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Research Articles

Exploration of the binding between cuminol and bovine serum albumin through spectroscopic, molecular docking and molecular dynamics methods

, ORCID Icon, & ORCID Icon
Pages 12404-12412 | Received 25 Apr 2021, Accepted 16 Aug 2021, Published online: 06 Sep 2021

References

  • AlAjmi, M. F., Rehman, M. T., Hussain, A., & Rather, G. M. (2018). Pharmacoinformatics approach for the identification of polo-like kinase-1 inhibitors from natural sources as anti-cancer agents. International Journal of Biological Macromolecules, 116, 173–181. https://doi.org/10.1016/j.ijbiomac.2018.05.023
  • Alekseev, R. J., & Rebane, A. L. (2012). Serum albumin: Structure, functions, and health impact. Nova Science Publishers.
  • Ali, M. S., & Al-Lohedan, H. A. (2013). Sulfadiazine binds and unfolds bovine serum albumin: An in vitro study. Molecular Biology Reports, 40(11), 6081–6090. https://doi.org/10.1007/s11033-013-2719-8
  • Ali, M. S., & Al-Lohedan, H. A. (2015). Biophysical characterization of the interaction between human serum albumin and n-dodecyl β-D-maltoside: A multi-technique approach. Colloids and Surfaces. B, Biointerfaces, 134, 392–400. https://doi.org/10.1016/j.colsurfb.2015.06.062
  • Ali, M. S., & Al-Lohedan, H. A. (2016). Multi-technique approach on the interaction between sugar-based surfactant n-dodecyl beta-D-maltoside and bovine serum albumin. Journal of Luminescence, 169, 35–42. https://doi.org/10.1016/j.jlumin.2015.08.049
  • Ali, M. S., & Al-Lohedan, H. A. (2017). Deciphering the interaction of procaine with bovine serum albumin and elucidation of binding site: A multi spectroscopic and molecular docking study. Journal of Molecular Liquids, 236, 232–240. https://doi.org/10.1016/j.molliq.2017.04.020
  • Ali, M. S., & Al-Lohedan, H. A. (2018). Spectroscopic and computational evaluation on the binding of safranal with human serum albumin: Role of inner filter effect in fluorescence spectral correction. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 203, 434–442. https://doi.org/10.1016/j.saa.2018.05.102
  • Ali, M. S., & Al-Lohedan, H. A. (2019). Experimental and computational investigation on the molecular interactions of safranal with bovine serum albumin: Binding and anti-amyloidogenic efficacy of ligand. Journal of Molecular Liquids, 278, 385–393. https://doi.org/10.1016/j.molliq.2019.01.034
  • Ali, M. S., & Al-Lohedan, H. A. (2020). Spectroscopic and molecular docking investigation on the noncovalent interaction of lysozyme with saffron constituent “Safranal”. Acs Omega, 5(16), 9131–9141. https://doi.org/10.1021/acsomega.9b04291
  • Ali, M. S., Amina, M., Al-Lohedan, H. A., & Al Musayeib, N. M. (2017). Elucidation of the interaction of human serum albumin with anti-cancer sipholane triterpenoid from the Red Sea sponge. Luminescence : The Journal of Biological and Chemical Luminescence, 32(2), 223–230. https://doi.org/10.1002/bio.3172
  • Ali, M. S., Amina, M., Al-Lohedan, H. A., & Al Musayeib, N. M. (2018). Human serum albumin binding to the biologically active labdane diterpene “leoheterin”: Spectroscopic and in silico analysis. Journal of Photochemistry and Photobiology. B, Biology, 182, 9–17. https://doi.org/10.1016/j.jphotobiol.2018.03.011
  • Ali, M. S., Muthukumaran, J., & Al-Lohedan, H. A. (2020). Molecular interactions of ceftazidime with bovine serum albumin: Spectroscopic, molecular docking, and DFT analyses. Journal of Molecular Liquids, 313, 113490. https://doi.org/10.1016/j.molliq.2020.113490
  • Ali, M. S., Muthukumaran, J., Jain, M., Al-Lohedan, H. A., Farah, M. A., & Alsowilem, O. I. (2021a). Experimental and computational investigation on the binding of anticancer drug gemcitabine with bovine serum albumin. Journal of Biomolecular Structure and Dynamics, 1–14.
  • Ali, M. S., Muthukumaran, J., Jain, M., Saad S. Al-Sanea, A., & Al-Lohedan, H. A. (2021b). Experimental and in silico investigation on the interaction of indomethacin with bovine serum albumin: Effect of sodium dodecyl sulfate surfactant monomers on the binding. Journal of Molecular Liquids, 336, 116858. https://doi.org/10.1016/j.molliq.2021.116858
  • Ali, M. S., Muthukumaran, J., Jain, M., Santos-Silva, T., Al-Lohedan, H. A., & Al-Shuail, N. S. (2021c). Molecular interactions of cefoperazone with bovine serum albumin: Extensive experimental and computational investigations. Journal of Molecular Liquids, 337, 116354. https://doi.org/10.1016/j.molliq.2021.116354
  • Ali, M. S., Waseem, M., Subbarao, N., & Al-Lohedan, H. A. (2021d). Dynamic interaction between lysozyme and ceftazidime: Experimental and molecular simulation approaches. Journal of Molecular Liquids, 328, 115412. https://doi.org/10.1016/j.molliq.2021.115412
  • Amina, M., Ali, M. S., Al-Musayeib, N. M., & Al-Lohedan, H. A. (2016). Biophysical characterization of the interaction of bovine serum albumin with anticancer sipholane triterpenoid from the Red Sea sponge. Journal of Molecular Liquids, 220, 931–938. https://doi.org/10.1016/j.molliq.2016.05.013
  • Aramesh-Boroujeni, Z., Jahani, S., Khorasani-Motlagh, M., Kerman, K., & Noroozifar, M. (2020). Evaluation of parent and nano-encapsulated terbium(III) complex toward its photoluminescence properties, FS-DNA, BSA binding affinity, and biological applications. Journal of Trace Elements in Medicine and Biology, 61, 126564. https://doi.org/10.1016/j.jtemb.2020.126564
  • Asadpour, S., Aramesh-Boroujeni, Z., & Jahani, S. (2020). In vitro anticancer activity of parent and nano-encapsulated samarium(iii) complex towards antimicrobial activity studies and FS-DNA/BSA binding affinity. RSC Advances, 10(53), 31979–31990. https://doi.org/10.1039/D0RA05280A
  • Atmaca, U., Alp, C., Akincioglu, H., Karaman, H. S., Gulcin, I., & Celik, M. (2021). Novel hypervalent iodine catalyzed synthesis of alpha-sulfonoxy ketones: Biological activity and molecular docking studies. Journal of Molecular Structure, 1239, 130492 (1-13).
  • Au, H. Y. N., Brand, S., Hutchinson, D. W., & Matejtschuk, P. (1984). Structures and ligand-binding properties of human-serum albumins. Biochemical Society Transactions, 12(4), 659–660. https://doi.org/10.1042/bst0120659
  • Carter, D. C., & He, X. M. (1990). Structure of human serum albumin. Science (New York, N.Y.), 249(4966), 302–303. https://doi.org/10.1126/science.2374930
  • Carter, D. C., & Ho, J. X. (1994). Structure of serum-albumin. Advances in Protein Chemistry, 45, 153–203.
  • Chen, Y.-H., Yang, J. T., & Martinez, H. M. (1972). Determination of the secondary structures of proteins by circular dichroism and optical rotatory dispersion. Biochemistry, 11(22), 4120–4131. https://doi.org/10.1021/bi00772a015
  • De, S., Girigoswami, A., & Das, S. (2005). Fluorescence probing of albumin-surfactant interaction. Journal of Colloid and Interface Science, 285(2), 562–573. https://doi.org/10.1016/j.jcis.2004.12.022
  • Dennis, M. S., Zhang, M., Meng, Y. G., Kadkhodayan, M., Kirchhofer, D., Combs, D., & Damico, L. A. (2002). Albumin binding as a general strategy for improving the pharmacokinetics of proteins. The Journal of Biological Chemistry, 277(38), 35035–35043. https://doi.org/10.1074/jbc.M205854200
  • DiPiro, J. T., & S.O.H.-S, A. (2010). Pharmacists, concepts in clinical pharmacokinetics. American Society of Health-System Pharmacists.
  • Eftink, M. R. (1991). Fluorescence quenching reactions. In: T. G. Dewey (Ed.,) Biophysical and biochemical aspects of fluorescence spectroscopy (pp. 1–41). Springer US.
  • Eftink, M. R., & Ghiron, C. A. (1981). Fluorescence quenching studies with proteins. Analytical Biochemistry, 114(2), 199–227. https://doi.org/10.1016/0003-2697(81)90474-7
  • Firdaus, M., Marliyana, S. D., & Razak, M. F. (2020). Initial study on the synthesis of 1-(4 '-Isopropilbenzil)-1,10-phenanthrolinium bromide from cuminyl alcohol, a potent antimalarial. AIP Conference Proceedings, 2237, 020036.
  • Gulcin, I. (2012). Antioxidant activity of food constituents: An overview. Archives of Toxicology, 86, 345–391.
  • Jiang, M., Xie, M. X., Zheng, D., Liu, Y., Li, X. Y., & Chen, X. (2004). Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin. Journal of Molecular Structure., 692(1–3), 71–80. https://doi.org/10.1016/j.molstruc.2004.01.003
  • Kayat, H. P., Gautam, S. D., & Jha, R. N. (2016). GC-MS analysis of hexane extract of Zanthoxylum armatum DC. fruits. Journal of Pharmacognosy and Phytochemistry, 5, 58.
  • Lakowicz, J. R. (2006). Principles of fluorescence spectroscopy. 3rd ed. Springer US.
  • Lee, G. S., Hong, E. J., Gwak, K. S., Park, M. J., Choi, K. C., Choi, I. G., Jang, J. W., & Jeung, E. B. (2010). The essential oils of Chamaecyparis obtusa promote hair growth through the induction of vascular endothelial growth factor gene. Fitoterapia, 81(1), 17–24. https://doi.org/10.1016/j.fitote.2009.06.016
  • Liu, M., Amini, A., & Ahmad, Z. (2017). Safranal and its analogs inhibit Escherichia coli ATP synthase and cell growth. International Journal of Biological Macromolecules, 95, 145–152. https://doi.org/10.1016/j.ijbiomac.2016.11.038
  • Malavya, B. K., & Dutt, S. (1942). Chemical examination of the essential oil derived from the seeds of Carum roxburghianum Benth. In Proceedings of the Indian Academy of Sciences-Section A, Springer, pp. 157.
  • Marchese, A., Arciola, C. R., Barbieri, R., Silva, A. S., Nabavi, S. F., Sokeng, A. J. T., Izadi, M., Jafari, N. J., Suntar, I., Daglia, M., & Nabavi, S. M. (2017). Update on monoterpenes as antimicrobial agents: A particular Focus on p-cymene. Materials, 10, 947. https://doi.org/10.3390/ma10080947
  • Moghaddam, M., Miran, S. N. K., Pirbalouti, A. G., Mehdizadeh, L., & Ghaderi, Y. (2015). Variation in essential oil composition and antioxidant activity of cumin (Cuminum cyminum L.) fruits during stages of maturity. Industrial Crops and Products, 70, 163–169. https://doi.org/10.1016/j.indcrop.2015.03.031
  • Moller, M., & Denicola, A. (2002). Study of protein-ligand binding by fluorescence. Biochemistry and Molecular Biology Education, 30(5), 309–312. https://doi.org/10.1002/bmb.2002.494030050089
  • Niroomand, S., Khorasani-Motlagh, M., Noroozifar, M., Jahani, S., & Moodi, A. (2017). Photochemical and DFT studies on DNA-binding ability and antibacterial activity of lanthanum(III)-phenanthroline complex. Journal of Molecular Structure, 1130, 940–950. https://doi.org/10.1016/j.molstruc.2016.10.076
  • Patil, S. B., Takalikar, S. S., Joglekar, M. M., Haldavnekar, V. S., & Arvindekar, A. U. (2013). Insulinotropic and β-cell protective action of cuminaldehyde, cuminol and an inhibitor isolated from Cuminum cyminum in streptozotocin-induced diabetic rats. The British Journal of Nutrition, 110(8), 1434–1443. https://doi.org/10.1017/S0007114513000627
  • Purcell, M., Neault, J. F., & Tajmir-Riahi, H. A. (2000). Interaction of taxol with human serum albumin. Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 1478(1), 61–68. https://doi.org/10.1016/S0167-4838(99)00251-4
  • Rahman, S., Rehman, M. T., Rabbani, G., Khan, P., AlAjmi, M. F., Hassan, M. I., Muteeb, G., & Kim, J. (2019). Insight of the interaction between 2,4-thiazolidinedione and human serum albumin: A spectroscopic, thermodynamic and molecular docking study. International Journal of Molecular Sciences., 20, 2727.
  • Rehman, M. T., Ahmed, S., & Khan, A. U. (2016). Interaction of meropenem with "N' and "B' isoforms of human serum albumin: A spectroscopic and molecular docking study. Journal of Biomolecular Structure and Dynamics., 34(9), 1849–1864. https://doi.org/10.1080/07391102.2015.1094411
  • Rehman, M. T., & Khan, A. U. (2015). Understanding the interaction between human serum albumin and anti-bacterial/ anti-cancer compounds. Current Pharmaceutical Design, 21(14), 1785–1799. https://doi.org/10.2174/1381612821666150304161201
  • Rehman, M. T., Shamsi, H., & Khan, A. U. (2014). Insight into the binding mechanism of imipenem to human serum albumin by spectroscopic and computational approaches. Molecular Pharmaceutics, 11(6), 1785–1797. https://doi.org/10.1021/mp500116c
  • Shirley, B. A. (1995). Protein stability and folding: Theory and practice. Humana Press.
  • Sirajuddin, M., Ali, S., & Badshah, A. (2013). Drug-DNA interactions and their study by UV-visible, fluorescence spectroscopies and cyclic voltametry. Journal of Photochemistry and Photobiology. B, Biology, 124, 1–19. https://doi.org/10.1016/j.jphotobiol.2013.03.013
  • Stern, O., & Volmer, M. (1919a). The extinction period of fluorescence. Physikalishce Zeitschrift., 20, 183–188.
  • Stern, O., & Volmer, M. (1919b). Über die abklingzeit der fluoreszenz. Physikalishce Zeitschrift., 20, 183–188.
  • Taslimi, P., Erden, Y., Mamedov, S., Zeynalova, L., Ladokhina, N., Tas, R., Tuzun, B., Sujayev, A., Sadeghian, N., Alwasel, S. H., & Gulcin, I. (2021). The biological activities, molecular docking studies, and anticancer effects of 1-arylsuphonylpyrazole derivatives. Journal of Biomolecular Structure & Dynamics, 39(9), 3336–3346. https://doi.org/10.1080/07391102.2020.1763838
  • Taslimi, P., & Gulcin, I. (2018). Antioxidant and anticholinergic properties of olivetol. Journal of Food Biochemistry, 42(3), e12516. https://doi.org/10.1111/jfbc.12516
  • Teissedre, P. L., & Waterhouse, A. L. (2000). Inhibition of oxidation of human low-density lipoproteins by phenolic substances in different essential oils varieties. Journal of Agricultural and Food Chemistry, 48(9), 3801–3805. https://doi.org/10.1021/jf990921x
  • Theodore Peters, J. (1995). All about albumin: Biochemistry, genetics, and medical applications. Academic Press.
  • Watanabe, K., Shono, Y., Kakimizu, A., Okada, A., Matsuo, N., Satoh, A., & Nishimura, H. (1993). New mosquito repellent from Eucalyptus-camaldulensis. Journal of Agricultural and Food Chemistry, 41(11), 2164–2166. https://doi.org/10.1021/jf00035a065
  • Yilmaztekin, M. (2014). Characterization of potent aroma compounds of Cape Gooseberry (Physalis peruviana L.) fruits grown in antalya through the determination of odor activity values. International Journal of Food Properties., 17(3), 469–480. https://doi.org/10.1080/10942912.2011.642446
  • Yinhua, D., Foroughi, M. M., Aramesh-Boroujeni, Z., Jahani, S., Peydayesh, M., Borhani, F., Khatami, M., Rohani, M., Dusek, M., & Eigner, V. (2020). The synthesis, characterization, DNA/BSA/HSA interactions, molecular modeling, antibacterial properties, and in vitro cytotoxic activities of novel parent and niosome nano-encapsulated Ho(iii) complexes. RSC Advances, 10(39), 22891–22908. https://doi.org/10.1039/D0RA03436C
  • Zouari, N., Ayadi, I., Fakhfakh, N., Rebai, A., & Zouari, S. (2012). Variation of chemical composition of essential oils in wild populations of Thymus algeriensis Boiss. et Reut., a North African endemic Species. Lipids in Health and Disease, 11, 28. https://doi.org/10.1186/1476-511X-11-28
  • Zsila, F. (2013). Subdomain IB is the third major drug binding region of human serum albumin: Toward the three-sites model. Molecular Pharmaceutics, 10(5), 1668–1682. https://doi.org/10.1021/mp400027q
  • Zvetanka, D. Z. (2015). Studies on drug – human serum albumin binding: The current state of the matter. Current Pharmaceutical Design, 21, 1817–1830.

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