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Yeni Bir NHC Tuzunun ve Palladyum-PEPPSI Kompleksinin Sentezi, Karakterizasyonu ve Moleküler Doking Analizi

Yıl 2023, , 15 - 23, 30.06.2023
https://doi.org/10.54370/ordubtd.1206005

Öz

PEPPSI tipi Pd kompleksleri son yıllarda geniş uygulama alanına sahiptir. Serum albümini oleik ve linoleik asitler, nitrik oksit, vitamin B6, tiroid gibi çok önemli molekülleri ve pek çok ilacı taşır. Bu çalışmada, yeni NHC molekülü ve onun Pd-PEPPSI kompleksi sentezlendi ve karakterize edildi. Hem ligand hem de kompleks, DFT tabanlı hesaplama yöntemleriyle optimize edildi. Moleküllerin HSA ile bağlanma özellikleri moleküler doking yöntemleri ile analiz edildi. NHC tuzu için -8.04 kcal/mol bağlanma afinitesi ve 1.29 uM inhibisyon sabiti belirlenirken, Pd-PEPPSI kompleksi için bağlanma afinitesi -7.04 kcal/mol ve inhibisyon sabiti 6.92 uM olarak hesaplandı.

Kaynakça

  • Akkoc, S., Ilhan, I. Ö., Gök, Y., Upadhyay, P. J., & Kayser, V. (2016). In vitro cytotoxic activities of new silver and PEPPSI palladium N-heterocyclic carbene complexes derived from benzimidazolium salts. Inorganica Chimica Acta, 449, 75-81. https://doi.org/10.1016/j.ica.2016.05.001
  • Akkoç, S., Kayser, V., İlhan, İ. Ö., Hibbs, D. E., Gök, Y., Williams, P. A., Hawkins, B., & Lai, F. (2017). New compounds based on a benzimidazole nucleus: Synthesis, characterization and cytotoxic activity against breast and colon cancer cell lines. Journal of Organometallic Chemistry, 839, 98-107. https://doi.org/10.1016/j.jorganchem.2017.03.037
  • Al-Harthi, S., Lachowicz, J. I., Nowakowski, M. E., Jaremko, M., & Jaremko, Ł. (2019). Towards the functional high-resolution coordination chemistry of blood plasma human serum albumin. Journal of Inorganic Biochemistry, 198, 110716. https://doi.org/10.1016/j.jinorgbio.2019.110716
  • Ata, A. Ç., Tanrıverdi, A. A., Yıldıko, Ü., & Çakmak, İ. (2022). A heterocyclic compound hispidulin: Theoretical investigation by DFT/TD-DFT öethods and öolecular docking studies. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 26(3), 515-522. https://doi.org/10.19113/sdufenbed.1126132
  • Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6), 3098. https://doi.org/10.1103/PhysRevA.38.3098
  • Bucur, P., Fülöp, I., & Sipos, E. (2022). Insulin complexation with cyclodextrins—A molecular modeling approach. Molecules, 27(2), 465. https://doi.org/10.3390/molecules27020465
  • Carter, D. C., & Ho, J. X. (1994). Structure of serum albumin. Advances in Protein Chemistry, 45, 153-203. https://doi.org/10.1016/S0065-3233(08)60640-3
  • Çelik, C., Üstün, E., Şahin, N., & Tutar, U. Antimicrobial and antibiofilm activity, and bovine serum albumin binding properties of benzimidazolium type NHC salts and their Ag (I)‐NHC complexes. Applied Organometallic Chemistry, 36(12) e6891. https://doi.org/10.1002/aoc.6891
  • Daşgın, S., Gök, Y., Celepci, D. B., Taslimi, P., Izmirli, M., Aktaş, A., & Gülçin, İ. (2021). Synthesis, characterization, crystal structure and bioactivity properties of the benzimidazole-functionalized PEPPSI type of Pd (II) NHC complexes. Journal of Molecular Structure, 1228, 129442. https://doi.org/10.1016/j.molstruc.2020.129442
  • Doǧan, Ö., Demir, S., Özdemir, İ., & Cetinkaya, B. (2011) Palladium (II)-NHC complexes containing benzimidazole ligand as a catalyst for C-N bond formation, Appl. Organomet. Chem. 25, 163-167. https://doi.org/10.1002/aoc.1731
  • Fowler, J. M., Britton, E., Pask, C. M., Willans, C. E., & Hardie, M. J. (2019). Cyclotriveratrylene-tethered trinuclear palladium (ii)–NHC complexes; reversal of site selectivity in Suzuki–Miyaura reactions. Dalton Transactions, 48(39), 14687-14695. https://doi.org/10.1039/C9DT03400E
  • Hussaini, S. Y., Haque, R. A., & Razali, M. R. (2019). Recent progress in silver (I)-, gold (I)/(III)-and palladium (II)-N-heterocyclic carbene complexes: A review towards biological perspectives. Journal of Organometallic Chemistry, 882, 96-111. https://doi.org/10.1016/j.jorganchem.2019.01.003
  • Jahanban-Esfahlan, A., & Panahi-Azar, V. (2016). Interaction of glutathione with bovine serum albumin: Spectroscopy and molecular docking. Food Chemistry, 202, 426-431. https://doi.org/10.1016/j.foodchem.2016.02.026
  • Kaloğlu, M., Kaloğlu, N., & Özdemir, İ. (2021). Palladium-PEPPSI-NHC complexes bearing imidazolidin-2-ylidene ligand: Efficient precatalysts for the direct C5-arylation of N-methylpyrrole-2-carboxaldehyde. Catalysis Letters, 151(11), 3197-3212. https://doi.org/10.1007/s10562-021-03561-4
  • Kaloğlu, N., & Özdemir, İ. (2019). PEPPSI-Pd-NHC catalyzed Suzuki-Miyaura cross-coupling reactions in aqueous media. Tetrahedron, 75(15), 2306-2313. https://doi.org/10.1016/j.tet.2019.02.062
  • Matin, M. M., Uzzaman, M., Chowdhury, S. A., & Bhuiyan, M. M. H. (2022). 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, 40(8), 3668-3680. https://doi.org/10.1080/07391102.2020.1850358
  • Meng, G., & Szostak, M. (2018). Palladium/NHC (NHC= N-heterocyclic carbene)-catalyzed B-alkyl suzuki cross-coupling of amides by selective N–C bond cleavage. Organic Şetters, 20(21), 6789-6793. https://doi.org/10.1021/acs.orglett.8b02911
  • Molaei, P., Mahaki, H., Manoochehri, H., & Tanzadehpanah, H. (2022). Binding sites of anticancer drugs on human serum albumin (HSA): A review. Protein and Peptide Letters, 29(8), 651-675 https://doi.org/10.2174/0929866529666220426124834
  • Morris, G. M., Huey, R., & Olson, A. J. (2008). Using autodock for ligand‐receptor docking. Current Protocols in Bioinformatics, 24(1), 8-14. https://doi.org/10.1002/0471250953.bi0814s24
  • Neese, F. (2007). Calculation of the zero-field splitting tensor on the basis of hybrid density functional and Hartree-Fock theory. The Journal of Chemical Physics, 127(16), 164112. https://doi.org/10.1063/1.2772857
  • Neese, F. (2012). The ORCA program system. Wiley interdisciplinary reviews: Computational Molecular Science, 2(1), 73-78. https://doi.org/10.1002/wcms.81
  • Neese, F., Wennmohs, F., Becker, U., & Riplinger, C. (2020). The ORCA quantum chemistry program package. The Journal of Chemical Physics, 152(22), 224108. https://doi.org/10.1063/5.0004608
  • Netherton, M.R., & Fu, G.C. (2005). Palladium-catalyzed cross-coupling reactions of unactivated alkyl electrophiles with organometallic compounds. In Tsuji, J. (eds) Palladium in Organic Synthesis. Topics in Organometallic Chemistry. Springer. https://doi.org/10.1007/b104127
  • Perdew, J. P. (1986). Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Physical Review B, 33(12), 8822. https://doi.org/10.1103/PhysRevB.33.8822
  • Peters Jr, T. (1985). Serum albumin. Advances in Pprotein Chemistry, 37, 161-245. https://doi.org/10.1016/S0065-3233(08)60065-0
  • Rabbani, G., & Ahn, S. N. (2019). Structure, enzymatic activities, glycation and therapeutic potential of human serum albumin: A natural cargo. International Journal of Biological Macromolecules, 123, 979-990. https://doi.org/10.1016/j.ijbiomac.2018.11.053
  • Scattolin, T., Voloshkin, V. A., Visentin, F., & Nolan, S. P. (2021). A critical review of palladium organometallic anticancer agents. Cell Reports Physical Science, 2(6), 100446. https://doi.org/10.1016/j.xcrp.2021.100446
  • Serdaroglu, G. (2022). Experimental and theoretical spectroscopic studies of the electronic structure of 2-Ethyl-2-phenylmalonamide. Physical Chemistry Research, 10(3), 333-344. https://doi.org/10.22036/PCR.2021.304087.1966
  • Serdaroğlu, G., Şahin, N., Üstün, E., Tahir, M. N., Arıcı, C., Gürbüz, N., & Özdemir, İ. (2021). PEPPSI type complexes: Synthesis, x-ray structures, spectral studies, molecular docking and theoretical investigations. Polyhedron, 204, 115281. https://doi.org/10.1016/j.poly.2021.115281
  • Slimani, I., Mansour, L., Özdemir, I., Gürbüz, N., & Hamdi, N. (2021). Synthesis, characterization and catalytic activity of PEPPSI-type palladium–NHC complexes. Inorganica Chimica Acta, 515, 120043. https://doi.org/10.1016/j.ica.2020.120043
  • Sugio, S., Kashima, A., Mochizuki, S., Noda, M., & Kobayashi, K. (1999). Crystal structure of human serum albumin at 2.5 Å resolution. Protein Engineering, 12(6), 439-446. https://doi.org/10.1093/protein/12.6.439
  • Tayyab, S., & Feroz, S. R. (2021). Serum albumin: Clinical significance of drug binding and development as drug delivery vehicle. Advances in Protein Chemistry and Structural Biology, 123, 193-218. https://doi.org/10.1016/bs.apcsb.2020.08.003
  • 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. https://doi.org/10.1002/jcc.21334
  • Türker, D., Üstün, E., Günal, S., Yıldız, H., D. Düşünceli, S., & Özdemir, İ. (2022). Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis. Archiv der Pharmazie, 355(6), e2200041. https://doi.org/10.1002/ardp.202200041
  • Umare, M., Alkathiri, F. A., & Chikhale, R. (2022). Development of nucleic acid targeting molecules: Molecular docking approaches and recent advances. In Erman Salih Istifli (Eds.), Molecular Docking. Intech. https://doi.org/10.5772/intechopen.107349
  • Üstün, E., Şakar, D., Ayvaz, M. Ç., Çelebi, M. S., & Ertürk, Ö. (2022). CO-Releasing, antioxidant, antibacterial, zeta potential,t, and electrochemical analysis of [Mn (CO) 3 (bpy) L] OTf type complexes. Polyhedron, 224, 115997. https://doi.org/10.1016/j.poly.2022.115997
  • Üstün, E., Şahin, N. (2022). Synthesis, and characterization and in-silico analysis against SARS CoV-2 of novel benzimidazolium salts. Orbital: The Electronic Journal of Chemistry, 14(4), 205-211. http://dx.doi.org/10.17807/orbital.v14i4.16834
  • Wani, T. A., Bakheit, A. H., Zargar, S., Alanazi, Z. S., & Al-Majed, A. A. (2021). Influence of antioxidant flavonoids quercetin and rutin on the in-vitro binding of neratinib to human serum albumin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 246, 118977. https://doi.org/10.1016/j.saa.2020.118977
  • Zhou, Y., Jiang, Y., & Chen, S. J. (2022). RNA–ligand molecular docking: Advances and challenges. Wiley Interdisciplinary Reviews: Computational Molecular Science, 12(3), e1571. https://doi.org/10.1002/wcms.1571

Synthesis, Characterization, and Molecular Docking Analysis of A Novel NHC Salt and Its Palladium-PEPPSI Complex

Yıl 2023, , 15 - 23, 30.06.2023
https://doi.org/10.54370/ordubtd.1206005

Öz

PEPPSI type Pd complexes have wide applications in recent years. Serum albumin carries very important molecules such as oleic and linoleic acids, nitric oxide, vitamin B6, thyroid and so do many drugs. In this study, a novel NHC molecule and its Pd-PEPPSI complex were synthesized and characterized. Both the ligand and the complex were optimized by DFT-based calculation methods. The binding properties of the molecules with HSA were analyzed by molecular docking methods. Binding affinity of -8.04 kcal/mol and inhibition constant of 1.29 µM were determined for NHC salt while the binding affinity was calculated as -7.04 kcal/mol and the inhibition constant as 6.92 µM for Pd-PEPPSI complex.

Kaynakça

  • Akkoc, S., Ilhan, I. Ö., Gök, Y., Upadhyay, P. J., & Kayser, V. (2016). In vitro cytotoxic activities of new silver and PEPPSI palladium N-heterocyclic carbene complexes derived from benzimidazolium salts. Inorganica Chimica Acta, 449, 75-81. https://doi.org/10.1016/j.ica.2016.05.001
  • Akkoç, S., Kayser, V., İlhan, İ. Ö., Hibbs, D. E., Gök, Y., Williams, P. A., Hawkins, B., & Lai, F. (2017). New compounds based on a benzimidazole nucleus: Synthesis, characterization and cytotoxic activity against breast and colon cancer cell lines. Journal of Organometallic Chemistry, 839, 98-107. https://doi.org/10.1016/j.jorganchem.2017.03.037
  • Al-Harthi, S., Lachowicz, J. I., Nowakowski, M. E., Jaremko, M., & Jaremko, Ł. (2019). Towards the functional high-resolution coordination chemistry of blood plasma human serum albumin. Journal of Inorganic Biochemistry, 198, 110716. https://doi.org/10.1016/j.jinorgbio.2019.110716
  • Ata, A. Ç., Tanrıverdi, A. A., Yıldıko, Ü., & Çakmak, İ. (2022). A heterocyclic compound hispidulin: Theoretical investigation by DFT/TD-DFT öethods and öolecular docking studies. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 26(3), 515-522. https://doi.org/10.19113/sdufenbed.1126132
  • Becke, A. D. (1988). Density-functional exchange-energy approximation with correct asymptotic behavior. Physical Review A, 38(6), 3098. https://doi.org/10.1103/PhysRevA.38.3098
  • Bucur, P., Fülöp, I., & Sipos, E. (2022). Insulin complexation with cyclodextrins—A molecular modeling approach. Molecules, 27(2), 465. https://doi.org/10.3390/molecules27020465
  • Carter, D. C., & Ho, J. X. (1994). Structure of serum albumin. Advances in Protein Chemistry, 45, 153-203. https://doi.org/10.1016/S0065-3233(08)60640-3
  • Çelik, C., Üstün, E., Şahin, N., & Tutar, U. Antimicrobial and antibiofilm activity, and bovine serum albumin binding properties of benzimidazolium type NHC salts and their Ag (I)‐NHC complexes. Applied Organometallic Chemistry, 36(12) e6891. https://doi.org/10.1002/aoc.6891
  • Daşgın, S., Gök, Y., Celepci, D. B., Taslimi, P., Izmirli, M., Aktaş, A., & Gülçin, İ. (2021). Synthesis, characterization, crystal structure and bioactivity properties of the benzimidazole-functionalized PEPPSI type of Pd (II) NHC complexes. Journal of Molecular Structure, 1228, 129442. https://doi.org/10.1016/j.molstruc.2020.129442
  • Doǧan, Ö., Demir, S., Özdemir, İ., & Cetinkaya, B. (2011) Palladium (II)-NHC complexes containing benzimidazole ligand as a catalyst for C-N bond formation, Appl. Organomet. Chem. 25, 163-167. https://doi.org/10.1002/aoc.1731
  • Fowler, J. M., Britton, E., Pask, C. M., Willans, C. E., & Hardie, M. J. (2019). Cyclotriveratrylene-tethered trinuclear palladium (ii)–NHC complexes; reversal of site selectivity in Suzuki–Miyaura reactions. Dalton Transactions, 48(39), 14687-14695. https://doi.org/10.1039/C9DT03400E
  • Hussaini, S. Y., Haque, R. A., & Razali, M. R. (2019). Recent progress in silver (I)-, gold (I)/(III)-and palladium (II)-N-heterocyclic carbene complexes: A review towards biological perspectives. Journal of Organometallic Chemistry, 882, 96-111. https://doi.org/10.1016/j.jorganchem.2019.01.003
  • Jahanban-Esfahlan, A., & Panahi-Azar, V. (2016). Interaction of glutathione with bovine serum albumin: Spectroscopy and molecular docking. Food Chemistry, 202, 426-431. https://doi.org/10.1016/j.foodchem.2016.02.026
  • Kaloğlu, M., Kaloğlu, N., & Özdemir, İ. (2021). Palladium-PEPPSI-NHC complexes bearing imidazolidin-2-ylidene ligand: Efficient precatalysts for the direct C5-arylation of N-methylpyrrole-2-carboxaldehyde. Catalysis Letters, 151(11), 3197-3212. https://doi.org/10.1007/s10562-021-03561-4
  • Kaloğlu, N., & Özdemir, İ. (2019). PEPPSI-Pd-NHC catalyzed Suzuki-Miyaura cross-coupling reactions in aqueous media. Tetrahedron, 75(15), 2306-2313. https://doi.org/10.1016/j.tet.2019.02.062
  • Matin, M. M., Uzzaman, M., Chowdhury, S. A., & Bhuiyan, M. M. H. (2022). 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, 40(8), 3668-3680. https://doi.org/10.1080/07391102.2020.1850358
  • Meng, G., & Szostak, M. (2018). Palladium/NHC (NHC= N-heterocyclic carbene)-catalyzed B-alkyl suzuki cross-coupling of amides by selective N–C bond cleavage. Organic Şetters, 20(21), 6789-6793. https://doi.org/10.1021/acs.orglett.8b02911
  • Molaei, P., Mahaki, H., Manoochehri, H., & Tanzadehpanah, H. (2022). Binding sites of anticancer drugs on human serum albumin (HSA): A review. Protein and Peptide Letters, 29(8), 651-675 https://doi.org/10.2174/0929866529666220426124834
  • Morris, G. M., Huey, R., & Olson, A. J. (2008). Using autodock for ligand‐receptor docking. Current Protocols in Bioinformatics, 24(1), 8-14. https://doi.org/10.1002/0471250953.bi0814s24
  • Neese, F. (2007). Calculation of the zero-field splitting tensor on the basis of hybrid density functional and Hartree-Fock theory. The Journal of Chemical Physics, 127(16), 164112. https://doi.org/10.1063/1.2772857
  • Neese, F. (2012). The ORCA program system. Wiley interdisciplinary reviews: Computational Molecular Science, 2(1), 73-78. https://doi.org/10.1002/wcms.81
  • Neese, F., Wennmohs, F., Becker, U., & Riplinger, C. (2020). The ORCA quantum chemistry program package. The Journal of Chemical Physics, 152(22), 224108. https://doi.org/10.1063/5.0004608
  • Netherton, M.R., & Fu, G.C. (2005). Palladium-catalyzed cross-coupling reactions of unactivated alkyl electrophiles with organometallic compounds. In Tsuji, J. (eds) Palladium in Organic Synthesis. Topics in Organometallic Chemistry. Springer. https://doi.org/10.1007/b104127
  • Perdew, J. P. (1986). Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Physical Review B, 33(12), 8822. https://doi.org/10.1103/PhysRevB.33.8822
  • Peters Jr, T. (1985). Serum albumin. Advances in Pprotein Chemistry, 37, 161-245. https://doi.org/10.1016/S0065-3233(08)60065-0
  • Rabbani, G., & Ahn, S. N. (2019). Structure, enzymatic activities, glycation and therapeutic potential of human serum albumin: A natural cargo. International Journal of Biological Macromolecules, 123, 979-990. https://doi.org/10.1016/j.ijbiomac.2018.11.053
  • Scattolin, T., Voloshkin, V. A., Visentin, F., & Nolan, S. P. (2021). A critical review of palladium organometallic anticancer agents. Cell Reports Physical Science, 2(6), 100446. https://doi.org/10.1016/j.xcrp.2021.100446
  • Serdaroglu, G. (2022). Experimental and theoretical spectroscopic studies of the electronic structure of 2-Ethyl-2-phenylmalonamide. Physical Chemistry Research, 10(3), 333-344. https://doi.org/10.22036/PCR.2021.304087.1966
  • Serdaroğlu, G., Şahin, N., Üstün, E., Tahir, M. N., Arıcı, C., Gürbüz, N., & Özdemir, İ. (2021). PEPPSI type complexes: Synthesis, x-ray structures, spectral studies, molecular docking and theoretical investigations. Polyhedron, 204, 115281. https://doi.org/10.1016/j.poly.2021.115281
  • Slimani, I., Mansour, L., Özdemir, I., Gürbüz, N., & Hamdi, N. (2021). Synthesis, characterization and catalytic activity of PEPPSI-type palladium–NHC complexes. Inorganica Chimica Acta, 515, 120043. https://doi.org/10.1016/j.ica.2020.120043
  • Sugio, S., Kashima, A., Mochizuki, S., Noda, M., & Kobayashi, K. (1999). Crystal structure of human serum albumin at 2.5 Å resolution. Protein Engineering, 12(6), 439-446. https://doi.org/10.1093/protein/12.6.439
  • Tayyab, S., & Feroz, S. R. (2021). Serum albumin: Clinical significance of drug binding and development as drug delivery vehicle. Advances in Protein Chemistry and Structural Biology, 123, 193-218. https://doi.org/10.1016/bs.apcsb.2020.08.003
  • 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. https://doi.org/10.1002/jcc.21334
  • Türker, D., Üstün, E., Günal, S., Yıldız, H., D. Düşünceli, S., & Özdemir, İ. (2022). Cyanopropyl functionalized benzimidazolium salts and their silver N‐heterocyclic carbene complexes: Synthesis, antimicrobial activity, and theoretical analysis. Archiv der Pharmazie, 355(6), e2200041. https://doi.org/10.1002/ardp.202200041
  • Umare, M., Alkathiri, F. A., & Chikhale, R. (2022). Development of nucleic acid targeting molecules: Molecular docking approaches and recent advances. In Erman Salih Istifli (Eds.), Molecular Docking. Intech. https://doi.org/10.5772/intechopen.107349
  • Üstün, E., Şakar, D., Ayvaz, M. Ç., Çelebi, M. S., & Ertürk, Ö. (2022). CO-Releasing, antioxidant, antibacterial, zeta potential,t, and electrochemical analysis of [Mn (CO) 3 (bpy) L] OTf type complexes. Polyhedron, 224, 115997. https://doi.org/10.1016/j.poly.2022.115997
  • Üstün, E., Şahin, N. (2022). Synthesis, and characterization and in-silico analysis against SARS CoV-2 of novel benzimidazolium salts. Orbital: The Electronic Journal of Chemistry, 14(4), 205-211. http://dx.doi.org/10.17807/orbital.v14i4.16834
  • Wani, T. A., Bakheit, A. H., Zargar, S., Alanazi, Z. S., & Al-Majed, A. A. (2021). Influence of antioxidant flavonoids quercetin and rutin on the in-vitro binding of neratinib to human serum albumin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 246, 118977. https://doi.org/10.1016/j.saa.2020.118977
  • Zhou, Y., Jiang, Y., & Chen, S. J. (2022). RNA–ligand molecular docking: Advances and challenges. Wiley Interdisciplinary Reviews: Computational Molecular Science, 12(3), e1571. https://doi.org/10.1002/wcms.1571
Toplam 39 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Mühendislik
Bölüm Araştırma Makaleleri
Yazarlar

Neslihan Şahin 0000-0003-1498-4170

Elvan Üstün 0000-0002-0587-7261

Yayımlanma Tarihi 30 Haziran 2023
Gönderilme Tarihi 16 Kasım 2022
Yayımlandığı Sayı Yıl 2023

Kaynak Göster

APA Şahin, N., & Üstün, E. (2023). Synthesis, Characterization, and Molecular Docking Analysis of A Novel NHC Salt and Its Palladium-PEPPSI Complex. Ordu Üniversitesi Bilim Ve Teknoloji Dergisi, 13(1), 15-23. https://doi.org/10.54370/ordubtd.1206005