Isostructurality and the conformational role of the 2′,3′-moieties in the diversity of lamivudine crystal forms probed in halide salts

Tenório, Juan C.; Guimarães, Fernando; Ellena, Javier; Martins, Felipe Terra

doi:10.1039/c4ce02373k

Cited by 11 publications

(5 citation statements)

References 23 publications

(31 reference statements)

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“…A more concise way of using this term could probably emerge from the effects of polymorphism itself. At a pharmaceutical level, the presence of polymorphs of a compound causes differences in solubility and stability, and in the formulation procedures for that particular compound [2][3][4][5][6][7][8][9][10][11]. In biomineral systems, organisms use different polymorphs according to the system and function that are needed [12][13][14].…”

Section: Definitionmentioning

confidence: 99%

Crystal Growth in Gels from the Mechanisms of Crystal Growth to Control of Polymorphism: New Trends on Theoretical and Experimental Aspects

et al. 2019

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A gel can be considered to be a two-phase (liquid and solid) system, which lacks flow once it reaches a stationary state. The solid phase is usually a tridimensional polymeric mesh, while the liquid phase is usually found in three forms: contained in great cavities, retained in the capillary pores between micelles, or adsorbed on the surface of a micelle. The influence of the use of gels in crystal growth is diverse and depends on the type of gel being used. A decrease in solubility of any solute in the liquid may occur if the solvent interacts extensively with the polymeric section, hence, the nucleation in gels in these cases apparently occurs at relatively low supersaturations. However, if the pore size is small enough, there is a possibility that a higher supersaturation is needed, due to the compartmentalization of solvents. Finally, this may also represent an effect in the diffusion of substances. This review is divided into three main parts; the first evaluates the theory and practice used for the obtainment of polymorphs. The second part describes the use of gels into crystallogenesis of different substances. The last part is related to the particularities of protein crystal polymorphism, as well as modern trends in gel growth for high-resolution X-ray crystallography.

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Section: Definitionmentioning

confidence: 99%

Crystal Growth in Gels from the Mechanisms of Crystal Growth to Control of Polymorphism: New Trends on Theoretical and Experimental Aspects

et al. 2019

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“…An example of this polymorphism is found in sodium dihydrogen citrate (NAHCIT 77 and NAHCIT01 78 ), where the citric carboxylic acid deprotonation is different in the two polymorphs. A particularly interesting example of this type of polymorphism is lamivudine hydrochloride (LASZAI 79 and LASZAI02 80 ) because the protonation at a different location in the lamivudine molecule is also related by tautomerism. Both tautomers of lamivudine (Table 4) are very weakly basic with calculated p K a of 0.21 and −0.05.…”

Section: Resultsmentioning

confidence: 99%

A to Z of polymorphs related by proton transfer

2023

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“…(5) or R 2 1 (6). In the structure, however, there is also a significant amount of Hbonding motifs that form larger rings, e.g., R 4 4 (12).…”

Section: Structural Description and Supramolecular Analysismentioning

confidence: 99%

“…Multicomponent crystal structures (MCSs) can be defined as crystals that contain two or more different residues in their crystal lattice. − The design of MCSs provides a means to alter the physicochemical properties of crystals without modifying the chemical properties of the molecule of interest, constituting any of these residues. This is an important current issue for the fields of crystalline engineering and pharmaceutical science, especially with regard to active pharmaceutical ingredients (APIs). − …”

Section: Introductionmentioning

confidence: 99%

Multicomponent Supramolecular Assemblies of Melamine and α-Hydroxycarboxylic Acids: Understanding the Hydrogen Bonding Patterns and Their Physicochemical Consequences

Castiñeiras

García‐Santos

González‐Pérez

et al. 2018

Crystal Growth & Design

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The reaction of 1,3,5-triazine-2,4,6-triamine (melamine, me) with alpha-hydroxycarboxylic acids, namely, glycolic acid (H 2 ga) and mandelic acid (H 2 ma), provided three ionic multicomponent crystal structures (MCSs) of composition:Those MCSs revealed the typical propensity of "me", and particularly of its monoprotonated form (Hme + ), to form supramolecular aggregates such as linear and crinkled tapes and molecular ribbons. The energetic landscape of those assemblies has been explored with the use of density functional theory calculations of various models of Hme + and "me" hydrogen-bonded aggregates. The stabilization energies of Hme + -based adducts are for the first time rationalized within the context of the anti-electrostatic hydrogen bonding concept. In addition, we discussed the supramolecular arrangement of I−III in terms of synthon formation and explored structural peculiarities imparted by hydration and solvation. The salt-to-cocrystal continuum is analyzed based on structural analysis and physicochemical properties such as vibrational characteristics, thermal stability, and solubility. Finally, the analysis of d norm -mapped Hirshfeld surfaces of melamine at different protonation states allowed us to establish strongly characteristic protonation-dependent features of those surfaces, whose peculiar features are reflected in associated fingerprint plots (FPs). By comparison with literature precedents, we have found that our findings on FP plots of "me" and Hme + species are indeed general.

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Isostructurality and the conformational role of the 2′,3′-moieties in the diversity of lamivudine crystal forms probed in halide salts

Cited by 11 publications

References 23 publications

Crystal Growth in Gels from the Mechanisms of Crystal Growth to Control of Polymorphism: New Trends on Theoretical and Experimental Aspects

Crystal Growth in Gels from the Mechanisms of Crystal Growth to Control of Polymorphism: New Trends on Theoretical and Experimental Aspects

A to Z of polymorphs related by proton transfer

Multicomponent Supramolecular Assemblies of Melamine and α-Hydroxycarboxylic Acids: Understanding the Hydrogen Bonding Patterns and Their Physicochemical Consequences

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