Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative
Улога интермолекулских интеракција у супрамолекулској организацији и биолошком препознавању деривата спирохидантоина
Authors
Lazić, AnitaĐorđević, Ivana
Radovanović, Lidija
Popović, Dragan
Rogan, Jelena
Janjić, Goran
Trišović, Nemanja
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A racemic spirohydantoin derivative bearing a tetralin and 4-methoxybenzyl group was synthesized
and its crystal structure was determined. The hierarchical development of the crystal packing was
discussed through cooperativity of various homo and heterohiral dimeric motifs associated with the
presence of different intermolecular interactions. A hallmark structural feature of the investigated
compound was alternation of double layers. A larger number of the contact fragments in the
environment of the tetralin unit results from its larger contact surface, while the 4-methoxybenzyl
unit provides a slightly greater contribution to the overall stabilization. Regarding the
pharmacological potential of the investigated compound, we performed a docking study on the
dopamine D3 receptor and IRAK 4 (Interleukin-1 Receptor-Associated Kinase 4) enzyme. The total
number of amino acid, which interact with the 4-methoxybenzyl unit, was slightly larger than the
number of amino acids in the n...eighborhood of the tetralin unit as a result of its greater flexibility. It
made the 4-methoxybenzyl unit more adaptable for interactions with the biological targets.
Keywords:
spirohydantoin / synthesis / crystal structure / dockingSource:
Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia, 2021, 93-93Publisher:
- Belgrade : Serbian Chemical Society
Funding / projects:
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-MESTD-inst-2020-200026)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200135 (University of Belgrade, Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200135)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200287 (Innovation Center of the Faculty of Technology and Metallurgy) (RS-MESTD-inst-2020-200287)
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IHTMTY - CONF AU - Lazić, Anita AU - Đorđević, Ivana AU - Radovanović, Lidija AU - Popović, Dragan AU - Rogan, Jelena AU - Janjić, Goran AU - Trišović, Nemanja PY - 2021 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/7124 AB - A racemic spirohydantoin derivative bearing a tetralin and 4-methoxybenzyl group was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of various homo and heterohiral dimeric motifs associated with the presence of different intermolecular interactions. A hallmark structural feature of the investigated compound was alternation of double layers. A larger number of the contact fragments in the environment of the tetralin unit results from its larger contact surface, while the 4-methoxybenzyl unit provides a slightly greater contribution to the overall stabilization. Regarding the pharmacological potential of the investigated compound, we performed a docking study on the dopamine D3 receptor and IRAK 4 (Interleukin-1 Receptor-Associated Kinase 4) enzyme. The total number of amino acid, which interact with the 4-methoxybenzyl unit, was slightly larger than the number of amino acids in the neighborhood of the tetralin unit as a result of its greater flexibility. It made the 4-methoxybenzyl unit more adaptable for interactions with the biological targets. PB - Belgrade : Serbian Chemical Society C3 - Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia T1 - Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative T1 - Улога интермолекулских интеракција у супрамолекулској организацији и биолошком препознавању деривата спирохидантоина SP - 93 EP - 93 UR - https://hdl.handle.net/21.15107/rcub_cer_7124 ER -
@conference{ author = "Lazić, Anita and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja", year = "2021", abstract = "A racemic spirohydantoin derivative bearing a tetralin and 4-methoxybenzyl group was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of various homo and heterohiral dimeric motifs associated with the presence of different intermolecular interactions. A hallmark structural feature of the investigated compound was alternation of double layers. A larger number of the contact fragments in the environment of the tetralin unit results from its larger contact surface, while the 4-methoxybenzyl unit provides a slightly greater contribution to the overall stabilization. Regarding the pharmacological potential of the investigated compound, we performed a docking study on the dopamine D3 receptor and IRAK 4 (Interleukin-1 Receptor-Associated Kinase 4) enzyme. The total number of amino acid, which interact with the 4-methoxybenzyl unit, was slightly larger than the number of amino acids in the neighborhood of the tetralin unit as a result of its greater flexibility. It made the 4-methoxybenzyl unit more adaptable for interactions with the biological targets.", publisher = "Belgrade : Serbian Chemical Society", journal = "Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia", title = "Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative, Улога интермолекулских интеракција у супрамолекулској организацији и биолошком препознавању деривата спирохидантоина", pages = "93-93", url = "https://hdl.handle.net/21.15107/rcub_cer_7124" }
Lazić, A., Đorđević, I., Radovanović, L., Popović, D., Rogan, J., Janjić, G.,& Trišović, N.. (2021). Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative. in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia Belgrade : Serbian Chemical Society., 93-93. https://hdl.handle.net/21.15107/rcub_cer_7124
Lazić A, Đorđević I, Radovanović L, Popović D, Rogan J, Janjić G, Trišović N. Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative. in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia. 2021;:93-93. https://hdl.handle.net/21.15107/rcub_cer_7124 .
Lazić, Anita, Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, "Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative" in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia (2021):93-93, https://hdl.handle.net/21.15107/rcub_cer_7124 .