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Induction of Petite Colonies in Candida glabrate via Rose Bengal-Mediated Photodynamic Therapy
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Fluconazolium picrate.

Grzegorz Dutkiewicz, C S Chidan Kumar, H S Yathirajan

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    The first structurally characterized salt of fluconazole, an antifungal agent, was identified. Crystal analysis revealed hydrogen bonding and C-H interactions stabilizing the structure into helical arrangements.

    Area of Science:

    • Crystallography
    • Medicinal Chemistry
    • Organic Chemistry

    Background:

    • Fluconazole is a widely used synthetic antifungal agent.
    • Structural characterization of drug salts can provide insights into their properties and interactions.
    • Picrate salts are often formed to aid in the crystallization and characterization of organic bases.

    Purpose of the Study:

    • To structurally characterize the first salt of the fluconazolium cation.
    • To elucidate the intermolecular interactions within the crystal lattice of this novel salt.
    • To understand the conformational preferences of the fluconazolium cation and picrate anion in the solid state.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.

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  • Analysis of hydrogen bonding (O-H⋯O, N-H⋯N, C-H⋯O) and other non-covalent interactions.
  • Geometric analysis of the fluconazolium cation and picrate anion, including ring planarity and dihedral angles.

    • Main Results:

    • The title compound, C(13)H(13)F(2)N(6)O(+)·C(6)H(2)N(3)O(7) (-), represents the first structurally characterized salt of fluconazolium.
    • The crystal structure is stabilized by a network of O-H⋯O, C-H⋯O, and N-H⋯N hydrogen bonds, forming helical arrangements.
    • The fluconazolium cation exhibits specific conformational arrangements of its aromatic and triazole rings, while the picrate anion shows variations in the planarity of its nitro groups.

    Conclusions:

    • The crystal structure provides a detailed understanding of the interactions governing the solid-state assembly of fluconazole picrate.
    • This characterization serves as a foundation for further studies on fluconazole salts and their potential applications.
    • The findings highlight the role of hydrogen bonding and other weak interactions in dictating the packing and stability of pharmaceutical salts.