRG: A tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr D Biol Crystallogr 60(Pt 8):1355-1363.
36. 1-acid glycoprotein genetic variants, the A and F1*S forms. J Biol Chem 286(16):14427-14434.
37. Potterton L, McNicholas S, Krissinel E, Gruber J, Cowtan K, Emsley P, Murshudov GN, Cohen S, Perrakis A, Noble M. 2004. Developments in the CCP4 molecular-graphics project. Acta Crystallogr D Biol Crystallogr 60(Pt 12 Pt 1):2288-2294.
38. Ausili A, Scire A, Damiani E, Zolese G, Bertoli E, Tanfani F. 2005. Temperature-induced molten globule-like state in human alpha(1)-acid glycoprotein: An infrared spectroscopic study. Biochemistry 44(49):15997-16006.
39. Barth A, Zscherp C. 2002. What vibrations tell us about proteins. Q Rev Biophys 35(4):369-430.
40. Tanfani F, Scire A, Masullo M, Raimo G, Bertoli E, Bocchini V. 2001. Salts induce structural changes in elongation factor 1alpha from the hyperthermophilic archaeon Sulfolobus solfataricus: A Fourier transform infrared spectroscopic study. Biochemistry 40(44):13143-13148.
41. Kuznetsova IM, Turoverov KK, Uversky VN. 2004. Use of the phase diagram method to analyze the protein unfolding-refolding reactions: Fishing out the "invisible" intermediates. J Proteome Res 3(3):485-494.
42. 1-acid glycoprotein. Biochim Biophys Acta 1336(2):349-359.
43. Albani JR. 2007. New insights in the interpretation of tryptophan fluorescence: Origin of the fluorescence lifetime and characterization of a new fluorescence parameter in proteins: The emission to excitation ratio. J Fluoresc 17(4):406-417.
44. 1-acid glycoprotein (orosomucoid). Straightforward fluorescence experiments revealing the presence of a binding pocket. Carbohydr Res 339(3):607-612.
45. Bi S, Song D, Kan Y, Xu D, Tian Y, Zhou X, Zhang H. 2005. Spectroscopic characterization of effective components anthraquinones in Chinese medicinal herbs binding with serum albumins. Spectrochim Acta A Mol Biomol Spectrosc 62(1-3):203-212.
46. Bi S, Song D, Tian Y, Zhou X, Liu Z, Zhang H. 2005. Molecular spectroscopic study on the interaction of tetracyclines with serum albumins. Spectrochim Acta A Mol Biomol Spectrosc 61(4):629-636.
47. Timaseff SN. 1972. Thermodynamics of protein interactions. In Proteins of biological fluids; Peeters H, Ed. Oxford: Pergamon Press, pp 511-519.
48. Ross PD, Subramanian S. 1981. Thermodynamics of protein association reactions: Forces contributing to stability. Biochemistry 20(11):3096-3102.
49. Bychkova VE, Berni R, Rossi GL, Kutyshenko VP, Ptitsyn OB. 1992. Retinol-binding protein is in the molten globule state at low pH. Biochemistry 31(33):7566-7571.
50. Scire A, Baldassarre M, Lupidi G, Tanfani F. 2011. Importance of pH and disulfide bridges on the structural and binding properties of human alpha(1)-acid glycoprotein. Biochimie 93(9):1529-1536.
51. Bychkova VE, Pain RH, Ptitsyn OB. 1988. The "molten globule" state is involved in the translocation of proteins across membranes? FEBS Lett 238(2):231-234.
52. Jeffrey PD, Bewley MC, MacGillivray RT, Mason AB, Woodworth RC, Baker EN. 1998. Ligand-induced conformational change in transferrins: Crystal structure of the open form of the N-terminal half-molecule of human transferrin. Biochemistry 37(40):13978-13986.
53. 1-acid glycoprotein to membrane results in a unique structural change and ligand release. Biochemistry 43(32):10513-10519.
54. Israili ZH, Dayton PG. 2001. Human alpha-1-glycoprotein and its interactions with drugs. Drug Metab Rev 33(2):161-235.
55. Maruyama T, Otagiri M, Takadate A. 1990. Characterization of drug binding sites on alpha 1-acid glycoprotein. Chem Pharm Bull (Tokyo) 38(6):1688-1691.