Amino acids and its pharmaceutical applications: A mini review

Bongioanni, Agustina; Bueno, Maria Soledad; Mezzano, Belén Alejandra; Longhi, Marcela Raquel; Garnero, Claudia

doi:10.1016/j.ijpharm.2021.121375

Cited by 36 publications

(20 citation statements)

References 106 publications

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“…An estimated 40% of commercially available drugs and up to 90% of newly discovered drug candidates have poor water solubility [ 1 , 2 ]. As a result, the development of solubilization techniques, as well as the search for new hydrotropes and potential water-soluble excipients to enhance the solubility and dissolution rates of poorly soluble drugs, has been an ongoing endeavor for formulation scientists [ 3 , 4 ]. Ketoprofen ( Figure 1 ) is a non-steroidal anti-inflammatory drug (NSAID) that was discovered in 1968 [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, there has been a growing interest in investigating and utilizing amino acids due to their safety and tolerability. Amino acids are classified as GRAS (Generally Recognized as Safe) and are used as dietary supplements [ 4 ]. In addition, amino acids have been successfully used to solubilize both ionizable and non-ionizable drugs.…”

Section: Introductionmentioning

confidence: 99%

“…They are small molecules with diverse chemical structures, and can be broadly classified into mainly amphoteric (e.g., glycine and alanine), acidic (e.g., aspartic acid and glutamic acid), or basic (e.g., arginine and lysine) amino acids ( Figure 1 ). Additional side chains, such as hydroxyl and sulfhydryl groups, can boost their solubilizing capacity [ 4 , 12 ].…”

Section: Introductionmentioning

confidence: 99%

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Exploration of the Safety and Solubilization, Dissolution, Analgesic Effects of Common Basic Excipients on the NSAID Drug Ketoprofen

et al. 2023

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Since its introduction to the market in the 1970s, ketoprofen has been widely used due to its high efficacy in moderate pain management. However, its poor solubility and ulcer side effects have diminished its popularity. This study prepared forms of ketoprofen modified with three basic excipients: tris, L-lysine, and L-arginine, and investigated their ability to improve water solubility and reduce ulcerogenic potential. The complexation/salt formation of ketoprofen and the basic excipients was prepared using physical mixing and coprecipitation methods. The prepared mixtures were studied for solubility, docking, dissolution, differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), in vivo evaluation for efficacy (the writhing test), and safety (ulcerogenic liability). Phase solubility diagrams were constructed, and a linear solubility (AL type) curve was obtained with tris. Docking studies suggested a possible salt formation with L-arginine using Hirshfeld surface analysis. The order of enhancement of solubility and dissolution rates was as follows: L-arginine > L-lysine > tris. In vivo analgesic evaluation indicated a significant enhancement of the onset of action of analgesic activities for the three basic excipients. However, safety and gastric protection indicated that both ketoprofen arginine and ketoprofen lysine salts were more favorable than ketoprofen tris.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Exploration of the Safety and Solubilization, Dissolution, Analgesic Effects of Common Basic Excipients on the NSAID Drug Ketoprofen

et al. 2023

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“…They are water-soluble carriers of relatively low molecular weights that have suitable structural characteristics (α-carboxylate, α-amino group, and side chains) for forming bonds with APIs. Numerous studies have demonstrated how amino acids can enhance the stability and safety of APIs [ 18 , 19 , 20 , 21 , 22 , 23 ].…”

Section: Introductionmentioning

confidence: 99%

Pharmaceutical Systems as a Strategy to Enhance the Stability of Oxytetracycline Hydrochloride Polymorphs in Solution

2023

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In order to improve the stability of oxytetracycline hydrochloride, a polymorphic antibiotic set of novel binary systems were developed using β-cyclodextrin and amino acids with different acid-basic characteristics as ligands. The formation constants for each system containing β-cyclodextrin, L-aspartic acid, histidine and N-acetylcysteine were determined by Scott’s method and statistical studies. The structure of the binary systems with β-cyclodextrin and N-acetylcysteine was elucidated by NMR experiments. The effect β-cyclodextrin and N-acetylcysteine on the polymorph’s chemical stability in aqueous and phosphate buffered saline solutions at 25 °C was monitored by an optimized and validated high-performance liquid chromatography method. The combination of N-acetylcysteine with the three polymorphs and the β-cyclodextrin system obtained with the form III demonstrated a reduction in the degradation rate of oxytetracycline hydrochloride in the aqueous solution when compared to each free form, with an increase of 20 h in the half time. It evidences that the use of amino acids as ligands constitutes an interesting alternative for pharmaceutical areas. In conclusion, based on the results obtained, these pharmaceutical systems could be candidates for the development of a pharmaceutical formulation for the administration of the drug through reconstituted solutions using the binary system as a promising tool for improving the stability of oxytetracycline hydrochloride polymorphs in solution.

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“…在人体内氨基酸能通过代谢转变成脂肪、碳水化合物、二氧化碳、尿素以及产生能量, 还可以合成蛋白质, 变成激素、肌酸、抗体等物质. 由于其功能和结构的多样性, 氨基酸在制药 [2] 、化妆品 [3] 、食品 [4] 以及饲料工业都有着重要作用 [5] . 将氘原子引入到药物分子中可改变其药动学参数(PK), 通常药物分子氘代后, 药物清除率会减少, 而药时曲线下面(AUC)、药峰浓度(C max )和末端消除半衰期(T 1/2 )则会增加.…”

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Asymmetric Transfer Hydrogenation of α-Aryl Amidates Using Methanol as Hydrogen Source

Ting¹,

Chen²,

Wang³

et al. 2022

Chinese Journal of Organic Chemistry

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As a kind of amino acid derivatives, chiral arylglycine not only has very important application value in the field of organic synthesis, but also serves as the key structure of many chiral drugs and biologically active compounds. A practical and economical method for the preparation of chiral α-arylglycines is reported herein. By using methanol as the hydrogen source, a series of chiral α-arylglycine derivatives were prepared by asymmetric transfer hydrogenation of α-aryl imine esters with Pd/Zn co-catalyzed system. By switching the hydrogen source to deuterated methanol, a series of chiral deuterated a-arylglycine derivatives were obtained. The catalytic system featured with good substrate suitability, and the product was obtained in up to 93% yield with up to 92% enantioselectivity, and the deuteration incorporation rate is up to 94%. The present method has provided an efficient and economic method for the synthesis of valuable deuterium-labeled chiral amino acids. Keywords methanol; imino acid; deuterium amino acid; asymmetric transfer hydrogenation 氨基酸是人体生长发育必不可少的基本物质 [1] . 在人体内氨基酸能通过代谢转变成脂肪、碳水化合物、二氧化碳、尿素以及产生能量, 还可以合成蛋白质, 变成激素、肌酸、抗体等物质. 由于其功能和结构的多样性, 氨基酸在制药 [2] 、化妆品 [3] 、食品 [4] 以及饲料工业都有着重要作用 [5] . 将氘原子引入到药物分子中可改变其药动学参数(PK), 通常药物分子氘代后, 药物清除率会减少, 而药时曲线下面(AUC)、药峰浓度(C max )和末端消除半衰期(T 1/2 )则会增加. 同时, 用氘取代单个立体异构的手性中心后, 它可能会降低原子提取率(the rate of atom ab-straction)以稳定其立体异构 [6] . 随着对氘代氨基酸的不断研究, 研究者发现用同位素稳定标记的氨基酸也可用于患者进行体内外代谢、疾病诊断的示踪研究 [7] .

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Amino acids and its pharmaceutical applications: A mini review

Cited by 36 publications

References 106 publications

Exploration of the Safety and Solubilization, Dissolution, Analgesic Effects of Common Basic Excipients on the NSAID Drug Ketoprofen

Exploration of the Safety and Solubilization, Dissolution, Analgesic Effects of Common Basic Excipients on the NSAID Drug Ketoprofen

Pharmaceutical Systems as a Strategy to Enhance the Stability of Oxytetracycline Hydrochloride Polymorphs in Solution

Asymmetric Transfer Hydrogenation of α-Aryl Amidates Using Methanol as Hydrogen Source

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