330
Views
68
CrossRef citations to date
0
Altmetric
Articles

Cytotoxicity and comparative binding mechanism of piperine with human serum albumin and α-1-acid glycoprotein

, , &
Pages 1336-1351 | Received 18 Jun 2014, Accepted 18 Jul 2014, Published online: 20 Aug 2014

References

  • Agudelo, D., Bourassa, P., Bruneau, J., Bérubé, G., Asselin, É., & Tajmir-Riahi, H.-A. (2012). Probing the binding sites of antibiotic drugs doxorubicin and N-(trifluoroacetyl) doxorubicin with human and bovine serum albumins. PLoS ONE, 7, e43814.10.1371/journal.pone.0043814
  • Atal, C., Dubey, R., & Singh, J. (1985). Biochemical basis of enhanced drug bioavailability by piperine: Evidence that piperine is a potent inhibitor of drug metabolism. Journal of Pharmacology and Experimental Therapeutics, 232, 258–262.
  • Atal, C., Zutshi, U., & Rao, P. (1981). Scientific evidence on the role of Ayurvedic herbals on bioavailability of drugs. Journal of Ethnopharmacology, 4, 229–232.10.1016/0378-8741(81)90037-4
  • Athineos, E., Kukral, J. C., & Winzler, R. J. (1964). Biosynthesis of glycoproteins: II. The site of glucosamine incorporation into canine plasma α-1 acid glycoprotein. Archives of Biochemistry and Biophysics, 106, 338–342.10.1016/0003-9861(64)90197-3
  • Bang, J. S., Choi, H. M., Sur, B.-J., Lim, S.-J., Kim, J. Y., Yang, H.-I., Kim, K. S. (2009). Anti-inflammatory and antiarthritic effects of piperine in human interleukin 1β-stimulated fibroblast-like synoviocytes and in rat arthritis models. Arthritis Research & Therapy, 11, R49.10.1186/ar2662
  • Baumann, H., Prowse, K., Marinković, S., Won, K. A., & Jahreis, G. (1989). Stimulation of hepatic acute phase response by cytokines and glucocorticoidsa. Annals of the New York Academy of Sciences, 557, 280–296.
  • Beauchemin, R., N'soukpoé-Kossi, C., Thomas, T., Thomas, T., Carpentier, R., & Tajmir-Riahi, H. (2007). Polyamine analogues bind human serum albumin. Biomacromolecules, 8, 3177–3183.10.1021/bm700697a
  • Berendsen, H. J., van der Spoel, D., & van Drunen, R. (1995). GROMACS: A message-passing parallel molecular dynamics implementation. Computer Physics Communications, 91, 43–56.10.1016/0010-4655(95)00042-E
  • Bhattacharya, A. A., Curry, S., & Franks, N. P. (2000). Binding of the general anesthetics propofol and halothane to human serum albumin. High resolution crystal structures. Journal of Biological Chemistry, 275, 38731–38738.10.1074/jbc.M005460200
  • Bourassa, P., Dubeau, S., Maharvi, G. M., Fauq, A. H., Thomas, T. J., & Tajmir-Riahi, H. A. (2011). Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin. Biochimie, 93, 1089–1101.10.1016/j.biochi.2011.03.006
  • Carter, D., He, X.-M., Munson, S. H., Twigg, P. D., Gernert, K. M., Broom, M. B., & Miller, T. Y. (1989). Three-dimensional structure of human serum albumin. Science, 244, 1195–1198.10.1126/science.2727704
  • Cheresh, D., Haynes, D., & Distasio, J. (1984). Interaction of an acute phase reactant, alpha 1-acid glycoprotein (orosomucoid), with the lymphoid cell surface: A model for non-specific immune suppression. Immunology, 51, 541.
  • Chuang, V. T. G., & Otagiri, M. (2006). Stereoselective binding of human serum albumin. Chirality, 18, 159–166.10.1002/(ISSN)1520-636X
  • Curry, S., Brick, P., & Franks, N. P. (1999). Fatty acid binding to human serum albumin: New insights from crystallographic studies. Biochimica et Biophysica Acta (BBA)-Molecular and Cell Biology of Lipids, 1441, 131–140.10.1016/S1388-1981(99)00148-1
  • Curry, S., Mandelkow, H., Brick, P., & Franks, N. (1998). Crystal structure of human serum albumin complexed with fatty acid reveals an asymmetric distribution of binding sites. Nature Structural & Molecular Biology, 5, 827–835.
  • Feroz, S. R., Mohamad, S. B., Bujang, N., Malek, S. N., & Tayyab, S. (2012). Multispectroscopic and molecular modeling approach to investigate the interaction of flavokawain B with human serum albumin. Journal of Agricultural and Food Chemistry, 60, 5899–5908.10.1021/jf301139h
  • Fey, G., & Fuller, G. (1987). Regulation of acute phase gene expression by inflammatory mediators. Molecular Biology & Medicine, 4, 323–338.
  • Fournier, T., Medjoubi-N, N., & Porquet, D. (2000). Alpha-1-acid glycoprotein. Biochimica et Biophysica Acta (BBA)-Protein Structure and Molecular Enzymology, 1482, 157–171.10.1016/S0167-4838(00)00153-9
  • Garg, A., Manidhar, D. M., Gokara, M., Malleda, C., Reddy, C. S., & Subramanyam, R. (2013). Elucidation of the binding mechanism of coumarin derivatives with human serum albumin. PLoS ONE, 8, e63805.10.1371/journal.pone.0063805
  • Ghuman, J., Zunszain, P. A., Petitpas, I., Bhattacharya, A. A., Otagiri, M., & Curry, S. (2005). Structural basis of the drug-binding specificity of human serum albumin. Journal of Molecular Biology, 353, 38–52.10.1016/j.jmb.2005.07.075
  • Gokara, M., Kimavath, G. B., Podile, A. R., & Subramanyam, R. (in press). Differential interactions and structural stability of chitosan oligomers with human serum albumin and alpha-1-glycoprotein. Journal of Biomolecular Structure & Dynamics 1–15. doi:10.1080/07391102.2013.868321
  • Gokara, M., Malavath, T., Kalangi, S. K., Reddana, P., & Subramanyam, R. (2014). Unraveling the binding mechanism of asiatic acid with human serum albumin and its biological implications. Journal of Biomolecular Structure & Dynamics, 32, 1290–1302. doi:10.1080/07391102.2013.817953
  • Gokara, M., Sudhamalla, B., Amooru, D. G., & Subramanyam, R. (2010). Molecular interaction studies of trimethoxy flavone with human serum albumin. PLoS ONE, 5, e8834. doi:10.1371/journal.pone.000883410.1371/journal.pone.0008834
  • Hein, K. L., Kragh-Hansen, U., Morth, J. P., Jeppesen, M. D., Otzen, D., Møller, J. V., & Nissen, P. (2010). Crystallographic analysis reveals a unique lidocaine binding site on human serum albumin. Journal of Structural Biology, 171, 353–360.10.1016/j.jsb.2010.03.014
  • He, X. M., & Carter, D. C. (1992). Atomic structure and chemistry of human serum albumin. Nature, 358, 209–215.10.1038/358209a0
  • Hussein, B. H. M. (2011). Spectroscopic studies of 7, 8-dihydroxy-4-methylcoumarin and its interaction with bovine serum albumin. Journal of Luminescence, 131, 900–908. doi:10.1016/j.jlumin.2010.12.02110.1016/j.jlumin.2010.12.021
  • Iranfar, H., Rajabi, O., Salari, R., & Chamani, J. (2012). Probing the interaction of human serum albumin with ciprofloxacin in the presence of silver nanoparticles of three sizes: Multispectroscopic and ζ potential investigation. The Journal of Physical Chemistry B, 116, 1951–1964.10.1021/jp210685q
  • Jiang, Y. L. (2008). Design, synthesis and spectroscopic studies of resveratrol aliphatic acid ligands of human serum albumin. Bioorganic & Medicinal Chemistry, 16, 6406–6414.
  • Jones, G., Willett, P., Glen, R. C., Leach, A. R., & Taylor, R. (1997). Development and validation of a genetic algorithm for flexible docking. Journal of Molecular Biology, 267, 727–748.10.1006/jmbi.1996.0897
  • Kalra, E. K. (2003). Nutraceutical-definition and introduction. Aaps Pharmsci, 5, 27–28.
  • Kanakis, C. D., Tarantilis, P. A., Tajmir-Riahi, H. A., & Polissiou, M. G. (2007). Crocetin, dimethylcrocetin, and safranal bind human serum albumin: Stability and antioxidative properties. Journal of Agricultural and Food Chemistry, 55, 970–977.10.1021/jf062638l
  • Kandagal, P., Kalanur, S., Manjunatha, D., & Seetharamappa, J. (2008). Mechanism of interaction between human serum albumin and N-alkyl phenothiazines studied using spectroscopic methods. Journal of Pharmaceutical and Biomedical Analysis, 47, 260–267.10.1016/j.jpba.2008.01.027
  • Kiselev, M., IuA, G., Dobretsov, G., & Komarova, M. (2001). Size of a human serum albumin molecule in solution. Biofizika, 46, 423.
  • Kragh-Hansen, U. (1981). Molecular aspects of ligand binding to serum albumin. Pharmacological Reviews, 33, 17–53.
  • Kragh-Hansen, U., Chuang, V. T. G., & Otagiri, M. (2002). Practical aspects of the ligand-binding and enzymatic properties of human serum albumin. Biological and Pharmaceutical Bulletin, 25, 695–704.10.1248/bpb.25.695
  • Kremer, J. M., Wilting, J., & Janssen, L. (1988). Drug binding to human alpha-1-acid glycoprotein in health and disease. Pharmacological Reviews, 40(1), 1–47.
  • Kulkarni, A. B., Reinke, R., & Feigelson, P. (1985). Acute phase mediators and glucocorticoids elevate alpha 1-acid glycoprotein gene transcription. Journal of Biological Chemistry, 260, 15386–15389.
  • Kumar, G., Walle, U., Bhalla, K., & Walle, T. (1993). Binding of taxol to human plasma, albumin and alpha 1-acid glycoprotein. Research Communications in Chemical Pathology and Pharmacology, 80, 337–344.
  • Lakowicz, J. R. (2009). Principles of fluorescence spectroscopy. Berlin: Springer.
  • Lee, E. B., Shin, K. H., & Woo, W. S. (1984). Pharmacological study on piperine. Archives of Pharmacal Research, 7, 127–132.10.1007/BF02856625
  • Li, D., Ji, B., & Sun, H. (2009). Probing the binding of 8-Acetyl-7-hydroxycoumarin to human serum albumin by spectroscopic methods and molecular modeling. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 73, 35–40.10.1016/j.saa.2009.01.023
  • Liang, L., Tajmir-Riahi, H., & Subirade, M. (2007). Interaction of β-lactoglobulin with resveratrol and its biological implications. Biomacromolecules, 9, 50–56.
  • Malleda, C., Ahalawat, N., Gokara, M., & Subramanyam, R. (2012). Molecular dynamics simulation studies of betulinic acid with human serum albumin. Journal of Molecular Modeling, 18, 2589–2597.10.1007/s00894-011-1287-x
  • Mandeville, J.-S., Froehlich, E., & Tajmir-Riahi, H. A. (2009). Study of curcumin and genistein interactions with human serum albumin. Journal of Pharmaceutical and Biomedical Analysis, 49, 468–474.10.1016/j.jpba.2008.11.035
  • Mansouri, M., Pirouzi, M., Saberi, M. R., Ghaderabad, M., & Chamani, J. (2013). Investigation on the interaction between cyclophosphamide and lysozyme in the presence of three different kind of cyclodextrins: Determination of the binding mechanism by spectroscopic and molecular modeling techniques. Molecules, 18, 789–813.10.3390/molecules18010789
  • Matsumoto, K., Sukimoto, K., Nishi, K., Maruyama, T., Suenaga, A., & Otagiri, M. (2002). Characterization of ligand binding sites on the alpha1-acid glycoprotein in humans, bovines and dogs. Drug Metabolism and Pharmacokinetics, 17, 300.10.2133/dmpk.17.300
  • Min, J., Meng-Xia, X., Dong, Z., Yuan, L., Xiao-Yu, L., & Xing, C. (2004). Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin. Journal of Molecular Structure, 692, 71–80.10.1016/j.molstruc.2004.01.003
  • Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K., & Olson, A. J. (1998). Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. Journal of Computational Chemistry, 19, 1639–1662.10.1002/(ISSN)1096-987X
  • Morris, G. M., Huey, R., Lindstrom, W., Sanner, M. F., Belew, R. K., Goodsell, D. S., & Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30, 2785–2791.10.1002/jcc.v30:16
  • Mosmann, T. (1983). Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. Journal of Immunological Methods, 65, 55–63.10.1016/0022-1759(83)90303-4
  • Neelam, S., Gokara, M., Sudhamalla, B., Amooru, D. G., & Subramanyam, R. (2010). Interaction studies of coumaroyltyramine with human serum albumin and its biological importance. The Journal of Physical Chemistry B, 114, 3005–3012.10.1021/jp910156k
  • N’soukpoé-Kossi, C., Sedaghat-Herati, R., Ragi, C., Hotchandani, S., & Tajmir-Riahi, H. (2007). Retinol and retinoic acid bind human serum albumin: Stability and structural features. International Journal of Biological Macromolecules, 40, 484–490.10.1016/j.ijbiomac.2006.11.005
  • Otagiri, M. (2009). Study on binding of drug to serum protein. Yakugaku zasshi: Journal of the Pharmaceutical Society of Japan, 129, 413.10.1248/yakushi.129.413
  • Pandey, R. K., Saraf, S., & Saraf, S. (2010). Development of fingerprint for single component analysis of an ayurvedic formulation (Sitopaladi Churna) by high performance liquid chromatography. Scholar Research Library Der Pharmacia Lettre, 2, 464–470.
  • Pei, Y. Q. (1983). A review of pharmacology and clinical use of piperine and its derivatives. Epilepsia, 24, 177–182.10.1111/epi.1983.24.issue-2
  • Peters, T., Jr. (1995). All about albumin: Biochemistry, genetics, and medical applications. San Diego, CA: Academic Press.
  • Petitpas, I., Grüne, T., Bhattacharya, A. A., & Curry, S. (2001). Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids. Journal of Molecular Biology, 314, 955–960.10.1006/jmbi.2000.5208
  • Platel, K., & Srinivasan, K. (2004). Digestive stimulant action of spices: A myth or reality? The Indian Journal of Medical Research, 119, 167–179.
  • Sattar, Z., Iranfar, H., Asoodeh, A., Saberi, M. R., Mazhari, M., & Chamani, J. (2012). Interaction between holo transferrin and HSA–PPIX complex in the presence of lomefloxacin: An evaluation of PPIX aggregation in protein–protein interactions. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 1089–1100.10.1016/j.saa.2012.07.034
  • Schüttelkopf, A. W., & van Aalten, D. M. (2004). PRODRG: A tool for high-throughput crystallography of protein–ligand complexes. Acta Crystallographica, Section D: Biological Crystallography, 60, 1355–1363.10.1107/S0907444904011679
  • Singh, N., Kulshrestha, V., Srivastava, R., & Kohli, R. (1973). A comparative evaluation of piperine and nalorphine against morphine induced respiratory depression and analgesia. Indian Journal of Medical Research, 8, 21–26.
  • Sreerama, N., & Woody, R. W. (2004). Computation and analysis of protein circular dichroism spectra. Methods in Enzymology, 318–351.10.1016/S0076-6879(04)83013-1
  • Srinivasan, K. (2007). Black pepper and its pungent principle-piperine: A review of diverse physiological effects. Critical Reviews in Food Science and Nutrition, 47, 735–748.10.1080/10408390601062054
  • Stadnyk, A. W., & Gauldie, J. (1991). The acute phase protein response during parasitic infection. Parasitology Today, 7, 7–12.10.1016/0169-4758(91)90021-F
  • Stekleneva, N., Shevtsova, A., Brazaluk, O., & Kulinich, A. (2010). Expression and structural-functional alterations of α-1-acid glycoprotein at the pathological state. Biopolymers and Cell, 26, 265–272.10.7124/bc
  • Subramanyam, R., Gollapudi, A., Bonigala, P., Chinnaboina, M., & Amooru, D. G. (2009). Betulinic acid binding to human serum albumin: A study of protein conformation and binding affinity. Journal of Photochemistry and Photobiology B: Biology, 94, 8–12.10.1016/j.jphotobiol.2008.09.002
  • Subramanyam, R., Goud, M., Sudhamalla, B., Reddeem, E., Gollapudi, A., Nellaepalli, S., Amooru, D. G. (2009). Novel binding studies of human serum albumin with trans-feruloyl maslinic acid. Journal of Photochemistry and Photobiology B: Biology, 95, 81–88.10.1016/j.jphotobiol.2009.01.002
  • Sudhamalla, B., Gokara, M., Ahalawat, N., Amooru, D. G., & Subramanyam, R. (2010). Molecular dynamics simulation and binding studies of β-sitosterol with human serum albumin and its biological relevance. The Journal of Physical Chemistry B, 114, 9054–9062.10.1021/jp102730p
  • Sudlow, G., Birkett, D., & Wade, D. (1975). The characterization of two specific drug binding sites on human serum albumin. Molecular Pharmacology, 11, 824–832.
  • Sudlow, G., Birkett, D., & Wade, D. (1976). Further characterization of specific drug binding sites on human serum albumin. Molecular Pharmacology, 12, 1052–1061.
  • Sugio, S., Kashima, A., Mochizuki, S., Noda, M., & Kobayashi, K. (1999). Crystal structure of human serum albumin at 2.5 Å resolution. Protein Engineering Design and Selection, 12, 439–446.10.1093/protein/12.6.439
  • Sułkowska, A. (2002). Interaction of drugs with bovine and human serum albumin. Journal of Molecular Structure, 614, 227–232.10.1016/S0022-2860(02)00256-9
  • Tayeh, N., Rungassamy, T., & Albani, J. R. (2009). Fluorescence spectral resolution of tryptophan residues in bovine and human serum albumins. Journal of Pharmaceutical and Biomedical Analysis, 50, 107–116.10.1016/j.jpba.2009.03.015
  • Urien, S., Albengres, E., Pinquier, J.-L., & Tillement, J.-P. (1986). Role of alpha-1 acid glycoprotein, albumin, and nonesterified fatty acids in serum binding of apazone and warfarin. Clinical Pharmacology and Therapeutics, 39, 683–689.10.1038/clpt.1986.119
  • van Gunsteren, W. F., Billeter, S., Eising, A., Hünenberger, P. H., Krüger, P., Mark, A. E., Tironi, I. G. (1996). Biomolecular simulation: The GROMOS96 manual and user guide. Zurich: vdf Hochschulverlag AG an der ETH Ziirich and BIOMOS b.v.
  • van Gunsteren, W. F., Daura, X., & Mark, A. E. (1998). GROMOS force field. Encyclopedia of Computational Chemistry, 2, 1211–1216.
  • Varshney, A., Sen, P., Ahmad, E., Rehan, M., Subbarao, N., & Khan, R. H. (2010). Ligand binding strategies of human serum albumin: How can the cargo be utilized? Chirality, 22, 77–87.10.1002/chir.v22:1
  • Wallace, A. C., Laskowski, R. A., & Thornton, J. M. (1995). LIGPLOT: A program to generate schematic diagrams of protein–ligand interactions. Protein Engineering, Design and Selection, 8, 127–134.10.1093/protein/8.2.127
  • Wanwimolruk, S., Birkett, D., & Brooks, P. (1983). Structural requirements for drug binding to site II on human serum albumin. Molecular Pharmacology, 24, 458–463.
  • Yeggoni, D. P., Gokara, M., Mark Manidhar, D., Rachamallu, A., Nakka, S., Reddy, C. S., & Subramanyam, R. (2014). Binding and molecular dynamics studies of 7-hydroxycoumarin derivatives with human serum albumin and its pharmacological importance. Molecular Pharmaceutics, 11, 1117–1131.10.1021/mp500051f
  • Zhang, M. F., Xu, Z. Q., Ge, Y.-S., Jiang, F. L., & Liu, Y. (2012). Binding of fullerol to human serum albumin: Spectroscopic and electrochemical approach. Journal of Photochemistry and Photobiology B: Biology, 108, 34–43.10.1016/j.jphotobiol.2011.12.006
  • Zhang, G., Que, Q., Pan, J., & Guo, J. (2008). Study of the interaction between icariin and human serum albumin by fluorescence spectroscopy. Journal of Molecular Structure, 881, 132–138.10.1016/j.molstruc.2007.09.002
  • Zsila, F., Bikádi, Z., & Simonyi, M. (2003). Probing the binding of the flavonoid, quercetin to human serum albumin by circular dichroism, electronic absorption spectroscopy and molecular modelling methods. Biochemical Pharmacology, 65, 447–456.10.1016/S0006-2952(02)01521-6

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.