Structural studies of crystalline forms of triamterene with carboxylic acid, GRAS and API molecules

Rehman, Abida; Delori, Amit; Hughes, David S.; Jones, William

doi:10.1107/s2052252518003317

Cited by 5 publications

(3 citation statements)

References 57 publications

(56 reference statements)

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“…The strategies hover around the possibility of predicting different hydrogen bonding propensity based on the approach developed at Cambridge Crystallographic Data Center (CCDC). , An equally successful approach uses the molecular shape and polarity descriptors . In a recent study of the drug triamterene, diversity created by variations in hydrogen bond donors and acceptors in two classes of coformers, mono and dicarboxylic acids, has been analyzed to arrive at several useful insights into the propensity of salt formation. In the present study, the role of an additional amino group on LH unlike that of UA and the proximity and number of hydroxyl groups on the benzoic acid moiety organize the supramolecular assembly to accommodate hydration levels …”

Section: Introductionmentioning

confidence: 99%

Role of Functionalities in Structural Analogues Urocanic Acid and l-Histidine, toward the Formation of Anhydrous and Hydrated Molecular Salts

Ganduri

Swain

Cherukuvada

et al. 2019

Crystal Growth & Design

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Cocrystallization of structural analogues urocanic acid and l-histidine with mono-, di-, and trisubstituted hydroxy benzoic acids has been carried out to gain insights into the formation of anhydrous and hydrated molecular salts. Urocanic acid generated anhydrous molecular salts with 2-hydroxy, 3,5-dihydroxy, and 2,4,6-trihydroxybenzoic acids, whereas 2,3-dihydroxy, 3,4-dihydroxy, and 3,4,5-trihydroxybenzoic acids resulted in hydrated salts. Cocrystallization experiments of anhydrous l-histidine with 2,3-dihydroxy, 3,4-dihydroxy, 3,5-dihydroxy, 3,4,5-trihydroxy, and 2,4,6-trihydroxybenzoic acids resulted in hydrated molecular salts. However, l-histidine 2-hydroxybenzoic acid formed an anhydrous molecular salt. In this context, the hitherto elusive structure of native urocanic acid (anhydrous form) has been determined. The rationale for the formation of hydrated and anhydrous salts is evaluated in terms of the hydroxyl substituents on benzoic acids and the presence of additional amino group in l-histidine. Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) proved the presence or absence of hydration, whereas Fourier-transform infrared (FT-IR) experiments confirmed proton transfer suggesting the formation of molecular salts for those combinations that did not produce good quality single crystals for diffraction.

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Section: Introductionmentioning

confidence: 99%

Role of Functionalities in Structural Analogues Urocanic Acid and l-Histidine, toward the Formation of Anhydrous and Hydrated Molecular Salts

Ganduri

Swain

Cherukuvada

et al. 2019

Crystal Growth & Design

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“…Since ibuprofen is deprotonated inside the enzyme, ibuprofenate salt crystal structures are most relevant for this study, in which we aim for a comparison of the enzyme and crystal environments. Most examples of ibuprofenate salts comprise ammonium countercations where the related amine is basic enough to deprotonate the carboxylic acid group of ibuprofen (Kumar et al, 2017;Lemmerer et al, 2010;Rehman et al, 2018;Ma et al, 2019). In this study, we will use R-or S-1-phenylethan-1-amine (PEA) to produce salts of ibuprofen and sila-ibuprofen (Lemmerer et al, 2010;Molna ´r et al, 2009), and also report on the new crystal structure of argininium ibuprofenate.…”

Section: Introductionmentioning

confidence: 99%

Ibuprofen and sila-ibuprofen: polarization effects in the crystal and enzyme environments

Kleemiss

Puylaert

Duvinage

et al. 2021

Acta Crystallogr Sect B

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Sila-ibuprofen is a new potential nonsteroidal anti-inflammatory drug which deviates from its parent ibuprofen in terms of the electrostatic potential around the carbon/silicon-switched C/Si—H group. Therefore, sila-ibuprofen is more water soluble and has a lower melting enthalpy. However, its binding and inhibition properties of cyclooxygenases appear to be very similar to regular ibuprofen. Therefore, in this study, intermolecular interactions and interaction densities of both ibuprofen and sila-ibuprofen in their biologically active forms, i.e. deprotonated and as the pure S-enantiomers are investigated. Quantum-crystallographically refined salts with argininium and 1-phenylethan-1-amoninium (PEA) counter-cations as crystalline models of the interactions with the guanidine functional group of arginine inside cyclooxygenases are presented. The similarities and differences between the polarization of ibuprofen and sila-ibuprofen in the crystal, enzyme, solvent and isolated environments are discussed based on quantum-chemical calculations. For the explicit crystal and enzyme environments, specifically, molecular dynamics simulations starting from the crystal models were combined with QM/MM calculations.

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“…Researchers constantly strive to pick out an alternative solid form to improve the poor physicochemical properties of special biocompatible ingredients (Sanphui et al, 2014;Kerr et al, 2017;Cerreia Vioglio et al, 2017;Swinton Darious et al, 2018;Rehman et al, 2018). The desired improvements can be alterations of melting point, crystallinity, density, solubility, stability, particle size and filterability (Mnguni et al, 2018;Nisar et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

The salt–cocrystal spectrum in salicylic acid–adenine: the influence of crystal structure on proton-transfer balance

Sedghiniya

Soleimannejad

Janczak

2019

Acta Crystallogr C Struct Chem

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At one extreme of the proton-transfer spectrum in cocrystals, proton transfer is absent, whilst at the opposite extreme, in salts, the proton-transfer process is complete. However, for acid-base pairs with a small ÁpK a (pK a of base À pK a of acid), prediction of the extent of proton transfer is not possible as there is a continuum between the salt and cocrystal ends. In this context, we attempt to illustrate that in these systems, in addition to ÁpK a , the crystalline environment could change the extent of proton transfer. To this end, two compounds of salicylic acid (SaH) and adenine (Ad) have been prepared. Despite the same small ÁpK a value (%1.2), different ionization states are found. Both crystals, namely adeninium salicylate monohydrate, C 5 H 6 N 5 + ÁC 7 H 5 O 3 À ÁH 2 O, I, and adeninium salicylate-adenine-salicylic acid-water (1/2/1/2), C 5 H 6 N 5 + ÁC 7 H 5 O 3 À Á-2C 5 H 5 N 5 ÁC 7 H 6 O 3 Á2H 2 O, II, have been characterized by single-crystal X-ray diffraction, IR spectroscopy and elemental analysis (C, H and N) techniques. In addition, the intermolecular hydrogen-bonding interactions of compounds I and II have been investigated and quantified in detail on the basis of Hirshfeld surface analysis and fingerprint plots. Throughout the study, we use crystal engineering, which is based on modifications of the intermolecular interactions, thus offering a more comprehensive screening of the salt-cocrystal continuum in comparison with pure pK a analysis.

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Structural studies of crystalline forms of triamterene with carboxylic acid, GRAS and API molecules

Cited by 5 publications

References 57 publications

Role of Functionalities in Structural Analogues Urocanic Acid and l-Histidine, toward the Formation of Anhydrous and Hydrated Molecular Salts

Role of Functionalities in Structural Analogues Urocanic Acid and l-Histidine, toward the Formation of Anhydrous and Hydrated Molecular Salts

Ibuprofen and sila-ibuprofen: polarization effects in the crystal and enzyme environments

The salt–cocrystal spectrum in salicylic acid–adenine: the influence of crystal structure on proton-transfer balance

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