مطالعه برهمکنش نیکوتین‌آمید با آلبومین سرم انسانی با استفاده از روش‌های طیف‌سنجی و شبیه‌سازی داکینگ مولکولی

نویسندگان

1 گروه شیمی تجزیه، دانشکده شیمی، دانشگاه تبریز، تبریز، ایران

2 مرکز تحقیقات کاربردی دارویی، دانشگاه علوم پزشکی تبریز، تبریز، ایران

3 گروه زیست شناسی، دانشکده علوم، دانشگاه پیام نور، تهران، ایران

4 گروه تغذیه، دانشکده تغذیه و علوم غذایی، دانشگاه علوم پزشکی تبریز، تبریز، ایران

5 گروه شیمی دارویی، دانشکده داروسازی، دانشگاه علوم پزشکی تبریز، تبریز، ایران

چکیده
آلبومین سرم انسانی یکی از مهمترین پروتئین‌های خون است که توانایی اتصال به ‌گستره زیادی از ترکیبات و داروهای مختلف را دارا است. از اینرو آگاهی از چگونگی پیوند داروها با آلبومین برای درک بهتر خصوصیات فارماکوکینتیک و فارماکودینامیک داروها حائز اهمیت است. برهمکنش دارو با آلبومین بر روی توزیع، دفع و برهمکنش دارو با بافتهای هدف اثرگذار است. نیکوتین­آمید یک مکمل دارویی ایمن و ارزان است که برای پیشگیری و درمان کمبود ویتامین ب3 مصرف می‌شود. در این پژوهش برای مطالعه مکانیسم برهمکنش مولکولی نیکوتین‌آمید با آلبومین سرم انسانی از روش‌های اسپکتروسکوپی و داکینگ مولکولی استفاده ‌شده است. تاثیر دما، pH های اسیدی/ بازی و حضور یون‌های فلزی، اوره و گلوکز روی برهمکنش نیکوتین­آمید و آلبومین سرم انسانی بررسی شده است. مطالعات اسپکتروسکوپی نشان دادند که برهمکنش نیکوتین‌آمید با آلبومین سرم انسانی عمدتاً تحت کنترل نیروهای آب‌گریز بوده و واکنش به‌صورت خودبه‌خودی است. تعداد جایگاه اتصال و ثابت اتصال به‌ترتیب برابر با 1 و 104×6/4 (لیتر/مول) است که در حضور گلوکز افزایش مییابند. حضور یون‌های فلزی و pH قلیائی ثابت اتصال نیکوتین­آمید به آلبومین را کاهش می‌دهد. نتایج حاصل نشانگر این است که نیکوتین‌آمید تمایل دارد به نواحی مشابهی که مولکول‌هایی با دنباله اسیدی به آنها می‌چسبند، متصل شود. در تفسیر مکانیسم برهمکنش و نیز حضور نیکوتین‌آمید در پدیده‌های مختلف فیزیولوژیکی بدن انسان نتایج میتواند مفید باشد.


کلیدواژه‌ها


عنوان مقاله English

Study of interaction between nicotinamide and human serum albumin using spectroscopic techniques and molecular docking simulation simulation

نویسندگان English

Golnaz Parvizi Fard 1
Lale Solouki 2
Mostafa Zakariazadeh 3
Hossein Haghaei 4
Somaieh Soltani 5
1 Department of Analytical Chemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran
2 Drug Applied Research Center, Tabriz University of Medical Sciences, Tabriz, Iran
3 Department of Biology, Faculty of Sciences, Payame Noor University, Tehran, Iran
4 Department of Nutrition, Faculty of Nutrition and Food Sciences, Tabriz University of Medical Sciences, Tabriz, Iran
5 Department of Medicinal Chemistry, Faculty of Pharmacy, Tabriz University of Medical Sciences, Tabriz, Iran
چکیده English

Human serum albumin is one of the most important blood proteins that has the ability to bind a wide range of compounds and different drugs. Hence, knowing how drugs bind to albumin is crucial to understand their pharmacokinetics and pharmacodynamic properties. The binding of drugs to protein affects the drug's excretion, distribution and interaction in the target tissues. Nicotinamide (NA) is a safe and inexpensive medical supplement that used to prevent and treat vitamin B3 deficiency. In this research, the molecular mechanism of the interaction between nicotinamide and human serum albumin was studied by the utilization of spectroscopic and molecular docking methods. The effects of temperature, acidic/basic pHs, metal ions, urea, and glucose on the interaction between nicotinamide and human serum albumin were also investigated. The spectroscopic studies indicated that the interaction between nicotinamide and human serum albumin is mainly controled by hydrophobic forces and the interaction is spontaneous. The number of binding site and binding constant is 1 and 4.6×104 (L/mol), respectively, which were increased in the presence of glucose. The presence of metallic ions and basic pH decreased the binding constant of nicotinamide to albumin. The obtained results indicated that nicotinamide tend to binds to the similar sites wherever the molecules with acidic moieties bind. The results could be helpful to interpret the mechanisms of actions of nicotinamide in the various physiological phenomena in the human body.









کلیدواژه‌ها English

carrier protein
drug-protein interaction
molecular simulation
spectroscopy
vitamin B3
Afkham, S., Hanaee, J., Zakariazadeh, M., Fathi, F., Shafiee, S. & Soltani, S. 2020. Molecular mechanism and thermodynamic study of Rosuvastatin interaction with human serum albumin using a surface plasmon resonance method combined with a multi-spectroscopic, and molecular modeling approach. European Journal of Pharmaceutical Sciences 168: 1-10.
Al-Shabib, N.A., Khan, J.M., Malik, A., Rehman, M.T., AlAjmi, M.F., Husain, F.M., Ahmed, M.Z. & Alamery, S.F. 2020. Molecular interactions of food additive dye quinoline yellow (Qy) with alpha-lactalbumin: Spectroscopic and computational studies. Journal of Molecular Liquids 311: 1-8.
Alhumaydhi, F.A., Aljasir, M.A., Aljohani, A.S., Alsagaby, S.A., Alwashmi, A.S., Shahwan, M., Hassan, M.I., Islam, A. & Shamsi, A. 2021.Probing the interaction of memantine, an important Alzheimer's drug, with human serum albumin: In silico and In vitro approach. Journal of Molecular Liquids 340: 116888.
Alvarado, Y.J., Vera-Parra, E., Mendez, A., Romero, F., Gonzalez-Paz, L.A., Moncayo, L.S., Restrepo, J., Rodríguez-Lugo, P., Paz, J.L. & Vera-Villalobos, J. 2021. Conformational change of ovalbumin induced by surface cavity binding of N-Phthaloyl gamma-aminobutyric acid derivative: a study theoretical and experimental. Biointerface Research in Applied Chemistry 11: 9566-9586.
Amézqueta, S., Beltrán, J.L., Bolioli, A.M., Campos-Vicens, L., Luque, F.J. & Ràfols, C. 2021. Evaluation of the interactions between Human Serum Albumin (HSA) and Non-Steroidal Anti-Inflammatory (NSAIDs) drugs by multiwavelength molecular fluorescence, structural and computational analysis. Pharmaceuticals 14: 214.
Andrade, J., Ramirez, R., Conde, M., Sobrino, F. & Bedoya, F.J. 1997. Nicotinamide inhibits inducible nitric oxide synthase enzyme activity in macrophages by allowing nitric oxide to inhibit its own formation. Life Sciences 61: 1843-1850.
Awasthi, S. & Saraswathi, N.T. 2016. Non-enzymatic glycation mediated structure–function changes in proteins: case of serum albumin. RSC Advances 6: 90739-90753.
Barzegar, A., Naghizadeh, E., Zakariazadeh, M. & Azamat, J. 2017. Molecular dynamics simulation study of the HIV-1 protease inhibit ion using fullerene and new fullerene derivatives of carbon nanostructures. Mini Reviews in Medicinal Chemistry 17: 633-647.
Byadagi, K., Meti, M., Nandibewoor, S. & Chimatadar, S. 2017. Investigation of binding behaviour of procainamide hydrochloride with human serum albumin using synchronous, 3D fluorescence and circular dichroism. Journal of Pharmaceutical Analysis 7: 103-109.
Bryszewska, M. 2012. Photo-physical and structural interactions between viologen phosphorus-based dendrimers and human serum albumin. Journal of Luminescence 132: 1553-1563.
Ciepluch, K., Katir, N., Kadib, A.El., Weber, M., Caminade, A.M., Bousmina, M., Majoral, J.P. & Collins, T. M., Caimi, R., Lynch, P.R., Sheffield, J., Mitra, A., Stueber, K. & Smith, Y.R. 1991. The effects of nicotinamide and hyperbaric oxygen on skin flap survival. Scandinavian Journal of Plastic and Reconstructive Surgery and Hand Surgery 25: 5-7.
Ding, F., Liu, W., Zhang, L., Yin, B. & Sun, Y. 2010. Sulfometuron-methyl binding to human serum albumin: Evidence that sulfometuron-methyl binds at the Sudlow's site I. Journal of Molecular Structure 968: 59-66.
Dubey, S., Madana, S.K., Kallubai, M., Sarkar, A. & Subramanyam, R. 2020. Unraveling the stability of plasma proteins upon interaction of synthesized uridine products: biophysical and molecular dynamics approach. Journal of Biomolecular Structure and Dynamics 38: 1927-1937.
Fanali, G., Masi, A.Di., Trezza,V., Marino, M., Fasano, M. & Ascenzi, P. 2012. Human serum albumin: from bench to bedside. Molecular Aspects of Medicine 33: 209-290.
Farsad, S.A., Haghaei, H., Shaban, M., Zakariazadeh, M. & Soltani, S. 2021. Investigations of the molecular mechanism of diltiazem binding to human serum albumin in the presence of metal ions, glucose and urea. Journal of Biomolecular Structure and Dynamics: 1-12.
Francis, J.A., Shalauddin, M., Ridzwan, N.F., Mohamad, S.B., Basirun, W.J. & Tayyab, S. 2020. Interaction mechanism of an antimalarial drug, sulfadoxine with human serum albumin. Spectroscopy Letters 53: 391-405.
Fratoni, V. & Brandi, M.L. 2015. B vitamins, homocysteine and bone health. Nutrients 74: 2176-2192.
Fukuwatari, T. & Shibata, K. 2007. Effect of nicotinamide administration on the tryptophan-nicotinamide pathway in humans. International Journal for Vitamin and Nutrition Research 77: 255-262.
Fujimura, M., Tominaga, T. & Yoshimoto, T. 1997. Nicotinamide inhibits inducible nitric oxide synthase mRNA in primary rat glial cells. Neuroscience Letters 228: 107-110.
Gao, W., Li, N., Chen, Y., Xu, Y., Lin, Y., Yin, Y. & Hu, Z. 2010. Study of interaction between syringin and human serum albumin by multi-spectroscopic method and atomic force microscopy. Journal of Molecular Structure 983: 133-140.
Gholizadeh, S., Haghaei, H., Karami, H., Zakariazadeh, M., Shokri, J. & Soltani, S. 2021. Mode of binding, kinetic and thermodynamic properties of a lipid like drug (Fingolimod) interaction with human serum albumin. BioImpacts. In press.
Greenfield, N.J. 2006. Using circular dichroism spectra to estimate protein secondary structure. Nature Protocols 1: 2876-2890.
Gull, N., Sen, P., Kabir-ud-Din. & Khan, R.H. 2007. Effect of physiological concentration of urea on the conformation of human serum albumin. The Journal of Biochemistry 141: 261-268.
Haghaei, H., Hosseini, S.R.A., Soltani, S., Fathi, F., Mokhtari, F., Karima, S. & Rashidi, M.R. 2020. Kinetic and thermodynamic study of beta-Boswellic acid interaction with Tau protein investigated by surface plasmon resonance and molecular modeling methods. BioImpacts 10: 17-25.
Harding, S.E., Gillis, R.B., Almutairi, F., Erten, T., Kök, M.Ş. & Adams, G.G. 2015. Recent advances in the analysis of macromolecular interactions using the matrix-free method of sedimentation in the analytical ultracentrifuge. Biology 4: 237-250.
Hou, H.N., Qi, Z.D., Yang, Y.W.Ou., Liao, F.L., Zhang, Y. & Liu, Y. 2008. Studies on interaction between Vitamin B12 and human serum albumin. Journal of Pharmaceutical and Biomedical Analysis 47: 134-139.
Huang, S., Qiu, H., Lu, S., Zhu, F. & Xiao, Q. 2015. Study on the molecular interaction of graphene quantum dots with human serum albumin: combined spectroscopic and electrochemical approaches. Journal of Hazardous Materials 285: 18-26.
Jayabharathi, J., Thanikachalam, V., Jayamoorthy, K. & Perumal, M.V. 2011. A physiochemical study of excited state intramolecular proton transfer process: luminescent chemosensor by spectroscopic investigation supported by ab initio calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 79: 6-16.
Karami, K., Rahimi, M., Zakariazadeh, Mostafa., Buyukgungor, Orhan. & Amirghofran, Z. 2018. New phosphorous ylide palladacyclic: Synthesis, characterization, X-Ray crystal structure, biomolecular interaction studies, molecular docking and in vitro cytotoxicity evaluations. Journal of Organometallic Chemistry 878: 60-76.
Karami, K., Rahimi, M., Zakariazadeh, Mostafa., Buyukgungor, Orhan., Momtazi-borojeni, A.A. & Esmaeili, S.A. 2019. A novel silver (I) complex of α-keto phosphorus ylid: Synthesis, characterization, crystal structure, biomolecular interaction studies, molecular docking and in vitro cytotoxic evaluation. Journal of Molecular Structure 1177: 430-443.
Kennedy, D.O. 2016. B vitamins and the brain: mechanisms, dose and efficacy—a review. Nutrients 8: 68.
Kharazian, B., Ahmad, A. & Mabudi, A. 2021. A molecular dynamics study on the binding of gemcitabine to human serum albumin. Journal of Molecular Liquids 337: 116496.
Kotani, A., Watanabe, M., Yamamoto, K., Kusu, F. & Hakamata, H. 2016. Determination of eicosapentaenoic, docosahexaenoic, and arachidonic acids in human plasma by high-performance liquid chromatography with electrochemical detection. Analytical Sciences 32: 1011-1014.
Li, X., Ou, X., Wang, B., Rong, H., Wang, B., Chang, C., Shi, B., Yu, L. & Lu, M. 2020. Rich polymorphism in nicotinamide revealed by melt crystallization and crystal structure prediction. Communications Chemistry 3: 1-8.
Mamizadeh, R. & Razzaghi-Asl, N. 2018. Molecular modeling of drug-albumin interactions: A case study on antifungal agents. Journal of Ardabil University of Medical Sciences 18: 173-190.
Maqbool, M.A., Aslam, M., Akbar, W. & Iqbal, Z. 2018. Biological importance of vitamins for human health: A review. Journal of Agriculture and Basic Science 2: 50-58.
Nakajou, K., Watanabe, H., Kragh-Hansen, U., Maruyama, T. & Otagiri, M. 2003. The effect of glycation on the structure, function and biological fate of human serum albumin as revealed by recombinant mutants. Biochimica et Biophysica Acta (BBA)-General Subjects 1623: 88-97.
Nusrat, S., Siddiqi, M.K., Zaman, M., Zaidi, N., Ajmal, M.R., Alam, P., Qadeer, A., Abdelhameed, A.S. & Khan, R.H. 2016. A comprehensive spectroscopic and computational investigation to probe the interaction of antineoplastic drug nordihydroguaiaretic acid with serum albumins. PLoS One 11: 1-20.
Otagiri, M. & Chuang, V.T.G. 2009. Pharmaceutically important pre-and posttranslational modifications on human serum albumin. Biological and Pharmaceutical Bulletin 32: 527-534.
Otsuka, A., Hanafusa, T., Miyagawa, J., Kono, N. & Tarui, S. 1991. Nicotinamide and 3-aminobenzamide reduce interferon-gamma-induced class Ii MHC (HLA-DR and -DP) molecule expression on cultured human endothelial cells and fibroblasts. Immunopharmacology and Immunotoxicology 13: 263-280.
Pietrzak, L., Mogielnicki, A. & Buczko, W. 2009. Nicotinamide and its metabolite N-methylnicotinamide increase skin vascular permeability in rats. Clinical and Experimental Dermatology 34: 380-384.
Poureshghi, F., Ghandforoushan, P., Safarnejad, A. & Soltani, S. 2017. Interaction of an antiepileptic drug, lamotrigine with human serum albumin (HSA): Application of spectroscopic techniques and molecular modeling methods. Journal of Photochemistry and Photobiology B: Biology 166: 187-192.
Qais, F.A., Sarwar, T., Ahmad, I., Khan, R.A., Shahzad, S.A. & Husain, F.M. 2021. Glyburide inhibits non-enzymatic glycation of HSA: An approach for the management of AGEs associated diabetic complications. International Journal of Biological Macromolecules 169: 143-152.
Rampogu, S. & Lemuel, M.R. 2016. Network based approach in the establishment of the relationship between type 2 diabetes mellitus and its complications at the molecular level coupled with molecular docking mechanism. BioMed Research International 2016: 1-6.
Ravindranath, P.A., Forli, S., Goodsell, D.S., Olson, A.J. & Sanner, M.F. 2015. AutoDockFR: advances in protein-ligand docking with explicitly specified binding site flexibility. PLoS Computational Biology 11: 1-28.
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: 1785-1797.
Rolfe, H.M. 2014. A review of nicotinamide: treatment of skin diseases and potential side effects. Journal of Cosmetic Dermatology 13: 324-328.
Safarnejad, A., Shaghaghi, M., Dehghan, G. & Soltani, S. 2016. Binding of carvedilol to serum albumins investigated by multi-spectroscopic and molecular modeling methods. Journal of Luminescence 176: 149-158.
Sengupta, P., Sardar, P.S., Roy, P., Dasgupta, S. & Bose, A. 2018. Investigation on the interaction of Rutin with serum albumins: Insights from spectroscopic and molecular docking techniques. Journal of Photochemistry and Photobiology B: Biology 183: 101-110.
Snaidr, V.A., Damian, D.L. & Halliday, G.M. 2019. Nicotinamide for photoprotection and skin cancer chemoprevention: A review of efficacy and safety. Experimental Dermatology 28: 15-22.
Soltani, S., Babaei, H., Asadpour-Zeynali, K. & Jouyban, A. 2007. Modeling vasorelaxant activity of some drugs/drug candidates using artificial neural networks. Journal of Pharmacology and Toxicology 2: 411-426.
Steinhardt, J., Krijn, J. & Leidy, J.G. 1971. Differences between bovine and human serum albumins. Binding isotherms, optical rotatory dispersion, viscosity, hydrogen ion titration, and fluorescence effects. Biochemistry 10: 4005-4015.
Sudlow, G., Birkett, D. & Wade, D. 1976. Further characterization of specific drug binding sites on human serum albumin. Molecular Pharmacology 12: 1052-1061.
Szkudlarek, A., Sułkowska, A., Maciążek-Jurczyk, M., Chudzik, M. & Równicka-Zubik, J. 2016. Effects of non-enzymatic glycation in human serum albumin. Spectroscopic analysis. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 152: 645-653.
Taghipour, P., Zakariazadeh, M., Sharifi, M., Dolatabadi, J.E.N. & Barzegar, A. 2018. Bovine serum albumin binding study to erlotinib using surface plasmon resonance and molecular docking methods. Journal of Photochemistry and Photobiology B: Biology 183: 11-15.
Tatardar, S., Jouyban, A., Soltani, S. & Zakariazadeh, M. 2015. QSAR analysis of cyclooxygenase inhibitors selectivity index (COX1/COX2): Application of SVM-RBF and MLR methods. Pharmaceutical Sciences 21: 86-93.
Thakur, A., Patwa, J., Pant, S., Sharma, A. & Flora, S.J.S. 2021. Interaction study of monoisoamyl dimercaptosuccinic acid with bovine serum albumin using biophysical and molecular docking approaches. Scientific Reports 11: 4068.
Trott, O. & Olson, A. 2010. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry 31: 455-461.
Usoltsev, D., Sitnikova, V., Kajava, A. & Uspenskaya, M. 2019. Systematic FTIR spectroscopy study of the secondary structure changes in human serum albumin under various denaturation conditions. Biomolecules 9: 1-17.
Williams, A. & Ramsden, D. 2005. Nicotinamide homeostasis: a xenobiotic pathway that is key to development and degenerative diseases. Medical Hypotheses 65: 353-362.
Wohlrab, J. & Kreft, D. 2014. Niacinamide – mechanisms of action and its topical use in dermatology. Skin Pharmacology and Physiology 27: 311-315.
Xu, H., Liu, Q. & Wen, Y. 2008. Spectroscopic studies on the interaction between nicotinamide and bovine serum albumin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 71: 984-988.
Yadav, R., Sengupta, B. & Sen, P. 2014. Conformational fluctuation dynamics of domain I of human serum albumin in the course of chemically and thermally induced unfolding using fluorescence correlation spectroscopy. The Journal of Physical Chemistry B 118: 5428-5438.
Yang, F., Zhang, Y. & Liang, H. 2014. Interactive association of drugs binding to human serum albumin. International Journal of Molecular Sciences 15: 3580-3595.
Yaseen, Z., Aswal, V., Zhou, X. & Haider, S. 2018. Morphological changes in human serum albumin in the presence of cationic amphiphilic drugs. New Journal of Chemistry 42: 2270-2277.
Yu, J., Liu, J.Y., Xiong, W.M., Zhang, X.Y. & Zheng, Y. 2019. Binding interaction of sodium benzoate food additive with bovine serum albumin: multi-spectroscopy and molecular docking studies. BMC Chemistry 13: 1-8.
Zakariazadeh, M., Barzegar, A., Soltani, S. & Aryapour, H. 2015. Developing 2D-QSAR models for naphthyridine derivatives against HIV-1 integrase activity. Medicinal Chemistry Research 24: 2485-2504.
Zhang, J., Gao, X., Huang, J. & Wang, H. 2020. Probing the interaction between human serum albumin and 9-hydroxyphenanthrene: a spectroscopic and molecular docking study. ACS Omega 5: 16833-16840.
Zhao, T., Liu, Z., Niu, J., Lv, B., Xiao, Y. & Li, Y. 2020. Investigation of the interaction mechanism between salbutamol and human serum albumin by multispectroscopic and molecular docking. BioMed Research International 2020: 1-8.

  • تاریخ دریافت 18 خرداد 1405
  • تاریخ انتشار 18 خرداد 1405