Evaluation of the effectiveness of new mixed ligand complexes against the vector of Dengue fever Aedes aegypti (Diptera; Culicidae)
Main Article Content
Abstract
Chloroquine phosphate with ibuprofen and sulphamethoxazole were used as mixed ligands with Ni(II), Co(II), Cu(II), and Zn(II) to prepare new transition metal complexes. Metal analysis, IR, and X-ray diffraction (XRD) spectrum analyzes were used to describe them, with some modifications to the World Health Organization (WHO) standard susceptibility test under laboratory conditions. The biological effects of ligands and new complexes against Aedes aegypti mosquito larvae were evaluated at various concentrations. To assess larvicidal efficacy, late third or early fourth instar larvae were exposed to multiple concentrations of the examined compounds, ranging from 50 to 1000 ppm. Cu(II) complexes revealed significant high activity (LC50 = 100 ppm against Ae. Aegypti was compared with the rest of the metal complexes. On the other hand, the Co(II) complex showed no activity against Ae. aegypti. These mixed ligand complexes seemed to be an alternative method for manufactured insecticides to control larvae of this medically important mosquito vector Ae. aegypti. Further research on other metal complex compounds responsible for larvicidal efficacy will be required.
Metrics
Article Details
This work is licensed under a Creative Commons Attribution 4.0 International License.
The corresponding author transfers the copyright of the submitted manuscript and all its versions to Eclet. Quim., after having the consent of all authors, which ceases if the manuscript is rejected or withdrawn during the review process.
When a published manuscript in EQJ is also published in other journal, it will be immediately withdrawn from EQ and the authors informed of the Editor decision.
Self-archive to institutional, thematic repositories or personal webpage is permitted just after publication. The articles published by Eclet. Quim. are licensed under the Creative Commons Attribution 4.0 International License.
References
Abbas, A. M.; Aboelmagd, A.; Kishk, S. M.; Nasrallah, H. H.; Boyd, W. C.; Kalil, H. and Orabi, A.S. A Novel Ibuprofen Derivative and Its Complexes Physicochemical Characterization, DFT Modeling, Docking, In Vitro Anti–Inflammatory Studies, and DNA Interaction. Molecules. 2022, 27 (21), 7540. https://doi.org/10.3390/molecules27217540
Abbott, W. S. A Method of Computing the Effectiveness of an Insecticide. Journal of Economic Entomology. 1925, 18 (2), 265–267. https://doi.org/10.1093/jee/18.2.265a
Adediji, J. F.; Olayinka, E. T.; Adebayo, M. A.; Babatunde, O. A study of the mode of coordination of mixed antimalarial metal complexes. African Journal of Malaria and Tropical Diseases. 2018, 6 (10), 444–449.
Al–Azab, A. M.; Zaituon, A. A.; Al–Ghamdi, K. M.; Abd Al–Galil, F. M. Effect of Four Indigenous Medicinal Plants on Dengue Fever, Vector Aedes aegypti from Jeddah, Saudi Arabia. Biosc. Biotech. Res. Comm. 2020, 13 (1), 212–218. https://doi.org/10.21786/bbrc/13.1/37
Al–Noor, T. H.; Mahdi, R. T.; Ismael, A. H. Preparation, characterization, and antibacterial properties of mixed ligand complexes of L–aspargine and sulfamethoxazole(antibiotic) with Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) ions. Journal of Chemical and Pharmaceutical Research. 2014, 6 (5), 1286–1294. https://doi.org/10.18488/journal.65/2014.1.6/65.6.109.120
Alosaimi, E. H. Spectroscopic Characterization, Thermogravimetry and Biological Studies of Ru(III), Pt(IV), Au(III) Complexes with Sulfamethoxazole Drug Ligand. Crystals. 2022, 12 (3), 340. https://doi.org/10.3390/cryst12030340
Alyousefi, T. A. A.; Abdul–Ghani, R.; Mahdy, M. A. K.; Al–Eryani, S. M. A.; Al–Mekhlafi, A. M.; Raja Y. A.; Shah, S. A.; Beier, J. C. A household–based survey of knowledge, attitudes and practices towards dengue fever among local urban communities in Taiz Governorate, Yemen. BMC Infect Dis. 2016, 16 (1), 543. https://doi.org/10.1186/s12879–016–1895–2
Aroyo, M. I. International Tables for Crystallography Volume A: Space–Group Symmetry. John Wiley and Sons, 2016. https://doi.org/10.1107/97809553602060000114
Bader, N. R. Sample preparation for flame atomic absorption spectroscopy: an overview. RJC. 2011, 4 (1), 49–55.
Bamigboye, O. M.; Ejidike, I. P.; Ahmed, R. N.; Lawal, M.; Nnabuike, G. G. Medubi, K. Chelation, characterization, and antibacterial activities of some mixed isonicotinic acid hydrazide–Paracetamol metal drug complexes. Suranaree J. Sci. Technol. 2020, 27 (3), 030026.
Bar, A.; Andrew, J. Morphology and Morphometry of Aedes aegypti Larvae. Annual Review & Research in Biology. 2013, 3 (1), 1–21.
Bhatt, S.; Gething, P. W.; Brady, O. J.; Messina, J. P.; Farlow, A. W.; Moyes, C. L.; Drake, J. M.; Brownstein, J. S.; Hoen, A. G.; Sankoh, O.; Myers, M. F.; George, D. B.; Jaenisch, T.; Wint, G. R. W.; Simmons, C. P.; Scott, T. W.; Farrar, J. J.; Simon I. Hay, S. I. The global distribution and burden of dengue. Nature. 2013, 496, 504–507. https://doi.org/10.1038/nature12060
Bin Ghouth A. S. B.; Amarasinghe, A.; Letson, G. W. Dengue outbreak in Hadramout, Yemen, 2010: an epidemiological perspective. Am J Trop Med Hyg. 2012, 86 (6),1072. https://doi.org/10.4269/ajtmh.2012.11–0723
Biot, C.; Nosten, F.; Fraisse, L.; Ter–Minassian, D.; Khalife, J.; Dive, D. The antimalarial ferroquine: From bench to clinic. Parasite, 2011, 18, 207–214. https://doi.org/10.1051/parasite/2011183207
Boverhof, D. R.; Bramante, C. M.; Butala, J. H.; Clancy, S. F.; Lafranconi, M.; West, J.; Gordon, S. C. Comparative assessment of nanomaterial definitions and safety evaluation considerations. Regulatory Toxicology and Pharmacology. 2015, 73 (1), 137–150. https://doi.org/10.1016/j.yrtph.2015.06.001
Charrel, R. N.; Leparc–Gofart, I.; Gallian, P.; Lamballerie, X. Globalization of chikungunya: 10 years to invade the world. Clin Microbiol Infect. 2014, 20 (7), 662–663. https://doi.org/10.1111/1469-0691.12694
Chavda, B. R.; Socha, B. N.; Pandya, S. B.; Chaudhary, K. P.; Padariya, T. J.; Alalawy, M. D.; Patel, M. K.; Dubey, R. P.; Patel, U. H. Coordination behavior of dinuclear silver complex of sulfamethoxazole with solvent molecule having static rotational d isorder: Spectroscopic characterization, crystal structure, Hirshfeld surface and antimicrobial activity. J. Mol. Struct. 2021, 1228, 129777. https://doi.org/10.1016/j.molstruc.2020.129777
Chew, T.; Pakasi, T.; Taylor–Robinson, A. Dengue Infection in Indonesia: Improved Clinical Profiling is Needed to Better Inform Patient Management and Disease Outbreak Control. Journal of Tropical Medicine and Health. 2019, 3, 142. https://doi.org/10.29011/2688-6383.000042
David, M. R.; Dantas, E. S.; Maciel–de–Freitas, R.; Codeço, C. T.; Prast, A. E.; Lourenço–de–Oliveira, R. Influence of Larval Habitat Environmental Characteristics on Culicidae Immature Abundance and Body Size of Adult Aedes Aegypti. Front. Ecol. Evol. 2021, 9, 626757. https://doi.org/10.3389/fevo.2021.626757
Fauci, A. S.; Morens, D. M. Zika virus in the Americas—yet another arbovirus threat. New Eng Jour Med. 2016, 374 (7), 601–604. https://doi.org/10.1056/nejmp1600297
Gutu, M. A.; Bekele, A.; Seid, Y.; Mohammed, Y.; Gemechu, F.; Woyessa, A. B.; Tayachew, A.; Dugasa, Y.; Gizachew, L.; Idosa, M.; Tokarz, R. E.; Sugerman, D. Another dengue fever outbreak in eastern Ethiopia—an emerging public health threat. PLOS Negl Trop Dis. 2021, 15 (1), e0008992. https://doi.org/10.1371/journal.pntd.0008992
Jamil, Y. M. S.; Al–Maqtari, M. A.; Al–Qadasi, M. K. Ligational and Spectroscopic On Some Sulfamethoxazole Metal Complexes As Antimicrobial Agents, European Journal Of Pharmaceutical And Medical Research. Ejpmr. 2017, 4 (7), 95–105.
Jamil, Y. M. S.; Al–Azab, F. M.; Al–Selwi, N. A.; Alorini, Th. and Al–Hakimi, A. N. P. Preparation, physicochemical characterization, molecular docking and biological activity of a novel schiff–base and organophosphorus schiff base with some transition metal(II) ions. Main Group Chemistry. 2022a, 1–26. https://doi.org/10.3233/MGC-220101
Jamil, Y. M. S.; Al–Azab, F.; Al–Selwi, N.; Al–duais, F.; Al–Hakimi, A.; Alhagri, I.; El–Sayed, S. Synthesis, Spectroscopic and Antibacterial Studies of New Schiff–base and Organophosphorus Schiff–base with Some Transition Metal (II) Ions. Journal of Qassim University for Science. 2022b, 1 (1), 129–153.
Jamil, Y. M. S.; Al–Azab, F. M.; Al–Selwi, N. A. Novel organophosphorus schiff base ligands: synthesis characterization, ligational aspcts, XRD and biological activity studies. Eclét. Quím. 2023a, 48 (3), 36–53. https://doi.org/10.26850/1678-4618eqj.v48.3.2023.p36-53
Jamil, Y. M. S.; Al–Azab, A.; Al–Azab, F.; Al–Selwi, N. A. Larvicidal Effects of New Organophosphorus Schiff base compounds against Dengue Fever Vector Aedes aegypti (Diptera; Culicidae). Sana’a University Journal of Applied Sciences and Technology 2023b, 1(1) 78 – 87. https://doi.org/10.59628/jast.v1i1.156
Jasim, D. J.; Abbas, A. K. Synthesis, identification, antibacterial, medical and dying performance studies for azosulfamethoxazole metal complexes. Eurasian Chem. Commun. 2022, 4, 16–40. https://doi.org/10.22034/ecc.2022.310593.1251
Kucharski, D. J.; Jaszczak, M. K.; Przemysław Boraty´nski, J. A. Review of Modifications of Quinoline Antimalarials Mefloquine and (hydroxy)Chloroquine. Molecules. 2022, 27 (3), 1003. https://doi.org/10.3390/molecules27031003
Kumar, K. S.; Reena, V. N.; Aravindakshan, K. K. Synthesis, anticancer and larvicidal activities of a novel Schiff base ligand, 3–((2–((1–(4–hydroxyphenyl)ethylidene)amino)ethyl)imino)–N–(p–tolyl) butanamide and its Mn(II), Fe(III), Co(II), Ni(II) and Zn(II) complexes. Results in Chemistry, 2021, 3, 100166. https://doi.org/10.1016/j.rechem.2021.100166
Leandro, A. D. S.; Ayala, M. J. C.; Lopes, R. D.; Martins, C. A.; Maciel–de–Freitas R.; Villela, D. A. M. Entomo–Virological Aedes aegypti Surveillance Applied for Prediction of Dengue Transmission: A SpatioTemporal Modeling Study. Pathogens. 2023, 12 (1), 4. https://doi.org/10.3390/pathogens12010004
Maciel-de-Freitas, R.; Marques, W. A.; Peres, R. C.; Cunha, S. P.; Lourenço-de-Oliveira, R. Variation in Aedes aegypti (Diptera: Culicidae) Container Productivity in a Slum and a Suburban District of Rio de Janeiro during Dry and Wet Seasons. Mem. Inst. Oswaldo Cruz. 2007, 102, 489–496. https://doi.org/10.1590/s0074–02762007005000056
Marcondes, C. B.; Ximenes, F. F. M. Zika virus in Brazil and the danger of infestation by Aedes (Stegomyia) mosquitoes. Rev. Soc. Bras. Med. Trop. 2015, 49 (1), 4–10. https://doi.org/10.1590/0037-8682-0220-2015
Meshnick, S. R.; Dobson, M. J. The history of antimalarial drugs. Antimalarial chemotherapy. P. J. Rosenthal (ed.). 2001, 15–26. https://doi.org/10.1385/1-59259-111-6:15
Mohammad, T.; Abdullah, A. Analytical profiles of drug substances. King Saud University, 1984.
Muthuppalani, M.; Al Otaibi, A.; Balasubramaniyan, S.; Manikandan, S.; Manimaran, P.; Mathubala, G.; Manikandan, A.; Arshad, M. N.; Puttegowda, M.; Alorfi, H. S.; Khan, A.; Asiri, A. M.; Rahman, M. M. Synthesis, Characterization and Bio–Potential Activities of Co(II) and Ni(II) Complexes with O and N Donor Mixed Ligands. Crystals, 2022, 12 (3), 326. https://doi.org/10.3390/cryst12030326
Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. John Wiley and Sons, 1978.
Netoi, A.; Junior, P.; Silva, M.; Lima, S.; Yara, R.; Guimavaes, E.; Santana, E.; Selva, L.; Delira, E.; Vieir, J. Evaluation of Embryotoxic and Embryostatic Effects of the Aqueous Extract of Rhizophora mangle and Tannic Acid on Eggs and Larvae of Aedes aegypti. Anais da Academia Brasileira de Ciencias. 2018, 2 (1), 2141–2148. https://doi.org/10.1590/0001–3765201720170297
Otuokere, I. E.; Okpara, L. O.; Amadi, K. C.; Alisa,C. O.; Okoyeag, A.; Nwadire, F. C. Synthesis, Characterization and Complexation Behaviour of Chloroquine towards Ti (II) Ion. Journal of Pharmaceutical Research International. 2019, 27 (3), 1–6. https://doi.org/10.9734/jpri/2019/v27i330168
Patterson, A. The Scherrer formula for X–ray particle size determination. Phys. Rev. 1939, 56, 978. https://doi.org/10.1103/PhysRev.56.978
Rajaganesh, R.; Murugan, K.; Panneerselvam, C.; Jayashanthini, S.; Roni, M.; Suresh, U.; Trivedi, S.; Rehman, H.; Higuchi, A.; Nicoletti, M.; Benelli, G. Fern–synthesized silver nanocrystals: Towards a new class of mosquito oviposition deterrents. Res. Vet. Sci. 2016, 109, 40–51. https://doi.org/10.1016/j.rvsc.2016.09.012
Rauseo, J.; Barra Caracciolo, A.; Ademollo, N.; Cardoni, M.; Di Lenola, M.; Gaze, W.; Stanton, I.; Grenni, P.; Pescatore, T.; Spataro, F.; Patrolecco, L. Dissipation of the antibiotic sulfamethoxazole in a soil amended with anaerobically digested cattle manure. Mater. 2019, 378, 120769. https://doi.org/10.1016/j.jhazmat.2019.120769
Rayms–Keller, A.; Olson, K. E.; McGaw, M.; Oray, C.; Carlson, J. O.; Beaty, B. J. Effect of Heavy Metals on Aedes aegypti (Diptera: Culicidae) Larva. Ecotoxicology and environmental safety. 1998, 39 (1), 41–47. https://doi.org/10.1006/eesa.1997.1605
Refat, M. S.; Al-Azab F. M.; Al-Maydama H. M.; Amin R. R.; Jamil, Y.M.S. Synthesis and in vitro microbial evaluation of La(III), Ce(III), Sm(III) and Y(III) metal complexes of vitamin B6 drug. Spectrochim. Acta - A: Mol. Biomol. Spectrosc. 2014 127 (2014) 196–215. https://doi.org/10.1016/j.saa.2014.02.043
Saeed, M.; Alenad, A. A.; Malik, M. A. Synthesis of mackinawite FeS thin films from acidic chemical baths. Materials Science in Semiconductor Processing. 2015, 32, 1–5. https://doi.org/10.1016/j.mssp.2014.12.073
Schrauf, S.; Tschismarov, R.; Tauber, E.; Ramsauer, K. Current eforts in the development of vaccines for the prevention of Zika and chikungunya virus Infections. Front Immunol. 2020, 11, 592. https://doi.org/10.3389/fimmu.2020.00592
Scott, T. W.; Chow, E.; Strickman, D.; Kittayapong, P.; Wirtz, R. A.; Lorenz, L. H.; Edman, J. D. Blood–Feeding Patterns of Aedes aegypti (Diptera: Culicidae) Collected in a Rural Thai Village. J. Med. Entomol. 1993, 30, 922–927. https://doi.org/10.1093/jmedent/30.5.922
Shah, B.; Kakumanu, V. K.; Bansal, A. K. Analytical techniques for quantification of amorphous/crystalline phases in pharmaceutical solids. J. Pharm Sci. 2006, 95 (8), 1641–1665. https://doi.org/10.1002/jps.20644
Simmons, C.; Farrar, J. Changing Patterns of Dengue Epidemiology and Implications for Clinical Management and Vaccines. PLoS Med. 2009, 6 (9), e1000129. https://doi.org/10.1371/journal.pmed.1000129
Singh, V. Metal complexes as antimalarial potential: A review. The Pharma Innovation Journal. 2019, 8 (5), 403–406.
Singh, A.; Sharma, J.; Paichha, M.; Chakrabarti, R. Achyranthes aspera (prickly chaff flower) leaves- and seeds-supplemented diets regulate growth, innate immunity, and oxidative stress in Aeromonas hydrophila-challenged Labeo rohita. J. Appl. Aquacult. 2020, 32 (3), 250-267. https://doi.org/10.1080/10454438.2019.1615594
Stork, G.; Niu, D.; Fujimoto, A.; Koft, E. R.; Balkovec, J. M.; Tata, J. R.; Dake, G. R. The first stereoselective total synthesis of quinine. Journal of the American Chemical Society. 2001, 123 (14), 3239–3242. https://doi.org/10.1021/ja004325r
Suresh, U.; Murugan, K.; Benelli, G.; Nicoletti, M.; Barnard, D. R.; Panneerselvam, C.; Kumar, P. M.; Subramaniam, J.; Dinesh, D.; Chandramohan, B. Tackling the growing threat of dengue: Phyllanthus nirurimediated synthesis of silver nanoparticles and their mosquitocidal properties against the dengue vector Aedes aegypti (Diptera: Culicidae). Parasitol Res. 2015, 114 (4), 1551–1562. https://doi.org/10.1007/s00436–015–4339–9
Szafran, Z.; Pike, R. M.; Singh, M. M. Microscale inorganic chemistry. John Wiley & Sons, 1991.
Tisgratog, R.; Sanguanpong, U, Grieco, J. P.; Ngoen–Kluan, R.; Chareonviriyaphap, T. Plants traditionally used as mosquito repellents and the implication for their use in vector control. Acta Tropica. 2016, 157, 136–144. https://doi.org/10.1016/j.actatropica.2016.01.024
Torre, M.; Calvo, S.; Pardo, H.; Mombru, A. W. Synthesis, spectroscopic characterization and crystal structure of disulfamethoxazole diaquo Ni(II) monohydrate. J. Coord. Chem. 2005, 58 (6), 513–520. https://doi.org/10.1080/00958970500037516
Wells, T. N. C. Natural products as starting points for future anti–malarial therapies: going back to our roots. Malaria Journal. 2011, 10 (1), 1–12. https://doi.org/10.1186/1475–2875–10–S1–S3
Wongsrichanalai, C.; Pickard, A. L.; Wernsdorfer, W. H.; Meshnick, S. R. Epidemiology of drug–resistant malaria. The Lancet Infectious Diseases. 2002, 2 (4), 209–218. https://doi.org/10.1016/s1473–3099(02)00239–6
World Health Organization [WHO]. Weekly Epidemiological Record – Malaria, (1982–1997); Technical Report Number 32. Geneva: WHO, 1999. http://www.who.int/wer. Accessed 9 Sept. 2021
World Health Organization [WHO]. UNICEF. The Africa Malaria Report. Geneva: WHO, 2003. https://iris.who.int/handle/10665/67869. Accessed 9 Sept. 2021
World Health Organization [WHO]. Dengue and dengue haemorrhagic fever. Factsheet N°117. Geneva: WHO, 2008.
World Health Organization [WHO]. Dengue Guidelines for diagnosis, treatment, prevention and control 2009. Geneva: WHO, 2009. https://iris.who.int/handle/10665/44188. Accessed 9 Sept. 2021