Identification of essential oil phytocompounds as natural inhibitors of Odorant-binding protein to prevent malaria through in silico approach

References

• Abdel-Rahman, A., Abou-Donia, S., El-Masry, E., Shetty, A., & Abou-Donia, M. (2004). Stress and combined exposure to low doses of pyridostigmine bromide, DEET, and permethrin produce neurochemical and neuropathological alterations in cerebral cortex, hippocampus, and cerebellum. Journal of Toxicology and Environmental Health, Part A, 67(2), 163–192.
   PubMed Web of Science ®Google Scholar
• Abou-Donia, M. B., Goldstein, L. B., Dechovskaia, A., Bullman, S., Jones, K. H., Herrick, E. A., Abdel-Rahman, A. A., & Khan, W. A. (2001). Effects of daily dermal application of DEET and epermethrin, alone and in combination, on sensorimotor performance, blood-brain barrier, and blood-testis barrier in rats. Journal of Toxicology and Environmental Health, Part A, 62(7), 523–541. https://doi.org/10.1080/152873901300007824
   PubMed Web of Science ®Google Scholar
• Adebayo, T. A., Gbolade, A. A., & Olaifa, J. I. (1999). Comparative study of toxicity of essential oils to larvae of three mosquito species. Nigerian Journal of Natural Products and Medicine, 3, 74–76.
   Google Scholar
• Anvikar, A. R., Sharma, B., Sharma, S. K., Ghosh, S. K., Bhatt, R. M., Kumar, A., Mohanty, S. S., Pillai, C. R., Dash, A. P., & Valecha, N. (2012). In vitro assessment of drug resistance in Plasmodium falciparum in five States of India. The Indian Journal of Medical Research, 135(4), 494–499.
   PubMed Web of Science ®Google Scholar
• Banerjee, P., Eckert, A. O., Schrey, A. K., & Preissner, R. (2018). ProTox-II: A webserver for the prediction of toxicity of chemicals. Nucleic Acids Research, 46(W1), W257–W263.
   PubMed Web of Science ®Google Scholar
• Briassoulis, G., Narlioglou, M., & Hatzis, T. (2001). Toxic encephalopathy associated with use of DEET insect repellents: A case analysis of its toxicity in children. Human & Experimental Toxicology, 20(1), 8–14. https://doi.org/10.1191/096032701676731093
   PubMed Web of Science ®Google Scholar
• Caputo, A., & Garavelli, P. L. (2016). Climate, environment and transmission of malaria. InfezMed, 2, 93–104.
   Google Scholar
• Choochote, W., Chaithong, U., Kamsuk, K., Jitpakdi, A., Tippawangkosol, P., Tuetun, B., Champakaew, D., & Pitasawat, B. (2007). Repellent activity of selected essential oils against Aedes aegypti. Fitoterapia, 78(5), 359–364. https://doi.org/10.1016/j.fitote.2007.02.006
   PubMed Web of Science ®Google Scholar
• Clyne, P. J., Warr, C. G., Freeman, M. R., Lessing, D., Kim, J., & Carlson, J. R. (1999). A novel family of divergent seven-transmembrane proteins: Candidate odorant receptors in Drosophila. Neuron, 22(2), 327–338.
   PubMed Web of Science ®Google Scholar
• Costa, E. B., Silva, R. C., Espejo-Román, J. M., Neto, M. F. d. A., Cruz, J. N., Leite, F. H. A., Silva, C. H. T. P., Pinheiro, J. C., Macêdo, W. J. C., & Santos, C. B. R. (2020). Chemometric methods in antimalarial drug design from 1, 2, 4, 5-tetraoxanes analogues. SAR and QSAR in Environmental Research, 31(9), 677–695. https://doi.org/10.1080/1062936X.2020.1803961
   PubMed Web of Science ®Google Scholar
• Galucio, N. C. d. R., Moysés, D. d. A., Pina, J. R. S., Marinho, P. S. B., Gomes Júnior, P. C., Cruz, J. N., Vale, V. V., Khayat, A. S., & Marinho, A. M. d. R. (2022). Antiproliferative, genotoxic activities and quantification of extracts and cucurbitacin B obtained from Luffa operculata (L.) Cogn. Arabian Journal of Chemistry, 15(2), 103589. https://doi.org/10.1016/j.arabjc.2021.103589
   Web of Science ®Google Scholar
• Daina, A., Michielin, O., & Zoete, V. (2017). SwissADME: A free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules. Scientific Reports, 7(1), 42717–42713. https://doi.org/10.1038/srep42717
   PubMed Web of Science ®Google Scholar
• Debboun, M., & Strickman, D. (2013). Insect repellents and associated personal protection for a reduction in human disease. Medical and Veterinary Entomology, 27(1), 1–9.
   PubMed Web of Science ®Google Scholar
• Di Pietrantonio, F., Benetti, M., CannatÃ, D., Varriale, A., D'Auria, S., & Palla-Papavlu, A. (2013). Surface acoustic wave biosensor based on odorant binding proteins deposited by laser induced forward transfer. Paper presented at the 2013 IEEE International Ultrasonics Symposium (IUS). https://doi.org/10.1109/ULTSYM.2013.0548
   Google Scholar
• Diaz, J. H. (2016). Chemical and plant-based insect repellents: Efficacy, safety, and toxicity. Wilderness & Environmental Medicine, 27(1), 153–163.
   PubMed Web of Science ®Google Scholar
• Dua, V. K., Dev, V., Phookan, S., Gupta, N. C., Sharma, V. P., & Subbarao, S. K. (2003). Multi-drug resistant Plasmodium falciparum malaria in Assam, India: Timing of recurrence and anti-malarial drug concentrations in whole blood. The American Journal of Tropical Medicine and Hygiene, 69(5), 555–557.
   PubMed Web of Science ®Google Scholar
• Duan, L., Guo, X., Cong, Y., Feng, G., Li, Y., & Zhang, J. Z. H. (2019). Accelerated molecular dynamics simulation for helical proteins folding in explicit water. Frontiers in Chemistry, 540, 1–18.
   Google Scholar
• Egor, G. P. (2015). Malaria related knowledge, perception and use of artemisinin-based combination therapy among students of school of nursing Eleyele, Ibadan. Oyo State, Nigeria.
   Google Scholar
• Frances, S. P., Cooper, R. D., Popat, S., & Beebe, N. W. (2001). Field evaluation of repellents containing deet and AI3-37220 against Anopheles koliensis in Papua New Guinea. Journal of the American Mosquito Control Association, 17(1), 42–44.
   PubMed Web of Science ®Google Scholar
• Gachelin, G., Garner, P., Ferroni, E., Verhave, J. P., & Opinel, A. (2018). Evidence and strategies for malaria prevention and control: A historical analysis. Malaria Journal, 17(1), 1–18. https://doi.org/10.1186/s12936-018-2244-2
   PubMedGoogle Scholar
• Gbolade, A. A. (2001). Plant-derived insecticides in the control of malaria vector. Journal of Tropical Medicinal Plants, 2, 91–97.
   Google Scholar
• Ghasemi, F., Zomorodipour, A., Karkhane, A. A., & Khorramizadeh, M. R. (2016). In silico designing of hyper-glycosylated analogs for the human coagulation factor IX. Journal of Molecular Graphics & Modelling, 68, 39–47.
   PubMed Web of Science ®Google Scholar
• Goodsell, D. S., Morris, G. M., & Olson, A. J. (1996). Automated docking of flexible ligands: Applications of AutoDock. Journal of Molecular Recognition, 9(1), 1–5. https://doi.org/10.1002/(SICI)1099-1352(199601)9:1<1::AID-JMR241>3.0.CO;2-6
   PubMed Web of Science ®Google Scholar
• Gruell, H., Hamacher, L., Jennissen, V., Tuchscherer, A., Ostendorf, N., Löffler, T., Hallek, M., Kochanek, M., Tannich, E., Böll, B., & Fätkenheuer, G. (2017). On taking a different route: An unlikely case of malaria by nosocomial transmission. Clinical Infectious Diseases, 65(8), 1404–1406. https://doi.org/10.1093/cid/cix520
   PubMed Web of Science ®Google Scholar
• Gupta, M., Sharma, R., & Kumar, A. (2020). Docking techniques in toxicology: An overview. Current Bioinformatics, 15(6), 600–610. https://doi.org/10.2174/1574893614666191003125540
   Web of Science ®Google Scholar
• Halgren, T. A., Murphy, R. B., Friesner, R. A., Beard, H. S., Frye, L. L., Pollard, W. T., & Banks, J. L. (2004). Glide: A new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. Journal of Medicinal Chemistry, 47(7), 1750–1759.
   PubMed Web of Science ®Google Scholar
• Huang, J., Hua, W., Li, J., & Hua, Z. (2015). Molecular docking to explore the possible binding mode of potential inhibitors of thioredoxin glutathione reductase. Molecular Medicine Reports, 12(4), 5787–5795.
   PubMed Web of Science ®Google Scholar
• Husain, A., Ahmad, A., Khan, S. A., Asif, M., Bhutani, R., & Al-Abbasi, F. A. (2016). Synthesis, molecular properties, toxicity and biological evaluation of some new substituted imidazolidine derivatives in search of potent anti-inflammatory agents. Saudi Pharmaceutical Journal: SPJ, 24(1), 104–114.
   PubMed Web of Science ®Google Scholar
• Jacobson, M. I. W. P. (1983). Plants – The potentials for extracting protein, medicines, and other useful chemicals. Congressional Office of Technology, Washington (DC), 138–146.
   Google Scholar
• Jorgensen, W. L., Chandrasekhar, J., Madura, J. D., Impey, R. W., & Klein, M. L. (1983). Comparison of simple potential functions for simulating liquid water. The Journal of Chemical Physics, 79(2), 926–935. https://doi.org/10.1063/1.445869
   Web of Science ®Google Scholar
• Kar, S., & Kar, S. (2010). Control of malaria. Nature Reviews. Drug Discovery, 9(7), 511–512. https://doi.org/10.1038/nrd3207
   PubMed Web of Science ®Google Scholar
• Kumari, R., Kumar, R., Open Source Drug Discovery Consortium, & Lynn, A. (2014). g_mmpbsaî—A GROMACS tool for high-throughput MM-PBSA calculations. Journal of Chemical Information and Modeling, 54(7), 1951–1962. https://doi.org/10.1021/ci500020m
   PubMed Web of Science ®Google Scholar
• Kuzmanic, A., & Zagrovic, B. (2010). Determination of ensemble-average pairwise root mean-square deviation from experimental B-factors. Biophysical Journal. 98(5), 861–871. https://doi.org/10.1016/j.bpj.2009.11.011
   PubMed Web of Science ®Google Scholar
• Lagunin, A., Zakharov, A., Filimonov, D., & Poroikov, V. (2011). QSAR modelling of rat acute toxicity on the basis of PASS prediction. Molecular Informatics, 30(2–3), 241–250.
   PubMed Web of Science ®Google Scholar
• Lee, M. Y. (2018). Essential oils as repellents against arthropods. BioMed Research International, 2018, 6860271. https://doi.org/10.1155/2018/6860271
   PubMed Web of Science ®Google Scholar
• Lobanov, M., Bogatyreva, N. S., & Galzitskaia, O. V. (2008). Radius of gyration is indicator of compactness of protein structure. Molekuliarnaia Biologiia, 42(4), 701–706.
   PubMed Web of Science ®Google Scholar
• Loutan, L. (2003). Malaria: Still a threat to travellers. International Journal of Antimicrobial Agents, 21(2), 158–163. https://doi.org/10.1016/S0924-8579(02)00367-9
   PubMed Web of Science ®Google Scholar
• Maia, M. F., & Moore, S. J. (2011). Plant-based insect repellents: A review of their efficacy, development and testing. Malaria Journal, 10(S1), 1–15. https://doi.org/10.1186/1475-2875-10-S1-S11
   Google Scholar
• Marsh, J. A., & Teichmann, S. A. (2011). Relative solvent accessible surface area predicts protein conformational changes upon binding. Structure, 19(6), 859–867. https://doi.org/10.1016/j.str.2011.03.010
   PubMed Web of Science ®Google Scholar
• Mccabe, W. F., Barthel, W. F., Gertler, S. I., & Hall, S. A. (1954). Insect repellents. 3. N,N-diethylamides. The Journal of Organic Chemistry, 19(4), 493–498. https://doi.org/10.1021/jo01369a003
   Web of Science ®Google Scholar
• Mischlinger, J., Rönnberg, C., Álvarez-Martínez, M. J., Bühler, S., Paul, M., Schlagenhauf, P., Petersen, E., & Ramharter, M. (2020). Imported malaria in countries where malaria is not endemic: A comparison of semi-immune and nonimmune travelers. Clinical Microbiology Reviews, 33(2), e00104–e00119. https://doi.org/10.1128/CMR.00104-19
   PubMed Web of Science ®Google Scholar
• Mohammadi, T., & Ghayeb, Y. (2018). Atomic insight into designed carbamate-based derivatives as acetylcholine esterase (AChE) inhibitors: A computational study by multiple molecular docking and molecular dynamics simulation. Journal of Biomolecular Structure & Dynamics, 36(1), 126–138.
   PubMed Web of Science ®Google Scholar
• Murty, U. S., & Jamil, K. (1987). Effect of south Indian vetiver against immatures of Culex quinquefasciatus. International Pest Control, 29(1), 8–9.
   Google Scholar
• Norman, F. F., Comeche, B., Chamorro, S., Pérez-Molina, J.-A., & López-Vélez, R. (2020). Update on the major imported protozoan infections in travelers and migrants. Future Microbiology, 15(3), 213–225.
   PubMed Web of Science ®Google Scholar
• O'Boyle, N. M., Banck, M., James, C. A., Morley, C., Vandermeersch, T., & Hutchison, G. R. (2011). Open Babel: An open chemical toolbox. Journal of Cheminformatics, 3, 33.
   PubMed Web of Science ®Google Scholar
• Osimitz, T. G., & Grothaus, R. H. (1995). The present safety assessment of deet. Journal of the American Mosquito Control Association, 11(2 Pt 2), 274–278.
   PubMed Web of Science ®Google Scholar
• Osimitz, T. G., & Murphy, J. V. (1997). Neurological effects associated with use of the insect repellent N,N-diethyl-m-toluamide (DEET. Journal of Toxicology. Clinical Toxicology, 35(5), 435–441.
   PubMed Web of Science ®Google Scholar
• Oyedele, A. O., Gbolade, A. A., Sosan, M. B., Adewoyin, F. B., Soyelu, O. L., & Orafidiya, O. O. (2002). Formulation of an effective mosquito-repellent topical product from lemongrass oil. Phytomedicine, 9(3), 259–262.
   PubMed Web of Science ®Google Scholar
• Pelosi, P., Zhou, J. J., Ban, L. P., & Calvello, M. (2006). Soluble proteins in insect chemical communication. Cellular and Molecular Life Sciences: CMLS, 63(14), 1658–1676.
   PubMed Web of Science ®Google Scholar
• Possas-Abreu, M., Rousseau, L., Ghassemi, F., Lissorgues, G., Habchi, M., & Scorsone, E. (2017). Biomimetic diamond MEMS sensors based on odorant-binding proteins: Sensors validation through an autonomous electronic system. Paper presented at the 2017 ISOCS/IEEE International Symposium on Olfaction and Electronic Nose (ISOEN). https://doi.org/10.1109/ISOEN.2017.7968909
   Google Scholar
• Pronk, S., Páll, S., Schulz, R., Larsson, P., Bjelkmar, P., Apostolov, R., Shirts, M. R., Smith, J. C., Kasson, P. M., van der Spoel, D., Hess, B., & Lindahl, E. (2013). GROMACS 4.5: A high-throughput and highly parallel open source molecular simulation toolkit. Bioinformatics (Oxford, England), 29(7), 845–854. https://doi.org/10.1093/bioinformatics/btt055
   PubMed Web of Science ®Google Scholar
• Sankaran, S., Panigrahi, S., & Mallik, S. (2011). Olfactory receptor based piezoelectric biosensors for detection of alcohols related to food safety applications. Sensors and Actuators B: Chemical, 155(1), 8–18. https://doi.org/10.1016/j.snb.2010.08.003
   Web of Science ®Google Scholar
• Shah, N. K., Dhillon, G. P., Dash, A. P., Arora, U., Meshnick, S. R., & Valecha, N. (2011). Antimalarial drug resistance of Plasmodium falciparum in India: Changes over time and space. The Lancet. Infectious Diseases, 11(1), 57–64.
   PubMed Web of Science ®Google Scholar
• Snyder, J. W., Poe, R. O., Stubbins, J. F., & Garrettson, L. K. (1986). Acute manic psychosis following the dermal application of N,N-diethyl-m-toluamide (DEET) in an adult. Journal of Toxicology, Clinical Toxicology. 24(5), 429–439. https://doi.org/10.3109/15563658608992605
   PubMed Web of Science ®Google Scholar
• Sun, J. S., Xiao, S., & Carlson, J. R. (2018). The diverse small proteins called odorant-binding proteins. Open Biology, 8(12), 180208. https://doi.org/10.1098/rsob.180208
   PubMed Web of Science ®Google Scholar
• Thomsen, R., & Christensen, M. H. (2006). MolDock: A new technique for high-accuracy molecular docking. Journal of Medicinal Chemistry, 49(11), 3315–3321.
   PubMed Web of Science ®Google Scholar
• Thorsell, W., Mikiver, A., Malander, I., & Tunon, H. (1998). Efficacy of plant extracts and oils as mosquito repellents. Phytomedicine, 5(4), 311–323.
   PubMed Web of Science ®Google Scholar
• Vanommeslaeghe, K., Hatcher, E., Acharya, C., Kundu, S., Zhong, S., Shim, J., Darian, E., Guvench, O., Lopes, P., Vorobyov, I., & Mackerell, A. D. (2010). CHARMM general force field: A force field for drug-like molecules compatible with the CHARMM all-atom additive biological force fields. Journal of Computational Chemistry, 31(4), 671–690.
   PubMed Web of Science ®Google Scholar
• Vogt, R. G. (2002). Odorant binding protein homologues of the malaria mosquito Anopheles gambiae; possible orthologues of the OS-E and OS-F OBPs of Drosophila melanogaster. Journal of Chemical Ecology, 28(11), 2371–2376. https://doi.org/10.1023/A:1021009311977
   PubMed Web of Science ®Google Scholar
• Vosshall, L. B., Wong, A. M., & Axel, R. (2000). An olfactory sensory map in the fly brain. Cell, 102(2), 147–159.
   PubMed Web of Science ®Google Scholar
• Wallace, A. C., Laskowski, R. A., & Thornton, J. M. (1995). LIGPLOT: A program to generate schematic diagrams of protein-ligand interactions. Protein Engineering, Design and Selection, 8(2), 127–134. https://doi.org/10.1093/protein/8.2.127
   Web of Science ®Google Scholar
• World Health Organization. (2019). World malaria report. World Health Organization.
   Google Scholar
• World Health Organization. (2020). World malaria report 2020. World Health Organization.
   Google Scholar
• Xue, R. D., Ali, A., & Barnard, D. R. (2003). Laboratory evaluation of toxicity of 16 insect repellents in aerosol sprays to adult mosquitoes. Journal of the American Mosquito Control Association 19(3), 271–274.
   PubMed Web of Science ®Google Scholar