Araştırma Makalesi
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p-asetamid ve MPAEMA'nın model organizma Galleria mellonella (Lepidoptera: Pyralidae) üzerindeki etkisinin in vivo ve in silico değerlendirilmesi

Yıl 2025, Cilt: 28 Sayı: 3, 625 - 635

Nevin Çankaya , Serap Yalcin , Fahriye Ercan

https://doi.org/10.18016/ksutarimdoga.vi.1591091

Öz

Bu çalışmada 2-kloro-N-(4-metoksifenil)asetamid (p-asetamid) ve 2-(4-metoksifenilamino)-2-oksoetil metakrilat (MPAEMA), tarımsal zararlı Galleria mellonella üzerindeki etkilerini değerlendirmek amacıyla yeniden sentezlenmiştir. p-asetamid ve MPAEMA'nın G. mellonella'nın larva evresine karşı toksisiteleri eş zamanlı olarak değerlendirilmiştir. Sonuçlar, p-asetamidin daha düşük dozlarda böcek larvaları üzerinde öldürücü etkiye sahip olduğunu göstermektedir. p-asetamid ve MPAEMA'nın LC50 dozları sırasıyla 873.572 ve 687.355 uM'dir. Bu değerler, bu maddelere maruz kalan larvaların %50'sinin ölmesinin beklendiği madde konsantrasyonlarını temsil etmektir. p-asetamid ve MPAEMA'nın süperoksit dismutaz (SOD), katalaz (CAT), glutatyon peroksidaz (GPx) ve glutatyon-S-transferaz (GST) proteinleriyle moleküler yerleştirme etkileşimleri analiz edildi. MPAEMA ve glutatyon peroksidaz arasındaki bağlanma enerjisi -6,8 kcal/mol olarak belirlendi. Bu, MPAEMA'nın glutatyon peroksidaz üzerinde inhibitör bir etkiye sahip olabileceğini ve bu enzimi hedef alan pestisitlerin geliştirilmesi için daha fazla araştırılabileceğini düşündürmektedir.

Anahtar Kelimeler

Galleria mellonella Toxicity Molecular docking p-acetamide MPAEMA

Kaynakça

  • Abbott, W.S. (1925). A method of computing the effectiveness of an insecticide. Journal of Economic Entomology, 18(2), 265-267.
  • Abdelaziz, N., Abdelrahman, A. & Elbanna, S. (2024). Toxicity and Physiological Effect of Lemongrass Essential Oil Nano-capsules on the Greater Wax Moth Larvae Galleria mellonella L. (Lepidoptera: Pyralidae). Catrina:The International Journal of Environmental Sciences, 32(1), 61-71.
  • Acikbas, Y., Cankaya, N., Capan, R., Erdogan, M. & Soykan, C. (2016). Swelling behaviour of the 2-(4-methoxyphenylamino)-2-oxoethyl methacrylate monomer LB thin film exposed to various organic vapours by quartz crystal microbalance technique. Journal of Macromolecular Science, Part A, Pure and Applied Chemistry, 53(1), 18–25.
  • Aioub, A.A.A., Hashem, A.S., El-Sappah, A.H., El-Harairy, A., Abdel-Hady, A.A.A., Al-Shuraym, L.A., Sayed, S., Huang, Q. & Abdel-Wahab, S.I.Z. (2023). Identification and Characterization of Glutathione S-transferase Genes in Spodoptera frugiperda (Lepidoptera: Noctuidae) under Insecticides Stress. Toxics, 11(6), 542.
  • Allegra, E., Titball, R.W., Carter, J. & Champion, O.L. (2018). Galleria mellonella larvae allow the discrimination of toxic and non-toxic chemicals, Chemosphere, 198, 469-472.
  • Altıkat, A., Turan, T., Torun, F.E. & Bingül, Z. (2009). Use of Pesticides in Turkey and its Effects on Environment, Atatürk Üniversitesi Ziraat Fakültesi Dergisi, 40(2), 87-92.
  • Alvandial, A., Jawadi M.H., Altıntaş Z.N., Yıldız N. & Karaman, M (2016.) Candida albicans’ın Salgısal Asit Proteinaz Etkinliğinin Araştırılmasında In Vivo Model Olarak Galleria mellonella Larvanın Kullanılması. Türk Mikrobiyoloji Cemiyeti Dergisi, 46(2), 69-75.
  • Banfi, D., Bianchi, T., Mastore, M. & Brivio, M.F. (2024). Optimization of Experimental Infection of the Animal Model Galleria mellonella Linnaeus 1758 (Lepidoptera: Pyralidae) with the Gram-Positive Bacterium Micrococcus luteus. Insects, 15(8), 618.
  • Borase, D.N., Thorat, Y.E., Baitha, A. et al. (2024). Parasitizing efficiency of Tetrastichus howardi (Olliff) (Hymenoptera: Eulophidae) on Galleria mellonella (Linnaeus) (Lepidoptera: Pyralidae) larva and pupa. Egyptian Journal of Biological Pest Control, 34(1), 14.
  • Bugyna, L., Kendra, S. & Bujdáková, H. (2023). Galleria mellonella—A Model for the Study of aPDT—Prospects and Drawbacks. Microorganisms, 11(6), 1455.
  • Cankaya, N. Izdal, M, Azarkan, S.Y. (2021). Synthesis, characterization, biological evaluation and molecular docking studies of new oxoacrylate and acetamide on hela cancer cell lines. Current Computer-Aided Drug Design, 17(6), 838−848.
  • Chowdhury, S.K., Banerjee, M., Basnett, D. & Mazumdar, T. (2023). Natural pesticides for pest control in agricultural crops: an alternative and eco-friendly method, Plant Science Today, 11(1), 433–450.
  • Coates, C.J., Lim, J., Harman, K., Rowley, A.F., Griffiths, D.J., Emery, H. & Layton, W. (2019). The insect, Galleria mellonella, is a compatible model for evaluating the toxicology of okadaic acid, Cell Biology and Toxicology, 35, 219–232.
  • Çelik, C., Stanley, D. & Büyükgüzel, E. (2024). Dietary oxyclozanide influences antioxidant enzyme activities and damages DNA in Galleria mellonella (Lepidoptera: Pyralidae), Environmental Entomology, 53(5), 789–800.
  • Çoban, V., Çankaya, N. & Azarkan, S.Y. (2024). New Oxomethacrylate and Acetamide: Synthesis, Characterization and their Computational Approaches: Molecular Docking, Molecular Dynamic, ADME, Drug and Chemical Toxicology, 47(6), 1175–1184.
  • Dent, D. & Binks, R.H., Insect pest management. 3rd ed. Wallingford (Oxfordshire, UK): CABI; 2020. p. 380. Firacative, C., Khan, A., Duan, S., Ferreira-Paim, K., Leemon, D. & Meyer, W. (2020). Rearing and Maintenance of Galleria mellonella and Its Application to Study Fungal Virulence, Journal of Fungi (Basel). 6(3), 130.
  • Humphrey, W., Dalke, A. & Schulten, K. (1996). VMD: visual molecular dynamics. Journal of Molecular Graphics, 14(1), 33–28.
  • Karimi-Maleh, H., Ghalkhani, M., Dehkordi, Z.S., Tehran, M.M., Singh, J., Wen, Y., Baghayeri, M., Rouhi, J., Fu, L. & Rajendran, S. (2024). Mof-enabled pesticides as developing approach for sustainable agriculture and reducing environmental hazards, Journal of Industrial and Engineering Chemistry, 129, 105-123.
  • Kelly, L.A., Mezulis, S., Yates, C., Wass, M. & Sternberg, M. (2015). The Phyre2 Web Portal for Protein Modelling, Prediction, and Analysis. Nature Protocols, 10(6), 845–858.
  • Kwadha, A.C.,Ong’amo, G.O, Ndegwa, P.N., Raina, S.K. & Fombong, A.T. (2017). The Biology and Control of the Greater Wax Moth, Galleria mellonella. Insects, 8(2), 61.
  • Maiorino, M., Gregolin, C. & Ursini, F. (1990). Phospholipid hydroperoxide glutathione peroxidase. Methods Enzymol. 186, 448-457.
  • Ménard, G., Rouillon, A., Cattoir, V. & Donnio, P.Y. (2021). Galleria mellonella as a Suitable Model of Bacterial Infection: Past, Present and Future, Frontiers in Cellular and Infection Microbiology, 11, 782733.
  • Moya-Anderico, L., Vukomanovic, M., del Mar Cendra, M., Segura-Feliu, M., Gil, V., del Río, J.A. & Torrents, E. (2021). Utility of Galleria mellonella larvae for evaluating nanoparticle toxicology, Chemosphere, 266, 129235.
  • Murail, S., Vries, S., Rey, J., Moroy, G. & Tufféry, P. (2021). SeamDock: An Interactive and Collaborative Online Docking Resource to Assist Small Compound Molecular Docking. Frontiers in Molecular Biosciences, 8, 716466.
  • Sefer, N.E. & Büyükgüzel, K. (2018). The effect of piperazine on the survival and development of Galleria mellonella. Karaelmas Science and Engineering Journal, 8(1), 365–372.
  • Tanış, E., Çankaya, N. & Yalçın, S. (2019). Synthesis, Experimental and Theoretical Analysis, and Antiproliferative Activity of 2-(4-methoxyphenylamino)-2-oxoethyl methacrylate, Chinese Journal of Physics, 57, 348-361.
  • Temüz, M. M., Çankaya, N., Korcan, S. E., Azarkan, S. Y., Kahraman, T. (2024). First in vitro-in silico Analysis’s for Determination of Antimicrobial and Antioxidant Properties of 2-(4-methoxyphenylamino)-2-oxoethylmethacrylate and p-acetamide, ACS Omega, 9(7), 7910-7922.
  • Tiwari, N., Mishra, A. (2023). Computational perspectives on Chlorpyrifos and its degradants as human glutathione S-transferases inhibitors: DFT calculations, molecular docking study and MD simulations. Computational Toxicology, 26, 100264.
  • Trott, O., Olson, A. J. (2010). AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry, 31(2), 455–461.
  • Tufféry, P. & Murail, S. (2020). Samuelmurail/docking_py: Docking_py, a python Library for Ligand Protein Docking. Paris, France, Zenodo. http://doi.org/10.5281/zenodo.4506970
  • Yalçın, S., Sas, E. B., Çankaya, N., Ercan, F., Kurt, M. (2019). The physical studies and interaction with anti-apoptotic proteins of 2-(bis(cyanomethyl)amino)-2-oxoethyl methacrylate molecule, Condensed Matter Physics, 22(3), 33301, 1–8.
  • Yang, J., Yan, R., Roy, A., Xu, D., Poisson, J., Zhang, Y. (2015). The I-TASSER Suite: Protein Structure and Function Prediction. Nature Methods, 12(1), 7–8.
  • Zheng, W. et al. (2021). Protein structure prediction using deep learning distance and hydrogen‐bonding restraints in CASP14. Proteins, 89, 1734–1751.
  • Zhou, W., Li, M., Achal, V. (2025). A comprehensive review on environmental and human health impacts of chemical pesticide usage. Emerging Contaminants, 11(1), 100410.

In Vivo and in Silico Evaluation of the Effect of p-Acetamide and MPAEMA on the Model Organism Galleria Mellonella (Lepidoptera: Pyralidae)

Yıl 2025, Cilt: 28 Sayı: 3, 625 - 635

Nevin Çankaya , Serap Yalcin , Fahriye Ercan

https://doi.org/10.18016/ksutarimdoga.vi.1591091

Öz

In this study, 2-chloro-N-(4-methoxyphenyl)acetamide (p-acetamide) and 2-(4-methoxyphenylamino)-2-oxoethyl methacrylate (MPAEMA) were resynthesized to evaluate their effect on the agricultural pest Galleria mellonella. The toxicities of p-acetamide and MPAEMA against the larval stage of G. mellonella were evaluated concurrently. The results indicate that p-acetamide has a lethal effect on insect larvae at lower doses. LC50 doses of p-acetamide and MPAEMA were 873,572 and 687,355 uM, respectively. These values represent the concentrations of the substances at which 50% of the larvae exposed to them are expected to die. The molecular docking interactions of p-acetamide and MPAEMA with the proteins superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx), and glutathione-S-transferase (GST) were analyzed. The binding energy between MPAEMA and glutathione peroxidase was determined to be -6.8 kcal/mol. This suggests that MPAEMA may have an inhibitory effect on glutathione peroxidase and could be further investigated for developing pesticides that target this enzyme.

Anahtar Kelimeler

Galleria mellonella Toxicity Molecular docking p-acetamide MPAEMA

Kaynakça

  • Abbott, W.S. (1925). A method of computing the effectiveness of an insecticide. Journal of Economic Entomology, 18(2), 265-267.
  • Abdelaziz, N., Abdelrahman, A. & Elbanna, S. (2024). Toxicity and Physiological Effect of Lemongrass Essential Oil Nano-capsules on the Greater Wax Moth Larvae Galleria mellonella L. (Lepidoptera: Pyralidae). Catrina:The International Journal of Environmental Sciences, 32(1), 61-71.
  • Acikbas, Y., Cankaya, N., Capan, R., Erdogan, M. & Soykan, C. (2016). Swelling behaviour of the 2-(4-methoxyphenylamino)-2-oxoethyl methacrylate monomer LB thin film exposed to various organic vapours by quartz crystal microbalance technique. Journal of Macromolecular Science, Part A, Pure and Applied Chemistry, 53(1), 18–25.
  • Aioub, A.A.A., Hashem, A.S., El-Sappah, A.H., El-Harairy, A., Abdel-Hady, A.A.A., Al-Shuraym, L.A., Sayed, S., Huang, Q. & Abdel-Wahab, S.I.Z. (2023). Identification and Characterization of Glutathione S-transferase Genes in Spodoptera frugiperda (Lepidoptera: Noctuidae) under Insecticides Stress. Toxics, 11(6), 542.
  • Allegra, E., Titball, R.W., Carter, J. & Champion, O.L. (2018). Galleria mellonella larvae allow the discrimination of toxic and non-toxic chemicals, Chemosphere, 198, 469-472.
  • Altıkat, A., Turan, T., Torun, F.E. & Bingül, Z. (2009). Use of Pesticides in Turkey and its Effects on Environment, Atatürk Üniversitesi Ziraat Fakültesi Dergisi, 40(2), 87-92.
  • Alvandial, A., Jawadi M.H., Altıntaş Z.N., Yıldız N. & Karaman, M (2016.) Candida albicans’ın Salgısal Asit Proteinaz Etkinliğinin Araştırılmasında In Vivo Model Olarak Galleria mellonella Larvanın Kullanılması. Türk Mikrobiyoloji Cemiyeti Dergisi, 46(2), 69-75.
  • Banfi, D., Bianchi, T., Mastore, M. & Brivio, M.F. (2024). Optimization of Experimental Infection of the Animal Model Galleria mellonella Linnaeus 1758 (Lepidoptera: Pyralidae) with the Gram-Positive Bacterium Micrococcus luteus. Insects, 15(8), 618.
  • Borase, D.N., Thorat, Y.E., Baitha, A. et al. (2024). Parasitizing efficiency of Tetrastichus howardi (Olliff) (Hymenoptera: Eulophidae) on Galleria mellonella (Linnaeus) (Lepidoptera: Pyralidae) larva and pupa. Egyptian Journal of Biological Pest Control, 34(1), 14.
  • Bugyna, L., Kendra, S. & Bujdáková, H. (2023). Galleria mellonella—A Model for the Study of aPDT—Prospects and Drawbacks. Microorganisms, 11(6), 1455.
  • Cankaya, N. Izdal, M, Azarkan, S.Y. (2021). Synthesis, characterization, biological evaluation and molecular docking studies of new oxoacrylate and acetamide on hela cancer cell lines. Current Computer-Aided Drug Design, 17(6), 838−848.
  • Chowdhury, S.K., Banerjee, M., Basnett, D. & Mazumdar, T. (2023). Natural pesticides for pest control in agricultural crops: an alternative and eco-friendly method, Plant Science Today, 11(1), 433–450.
  • Coates, C.J., Lim, J., Harman, K., Rowley, A.F., Griffiths, D.J., Emery, H. & Layton, W. (2019). The insect, Galleria mellonella, is a compatible model for evaluating the toxicology of okadaic acid, Cell Biology and Toxicology, 35, 219–232.
  • Çelik, C., Stanley, D. & Büyükgüzel, E. (2024). Dietary oxyclozanide influences antioxidant enzyme activities and damages DNA in Galleria mellonella (Lepidoptera: Pyralidae), Environmental Entomology, 53(5), 789–800.
  • Çoban, V., Çankaya, N. & Azarkan, S.Y. (2024). New Oxomethacrylate and Acetamide: Synthesis, Characterization and their Computational Approaches: Molecular Docking, Molecular Dynamic, ADME, Drug and Chemical Toxicology, 47(6), 1175–1184.
  • Dent, D. & Binks, R.H., Insect pest management. 3rd ed. Wallingford (Oxfordshire, UK): CABI; 2020. p. 380. Firacative, C., Khan, A., Duan, S., Ferreira-Paim, K., Leemon, D. & Meyer, W. (2020). Rearing and Maintenance of Galleria mellonella and Its Application to Study Fungal Virulence, Journal of Fungi (Basel). 6(3), 130.
  • Humphrey, W., Dalke, A. & Schulten, K. (1996). VMD: visual molecular dynamics. Journal of Molecular Graphics, 14(1), 33–28.
  • Karimi-Maleh, H., Ghalkhani, M., Dehkordi, Z.S., Tehran, M.M., Singh, J., Wen, Y., Baghayeri, M., Rouhi, J., Fu, L. & Rajendran, S. (2024). Mof-enabled pesticides as developing approach for sustainable agriculture and reducing environmental hazards, Journal of Industrial and Engineering Chemistry, 129, 105-123.
  • Kelly, L.A., Mezulis, S., Yates, C., Wass, M. & Sternberg, M. (2015). The Phyre2 Web Portal for Protein Modelling, Prediction, and Analysis. Nature Protocols, 10(6), 845–858.
  • Kwadha, A.C.,Ong’amo, G.O, Ndegwa, P.N., Raina, S.K. & Fombong, A.T. (2017). The Biology and Control of the Greater Wax Moth, Galleria mellonella. Insects, 8(2), 61.
  • Maiorino, M., Gregolin, C. & Ursini, F. (1990). Phospholipid hydroperoxide glutathione peroxidase. Methods Enzymol. 186, 448-457.
  • Ménard, G., Rouillon, A., Cattoir, V. & Donnio, P.Y. (2021). Galleria mellonella as a Suitable Model of Bacterial Infection: Past, Present and Future, Frontiers in Cellular and Infection Microbiology, 11, 782733.
  • Moya-Anderico, L., Vukomanovic, M., del Mar Cendra, M., Segura-Feliu, M., Gil, V., del Río, J.A. & Torrents, E. (2021). Utility of Galleria mellonella larvae for evaluating nanoparticle toxicology, Chemosphere, 266, 129235.
  • Murail, S., Vries, S., Rey, J., Moroy, G. & Tufféry, P. (2021). SeamDock: An Interactive and Collaborative Online Docking Resource to Assist Small Compound Molecular Docking. Frontiers in Molecular Biosciences, 8, 716466.
  • Sefer, N.E. & Büyükgüzel, K. (2018). The effect of piperazine on the survival and development of Galleria mellonella. Karaelmas Science and Engineering Journal, 8(1), 365–372.
  • Tanış, E., Çankaya, N. & Yalçın, S. (2019). Synthesis, Experimental and Theoretical Analysis, and Antiproliferative Activity of 2-(4-methoxyphenylamino)-2-oxoethyl methacrylate, Chinese Journal of Physics, 57, 348-361.
  • Temüz, M. M., Çankaya, N., Korcan, S. E., Azarkan, S. Y., Kahraman, T. (2024). First in vitro-in silico Analysis’s for Determination of Antimicrobial and Antioxidant Properties of 2-(4-methoxyphenylamino)-2-oxoethylmethacrylate and p-acetamide, ACS Omega, 9(7), 7910-7922.
  • Tiwari, N., Mishra, A. (2023). Computational perspectives on Chlorpyrifos and its degradants as human glutathione S-transferases inhibitors: DFT calculations, molecular docking study and MD simulations. Computational Toxicology, 26, 100264.
  • Trott, O., Olson, A. J. (2010). AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. Journal of Computational Chemistry, 31(2), 455–461.
  • Tufféry, P. & Murail, S. (2020). Samuelmurail/docking_py: Docking_py, a python Library for Ligand Protein Docking. Paris, France, Zenodo. http://doi.org/10.5281/zenodo.4506970
  • Yalçın, S., Sas, E. B., Çankaya, N., Ercan, F., Kurt, M. (2019). The physical studies and interaction with anti-apoptotic proteins of 2-(bis(cyanomethyl)amino)-2-oxoethyl methacrylate molecule, Condensed Matter Physics, 22(3), 33301, 1–8.
  • Yang, J., Yan, R., Roy, A., Xu, D., Poisson, J., Zhang, Y. (2015). The I-TASSER Suite: Protein Structure and Function Prediction. Nature Methods, 12(1), 7–8.
  • Zheng, W. et al. (2021). Protein structure prediction using deep learning distance and hydrogen‐bonding restraints in CASP14. Proteins, 89, 1734–1751.
  • Zhou, W., Li, M., Achal, V. (2025). A comprehensive review on environmental and human health impacts of chemical pesticide usage. Emerging Contaminants, 11(1), 100410.
Toplam 34 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Bitki Hücresi ve Moleküler Biyoloji
Bölüm ARAŞTIRMA MAKALESİ (Research Article)
Yazarlar

Nevin Çankaya 0000-0002-6079-4987

Serap Yalcin 0000-0002-9584-266X

Fahriye Ercan 0000-0002-0111-8460

Erken Görünüm Tarihi 1 Mayıs 2025
Yayımlanma Tarihi
Gönderilme Tarihi 2 Aralık 2024
Kabul Tarihi 10 Nisan 2025
Yayımlandığı Sayı Yıl 2025Cilt: 28 Sayı: 3

Kaynak Göster

APA Çankaya, N., Yalcin, S., & Ercan, F. (2025). In Vivo and in Silico Evaluation of the Effect of p-Acetamide and MPAEMA on the Model Organism Galleria Mellonella (Lepidoptera: Pyralidae). Kahramanmaraş Sütçü İmam Üniversitesi Tarım Ve Doğa Dergisi, 28(3), 625-635. https://doi.org/10.18016/ksutarimdoga.vi.1591091
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