In Silico Investigation of Some Glucose-Aspirin as COX Inhibitor
DOI:
https://doi.org/10.33736/jaspe.4065.2022Keywords:
Anti-inflammatory drug, Cyclooxygenase (COX), Aspirin, Molecular docking,, Sugar estersAbstract
Monosaccharide derived glucose-aspirin (GA) can be prepared by conjugation between glucose and aspirin (ASA). The GA is reported to show higher analgesic and anti-inflammatory properties than ASA itself. In this perspective, six GAs which are composed of β-D-glucopyranose, ASA and acetyl groups are considered for the present investigations. The glucose unit in these GAs possesses regular chair conformation with slightly lower dipole moments. Molecular orbitals indicated a higher HOMO-LUMO gap of the molecules. All GAs showed more prone to electrophilic interactions than aspirin. Overall, glucose-aspirin esters are found to have better non-steroidal anti-inflammatory properties than the original aspirin. These GAs are better inhibitors of cyclooxygenase-2 (COX2, 5f19) compared to cyclooxygenase-1 (COX1, 6y3c) indicating that these GAs are potential drug candidates for COX2 related inflammation. Additionally, aspirinyl group at C-6 or C-3 position of the glucopyranose unit is found more suitable for anti-inflammatory activities as compared to C-4 position.
References
Flower, R. (2003). What are all the things that aspirin does? British Medical Journal, 327, 572–573. https://doi.org/10.1136/bmj.327.7415.572
Chen, H., Zhang, S. M., Hernan, M. A., Schwarzschild, M. A., Willett, W. C., Colditz, G. A., Speizer, F. E., & Ascherio, A. (2003). Non-steroidal anti-inflammatory drugs and the risk of Parkinson’s disease. Archives of Neurology, 60, 1059–1064. http://dx.doi.org/10.1001/archneur.60.8.1059
Entminan, M., Sudeep, G., & Samii, A. (2003). Effect on non-steroidal anti-inflammatory drugs on risk of Alzheimer’s disease: systematic review and meta-analysis of observational studies. British Medical Journal, 327, 128–130. http://dx.doi.org/10.1136/bmj.327.7407.128
Ittaman, S. V., VanWormer, J. J., & Rezkalla, S. H. (2014). The role of aspirin in the prevention of cardiovascular disease. Clinical Medicine & Research, 12(3-4), 147–54. http://dx.doi.org/10.3121/cmr.2013.1197.
Bartolucci, A. A., Tendera, M., Howard, G. (2011). Meta-analysis of multiple primary prevention trials of cardiovascular events using aspirin. American Journal of Cardiology, 107, 1796–1801. http://dx.doi.org/10.1016/j.amjcard.2011.02.325
Soni, A. (2013). Aspirin use among the adult U.S. non-institutionalized population, with and without indicators of heart disease, 2005. Statistical Brief #129. Agency for Healthcare Research and Quality, Medical Expenditure Panel Survey. Link: http://meps.ahrq.gov/mepsweb/data_files/publications/st179/stat179.pdf
Vane, J. R., & Botting, R. M. (2003). The mechanism of action of aspirin. Thrombosis Research, 110, 255-8. http://dx.doi.org/10.1016/s0049-3848(03)00379-7
Mekaj, Y., Daci, F., & Mekaj, A. (2015). New insights into the mechanisms of action of aspirin and its use in the prevention and treatment of arterial and venous thromboembolism. Therapeutics and Clinical Risk Management, 11, 1449-1456. https://doi.org/10.2147/TCRM.S92222
Miner, J., & Hoffhines, A. (2007). The discovery of aspirin’s antithrombotic effects. Texas Heart Institute Journal, 34(2), 179–186.
Krupski, W. C., Weiss, D. G., Rapp, J. H., Corson, J. D., Hobson, R. W. (1992). Adverse effects of aspirin in the treatment of asymptomatic carotid artery stenosis. Journal of Vascular Surgery, 16(4), 588-600. https://doi.org/10.1016/0741-5214(92)90166-6
Karsh, J. (1990). Adverse reactions and interactions with aspirin. Considerations in the treatment of the elderly patient. Drug Safety, 5(5), 317-27. http://dx.doi.org/10.2165/00002018- 199005050-00002
Weinberger, J. (2005). Adverse effects and drug interactions of antithrombotic agents used in prevention of ischaemic stroke. Drugs, 65(4), 461-71. http://dx.doi.org/10.2165/00003495-200565040-00003
Jacob, J. N., & Tazawa, M. J. (2012). Glucose–aspirin: Synthesis and in vitro anti-cancer activity studies. Bioorganic & Medicinal Chemistry Letters, 22, 3168–3171. http://dx.doi.org/10.1016/j.bmcl.2012.03.053
Jacob, J. N., Badyal, D. K. & Bala, S. (2013). Evaluation of the in vivo anti-inflammatory and analgesic activity of a highly water-soluble aspirin conjugate. Basic & Clinical Pharmacology & Toxicology, 112, 171–174. http://dx.doi.org/10.1111/bcpt.12006
Dhavale, D. D., Matin, M. M., Sharma, T., & Sabharwal, S. G. (2003). N-Hydroxyethyl-piperidine and –pyrrolidine homoazasugars: preparation and evaluation of glycosidase inhibitory activity. Bioorganic & Medicinal Chemistry, 11(15), 3295–3305. https://doi.org/10.1016/S0968-0896(03)00231-1
Dhavale, D. D., & Matin, M. M. (2004). Selective sulfonylation of 4-C-hyroxymethyl-β-L-threo-pento-1,4-furanose: Synthesis of bicyclic diazasugars. Tetrahedron, 60(19), 4275–4281. https://doi.org/10.1016/j.tet.2004.03.034
Muhammad, D., Matin, M. M., Miah, S. M. R., Devi, P. (2021). Synthesis, antimicrobial, and DFT studies of some benzyl 4-O-acyl-α-L-rhamnopyranosides. Orbital: The Electronic Journal of Chemistry, 13(3), 250–258. http://dx.doi.org/10.17807/orbital.v13i3.1614
Matin, M. M., Bhuiyan, M. M. H., Afrin, A., & Debnath, D. C. (2013). Comparative antimicrobial activities of some monosaccharide and disaccharide acetates. Journal of Scientific Research, 5(3), 515–525. http://dx.doi.org/10.3329/jsr.v5i3.15695
Kabir, A. K. M. S., Matin, M. M., Hossain, A., & Sattar, M. A. (2003). Synthesis and antimicrobial activities of some rhamnopyranoside derivatives. Journal of the Bangladesh Chemical Society, 16(2), 85–93. ISSN: 1022-016X
Matin, M. M. (2014). Synthesis and antimicrobial study of some methyl 4-O-palmitoyl-α-L-rhamnopyranoside derivatives. Orbital: The Electronic Journal of Chemistry, 6(1), 20–28. https://doi.org/10.17807/orbital.v6i1.553
Matin, M. M., Bhuiyan, M. M. H., Debnath, D. C., & Manchur, M. A. (2013). Synthesis and comparative antimicrobial studies of some acylated D-glucofuranose and D-glucopyranose derivatives. International Journal of Biosciences, 3(8), 279–287. http://dx.doi.org/10.12692/ijb/3.8.279-287
Kabir, A. K. M. S., & Matin, M. M. (1994). Regioselective acylation of a derivative of L-rhamonse using the dibutyltin oxide method. Journal of the Bangladesh Chemical Society, 7(1), 73–79. ISSN: 1022-016X
Ali, M., Karim, M. H., & Matin, M. M. (2021). Efficient synthetic technique, PASS predication, and ADMET studies of acylated n-octyl glucopyranosides. Journal of Applied Science & Process Engineering, 8(1), 648–659. https://doi.org/10.33736/jaspe.2823.2021
Kabir, A. K. M. S., Matin, M. M., Mridha, M. A. U., & Shahed, S. M. (1998). Antifungal activities of some methyl 6-O-trityl-α-D-mannopyranosides. The Chittagong University Journal of Science, 22(1), 41–46. ISSN: 1561-1167
Kabir, A. K. M. S., Matin, M. M., Sanaullah, A. F. M., Sattar, M. A., & Rahman, M. S. (2001). Antimicrobial activities of some lyxoside derivatives. Bangladesh Journal of Microbiology, 18(1), 89–95. ISSN: 1011-9981
Kabir, A. K. M. S., Matin, M. M., Bhuiyan, M. M. R., Rahim, M. A., Rahman, M. S. (2005). Biological evaluation of some monosaccharide derivatives. International Journal of Agriculture and Biology, 7(2), 218–221. ISSN: 1560-8530
Matin, M. M., & Iqbal, M. Z. (2021). Methyl 4-O-(2-chlorobenzoyl)-α-L-rhamnopyranosides: Synthesis, characterization, and thermodynamic studies. Orbital: The Electronic Journal of Chemistry, 13(1), 19–27. http://dx.doi.org/10.17807/orbital.v13i1.1532
Matin, M. M., Bhuiyan, M. M. H., Azad, A. K. M. S., Akther, N. (2017). Design and synthesis of benzyl 4-O-lauroyl-α-L-rhamnopyranoside derivatives as antimicrobial agents. Current Chemistry Letters, Vol.6, No.1, 31–40. https://doi.org/10.5267/j.ccl.2016.10.001
Matin, M. M., & Ibrahim, M. (2010). Synthesis of some methyl 4-O-octanoyl-α-L-rhamnopyranoside derivatives. Journal of Applied Sciences Research, 6(10), 1527–1532. ISSN: 1816-157X
Kim, H. J., Kang, S. H., Choi, S. S., & Kim, E. S. (2017). Redesign of antifungal polyene glycosylation: engineered biosynthesis of disaccharide-modified NPP. Applied Microbiology & Biotechnology, 101, 5131–5137. https://doi.org/10.1007/s00253-017-8303-8
Matin, M. M., Bhuiyan, M. M. H., Azad, A. K. M. S., & Rashid, M. H. O. (2015). Synthesis of 6-O-stearoyl-1,2-O-isopropylidene-α-D-gluco-furanose derivatives for antimicrobial evaluation. Journal of Physical Science, 26,(1), 1–12. ISSN: 1675-3402
Zago, E., Joly, N., Chaveriat, L., Vincent Lequart, V., & Martin, P., (2021). Enzymatic synthesis of amphiphilic carbohydrate esters: Influence of physicochemical and biochemical parameters, Biotechnology Reports, 30, e00631, https://doi.org/10.1016/j.btre.2021.e00631
Matin, M. M., Bhuiyan, M. H., Hossain, M. M., & Roshid, M. H. O. (2015). Comparative antibacterial activities of some monosaccharide and disaccharide benzoates. Orbital: The Electronic Journal of Chemistry, 7(2), 160–167. https://doi.org/10.17807/orbital.v7i2.699
Matin, M. M. (2006). Synthesis of some silyl protected 1,4-galactonolactone derivatives. Journal of Applied Sciences Research, 2(10), 753–756. ISSN: 1816-157X
Chowdhury, A. Z. M. S., & Matin, M. M. (1997). Synthesis of imidazo[1,2-c]pyrido[4¢,3¢:4,5]thieno[3,2-e]-pyrimidine. Chittagong University Studies, Part II: Science, 21(2), 47–52. ISSN: 0253-5459
Khairulzaim, A. A. B. M., Rahman, M. R., Roslan, L., Bakri, M. K. B., Khan, A., Matin, M. M. (2021). Analysis of char prepared by pyrolysis of dabai (Canarium odontophyllum) nutshells as a potential precursor of biocarbon used for wastewater treatment. BioResources, 16(3), 5036–5046. https://doi.org/10.15376/biores.16.3.5036-5046
Santos, C. B. R., Lobato, C. C., Braga, F. S., Morais, S. S. S., Santos, C. F., Fernandes, C. P., Brasil, D. S. B., Hage-Melim, L. I. S., Macedo, W. J. C., & Carvalho, J. C. T. (2014). Application of Hartree-Fock method for modeling of bioactive molecules using SAR and QSPR, Computational Molecular Bioscience, 4, 1–24. http://dx.doi.org/10.4236/cmb.2014.41001
Matin, M. M., Uzzaman, M., Chowdhury, S. A., & Bhuiyan, M. M. H. (2020). In vitro antimicrobial, physicochemical, pharmacokinetics, and molecular docking studies of benzoyl uridine esters against SARS-CoV-2 main protease. Journal of Biomolecular Structure and Dynamics, 1-13. https://doi.org/10.1080/07391102.2020.1850358
Matin, M. M., Hasan, M. S., Uzzaman, M., Bhuiyan, M. M. H., Kibria, S. M., Hossain, M. E., & Roshid, M. H. O. (2020). Synthesis, spectroscopic characterization, molecular docking, and ADMET studies of mannopyranoside esters as antimicrobial agents. Journal of Molecular Structure, 1222, 128821. https://doi.org/10.1016/j.molstruc.2020.128821
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., et al. (2013). Gaussian 09W, Revision D.01. Gaussian, Inc., Wallingford CT.
Matin, M. M., Chakraborty, P., Alam M. S., Islam, M. M., & Hanee, U. (2020) Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies. Carbohydrate Research, 496, 108130. https://doi.org/10.1016/j.carres.2020.108130
Pehkonen, S. O., & Yuan, S. (2018). Chapter 1 - Introduction and Background. Interface Science and Technology, 23, 1-11. https://doi.org/10.1016/B978-0-12-813584-6.00001-6
Matin, M. M., Bhuiyan, M. M. H., Kabir, E., Sanaullah, A. F. M., Rahman, M. A., Hossain, M. E., & Uzzaman, M. (2019). Synthesis, characterization, ADMET, PASS predication, and antimicrobial study of 6-O-lauroyl mannopyranosides. Journal of Molecular Structure, 1195, 189–197. https://doi.org/10.1016/j.molstruc.2019.05.102
Filimonov, D.,A., Lagunin, A. A., Gloriozova, T. A., Rudik, A. V., Druzhilovskii, D. S., Pogodin, P. V., Poroikov, V. V. (2014). Prediction of the biological activity spectra of organic compounds using the PASS online web resource. Chemistry of Heterocyclic Compounds, 50(3), 444–457. https://doi.org/10.1007/s10593-014-1496-1
Matin, M. M., Bhattacharjee, S. C., Chakraborty, P., & Alam M. S. (2019). Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters. Carbohydrate Research, 485, 107812. https://doi.org/10.1016/j.carres.2019.107812
Devi, P., Matin, M. M., Bhuiyan, M. M. H., & Hossain, M. E. (2021). Synthesis, and spectral characterization of 6-O-octanoyl-1,2-O-isopropylidene-α-D-glucofuranose derivatives. Journal of the Turkish Chemical Society Section A: Chemistry, 8(4), 1003-1024. https://doi.org/10.18596/jotcsa.929996
Bakri, M. K. B., Rahman, M. R., & Matin, M. M. (2021). Cellulose reinforcement in thermoset composites. In: Fundamentals and Recent Advances in Nanocomposites Based on Polymers and Nanocellulose, MR Rahman (Ed), 1st Ed, Elsevier Science, 127-142. https://doi.org/10.1016/B978-0-323-85771-0.00011-7
Taib, N-. A. B., Rahman, M. R., Bakri, M. K. B., & Matin, M. M. (2021). Advanced techniques for characterizing cellulose. In: Fundamentals and Recent Advances in Nanocomposites Based on Polymers and Nanocellulose, MR Rahman (Ed), 1st Ed, Elsevier Science, 2021, 53-84. https://doi.org/10.1016/B978-0-323-85771-0.00001-4
Islam, N., Islam, M. D., Rahman, M. R., & Matin, M. M. (2021). Octyl 6-O-hexanoyl-β-D-glucopyranosides: Synthesis, PASS, antibacterial, in silico ADMET, and DFT studies. Current Chemistry Letters, 10(4), 413-426. https://doi.org/10.5267/j.ccl.2021.5.003
Rahim, A., Bhuiyan, M. M. H., & Matin, M. M. (2020). Microwave assisted efficient synthesis of some flavones for antimicrobial and ADMET studies. Journal of Scientific Research, 12(4), 673-685. http://dx.doi.org/10.3329/jsr.v12i4.45523
Fraga, C. A. M. (2001). Razões da Atividade Biológica: Interações Micro- e Biomacromoléculas. Química Nova na Escola, São Paulo-SP, 33–42.
Downloads
Published
How to Cite
Issue
Section
License
Copyright Transfer Statement for Journal
1) In signing this statement, the author(s) grant UNIMAS Publisher an exclusive license to publish their original research papers. The author(s) also grant UNIMAS Publisher permission to reproduce, recreate, translate, extract or summarize, and to distribute and display in any forms, formats, and media. The author(s) can reuse their papers in their future printed work without first requiring permission from UNIMAS Publisher, provided that the author(s) acknowledge and reference publication in the Journal.
2) For open access articles, the author(s) agree that their articles published under UNIMAS Publisher are distributed under the terms of the CC-BY-NC-SA (Creative Commons Attribution-Non Commercial-Share Alike 4.0 International License) which permits unrestricted use, distribution, and reproduction in any medium, for non-commercial purposes, provided the original work of the author(s) is properly cited.
3) For subscription articles, the author(s) agree that UNIMAS Publisher holds copyright, or an exclusive license to publish. Readers or users may view, download, print, and copy the content, for academic purposes, subject to the following conditions of use: (a) any reuse of materials is subject to permission from UNIMAS Publisher; (b) archived materials may only be used for academic research; (c) archived materials may not be used for commercial purposes, which include but not limited to monetary compensation by means of sale, resale, license, transfer of copyright, loan, etc.; and (d) archived materials may not be re-published in any part, either in print or online.
4) The author(s) is/are responsible to ensure his or her or their submitted work is original and does not infringe any existing copyright, trademark, patent, statutory right, or propriety right of others. Corresponding author(s) has (have) obtained permission from all co-authors prior to submission to the journal. Upon submission of the manuscript, the author(s) agree that no similar work has been or will be submitted or published elsewhere in any language. If submitted manuscript includes materials from others, the authors have obtained the permission from the copyright owners.
5) In signing this statement, the author(s) declare(s) that the researches in which they have conducted are in compliance with the current laws of the respective country and UNIMAS Journal Publication Ethics Policy. Any experimentation or research involving human or the use of animal samples must obtain approval from Human or Animal Ethics Committee in their respective institutions. The author(s) agree and understand that UNIMAS Publisher is not responsible for any compensational claims or failure caused by the author(s) in fulfilling the above-mentioned requirements. The author(s) must accept the responsibility for releasing their materials upon request by Chief Editor or UNIMAS Publisher.
6) The author(s) should have participated sufficiently in the work and ensured the appropriateness of the content of the article. The author(s) should also agree that he or she has no commercial attachments (e.g. patent or license arrangement, equity interest, consultancies, etc.) that might pose any conflict of interest with the submitted manuscript. The author(s) also agree to make any relevant materials and data available upon request by the editor or UNIMAS Publisher.
To download Copyright Transfer Statement for Journal, click here
