Binding characteristics of Bruton’s tyrosine kinase inhibitor ibrutinib with bovine serum albumin: multi-spectroscopic combined with molecular simulation

References

• Kim, E. S.; Dhillon, S. Ibrutinib: A Review of Its Use in Patients with Mantle Cell Lymphoma or Chronic Lymphocytic Leukaemia. Drugs 2015, 75(7), 769–776. DOI: 10.1007/s40265-015-0380-3.
   PubMedGoogle Scholar
• Seftel, M. D.; Kuruvilla, J.; Kouroukis, T.; Banerji, V.; Fraser, G.; Crump, M.; Kumar, R.; Chalchal, H. I.; Salim, M.; Laister, R. C.; et al. The CDK Inhibitor AT7519M in Patients with Relapsed or Refractory Chronic Lymphocytic Leukemia (CLL) and Mantle Cell Lymphoma. A Phase II Study of the Canadian Cancer Trials Group. Leukemia & Lymphoma 2017, 58(6), 1358–1365. DOI: 10.1080/10428194.2016.1239259.
   PubMed Web of Science ®Google Scholar
• Honigberg, L. A.; Smith, A. M.; Sirisawad, M.; Verner, E.; Loury, D.; Chang, B.; Li, S.; Pan, Z.; Thamm, D. H.; Miller, R. A.; et al. The Bruton Tyrosine Kinase Inhibitor PCI-32765 Blocks B-cell Activation and Is Efficacious in Models of Autoimmune Disease and B-cell Malignancy. Proceedings of the National Academy of Sciences of the United States of America 2010, 107(29), 13075–13080. DOI: 10.1073/pnas.1004594107.
   PubMed Web of Science ®Google Scholar
• Bagcchi, S. Ibrutinib in Pretreated Waldenstrm’s Macroglobulinaemia. The Lancet. Oncology 2015, 16(5), E204. DOI: 10.1016/s1470-2045(15)70185-3.
   PubMedGoogle Scholar
• Du, W.; Teng, T.; Zhou, C. C.; Xi, L.; Wang, J.-Z. Spectroscopic Studies on the Interaction of Bovine Serum Albumin with Ginkgolic Acid: Binding Characteristics and Structural Analysis. Journal of Luminescense. 2012, 132(5), 1207–1214. DOI: 10.1016/j.jlumin.2011.12.067.
   Web of Science ®Google Scholar
• Merlot, A.M.; Kalinowski, D.S.; Richardson, D.R. Unraveling the Mysteries of Serum Albumin-more Than Just a Serum Protein. Frontiers in Physiology 2014, 5, 299–7. DOI: 10.3389/fphys.2014.00299.
   PubMed Web of Science ®Google Scholar
• Rahman, A. J.; Sharma, D.; Kumar, D.; Pathak, M.; Singh, A.; Kumar, V.; Chawla, R.; Ojha, H. Spectroscopic and Molecular Modelling Study of Binding Mechanism of Bovine Serum Albumin with Phosmet. Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 2021, 244, 118803. DOI: 10.1016/j.saa.2020.118803.
   PubMed Web of Science ®Google Scholar
• Safavi, M.S., Shojaosadati, S.A., Yang, H.G., Kim, Y., Park, E.J., Lee, K.C., Na, D.H., Reducing Agent-free Synthesis of Curcumin-loaded Albumin Nanoparticles by Self-Assembly at Room Temperature. International Journal of Pharmaceutics 2017, 529(1-2), 303–309. DOI: 10.1016/j.ijpharm.2017.06.087.
   PubMed Web of Science ®Google Scholar
• Fan, Y.; Yi, J.; Zhang, Y.; Yokoyama, W. Fabrication of Curcumin-loaded Bovine Serum Albumin (BSA)-dextran Nanoparticles and the Cellular Antioxidant Activity. Food Chemistry. 2018, 239, 1210–1218. DOI: 10.1016/j.foodchem.2018.04.055.
   PubMed Web of Science ®Google Scholar
• Verma, P.; Kaur, L.; Aswal, P.; Singh, A.; Ojha, H.; Rahman, A. J.; Singhal, R.; Tiwari, A. K.; Pathak, M. Luminescence Studies of Binding Affinity of Vildagliptin with Bovine Serum Albumin. Journal of Biomolecular Structure and Dynamics. 2022. DOI: 10.1080/07391102.2022.2043939.
   Google Scholar
• Rahman, A. J.; Kaur, L.; Pathak, M.; Singh, A.; Verma, P.; Singhal, R.; Kumar, V.; Ojha, H. Spectroscopic Studies of Binding Interactions of 2-Chloroethylphenyl Sulphide with Bovine Serum Albumin. Journal of Molecular Liquids. 2021, 340, 117144. DOI: 10.1016/j.molliq.2021.117144.
   Web of Science ®Google Scholar
• Zhou, X.Q.; Wang, B.L.; Kou, S.B.; Lin, Z.Y.; Lou, Y.Y.; Zhou, K.L.; Shi, J.H. Multi-spectroscopic Approaches Combined with Theoretical Calculation to Explore the Intermolecular Interaction of Telmisartan with Bovine Serum Albumin. Chemical Physics. 2019, 522, 285–293. DOI: 10.1016/j.chemphys.2019.03.019.
   Web of Science ®Google Scholar
• Chandrasekaran, S.; Sudha, N.; Premnath, D.; Enoch, I. Binding of a Chromen-4-one Schiff’s Base with Bovine Serum Albumin: Capping with Beta-cyclodextrin Influences the Binding. Journal of Biomolecular Structure & Dynamics 2015, 33(9), 1945–1956. DOI: 10.1080/07391102.2014.980323.
   PubMed Web of Science ®Google Scholar
• Sharma, D.; Ojha, H.; Pathak, M.; Singh, B.; Sharma, N.; Singh, A.; Kakkar, R.; Sharma, R. K. Spectroscopic and Molecular Modelling Studies of Binding Mechanism of Metformin with Bovine Serum Albumin. Journal of Molecular Structure. 2016, 1118, 267–274. DOI: 10.1016/j.molstruc.2016.04.030.
   Web of Science ®Google Scholar
• Guo, X.; Li, X.; Jiang, Y.; Yi, L.; Wu, Q.; Chang, H.; Diao, X.; Sun, Y.; Pan, X.; Zhou, N. A Spectroscopic Study on the Interaction between p-Nitrophenol and Bovine Serum Albumin. Journal of Luminescense. 2014, 149, 353–360. DOI: 10.1016/j.jlumin.2014.01.036.
   Web of Science ®Google Scholar
• Feng, J.-F.; Wu, M.; Wang, B.-L.; Kou, S.-B.; Lin, Z.-Y.; Shi, J.-H. In Vitro Investigation on Behavior of Pyriproxyfen Binding onto Bovine Serum Albumin by Mean of Various Spectroscopic Methodologies and In Silico. Chemistryselect 2019, 4(40), 11626–11635. DOI: 10.1002/slct.201902688.
   Google Scholar
• Wang, Y.; Wang, Y.; Luo, Q.; Zhang, H.; Cao, J. Molecular Characterization of the Effects of Ganoderma Lucidum Polysaccharides on the Structure and Activity of Bovine Serum Albumin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2019, 206, 538–546. DOI: 10.1016/j.saa.2018.08.051.
   PubMed Web of Science ®Google Scholar
• Roy, A.S.; Tripathy, D.R.; Chatterjee, A.; Dasgupta, S. The Influence of Common Metal Ions on the Interactions of the Isoflavone Genistein with Bovine Serum Albumin. Spectrochimica Acta A: Molecular and Biomolecular Spectroscopy 2013, 102, 393–402. DOI: 10.1016/j.saa.2012.09.053.
   PubMed Web of Science ®Google Scholar
• Shi, J.-H.; Lou, Y.-Y.; Zhou, K.-L.; Pan, D.-Q. Spectroscopic and Molecular Docking Approaches for the Investigation of Molecular Interactions between Herbicide Sulfosulfuron and Bovine Serum Albumin. Journal of Biomolecular Structure and Dynamics. 2018, 36(11), 2822–2830. DOI: 10.1080/07391102.2017.1375991.
   PubMed Web of Science ®Google Scholar
• Shi, J.-H.; Lou, Y.-Y.; Zhou, K.-L.; Pan, D.-Q. Elucidation of Intermolecular Interaction of Bovine Serum Albumin with Fenhexamid: A Biophysical Prospect. Journal of Photochemistry and Photobiology B: Biology 2018, 180, 125–133. DOI: 10.1016/j.jphotobiol.2018.01.025.
   PubMed Web of Science ®Google Scholar
• Satish, L.; Millan, S.; Sahoo, H. Spectroscopic Insight into the Interaction of Bovine Serum Albumin with Imidazolium-based Ionic Liquids in Aqueous Solution. Luminescence 2017, 32(5), 695–705. DOI: 10.1002/bio.3239.
   PubMedGoogle Scholar
• Samaroo, D.; Zahran, M.; Wills, A.C.; Guevara, J.; Tatonetti, A. In Vitro Interaction and Computational Studies of Glycosylated Photosensitizers with Plasma Proteins. Journal of Porphyrins and Phthalocyanines 2019, 23(04n05), 437–452. DOI: 10.1142/S1088424619500275.
   Google Scholar
• Sudha, N.; Enoch, I. M. V. Interaction of Curculigosides and Their Beta-cyclodextrin Complexes with Bovine Serum Albumin: A Fluorescence Spectroscopic Study. Journal of Solution Chemistry 2011, 40(10), 1755–1768. DOI: 10.1007/s10953-011-9750-y.
   Web of Science ®Google Scholar
• Elzoghby, A.O.; Samy, W.M.; Elgindy, N. Albumin-based Nanoparticles as Potential Controlled Release Drug Delivery Systems. Journal of Controlled Release. 2012, 157(2), 168–182. DOI: 10.1016/j.jconrel.2011.07.031.
   PubMed Web of Science ®Google Scholar
• Prajapati, R.; Somoza, A. Albumin Nanostructures for Nucleic Acid Delivery in Cancer: Current Trend, Emerging Issues, and Possible Solutions. Cancers 2021, 13(14), 3454. DOI: 10.3390/cancers13143454.
   PubMedGoogle Scholar
• Tang, B.; Tang, P.; He, J.; Yang, H.; Li, H. Characterization of the Binding of a Novel Antitumor Drug Ibrutinib with Human Serum Albumin: Insights from Spectroscopic, Calorimetric and Docking Studies. Journal of Photochemistry and Photobiology. B, Biology 2018, 184, 18–26. DOI: 10.1016/j.jphotobiol.2018.05.008.
   PubMed Web of Science ®Google Scholar
• Zhang, R.-J.; Kou, S.-B.; Hu, L.; Li, L.; Shi, J.-H.; Jiang, S.-L. Exploring Binding Interaction of Baricitinib with Bovine Serum Albumin (BSA): Multi-spectroscopic Approaches Combined with Theoretical Calculation. Journal of Molecular Liquids. 2022, 354, 118831. DOI: 10.1016/j.molliq.2022.118831.
   Web of Science ®Google Scholar
• Wang, B.-L.; Kou, S.-B.; Lin, Z.-Y.; Shi, J.-H. Investigation on the Binding Behavior between BSA and Lenvatinib with the Help of Various Spectroscopic and In Silico Methods. Journal of Molecular Structure. 2020, 1204, 127521. DOI: 10.1016/j.molstruc.2019.127521.
   Web of Science ®Google Scholar
• Kaur, L.; Rahman, A. J.; Singh, A.; Pathak, M.; Datta, A.; Singhal, R.; Ojha, H. Binding Studies for the Interaction between Hazardous Organophosphorus Compound Phosmet and Lysozyme: Spectroscopic and In-Silico Analyses. Journal of Molecular Liquids. 2022, 355, 118954. DOI: 10.1016/j.molliq.2022.118954.
   Google Scholar
• Hochepied, T.; Berger, F.G.; Baumann, H.; Libert, C. Alpha(1)-acid Glycoprotein: An Acute phase Protein with Inflammatory and Immunomodulating Properties. Cytokine & Growth Factor Reviews. 2003, 14(1), 25–34. DOI: 10.1016/S1359-6101(02)00054-0.
   PubMed Web of Science ®Google Scholar
• Bianco, G.; Forli, S.; Goodsell, D.S.; Olson, A.J. Covalent Docking Using Autodock: Two-point Attractor and Flexible Side Chain Methods. Protein Science. 2016, 25(1), 295–301. DOI: 10.1002/pro.2733.
   PubMed Web of Science ®Google Scholar
• Gandhi, S.; Roy, I. Synthesis and Characterization of Manganese Ferrite Nanoparticles, and Its Interaction with Bovine Serum Albumin: A Spectroscopic and Molecular Docking Approach. Journal of Molecular Liquids. 2019, 296, 111871. DOI: 10.1016/j.molliq.2019.111871.
   Web of Science ®Google Scholar
• Wang, Q.; Huang, C.R.; Jiang, M.; Zhu, Y.Y.; Wang, J.; Chen, J.; Shi, J.H. Binding Interaction of Atorvastatin with Bovine Serum Albumin: Spectroscopic Methods and Molecular Docking. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2016, 156, 155–163. DOI: 10.1016/j.saa.2015.12.003.
   PubMed Web of Science ®Google Scholar
• Zhang, Y.F.; Zhou, K.L.; Lou, Y.Y.; Pan, D.Q.; Shi, J.H. Investigation of the Binding Interaction between Estazolam and Bovine Serum Albumin: Multi-spectroscopic Methods and Molecular Docking Technique. Journal of Biomolecular Structure and Dynamics. 2017, 35(16), 3605–3614. DOI: 10.1080/07391102.2016.1264889.
   PubMed Web of Science ®Google Scholar
• Jahanban-Esfahlan, A.; Panahi-Azar, V. Interaction of Glutathione with Bovine Serum Albumin: Spectroscopy and Molecular Docking. Food Chemistry. 2016, 202, 426–431. DOI: 10.1016/j.foodchem.2016.02.026.
   PubMed Web of Science ®Google Scholar
• Bolel, P.; Mahapatra, N.; Halder, M. Optical Spectroscopic Exploration of Binding of Cochineal Red A with Two Homologous Serum Albumins. Journal of Agricultural and Food Chemistry 2012, 60(14), 3727–3734. DOI: 10.1021/jf205219w.
   PubMed Web of Science ®Google Scholar
• Liu, X.; Ling, Z.; Zhou, X.; Ahmad, F.; Zhou, Y. Comprehensive Spectroscopic Probing the Interaction and Conformation Impairment of Bovine Serum Albumin (BSA) by Herbicide Butachlor. Journal of Photochemistry and Photobiology B: Biology 2016, 162, 332–339. DOI: 10.1016/j.jphotobiol.2016.07.005.
   PubMed Web of Science ®Google Scholar
• Valdebenito, S.; Zapata-Torres, G.; Lemp, E.; Zanocco, A.L. Experimental and Theoretical Studies of the Photophysics of 7-Amino-3-phenyl-2H-benzo[b] [1,4]oxazin-2-one in Homogeneous Solvents and Beta-cyclodextrin Aqueous Solutions. Afinidad 2015, 72, 53–59.
   Google Scholar
• Aramesh-Boroujeni, Z.; Jahani, S.; Khorasani-Motlagh, M.; Kerman, K.; Aramesh, N.; Asadpour, S.; Noroozifar, M. Experimental and Theoretical Investigations of Dy(III) Complex with 2,2'-Bipyridine Ligand: DNA and BSA Interactions and Antimicrobial Activity Study. Journal of Biomolecular Structure and Dynamics. 2020, 38(16), 4746–4763. DOI: 10.1080/07391102.2019.1689170.
   PubMed Web of Science ®Google Scholar
• Ghuman, J.; Zunszain, P.A.; Petitpas, I.; Bhattacharya, A.A.; Otagiri, M.; Curry, S. Structural Basis of the Drug-binding Specificity of Human Serum Albumin. Journal of Molecular Biology 2005, 353(1), 38–52. DOI: 10.1016/j.jmb.2005.07.075.
   PubMed Web of Science ®Google Scholar
• Ross, P.D.; Subramanian, S. Thermodynamics of Protein Association Reactions: Forces Contributing to Stability. Biochemistry 1981, 20(11), 3096–3102. DOI: 10.1021/bi00514a017.
   PubMed Web of Science ®Google Scholar
• Shi, J.H.; Pan, D.Q.; Wang, X.X.; Liu, T.T.; Jiang, M.; Wang, Q. Characterizing the Binding Interaction between Antimalarial Artemether (AMT) and Bovine Serum Albumin (BSA): Spectroscopic and Molecular Docking Methods. Journal of Photochemistry and Photobiology B: Biology 2016, 162, 14–23. DOI: 10.1016/j.jphotobiol.2016.06.025.
   PubMed Web of Science ®Google Scholar
• Momeni, L.; Mahmodian, S.; Shareghi, B.; Saboury, A.A.; Farhadian, S. The Functional and Structural Stabilization of Trypsin by Sucrose. International Journal of Biological Macromolecules. 2017, 99, 343–349. DOI: 10.1016/j.ijbiomac.2017.02.090.
   PubMed Web of Science ®Google Scholar
• Roy, A.; Seal, P.; Sikdar, J.; Banerjee, S.; Haldar, R. Underlying Molecular Interaction of Bovine Serum Albumin and Linezolid: A Biophysical Outlook. Journal of Biomolecular Structure and Dynamics. 2018, 36(2), 387–397. DOI: 10.1080/07391102.2017.1278721.
   PubMed Web of Science ®Google Scholar
• Pal, S.; Saha, C.; Hossain, M.; Dey, S.K.; Kumar, G.S. Influence of Galloyl Moiety in Interaction of Epicatechin with Bovine Serum Albumin: A Spectroscopic and Thermodynamic Characterization. PLoS One. 2012, 7(8), e43321. DOI: 10.1371/journal.pone.0043321.
   PubMed Web of Science ®Google Scholar
• Wang, B.-L.; Pan, D.-Q.; Zhou, K.-L.; Lou, Y.-Y.; Shi, J.-H. Multi-spectroscopic Approaches and Molecular Simulation Research of the Intermolecular Interaction between the Angiotensin-converting Enzyme Inhibitor (ACE Inhibitor) Benazepril and Bovine Serum Albumin (BSA). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2019, 212, 15–24. DOI: 10.1016/j.saa.2018.12.040.
   PubMed Web of Science ®Google Scholar
• Pan, X.; Qin, P.; Liu, R.; Wang, J. Characterizing the Interaction between Tartrazine and Two Serum Albumins by a Hybrid Spectroscopic Approach. Journal of Agricultural and Food Chemistry 2011, 59(12), 6650–6656. DOI: 10.1021/jf200907x.
   PubMed Web of Science ®Google Scholar
• Jattinagoudar, L.; Meti, M.; Nandibewoor, S.; Chimatadar, S. Evaluation of the Binding Interaction between Bovine Serum Albumin and Dimethyl Fumarate, an Anti-inflammatory Drug by Multispectroscopic Methods. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2016, 156, 164–171. DOI: 10.1016/j.saa.2015.11.026.
   PubMed Web of Science ®Google Scholar
• Suryawanshi, V.D.; Walekar, L.S.; Gore, A.H.; Anbhule, P.V.; Kolekar, G.B. Spectroscopic Analysis on the Binding Interaction of Biologically Active Pyrimidine Derivative with Bovine Serum Albumin. Journal of Pharmaceutical Analysis. 2016, 6(1), 56–63. DOI: 10.1016/j.jpha.2015.07.001.
   PubMed Web of Science ®Google Scholar
• Abdelhameed, A.S.; Alanazi, A.M.; Bakheit, A.H.; Hassan, E.S.; Herqash, R.N.; Almutairi, F.M. Novel BTK Inhibitor Acalabrutinib (ACP-196) Tightly Binds to Site I of the Human Serum Albumin as Observed by Spectroscopic and Computational Studies. International Journal of Biological Macromolecules. 2019, 127, 536–543. DOI: 10.1016/j.ijbiomac.2019.01.083.
   PubMed Web of Science ®Google Scholar
• Kou, S.-B.; Lin, Z.-Y.; Wang, B.-L.; Shi, J.-H.; Liu, Y.-X. Evaluation of the Binding Behavior of Olmutinib (HM61713) with Model Transport Protein: Insights from Spectroscopic and Molecular Docking Studies. Journal of Molecular Structure. 2021, 1224, 129024. DOI: 10.1016/j.molstruc.2020.129024.
   Web of Science ®Google Scholar
• Peng, X.; Wang, X.; Qi, W.; Su, R.; He, Z. Affinity of Rosmarinic Acid to Human Serum Albumin and Its Effect on Protein Conformation Stability. Food Chemistry. 2016, 192, 178–187. DOI: 10.1016/j.foodchem.2015.06.109.
   PubMed Web of Science ®Google Scholar
• Zhang, G.; Wang, L.; Pan, J. Probing the Binding of the Flavonoid Diosmetin to Human Serum Albumin by Multispectroscopic Techniques. Journal of Agricultural and Food Chemistry 2012, 60(10), 2721–2729. DOI: 10.1021/jf205260g.
   PubMed Web of Science ®Google Scholar