Influence of N-protonation on electronic properties of acridine derivatives by quantum crystallography

Pawlędzio, Sylwia; Ziemniak, Marcin; Trzybiński, Damian; Arhangelskis, Mihails; Makal, Anna; Woźniak, Krzysztof

doi:10.1039/d3ra08081a

Title: Influence of N-protonation on electronic properties of acridine derivatives by quantum crystallography

Journal Article · 12 February 2024 · RSC Advances

DOI: https://doi.org/10.1039/d3ra08081a · OSTI ID:2301742

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^[2]; Makal, Anna ^[2];

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Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States); Univ. of Warsaw (Poland)
Univ. of Warsaw (Poland)

Applications of 9-aminoacridine (9aa) and its derivatives span fields such as chemistry, biology, and medicine, including anticancer and antimicrobial activities. Protonation of such molecules can alter their bioavailability as weakly basic drugs like aminoacridines exhibit reduced solubility at high pH levels potentially limiting their effectiveness in patients with elevated gastric pH. In this study, we analyse the influence of protonation on the electronic characteristics of the molecular organic crystals of 9-aminoacridine. The application of quantum crystallography, including aspherical atom refinement, has enriched the depiction of electron density in the studied systems and non-covalent interactions, providing more details than previous studies. Our experimental results, combined with a topological analysis of the electron density and its Laplacian, provided detailed descriptions of how protonation changes the electron density distribution around the amine group and water molecule, concurrently decreasing the electron density at bond critical points of N/O-H bonds. Protonation also alters the molecular architecture of the systems under investigation. This is reflected in different proportions of the N^...H and O^...H intermolecular contacts for the neutral and protonated forms. Periodic DFT calculations of the cohesive energies of the crystal lattice, as well as computed interaction energies between molecules in the crystal, confirm that protonation stabilises the crystal structure due to a positive synergy between strong halogen and hydrogen bonds. Our findings highlight the potential of quantum crystallography in predicting crystal structure properties and point to its possible applications in developing new formulations for poorly soluble drugs.

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Research Organization:: Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE; Polish National Science Centre (NCN)

Grant/Contract Number:: AC05-00OR22725; 2018/31/B/ST4/02142

OSTI ID:: 2301742

Alternate ID(s):: OSTI ID: 2320358

Journal Information:: RSC Advances, Vol. 14, Issue 8; ISSN 2046-2069

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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Title: Influence of N-protonation on electronic properties of acridine derivatives by quantum crystallography

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