Novel Hydrate and Anhydrate Cocrystals/Salts of Norfloxacin and Their Physicochemical Properties

Gunnam, Anilkumar; Nangia, Ashwini

doi:10.1021/acs.cgd.3c00023

Cited by 12 publications

(11 citation statements)

References 73 publications

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“…In addition, the pyridine ring in donors can form an N⋅⋅⋅H hydrogen bond with the acceptor, the strong binding between donor and acceptor gives the system excellent fluorescence properties. Hence, our cocrystal systems show strong water absorption ability and excellent fluorescence properties compared to previously reported water absorption cocrystal materials [39–43] . The DFT calculation revealed that the N‐H group of the donor molecules forms hydrogen bonding interactions with the oxygen atom of water molecules, causing the acceptance of excitation energy and subsequent fluorescence extinction [44] .…”

Section: Introductionmentioning

confidence: 59%

“…The special structure of the pyridyl benzimidazole-based system endows the obtained cocrystals with strong water absorption ability and excellent fluorescence properties compared to previously reported water absorption cocrystal materials. [40][41][42] Then, we also try to adopt the cocrystals of these systems in different organic solvents such as ACN, ethanol (ET), acetone (ACE), THF, DCM, chloroform (TCM), toluene (TL), dimethyl sulfoxide (DMSO), and ethyl acetate (EA), and with varied D-A ratios (1 : 1, 1 : 2, 2 : 1). The tables S11-S14 showed the cell data and powder X-ray diffraction data of cocrystals or cocrystal powders.…”

Section: Resultsmentioning

confidence: 99%

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Hydrophilic Cocrystals with Water Switched Luminescence

Gao,

Baryshnikov,

Ali

et al. 2024

Angewandte Chemie

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Utilizing water molecules to regulate the luminescence properties of solid materials is highly challenging. Herein, we develop a strategy to produce water‐triggered luminescence‐switching cocrystals by coassembling hydrophilic donors with electron‐deficient acceptors, where 1,2,4,5‐Tetracyanobenzene (TCNB) was used as the electron acceptor and pyridyl benzimidazole derivatives were used as the electron donors enabling multiple hydrogen‐bonds. Two cocrystals, namely 2PYTC and 4PYTC were obtained and showed heat‐activated emission, and such emission could be quenched or weakened by adding water molecules. The cocrystal structure exhibited the donor molecule that can form multiple hydro bonds with water and acceptor molecules due to the many nitrogen atoms of them. The analyses of the photophysical data, powder X‐ray diffraction, and other data confirmed the reversible fluorescence "on‐off" effects were caused by eliminating and adding water molecules in the crystal lattice. The density functional theory calculations indicate that the vibration of the O‐H bond of water molecules in the cocrystal can absorb the excitation energy and suppress fluorescence. Furthermore, the obtained cocrystals also showed temperature, humidity, and H+/NH4+ responsive emission behavior, which allows their applications as thermal and humidity sensors, and multiple information encryptions. This research paves the way for preparing intelligent hydrophilic organic cocrystal luminescent materials.

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Section: Introductionmentioning

confidence: 59%

Section: Resultsmentioning

confidence: 99%

Hydrophilic Cocrystals with Water Switched Luminescence

Gao,

Baryshnikov,

Ali

et al. 2024

Angewandte Chemie

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“…Further to these, going by literature, comparison of crystal structures and physicochemical behaviors of anhydrous and hydrated forms of the cocrystal/salt (norfloxacin) has also been discussed. 33 However, no reports are available for the effects of different configurational coformers on the conformations, crystal structure, and physicochemical properties of quinolones.…”

Section: ■ Introductionmentioning

confidence: 99%

“…It is important to emphasize that cocrystals/salts of many quinolones with straight-chain dicarboxylic acids, − tricarboxylic acids, , and phenolic acids , have been reported. Further to these, going by literature, comparison of crystal structures and physicochemical behaviors of anhydrous and hydrated forms of the cocrystal/salt (norfloxacin) has also been discussed . However, no reports are available for the effects of different configurational coformers on the conformations, crystal structure, and physicochemical properties of quinolones.…”

Section: Introductionmentioning

confidence: 99%

Salt Cocrystal and Salt of Marbofloxacin with Butenedioic Acid: Impact of cis–trans Isomerism of Coformer on the Conformation and Properties of Marbofloxacin

Li,

Zhang,

et al. 2024

Crystal Growth & Design

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Based on the study of the effect of positional isomerism of coformer functional groups on the cocrystallization and physicochemical properties of the active pharmaceutical ingredients, the impact of cis−trans isomeric butenedioic acid as coformers on the conformation, crystal structure, and its physicochemical properties of marbofloxacin was further explored. In this work, fumaric acid (FA) and maleic acid (MA) with different configurations were chosen as coformers to synthesize the pharmaceutical salt cocrystal (MBF-FA-H 2 FA) and salt (MBF-MA) of marbofloxacin (MBF), and their structures were fully characterized. Significant differences between the conformations of marbofloxacin in the salt cocrystal and in salt were found. In the salt cocrystal, the N atom of the piperazine group from marbofloxacin is coplanar with the pyridone ring, and the whole is straight like fumaric acid, whereas the marbofloxacin piperazine group in the salt is bent like the maleic acid configuration. Furthermore, the conformational variability of marbofloxacin in the salt cocrystal and the salt resulted in different crystal structures and opposite physicochemical properties. Notably, both multicomponent crystals have a surface hydrophilic intercalation structure. However, the salt cocrystal and salt exhibited different solubility and permeability. Specifically, the MBF-MA salt showed improved solubility and permeability, while the MBF-FA-H 2 FA salt cocrystal showed a decreased solubility and permeation rate compared to MBF. In addition, in vitro bacterial inhibitory activity assays indicated that the MBF-MA salt has stronger inhibitory activity against Gram-negative and Gram-positive bacterial strains than the MBF-FA-H 2 FA salt cocrystal and pure MBF.

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“…Each coformer can form a hydrated and anhydrous co-crystal or salt with norfloxacin. 23 In this work, we propose alternative salt forms of CIF with oxalic acid (OXA), a co-former in the generally recognized as safe (GRAS) list. The CIF-OXA crystallization was performed in a pure water solvent, which is a non-toxic and inexpensive media.…”

Section: Introductionmentioning

confidence: 99%