INTERACTIONS OF ANTIDEPRESSANT ESCITALOPRAM WITH ACETIC ACID AND LACTIC ACID: DFT AND MOLECULAR DOCKING ANALYSES

Yıl 2024, , 22 - 31, 27.02.2024

Cemal Parlak , İlkin Şengün

https://doi.org/10.20290/estubtdb.1346741

Öz

Many possible drugs have taken their places in the world market for the treatment of various medical diseases. Drug interactions involve combinations with drugs or other substances that alter the effect of a drug on the body. In this research, by using density functional theory, quantum theory of atoms in molecules, and in silico molecular docking against the receptor for antidepressant, we have investigated possible outcomes if antidepressant escitalopram comes across with an organic acid as acetic or lactic acids. The results suggest that escitalopram and acetic or lactic acids can interact spontaneously without requiring extra energy and depending on the interaction site different stabilities and reactivities are possible. Further, the findings show potential improvement in the effectiveness of antidepressant after interacting.

Anahtar Kelimeler

Escitalopram, Drug interactions, DFT, Molecular docking

INTERACTION OF ANTIDEPRESSANT ESCITALOPRAM AND ACETIC ACID OR LACTIC ACID: DFT AND MOLECULAR DOCKING ANALYSES

Öz

Many possible drugs have taken their places in the world market for the treatment of various medical diseases. Drug interactions involve combinations with drugs or other substances that alter the effect of a drug on the body. In this research, using the advantage of density functional theory, quantum theory of atoms in molecules and in silico molecular docking against the protein receptor 6HIS for antidepressants, we have investigated the possible outcomes if antidepressant escitalopram comes across with an organic acid as acetic or lactic acids. The results suggest that escitalopram and acetic or lactic acids can interact spontaneously without requiring extra energy and depending on the interaction site different stabilities and reactivities are possible. Further, the findings show potential improvement in the effectiveness of antidepressant after associating

Anahtar Kelimeler

Escitalopram, Acetic acid, Lactic acid, Drug interactions, DFT, 6HIS, Molecular docking.

Kaynakça

• [1] Lanser DAC, Van der Kleij MBA, Veerman GDM, Steeghs N, Huitema ADR, Mathijssen RHJ, Oomen-de Hoop E. Design and statistics of pharmacokinetic drug-drug, herb-drug, and food-drug interaction studies in oncology patients. Biomed Pharmacother 2023; 163: 114823.
• [2] Flynn E, Drug-Drug Interactions. 2007. xPharm: The Comprehensive Pharmacology Reference, Editor: Enna SJ, Bylund DB. Boston: Elsevier. 1–3.
• [3] Veerman GDM, Hussaarts K, Jansman FGA, Koolen SWL, van Leeuwen RWF, Mathijssen RHJ. Clinical implications of food-drug interactions with small-molecule kinase inhibitors. Lancet Oncol 2020; 21(5): 265─279.
• [4] Owens MJ, Knight DL, Nemeroff CB. Second-generation SSRIs: human monoamine transporter binding profile of escitalopram and R-fluoxetine. Biol Psychiatry 2001; 50: 345–350.
• [5] Jonathan RT, Davidson MD, Bose A, Korotzer A, Zheng H. Escitalopram in the treatment of generalized anxiety disorder: double-blind, placebo controlled, flexible-dose study. Depress and Anxiety 2004; 19: 234─240.
• [6] Cipriani A, Furukawa TA, Salanti G, Chaimani A, Atkinson LZ, Ogawa Y, Leucht S, Ruhe HG, Turner EH, Higgins JPT, Egger M, Takeshima N, Hayasaka Y, Imai H, Shinohara K, Tajika A, Ioannidis JPA, Geddes JR. Comparative efficacy and acceptability of 21 antidepressant drugs for the acute treatment of adults with major depressive disorder: a systematic review and network meta-analysis. Lancet 2018; 391: 1357–1366.
• [7] The Top 300 of 2020. ClinCalc. Retrieved 7 October 2022.
• [8] Narladkar A, Balnois E, Grohens Y. An AFM study of poly(L-lactic acid) and poly(D-lactic acid) macromolecules and their stereocomplexes at the solid-air interface. Macromol Symp 2006; 241: 34–44.
• [9] Kleerebezem M, Hugenholtz J. Metabolic pathway engineering in lactic acid bacteria. Curr Opin Biotechnol 2003; 14: 232–237.
• [10] Maki-Arvela P, Simakova IL, Salmi T, Murzin DY. Production of lactic acid/lactates from biomass and their catalytic transformations to commodities. Chem Rev 2014; 114: 1909–1971.
• [11] Sengun Yucel I, Kilic G, Charoenyingcharoen P, Yukphan P, Yamada Y. Investigation of the microbiota associated with traditionally produced fruit vinegars with focus on acetic acid bacteria and lactic acid bacteria. Food Biosci 2022; 47: 101636.
• [12] Chan BS, Endo S, Kanai N, Schuster VL. Identification of lactate as a driving force for prostanoid transport by prostaglandin transporter PGT. Am J Physiol Renal Physiol 2002; 282(6): F1097-1102.
• [13] Buckingham, J. Dictionary of Organic Compounds. 1996; 1 (6th ed.). London: Chapman & Hall.
• [14] Cheung H, Tanke RS, Torrence GP. Acetic Acid. Ullmann's Encyclopedia of Industrial Chemistry. 2011; Weinheim: Wiley-VCH.
• [15] Nemecz A, Prevost MS, Menny A, Corringer PJ. Emerging molecular mechanisms of signal transduction in pentameric ligand gated ion channels. Neuron 2016; 90(3): 452–470.
• [16] Fakhfouri G, Rahimian R, Dyhrfjeld-Johnsen J, Zirak MR, Beaulieu JM. 5-HT3 receptor antagonists in neurologic and neuropsychiatric disorders: The iceberg still lies beneath the surface. Pharmacol Rev 2019; 71(3): 383–412.
• [17] Parlak C, Alver Ö, Bağlayan Ö. Quantum mechanical simulation of Molnupiravir drug interaction with Si-doped C60 fullerene. Comput Theor Chem 2021; 1202; 113336.
• [18] Beaula TJ, Muthuraja P, Dhandapani M, Joe IH, Rastogi VK, Jothy VB. Biological applications and spectroscopic investigations of 4-nitrophenol-urea dimer: A DFT approach. Chem Phys Lett 2016; 645: 59-70.
• [19] Tamer Ö, Mahmoody H, Feyzioğlu KF, et al. Synthesis of the first mixed ligand Mn (II) and Cd (II) complexes of 4-methoxy-pyridine-2-carboxylic acid, molecular docking studies and investigation of their anti-tumor effects in vitro. Appl Organometal Chem 2020; 34: e5416.
• [20] Bader RFW. In Atoms in Molecules: A Quantum Theory (Oxford: Clarendon Press), 1990.
• [21] Grabowski SJ. What Is the Covalency of Hydrogen Bonding? Chem Rev 2011; 111: 2597─2625.
• [22] Ferreira LG, Dos Santos RN, Oliva G, Andricopulo AD. Molecular docking and structure-based drug design strategies. Molecules 2015; 20(7): 13384-13421.
• [23] Firouzabadi N, Alimoradi N, Najafizadeh M, Najafizadeh P. Effect of escitalopram on an acetic acid-induced ulcerative colitis model. Clin Exp Pharmacol Physiol 2021; 48(5): 782-790.
• [24] Wei F, Zhou L, Wang Q, Zheng G, Su S. Effect of Compound Lactic Acid Bacteria Capsules on the Small Intestinal Bacterial Overgrowth in Patients with Depression and Diabetes: A Blinded Randomized Controlled Clinical Trial. Disease Markers 2022; 6721695.
• [25] Daboe M, Parlak C, Direm A, Alver Ö, Ramasami P. Interaction between escitalopram and ibuprofen or paracetamol: DFT and molecular docking on the drug-drug interactions. J Biomol Struct Dyn 2024; 42(2): 672-686.
• [26] Guerraoui A, Goudjil M, Direm A, Guerraoui A, Yücel Sengün I, Parlak C, Djedouani A, Chelazzi L, Monti F, Lunedei E, Boumaza B. A rhodanine derivative as a potential antibacterial and anticancer agent: Crystal structure, spectral characterization, DFT calculations, Hirshfeld surface analysis, in silico molecular docking and ADMET studies. J Mol Struct 2023; 1280: 135025.
• [27] Tomasi J, Mennucci B, Cammi R. Quantum mechanical continuum solvation models. Chem Rev 2005; 105: 2999–3094.
• [28] Becke AD. Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 1993; 98: 5648-5652.
• [29] Lee C, Yang W, Parr RG. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 1988; 37: 785-789.
• [30] Parlak C, Alver Ö, Bağlayan Ö, Ramasami P. Theoretical insights of the drug-drug interaction between favipiravir and ibuprofen: a DFT, QTAIM and drug-likeness investigation. J Biomol Struc Dyn 2023; 41: 4313–4320.
• [31] Parr RG, Szentpaly Lv, Liu S. Electrophilicity index. J Am Chem Soc 1999: 121; 1922–1924.
• [32] Padmanabhan J, Parthasarathi R, Subramanian V, Chattaraj PK. Electrophilicity-Based Charge Transfer Descriptor. J Phys Chem A 2007; 111: 1358–1361.
• [33] Simon S, Duran M, Dannenberg J. How does basis set superposition error change the potential surfaces for hydrogen‐bonded dimers? J. Chem. Phys. 1996; 105: 11024–11031.
• [34] Frisch MJ, Trucks GW, Schlegel HB et al. Gaussian 16, Revision C.01, Gaussian Inc., Wallingford, CT. 2016.
• [35] Lu T, Chen F. Multiwfn: A multifunctional wavefunction analyser. Comput Chem 2012; 33: 580–592.
• [36] Dennington RD, Keith TA, Millam JM. GaussView 6.0.16, Gaussian Inc., 2016.
• [37] Morris GM, Huey R, Lindstrom W, Sanner MF, Belew RK, Goodsell DS, Olson AJ. Autodock4 and AutoDockTools4: automated docking with selective receptor flexiblity. J Comput Chem 2009; 16: 2785-2791.
• [38] Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE. The Protein Data Bank. Nucleic Acids Research 2000; 28: 235-242.
• [39] Polovinkin L, Hassaine G, Perot J, Neumann E, Jensen AA, Lefebvre SN, Corringer PJ, Neyton J, Chipot C, Dehez F, Schoehn G, Nury H. Conformational transitions of the serotonin 5-HT3 receptor. Nature 2018; 563 (7730): 275–279.
• [40] BIOVIA, Discovery Studio Visualizer Software, Version 21.1.0, San Diego 2021.