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

Author:

Flores-Rivera Mariola M.1ORCID,Carmona-Negrón José A.1ORCID,Rheingold Arnold L.2ORCID,Meléndez Enrique1ORCID

Affiliation:

1. Department of Chemistry, University of Puerto Rico, P.O. Box 9019, Mayaguez, PR 00681, USA

2. Department of Chemistry and Biochemistry, University of California–San Diego, Urey Hall 5128, 9500 Gilman Drive, La Jolla, CA 92093, USA

Abstract

3-ferrocenyl-estra-1,3,5 (10)-triene-17-one (2), [Fe(C5H5)(C24H25O3)], 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 2 via a static mechanism dominated by van der Waals interactions and hydrogen bonding interactions.

Funder

Bridge to the Doctorate Program

BioXFEL Science Technology Center

Alfred P. Sloan Foundation—UPRM Ph.D. Enrichment Program

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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