3-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking Studies
3-ferrocenyl-estra-1,3,5 (10)-triene-17-one (<b>2</b>), [Fe(C<sub>5</sub>H<sub>5</sub>)(C<sub>24</sub>H<sub>25</sub>O<sub>3</sub>)], crystallizes in the monoclinic space group C2. The cyclopentadienyl (Cp) rings adopt a nearly e...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/16/6147 |
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| author | Mariola M. Flores-Rivera José A. Carmona-Negrón Arnold L. Rheingold Enrique Meléndez |
| author_facet | Mariola M. Flores-Rivera José A. Carmona-Negrón Arnold L. Rheingold Enrique Meléndez |
| author_sort | Mariola M. Flores-Rivera |
| collection | DOAJ |
| description | 3-ferrocenyl-estra-1,3,5 (10)-triene-17-one (<b>2</b>), [Fe(C<sub>5</sub>H<sub>5</sub>)(C<sub>24</sub>H<sub>25</sub>O<sub>3</sub>)], crystallizes in the monoclinic space group C2. The cyclopentadienyl (Cp) rings adopt a nearly eclipsed conformation, and the Cp plane is tilted by 87.66° with respect to the substituted phenyl plane. An average Fe-C(Cp) bond length of 2.040(13) Å was determined, similar to the one reported for ferrocene. Hirshfeld surfaces and two-dimensional fingerprint plots were generated to analyze weak intermolecular C-H···π and C-H···O interactions. Density functional theory studies revealed a 1.15 kcal/mol rotational barrier for the C3-O1 single bound. Fluorescence quenching studies and in silico docking studies suggest that human serum albumin forms a complex with <b>2</b> via a static mechanism dominated by van der Waals interactions and hydrogen bonding interactions. |
| first_indexed | 2024-03-10T23:41:28Z |
| format | Article |
| id | doaj.art-692f26dc9fff455bbdd249c3a90950d6 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T23:41:28Z |
| publishDate | 2023-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-692f26dc9fff455bbdd249c3a90950d62023-11-19T02:25:39ZengMDPI AGMolecules1420-30492023-08-012816614710.3390/molecules281661473-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking StudiesMariola M. Flores-Rivera0José A. Carmona-Negrón1Arnold L. Rheingold2Enrique Meléndez3Department of Chemistry, University of Puerto Rico, P.O. Box 9019, Mayaguez, PR 00681, USADepartment of Chemistry, University of Puerto Rico, P.O. Box 9019, Mayaguez, PR 00681, USADepartment of Chemistry and Biochemistry, University of California–San Diego, Urey Hall 5128, 9500 Gilman Drive, La Jolla, CA 92093, USADepartment of Chemistry, University of Puerto Rico, P.O. Box 9019, Mayaguez, PR 00681, USA3-ferrocenyl-estra-1,3,5 (10)-triene-17-one (<b>2</b>), [Fe(C<sub>5</sub>H<sub>5</sub>)(C<sub>24</sub>H<sub>25</sub>O<sub>3</sub>)], crystallizes in the monoclinic space group C2. The cyclopentadienyl (Cp) rings adopt a nearly eclipsed conformation, and the Cp plane is tilted by 87.66° with respect to the substituted phenyl plane. An average Fe-C(Cp) bond length of 2.040(13) Å was determined, similar to the one reported for ferrocene. Hirshfeld surfaces and two-dimensional fingerprint plots were generated to analyze weak intermolecular C-H···π and C-H···O interactions. Density functional theory studies revealed a 1.15 kcal/mol rotational barrier for the C3-O1 single bound. Fluorescence quenching studies and in silico docking studies suggest that human serum albumin forms a complex with <b>2</b> via a static mechanism dominated by van der Waals interactions and hydrogen bonding interactions.https://www.mdpi.com/1420-3049/28/16/6147ferrocenecrystal structureHirshfeld surfaceDFTfluorescence quenching |
| spellingShingle | Mariola M. Flores-Rivera José A. Carmona-Negrón Arnold L. Rheingold Enrique Meléndez 3-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking Studies Molecules ferrocene crystal structure Hirshfeld surface DFT fluorescence quenching |
| title | 3-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking Studies |
| title_full | 3-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking Studies |
| title_fullStr | 3-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking Studies |
| title_full_unstemmed | 3-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking Studies |
| title_short | 3-Ferrocenyl-estra-1,3,5 (10)-triene-17-one: Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT Studies, and Its Binding to Human Serum Albumin Studied through Fluorescence Quenching and In Silico Docking Studies |
| title_sort | 3 ferrocenyl estra 1 3 5 10 triene 17 one synthesis crystal structure hirshfeld surface analysis dft studies and its binding to human serum albumin studied through fluorescence quenching and in silico docking studies |
| topic | ferrocene crystal structure Hirshfeld surface DFT fluorescence quenching |
| url | https://www.mdpi.com/1420-3049/28/16/6147 |
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