Structure-activity relationship of the ionic cocrystal: 5-amino-2-naphthalene sulfonate·ammonium ions for pharmaceutical applications

Sangeetha, M.; Mathammal, R.

doi:10.1016/j.molstruc.2017.10.060

Cited by 18 publications

(10 citation statements)

References 21 publications

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“…The electrophilic reactivity is represented by the negative potential, while the nucleophilic reactivity is denoted by the positive potential. 40 The values of MEP are closely related to the strength of intermolecular interactions between 2 molecules and could be used as an indicator to evaluate the possibility of formation of multicomponent solids such as co-crystals and salts. 41 The MEP mapped on the vdW surface of DAP and coformer molecules where red color represents the positive potential and cyan represents the negative potential (Fig.…”

Section: Molecular Electrostatic Potential (Mep) Surfacementioning

confidence: 99%

Eutectics and Salt of Dapsone With Hydroxybenzoic Acids: Binary Phase Diagrams, Characterization and Evaluation

Shi

Jia

et al. 2020

Journal of Pharmaceutical Sciences

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Section: Molecular Electrostatic Potential (Mep) Surfacementioning

confidence: 99%

Eutectics and Salt of Dapsone With Hydroxybenzoic Acids: Binary Phase Diagrams, Characterization and Evaluation

Shi

Jia

et al. 2020

Journal of Pharmaceutical Sciences

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“…MEPs mapped on the molecular surface provide clear information in terms of the electrophilic and nucleophilic attack regions of the molecule. The electrophilic reactivity is represented by the negative potential, while the nucleophilic reactivity is denoted by the positive potential . The values of MEP are closely related to the strength of intermolecular interactions between two molecules and are critical for understanding and evaluating the formation possibility of multicomponent crystals.…”

Section: Resultsmentioning

confidence: 86%

“…The electrophilic reactivity is represented by the negative potential, while the nucleophilic reactivity is denoted by the positive potential. 57 The values of MEP are closely related to the strength of intermolecular interactions between two molecules and are critical for understanding and evaluating the formation possibility of multicomponent crystals. Figure 11 shows the MEPs mapped on van der Waals (vdW) surface of APZ and coformer molecules, where the red color represents the value of positive potential, the blue color represents the negative potential value, and the black color represents the calculated pK a value.…”

Section: Molecular Electrostatic Potential Surface (Meps)mentioning

confidence: 80%

Tuning Physicochemical Properties of Antipsychotic Drug Aripiprazole with Multicomponent Crystal Strategy Based on Structure and Property Relationship

Zhao

Sun

Jia

et al. 2020

Crystal Growth & Design

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Poor solubility and dissolution property of pharmaceuticals largely limits their bioavailability and efficacy, and development of a multicomponent crystal is one of the effective approaches to potentially address the issue. Herein we investigated the structure and property relationship of multicomponent crystal aiming to improve the pharmaceutical property, using the Biopharmaceutics Drug Disposition Classification System class II antipsychotic drug Aripiprazole (APZ) as model compound. We reported six new discovered multicomponent crystals of APZ salts with all pharmaceutically acceptable coformers. The comprehensive characterizations were done using X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, and X-ray photoelectron spectroscopy (XPS) techniques. Four multicomponent crystals were structurally solved for the first time by single-crystal X-ray diffraction, demonstrating the proton transfer from the carboxyl group of acids to APZ piperazine. Molecular interactions, crystal packing, and structure similarity analyses performed by Hirshfeld surface and CrystalCMP confirmed the charge-assisted H-bonding sites and structural similarity among the solved crystal structures. The XPS characterization of the other two multicomponent crystals corroborates the salt form as evidenced by the significant chemical shift toward higher binding energy; the pharmaceutical properties including stability, hygroscopicity, and dissolution behavior of all multicomponent crystals were examined by dynamic vapor sorption and high-performance liquid chromatography. It was found all six multicomponent crystals display high stability and low hygroscopicity but divergent dissolution behavior. The variations of these physicochemical properties were further rationalized from their crystal structures and intermolecular interactions.

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“…MEPs has often been used as a straightforward interpretative tool for understanding and predicting the intermolecular interactions in organic crystal structures. It identifies the sites of electrophilic (the negative potential) and nucleophilic (the positive potential) attack and shows the state prior to crystal formation. MEP analysis was employed to investigate the reason behind the difference in formation of salts and cocrystals.…”

Section: Resultsmentioning

confidence: 99%

New Salts and Cocrystals of Pymetrozine with Improvements on Solubility and Humidity Stability: Experimental and Theoretical Study

Xiao

et al. 2021

Crystal Growth & Design

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For the purpose of enhancing the solubility and humidity stability of pymetrozine (PMZ), a highly active but nonbiocidal pesticide, new multicomponent crystals were developed based on the connotation of crystal engineering. In the coformer screening process, a combined method, the Conductor-like Screening Model for Realistic Solvents (COSMO-RS) approach together with Cambridge Structural Database (CSD) analysis, was employed to shorten the screening process. Further, seven single crystals of PMZ’s new multicomponent solids were obtained including three cocrystals and four salts. Single-crystal X-ray diffraction together with Hirshfeld surface analysis clarified the detailed structure and the molecular interactions in these new crystals. Thermodynamic properties and spectral data were characterized by thermogravimetric analysis, differential scanning calorimetry, and Fourier-transform infrared spectroscopy. Hygroscopicity and solubility of the seven cocrystals/salts were investigated by dynamic vapor sorption and equilibrium solubility measurement, respectively. Multicomponent crystals not only exhibit better stability against humidity and but also higher water solubility than PMZ. Meanwhile, the insecticidal activity of PMZ was preserved during the formation of cocrystals/salts. On this basis, we conducted the atoms-in-molecules (AIM) analysis and the molecular electrostatic potential surfaces (MEPs) analysis to assess the strength of hydrogen bonds and reveal the origins of salt/cocrystal formation. So, the variations and origins of these physicochemical properties were rationalized and explained on the atomic scale. On the whole, the efficiency of the novel combined coformers screening method was verified and new multicomponent crystalline forms of PMZ were successfully obtained to prevent the parent compound from hydrating transformation.

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Structure-activity relationship of the ionic cocrystal: 5-amino-2-naphthalene sulfonate·ammonium ions for pharmaceutical applications

Cited by 18 publications

References 21 publications

Eutectics and Salt of Dapsone With Hydroxybenzoic Acids: Binary Phase Diagrams, Characterization and Evaluation

Eutectics and Salt of Dapsone With Hydroxybenzoic Acids: Binary Phase Diagrams, Characterization and Evaluation

Tuning Physicochemical Properties of Antipsychotic Drug Aripiprazole with Multicomponent Crystal Strategy Based on Structure and Property Relationship

New Salts and Cocrystals of Pymetrozine with Improvements on Solubility and Humidity Stability: Experimental and Theoretical Study

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