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Article: Metronidazole Cocrystal Polymorphs with Gallic and Gentisic Acid Accessed through Slurry, Atomization Techniques, and Thermal Methods.

Dyba, Aleksandra J / Wiącek, Ewa / Nowak, Maciej / Janczak, Jan / Nartowski, Karol P / Braun, Doris E

Crystal growth & design

2023 Volume 23, Issue 11, Page(s) 8241–8260

Abstract: In this study, key features of metronidazole (MNZ) cocrystal polymorphs with gallic acid (GAL) and gentisic acid (GNT) were elucidated. Solvent-mediated phase transformation experiments in 30 solvents with varying properties were employed to control the ... ...

Abstract	In this study, key features of metronidazole (MNZ) cocrystal polymorphs with gallic acid (GAL) and gentisic acid (GNT) were elucidated. Solvent-mediated phase transformation experiments in 30 solvents with varying properties were employed to control the polymorphic behavior of the MNZ cocrystal with GAL. Solvents with relative polarity (RP) values above 0.35 led to cocrystal I°, the thermodynamically stable form. Conversely, solvents with RP values below 0.35 produced cocrystal II, which was found to be only 0.3 kJ mol
Language	English
Publishing date	2023-10-12
Publishing country	United States
Document type	Journal Article
ISSN	1528-7483
ISSN	1528-7483
DOI	10.1021/acs.cgd.3c00951
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Article ; Online: Unravelling the mechanisms of drugs partitioning phenomena in micellar systems via NMR spectroscopy.

Malec, Katarzyna / Monaco, Serena / Delso, Ignacio / Nestorowicz, Justyna / Kozakiewicz-Latała, Marta / Karolewicz, Bożena / Khimyak, Yaroslav Z / Angulo, Jesús / Nartowski, Karol P

Journal of colloid and interface science

2023 Volume 638, Page(s) 135–148

Abstract: Despite extensive use of micelles in materials and colloidal science, their supramolecular organization as well as host-guest interactions within these dynamic assemblies are poorly understood. Small guest molecules in the presence of micelles undergo ... ...

Abstract	Despite extensive use of micelles in materials and colloidal science, their supramolecular organization as well as host-guest interactions within these dynamic assemblies are poorly understood. Small guest molecules in the presence of micelles undergo constant exchange between a micellar aggregate and the surrounding solution, posing a considerable challenge for their molecular level characterisation. In this work we reveal the interaction maps between small guest molecules and surfactants forming micelles via novel applications of NMR techniques supported with state-of-the-art analytical methods used in colloidal science. Model micelles composed of structurally distinct surfactants (block non-ionic polymer Pluronic® F-127, non-ionic surfactant Tween 20 or Tween 80, and ionic surfactant sodium lauryl sulphate, SLS) were selected and loaded with model small molecules of biological relevance (i.e. the drugs fluconazole, FLU or indomethacin, IMC) known to have different partition coefficients. Molecular level organization of FLU or IMC within hydrophilic and hydrophobic domains of micellar aggregates was established using the combination of NMR methods (1D
MeSH term(s)	Micelles ; Surface-Active Agents/chemistry ; Sodium Dodecyl Sulfate/chemistry ; Polysorbates/chemistry ; Magnetic Resonance Spectroscopy
Chemical Substances	Micelles ; Surface-Active Agents ; Sodium Dodecyl Sulfate (368GB5141J) ; Polysorbates
Language	English
Publishing date	2023-01-20
Publishing country	United States
Document type	Journal Article
ZDB-ID	241597-5
ISSN	1095-7103 ; 0021-9797
ISSN (online)	1095-7103
ISSN	0021-9797
DOI	10.1016/j.jcis.2023.01.063
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Article ; Online: Unravelling the mechanisms of drugs partitioning phenomena in micellar systems via NMR spectroscopy

Malec, Katarzyna / Monaco, Serena / Delso, Ignacio / Nestorowicz, Justyna / Kozakiewicz-Latała, Marta / Karolewicz, Bożena / Khimyak, Yaroslav Z. / Angulo, Jesús / Nartowski, Karol P.

Journal of Colloid And Interface Science. 2023 May, v. 638 p.135-148

2023

Abstract: Despite extensive use of micelles in materials and colloidal science, their supramolecular organization as well as host–guest interactions within these dynamic assemblies are poorly understood. Small guest molecules in the presence of micelles undergo ... ...

Abstract	Despite extensive use of micelles in materials and colloidal science, their supramolecular organization as well as host–guest interactions within these dynamic assemblies are poorly understood. Small guest molecules in the presence of micelles undergo constant exchange between a micellar aggregate and the surrounding solution, posing a considerable challenge for their molecular level characterisation. In this work we reveal the interaction maps between small guest molecules and surfactants forming micelles via novel applications of NMR techniques supported with state-of-the-art analytical methods used in colloidal science. Model micelles composed of structurally distinct surfactants (block non-ionic polymer Pluronic® F-127, non-ionic surfactant Tween 20 or Tween 80, and ionic surfactant sodium lauryl sulphate, SLS) were selected and loaded with model small molecules of biological relevance (i.e. the drugs fluconazole, FLU or indomethacin, IMC) known to have different partition coefficients. Molecular level organization of FLU or IMC within hydrophilic and hydrophobic domains of micellar aggregates was established using the combination of NMR methods (1D ¹H NMR, 1D ¹⁹F NMR, 2D ¹H–¹H NOESY and 2D ¹H-¹⁹F HOESY, and the multifrequency-STD NMR) and corroborated with molecular dynamics (MD) simulations. This is the first application of multifrequency-STD NMR to colloidal systems, enabling us to elucidate intricately detailed patterns of drug/micelle interactions in a single NMR experiment within minutes. Importantly, our results indicate that flexible surfactants, such as block copolymers and polysorbates, form micellar aggregates with a surface composed of both hydrophilic and hydrophobic domains and do not follow the classical core–shell model of the micelle. We propose that the magnitude of changes in ¹H chemical shifts corroborated with interaction maps obtained from DEEP-STD NMR and 2D NMR experiments can be used as an indicator of the strength of the guest-surfactant interactions. This NMR toolbox can be adopted for the analysis of broad range of colloidal host–guest systems from soft materials to biological systems.
Keywords	composite polymers ; fluconazole ; hydrophilicity ; hydrophobicity ; indomethacin ; micelles ; models ; molecular dynamics ; nuclear magnetic resonance spectroscopy ; polysorbates
Language	English
Dates of publication	2023-05
Size	p. 135-148.
Publishing place	Elsevier Inc.
Document type	Article ; Online
ZDB-ID	241597-5
ISSN	1095-7103 ; 0021-9797
ISSN (online)	1095-7103
ISSN	0021-9797
DOI	10.1016/j.jcis.2023.01.063
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Article ; Online: Emulsion-Based Multicompartment Vaginal Drug Carriers: From Nanoemulsions to Nanoemulgels.

Smoleński, Michał / Karolewicz, Bożena / Gołkowska, Anna M / Nartowski, Karol P / Małolepsza-Jarmołowska, Katarzyna

International journal of molecular sciences

2021 Volume 22, Issue 12

Abstract: In order to overcome the limitations associated with vaginal administration of drugs, e.g., the short contact time of the drug form with the mucosa or continuous carrier wash-out, the development of new carriers for gynecological use is necessary. ... ...

Abstract	In order to overcome the limitations associated with vaginal administration of drugs, e.g., the short contact time of the drug form with the mucosa or continuous carrier wash-out, the development of new carriers for gynecological use is necessary. Furthermore, high individual anatomical and physiological variability resulting in unsatisfactory therapeutic efficacy of lipophilic active substances requires application of multicompartment drug delivery systems. This manuscript provides an up-to-date comprehensive review of the literature on emulsion-based vaginal dosage forms (EVDF) including macroemulsions, microemulsions, nanoemulsions, multiple emulsions and self-emulsifying drug delivery systems. The first part of the paper discusses (i) the influence of anatomical-physiological conditions on therapeutic efficacy of drug forms after local and systemic administration, (ii) characterization of EVDF components and the manufacturing techniques of these dosage forms and (iii) methods used to evaluate the physicochemical and pharmaceutical properties of emulsion-based vaginal dosage forms. The second part of the paper presents (iv) the results of biological and in vivo studies as well as (v) clinical evaluation of EVDF safety and therapeutic efficacy across different indications.
MeSH term(s)	Administration, Intravaginal ; Chemical Phenomena ; Drug Carriers/chemistry ; Drug Compounding ; Drug Delivery Systems ; Emulsions ; Female ; Humans ; Microbiota ; Mucous Membrane ; Pharmaceutical Preparations/administration & dosage ; Pharmaceutical Preparations/chemistry ; Theranostic Nanomedicine
Chemical Substances	Drug Carriers ; Emulsions ; Pharmaceutical Preparations
Language	English
Publishing date	2021-06-16
Publishing country	Switzerland
Document type	Journal Article ; Review
ZDB-ID	2019364-6
ISSN	1422-0067 ; 1422-0067 ; 1661-6596
ISSN (online)	1422-0067
ISSN	1422-0067 ; 1661-6596
DOI	10.3390/ijms22126455
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Article ; Online: Directing Crystallization Outcomes of Conformationally Flexible Molecules: Polymorphs, Solvates, and Desolvation Pathways of Fluconazole.

Nowak, Maciej / Dyba, Aleksandra J / Janczak, Jan / Morritt, Alexander / Fábián, László / Karolewicz, Bożena / Khimyak, Yaroslav Z / Braun, Doris E / Nartowski, Karol P

Molecular pharmaceutics

2022 Volume 19, Issue 2, Page(s) 456–471

Abstract: Control over polymorphism and solvatomorphism in API assisted by structural information, e.g., molecular conformation or associations via hydrogen bonds, is crucial for the industrial development of new drugs, as the crystallization products differ in ... ...

Abstract	Control over polymorphism and solvatomorphism in API assisted by structural information, e.g., molecular conformation or associations via hydrogen bonds, is crucial for the industrial development of new drugs, as the crystallization products differ in solubility, dissolution profile, compressibility, or melting temperature. The stability of the final formulation and technological factors of the pharmaceutical powders further emphasize the importance of precise crystallization protocols. This is particularly important when working with highly flexible molecules with considerable conformational freedom and a large number of hydrogen bond donors or acceptors (e.g., fluconazole, FLU). Here, cooling and suspension crystallization were applied to access polymorphs and solvates of FLU, a widely used azole antifungal agent with high molecular flexibility and several reported polymorphs. Each of four polymorphic forms, FLU I, II, III, or IV, can be obtained from the same set of alcohols (MeOH, EtOH, isPrOH) and DMF via careful control of the crystallization conditions. For the first time, two types of isostructural channel solvates of FLU were obtained (nine new structures). Type I solvates were prepared by cooling crystallization in Tol, ACN, DMSO, BuOH, and BuON. Type II solvates formed in DCM, ACN,
MeSH term(s)	Crystallization ; Fluconazole ; Molecular Conformation ; Solvents/chemistry ; Thermogravimetry
Chemical Substances	Solvents ; Fluconazole (8VZV102JFY)
Language	English
Publishing date	2022-01-20
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2138405-8
ISSN	1543-8392 ; 1543-8384
ISSN (online)	1543-8392
ISSN	1543-8384
DOI	10.1021/acs.molpharmaceut.1c00752
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Article ; Online: Hierarchical Macro-Mesoporous Silica Monolithic Tablets as a Novel Dose-Structure-Dependent Delivery System for the Release of Confined Dexketoprofen.

Kozakiewicz-Latała, Marta / Marciniak, Dominik / Krajewska, Karolina / Złocińska, Adrianna / Prusik, Krystian / Karolewicz, Bożena / Nartowski, Karol P / Pudło, Wojciech

Molecular pharmaceutics

2022 Volume 20, Issue 1, Page(s) 641–649

Abstract: This study reports the application of hierarchical porous monoliths as carriers for controlled and dose-adjustable release of model pharmaceutical (dexketoprofen, DEX). The synthesis and detailed characterization of the hierarchical porous scaffolds are ... ...

Abstract	This study reports the application of hierarchical porous monoliths as carriers for controlled and dose-adjustable release of model pharmaceutical (dexketoprofen, DEX). The synthesis and detailed characterization of the hierarchical porous scaffolds are provided before and after the adsorption of three doses of DEX─a widely used nonsteroidal anti-inflammatory drug. The drug incorporated in the mesopores of silica was stabilized in an amorphous state, while the presence of macropores provided sufficient space for drug crystallization as we demonstrated via a combination of powder X-ray diffraction, differential scanning calorimetry, and imaging techniques (scanning electron microscopy and EDX analysis). Drug release from silica matrices was tested, and a mechanistic model of this release based on the Fick diffusion equation was proposed. The hierarchical structure of the carrier, due to the presence of micrometric macropores and nanometric mesopores, turned out to be critical for the control of the drug phase and drug release from the monoliths. It was found that at low drug content, the presence of an amorphous component in the pores promoted the rapid release of the drug, while at higher drug contents, the presence of macropores favored the crystallization of DEX, which naturally slowed down its release. Both the hierarchical porous structure and the control of the drug phase (amorphous and/or crystalline) were proven important for adjustable (fast or prolonged) release kinetics, desirable for effective pharmacotherapy and patient compliance. Therefore, the developed materials may serve as a versatile formulation platform for the smart manipulation of drug release kinetics.
MeSH term(s)	Humans ; Solubility ; Silicon Dioxide/chemistry ; Drug Liberation ; Drug Carriers/chemistry ; X-Ray Diffraction ; Tablets/chemistry ; Porosity ; Calorimetry, Differential Scanning
Chemical Substances	Silicon Dioxide (7631-86-9) ; dexketoprofen trometamol (N674F7L21E) ; Drug Carriers ; Tablets
Language	English
Publishing date	2022-12-19
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2138405-8
ISSN	1543-8392 ; 1543-8384
ISSN (online)	1543-8392
ISSN	1543-8384
DOI	10.1021/acs.molpharmaceut.2c00834
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Article ; Online: Continuous, one-step synthesis of pharmaceutical cocrystals via hot melt extrusion from neat to matrix-assisted processing - State of the art.

Gajda, Maciej / Nartowski, Karol P / Pluta, Janusz / Karolewicz, Bożena

International journal of pharmaceutics

2019 Volume 558, Page(s) 426–440

Abstract: Use of hot melt extrusion (HME) as continuous manufacturing process in the cocrystal synthesis is of increasing interest from both industrial and academic perspective and it is seen as a newly developing branch of mechanochemistry with possible broad ... ...

Abstract	Use of hot melt extrusion (HME) as continuous manufacturing process in the cocrystal synthesis is of increasing interest from both industrial and academic perspective and it is seen as a newly developing branch of mechanochemistry with possible broad application in single step synthesis and formulation of pharmaceutical cocrystals. Furthermore, one-step formulation of pharmaceutical products results in combined processing of pharmaceutical cocrystal mixtures with polymers using HME, which may result in phase change or formation of amorphous solid dispersions during the material processing. The manuscript aims at providing selection guidelines and understanding of processing parameters and instrumental setup of importance to design the HME process for cocrystal synthesis. Furthermore, importance of stoichiometry control of the final product and the matrix selection criteria in simultaneous synthesis and formulation of pharmaceutical cocrystals via HME are provided. The first part of this review, introduce mechanochemical methods of cocrystals synthesis along brief explanation of the possible molecular mechanisms of cocrystal synthesis via mechanochemical approach. Subsequently, the critical process parameters i.e. temperature, screw speed, screw configuration or material feed rate of importance in successful synthesis of high quality product are described followed by literature examples of the processing of neat cocrystal compounds or matrix assisted cocrystallisation.
MeSH term(s)	Crystallization ; Drug Compounding/methods ; Hot Temperature ; Pharmaceutical Preparations/chemistry
Chemical Substances	Pharmaceutical Preparations
Language	English
Publishing date	2019-01-18
Publishing country	Netherlands
Document type	Journal Article ; Review
ZDB-ID	428962-6
ISSN	1873-3476 ; 0378-5173
ISSN (online)	1873-3476
ISSN	0378-5173
DOI	10.1016/j.ijpharm.2019.01.016
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Article ; Online: Tuning the cocrystal yield in matrix-assisted cocrystallisation via hot melt extrusion: A case of theophylline-nicotinamide cocrystal.

Gajda, Maciej / Nartowski, Karol P / Pluta, Janusz / Karolewicz, Bożena

International journal of pharmaceutics

2019 Volume 569, Page(s) 118579

Abstract: Polymer-assisted cocrystallisation via hot melt extrusion (HME) facilitates the cocrystallisation process and increases cocrystal yield compared with the HME of neat cocrystal components. This makes it an attractive method for the single-step continuous ... ...

Abstract	Polymer-assisted cocrystallisation via hot melt extrusion (HME) facilitates the cocrystallisation process and increases cocrystal yield compared with the HME of neat cocrystal components. This makes it an attractive method for the single-step continuous synthesis of pharmaceutical cocrystals. The aim of this study is to understand the effect of semicrystalline (Poloxamer P407, PXM) or amorphous (Soluplus®, SOL) polymers on the cocrystallisation of model theophylline-nicotinamide (TP:NA, 1:1) cocrystal with significantly different melting temperatures of API (TP, m.p. = 271.4 °C) and coformer (NA, m.p. = 128.7 °C) in neat and matrix-assisted cocrystallisation via HME. Compared with the processing of neat cocrystal components, the addition of PXM led to formulation of TP:NA cocrystal embedded in the polymer matrix and increased the cocrystal formation efficiency. On the other hand, the co-processing of cocrystal components with SOL resulted in the formation of cocrystal embedded in the amorphous polymer matrix or in the partially amorphous TP:NA/SOL composites. The one-step formulation of API:coformer mixtures with polymers using HME may result in phase changes or the formation of amorphous solid dispersions, which highlights the importance of matrix selection and phase control of the final product.
MeSH term(s)	Crystallization ; Hot Melt Extrusion Technology ; Hot Temperature ; Niacinamide/chemistry ; Poloxamer/chemistry ; Polyethylene Glycols/chemistry ; Polyvinyls/chemistry ; Theophylline/chemistry
Chemical Substances	Polyvinyls ; polyvinyl caprolactam-polyvinyl acetate-polyethylene glycol graft copolymer ; Poloxamer (106392-12-5) ; Niacinamide (25X51I8RD4) ; Polyethylene Glycols (3WJQ0SDW1A) ; Theophylline (C137DTR5RG)
Language	English
Publishing date	2019-07-27
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	428962-6
ISSN	1873-3476 ; 0378-5173
ISSN (online)	1873-3476
ISSN	0378-5173
DOI	10.1016/j.ijpharm.2019.118579
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Article ; Online: Pluronic F-127 Enhances the Antifungal Activity of Fluconazole against Resistant

Malec, Katarzyna / Mikołajczyk, Aleksandra / Marciniak, Dominik / Gawin-Mikołajewicz, Agnieszka / Matera-Witkiewicz, Agnieszka / Karolewicz, Bożena / Nawrot, Urszula / Khimyak, Yaroslav Z / Nartowski, Karol P

ACS infectious diseases

2023 Volume 10, Issue 1, Page(s) 215–231

Abstract: ... ...

Abstract	Candida
MeSH term(s)	Antifungal Agents/pharmacology ; Antifungal Agents/therapeutic use ; Fluconazole/pharmacology ; Candida ; Poloxamer ; Drug Resistance, Fungal ; Microbial Sensitivity Tests
Chemical Substances	Antifungal Agents ; Fluconazole (8VZV102JFY) ; Poloxamer (106392-12-5)
Language	English
Publishing date	2023-12-18
Publishing country	United States
Document type	Journal Article
ISSN	2373-8227
ISSN (online)	2373-8227
DOI	10.1021/acsinfecdis.3c00536
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Article ; Online: Probing fluconazole deposition inside mesoporous silica using solid-state NMR spectroscopy: Crystallization of a confined metastable form and phase transformations under storage conditions.

Nowak, Maciej / Dyba, Aleksandra J / Gołkowska, Anna M / Nieckarz, Aleksandra / Krajewska, Karolina / Malec, Katarzyna / Iuga, Dinu / Karolewicz, Bożena / Khimyak, Yaroslav Z / Nartowski, Karol P

International journal of pharmaceutics

2023 Volume 645, Page(s) 123403

Abstract: Encapsulation of molecules into mesoporous silica carriers continues to attract considerable interest in the area of drug delivery and crystal engineering. Here, MCM-41, SBA-15 and MCF silica matrices were used to encapsulate fluconazole (FLU), a ... ...

Abstract	Encapsulation of molecules into mesoporous silica carriers continues to attract considerable interest in the area of drug delivery and crystal engineering. Here, MCM-41, SBA-15 and MCF silica matrices were used to encapsulate fluconazole (FLU), a pharmaceutically relevant molecule with known conformational flexibility, using the melting method. The composites have been characterized using
MeSH term(s)	Crystallization ; Fluconazole ; Water/chemistry ; Silicon Dioxide/chemistry ; Magnetic Resonance Spectroscopy/methods ; Porosity
Chemical Substances	Fluconazole (8VZV102JFY) ; Water (059QF0KO0R) ; Silicon Dioxide (7631-86-9)
Language	English
Publishing date	2023-09-14
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	428962-6
ISSN	1873-3476 ; 0378-5173
ISSN (online)	1873-3476
ISSN	0378-5173
DOI	10.1016/j.ijpharm.2023.123403
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