Tris(hydroxymethyl)methyl ammonium salts of biologically active carboxylic acids. Synthesis, properties and crystal structure

Kondratenko, Yu. A.; Nikonorova, A.A.; Zolotarev, Andrey A.; Уголков, В. Л.; Кочина, Т. А.

doi:10.1016/j.molstruc.2020.127813

Cited by 15 publications

(5 citation statements)

References 41 publications

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“…The exception is BIS‐TRIS salts of dicarboxylic acids 7 , 9 , 11 , and 13 , obtained with a molar ratio of reagents equal to 1: 1, which led to the formation of acid salts of the composition [BIS‐TRIS](HOOC(CH 2 ) n COO), n=0‐2. In general, the FTIR spectra of BIS‐TRIS salts 1–14 are similar to the spectra of other hydroxyalkylammonium salts of carboxylic acids [12a,18] and are characterized by broadened bands in the spectral range 3600–3100 cm −1 (ν(OH)), medium‐intensity bands in the range 3050–2820 cm −1 (ν(CH), ν(CH 2 ), ν(CH 3 )), two intense bands in the range 1610–1540 (ν as (COO − )) and 1430–1340 (ν s (COO − )) cm −1 , as well as medium and intense bands in the region of 1600–1450 cm −1 (ν(Ar)) only in the case of salts 1–6 with aromatic groups in the anion.…”

Section: Resultsmentioning

confidence: 58%

Protic Ionic Liquids Based on BIS‐TRIS Carboxylates: Synthesis, Structural Characterization and Buffer Activity

et al. 2022

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Ionic liquids, which have their own buffer capacity, have been classified as Good's buffer ionic liquids (GB-ILs). GB-ILs have demonstrated their potential in biotechnology due to their biocompatibility and profitable self-buffering properties. A number of new GB-ILs based on BIS-TRIS (bis(2-hydroxyethyl)amino-tris(hydroxymethyl)methane) carboxylates have been synthesized. IR, NMR ( 1 H, 13 C) spectroscopy, and thermal analysis data confirming the formation of new BIS-TRIS salts are presented. The crystal structure of three BIS-TRIS salts with salicylate, hydrogen oxalate, and oxalate anions was determined by single-crystal X-ray diffraction. Screening of synthesized BIS-TRIS carboxylates as buffers in 68 Ga-radiolabeling reactions of the model chelator p-SCNÀ Bn-DOTA, which is prototype of DOTA-modified (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) peptides, was carried out.

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Section: Resultsmentioning

confidence: 58%

Protic Ionic Liquids Based on BIS‐TRIS Carboxylates: Synthesis, Structural Characterization and Buffer Activity

et al. 2022

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“…If the ∆pKa between solid active pharmaceutical ingredients and its coformers was more than three, the multicomponent crystal tended to form a salt-type crystal [17,27,28]. Ketoprofen and tromethamine had pKas of 4.13 and 8.6, respectively [29,30]. Thus, the ∆pKa between the ketoprofen and tromethamine was 4.47, which indicated a high likelihood of forming a salt-type multicomponent crystal phase.…”

Section: Solid-state Characterizationmentioning

confidence: 99%

Improved Solubility and Dissolution Rate of Ketoprofen by the Formation of Multicomponent Crystals with Tromethamine

Fitriani

Firdaus

Sidadang³

et al. 2022

Crystals

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This study aims to improve the dissolution rate of ketoprofen by preparing multicomponent crystals with tromethamine. The multicomponent crystals (equimolar ratio) of ketoprofen and tromethamine were prepared by the solvent co-evaporation method. The solid-state properties of the resulting powder were characterized by powder X-ray diffraction, DSC thermal analysis, FT–IR spectroscopy, solubility, and in vitro dissolution rate. The crystal structure of the multicomponent crystal was determined by single-crystal X-ray diffraction analysis. The results showed that the powder X-ray diffraction pattern of the ketoprofen–tromethamine binary system was different from that of the starting materials. This difference indicates the formation of a new crystalline phase between ketoprofen and tromethamine (equimolar ratio). The DSC thermogram of the ketoprofen–tromethamine binary system exhibited a single and sharp endothermic peak at 128.67 °C, attributed to the melting point of a multicomponent crystal of ketoprofen–tromethamine. A single-crystal X-ray analysis revealed that ketoprofen–tromethamine formed a layered structure, salt-type multicomponent crystal. The solubility and dissolution rate of the multicomponent crystal were notably enhanced compared to the intact ketoprofen. The ketoprofen–tromethamine binary system forms salt-type multicomponent crystals, which can significantly increase the solubility and dissolution rate.

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“…For example, tris(hydroxymethyl)methylammonium (TRIS) and tris(2-hydroxypropyl)ammonium (TPA) salts of analogous carboxylic acids (cinnamic, benzoic, etc.) have been obtained for the first time [93,94] to investigate the conformation of the hydroxyalkylammonium cation and the cationanion interactions. In the case of tris(hydroxymethyl)methylammonium cation, three conformations have been revealed (Fig.…”

Section: Sn Adamovich Et Al Have Elaboratedmentioning

confidence: 99%

Contribution of the Scientific School of Academician M.G. Voronkov to the Development of the Chemistry of Biologically Active Atranes (Protatranes and Hydrometallatranes) (A Review)

Kondratenko

Кочина

2021

Russ J Gen Chem

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The main results of the many years’ studies of the scientific school of Academician Mikhail G. Voronkov in the field of two subgroups of the atrane family (protatranes and hydrometallatranes) as well as the results of research in continuation of the studies initiated by Academician M. G. Voronkov have been summarized and presented. Long-term studies of atranes under the leadership of M. G. Voronkov have led to the discovery of their unique biological activity and the creation of a series of unique original drugs and means of agricultural chemicalization: biostimulants and adaptogens for agricultural plants, animals, useful insects and microorganisms.

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Tris(hydroxymethyl)methyl ammonium salts of biologically active carboxylic acids. Synthesis, properties and crystal structure

Cited by 15 publications

References 41 publications

Protic Ionic Liquids Based on BIS‐TRIS Carboxylates: Synthesis, Structural Characterization and Buffer Activity

Protic Ionic Liquids Based on BIS‐TRIS Carboxylates: Synthesis, Structural Characterization and Buffer Activity

Improved Solubility and Dissolution Rate of Ketoprofen by the Formation of Multicomponent Crystals with Tromethamine

Contribution of the Scientific School of Academician M.G. Voronkov to the Development of the Chemistry of Biologically Active Atranes (Protatranes and Hydrometallatranes) (A Review)

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