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Principles for Stereoselective Separation of Chiral Drug Compounds Enantiomers and Diastereomers in Pharmaceuticals and Biopharmaceuticals Using Liquid Chromatography
IF 2.8 4区 化学
Chirality Pub Date : 2025-02-03 DOI: 10.1002/chir.70017
Niroja Vadagam, Sharath Babu Haridasyam, Narasimha S. Lakka, Chandrasekar Kuppan, Poornima Ravinathan, Sanjeeva R. Chinnakadoori
{"title":"Principles for Stereoselective Separation of Chiral Drug Compounds Enantiomers and Diastereomers in Pharmaceuticals and Biopharmaceuticals Using Liquid Chromatography","authors":"Niroja Vadagam,&nbsp;Sharath Babu Haridasyam,&nbsp;Narasimha S. Lakka,&nbsp;Chandrasekar Kuppan,&nbsp;Poornima Ravinathan,&nbsp;Sanjeeva R. Chinnakadoori","doi":"10.1002/chir.70017","DOIUrl":"https://doi.org/10.1002/chir.70017","url":null,"abstract":"<div>\u0000 \u0000 <p>In the fields of pharmaceuticals and biopharmaceuticals, chiral liquid chromatography techniques including high-performance liquid chromatography and ultra-performance liquid chromatography are frequently used to isolate, identify, separate, and quantify chiral isomers, including enantiomers and diastereomers (stereoisomers), due to the significant differences in biological activity and therapeutic effects of stereoisomers. The authors have provided a comprehensive overview of the fundamental principles necessary for using liquid chromatography to separate and accurately estimate chiral compounds that exhibit stereoisomerism (both enantiomers and diastereomers). The development strategies outlined include the selection of chromatographic conditions, optimization of sample preparation, evaluation of degradation pathways, establishment of system suitability criteria, and execution of method validation studies. Additionally, this article supports the development of robust and stability-indicating methods by applying one factor at a time and design of experiments concepts for chiral drugs and their chiral impurities in pharmaceuticals and biopharmaceuticals. The method validation attributes essential to evaluate the characteristics of the developed method were discussed in this write-up. The validation parameters include specificity, linearity, detection limit, quantitation limit, accuracy, precision, solution stability.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143111351","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A Review on Carbazole and Its Derivatives as Anticancer Agents From 2013 to 2024
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-30 DOI: 10.1002/chir.70021
Priyanka Sanjay Waghmare, Anuruddha Rajaram Chabukswar, Kunal Ganesh Raut, Pooja Tanaji Giri
{"title":"A Review on Carbazole and Its Derivatives as Anticancer Agents From 2013 to 2024","authors":"Priyanka Sanjay Waghmare,&nbsp;Anuruddha Rajaram Chabukswar,&nbsp;Kunal Ganesh Raut,&nbsp;Pooja Tanaji Giri","doi":"10.1002/chir.70021","DOIUrl":"10.1002/chir.70021","url":null,"abstract":"<div>\u0000 \u0000 <p>Carbazole, a natural alkaloid, has been recognized as an effective anticancer agent for over 40 years. However, only a limited number of carbazole-based compounds have received FDA approval for cancer treatment. Current cancer therapies are often associated with significant side effects, causing physical, emotional, and financial burdens for patients. Additionally, despite advancements, cancer prevention and treatment remain challenging due to suboptimal clinical outcomes. The development of new drugs is crucial for achieving safer and more effective cancer therapies. This review focuses on various carbazole derivatives and hybrid composites, highlighting their interactions with distinct receptors and their mechanisms of anticancer action, along with a general structure–activity relationship (SAR). It also emphasizes carbazole-based compounds employed in chemoprevention, which aim to delay or prevent malignant progression. By covering carbazole derivatives and their anticancer potential from 2013 to the present, along with their current clinical status, this study offers valuable insights and updates for researchers in the field.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143064012","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
150 Years of the Tetrahedral Carbon: A Toast to Chirality
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-26 DOI: 10.1002/chir.70022
Pedro Cintas
{"title":"150 Years of the Tetrahedral Carbon: A Toast to Chirality","authors":"Pedro Cintas","doi":"10.1002/chir.70022","DOIUrl":"10.1002/chir.70022","url":null,"abstract":"<div>\u0000 \u0000 <p>We have recently celebrated the 150th anniversary of the tetrahedral carbon (1874–2024), as postulated by van't Hoff and Le Bel, who published their seminal breakthrough only 2-months apart, on September 5 and November 5, 1874, respectively. The concept is a fundamental pillar of structural chemistry and, if we may say so, of molecular sciences. How two young men in their early careers dared to disturb the established way of thinking constitutes the jumping-off of scientific theories as constructive elements, rather than arguments derived from experiments. Chirality makes no sense without geometry. Nor can we interpret a molecular scenario devoid of spatial considerations. All in all, a felicitous celebration to be highlighted.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143045719","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
On the Influence of Additives and Modifiers on the Chiral HPLC Separation of the Enantiomers of Nicotine
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-26 DOI: 10.1002/chir.70020
Mehdi Ashraf-Khorassini, William M. Coleman III, Weston J. Umstead
{"title":"On the Influence of Additives and Modifiers on the Chiral HPLC Separation of the Enantiomers of Nicotine","authors":"Mehdi Ashraf-Khorassini,&nbsp;William M. Coleman III,&nbsp;Weston J. Umstead","doi":"10.1002/chir.70020","DOIUrl":"10.1002/chir.70020","url":null,"abstract":"<p>The influence of additives and modifiers on the chiral HPLC separation of the nicotine enantiomers using UV/Vis detection is discussed. Selected alcohols as modifiers and selected amines as additives were found to have a significant effect on the resolution and retention times of nicotine enantiomers even to the point of eliminating component elution. Systematic variations in the concentration of ethanol, methanol, and isopropanol, as modifiers, along with variations in the concentration of diethylamine, triethylamine, tributylamine, ethylenediamine, isopropylamine, as additives, revealed that the average resolution (<i>R</i>) of the nicotine enantiomers ranged from 2.9 to 7.57, using a mobile phase flow rate of 0.80 mL/min. The average retention times of the nicotine enantiomer pairs ranged from 7.64 and 8.34 min to 13.47 and 14.97 min, with the S(−) enantiomer eluting first. As expected, faster flow rates of 1.0 mL/min reduced retention times by approximately 1–2 min, with a slight decrease in the <i>R</i> values. The %RSD values for both resolution and retention times consistently remained below 2%. The detection limits for the enantiomers were approximately 5 μg/mL. The optimized method successfully detected one part in 100 for the minor R(+) enantiomer in the presence of the dominate S(−) enantiomer and adhered to all established QuEChERS method protocols.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11771616/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143045724","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-23 DOI: 10.1002/chir.70013
Sevgi Sarigul Ozbek, Senel Teke Tuncel, Sule Erol Gunal, Ilknur Dogan
{"title":"Enantiodifferentiation of Thiohydantoin Derivatives by NMR in the Presence of Chiral Solvating Agent: (1R,2S)-Ephedrine and Chiral Symmetrical and Unsymmetrical Thioureas","authors":"Sevgi Sarigul Ozbek,&nbsp;Senel Teke Tuncel,&nbsp;Sule Erol Gunal,&nbsp;Ilknur Dogan","doi":"10.1002/chir.70013","DOIUrl":"10.1002/chir.70013","url":null,"abstract":"<div>\u0000 \u0000 <p>2-Thiohydantoin derivatives, including different substitutions at N-1 and C-5 (5-methyl-, 5-isopropyl-, 1-acetyl-5-methyl-, and 1-acetyl-5-isopropyl-) (<b>1–4</b>, respectively), were synthesized by the known literature methods. In these synthetic pathways, it was reported that enantiomerically pure 2-thiohydantions were obtained in the absence of any solvent via the reaction of <i>L</i>-amino acids with thiourea (<b>1&amp;2</b>) and via the reaction of <i>L</i>-amino acids with NH<sub>4</sub>SCN and acetic anhydride (<b>3&amp;4</b>). However, in this study, in contrary to the previous literature studies, racemic mixtures of 2-thiohydantoins were obtained although the same synthetic methods were used. The racemic nature of 2-thiohydantoin derivatives (<b>1–4</b>) was proved by using <sup>1</sup>H NMR analysis in the presence of (1<i>R</i>,2<i>S</i>)-(−)-ephedrine as a chiral auxiliary. In addition, the enantiomers of <b>3&amp;4</b> were also resolved on chiral stationary phases by HPLC analyses. Furthermore, newly synthesized unsymmetrical chiral thioureas (<b><i>S</i>-1&amp;<i>S</i>-2</b>) and previously synthesized symmetrical ones (<b><i>SS</i>-3&amp;<i>SS</i>-4</b>) were used as chiral solvating agent (CSA) for the enantiodiscrimination of the thiohydantoins (<b>5&amp;6</b>), previously reported. Optimal CSA/substrate ratios were determined for the best enantiodiscrimination.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143021639","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Optimizing Enantiomeric Resolution of Chiral Triazoles in Supercritical Fluid Chromatography
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-23 DOI: 10.1002/chir.70016
Codruţa Frîncul, Alina Ghinet, Dalila Belei, Bezhan Chankvetadze, Sergiu Shova, Emmanuelle Lipka, Anca-Elena Dascălu
{"title":"Optimizing Enantiomeric Resolution of Chiral Triazoles in Supercritical Fluid Chromatography","authors":"Codruţa Frîncul,&nbsp;Alina Ghinet,&nbsp;Dalila Belei,&nbsp;Bezhan Chankvetadze,&nbsp;Sergiu Shova,&nbsp;Emmanuelle Lipka,&nbsp;Anca-Elena Dascălu","doi":"10.1002/chir.70016","DOIUrl":"10.1002/chir.70016","url":null,"abstract":"<div>\u0000 \u0000 <p>Chirality plays a crucial role in the pharmacological activity of triazoles, a key scaffold in antifungal agents and various therapeutic applications. This study focuses on optimizing the enantiomeric resolution of chiral triazoles using supercritical fluid chromatography (SFC) and 10 different columns, either immobilized or coated, chlorinated or nonchlorinated, cellulose or amylose-based chiral stationary phases (CSPs). Four novel triazoles and two marketed ones (tebuconazole and hexaconazole) were separated to determine optimal resolution conditions. The best resolution was achieved using chlorinated amylose-based CSPs across the tested compounds. Optical rotation and X-ray crystallography were employed to determine the absolute configurations of the purified enantiomers.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143022129","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Controlling Sign and Magnitude of Circularly Polarized Luminescence of Axially Chiral Schiff-Base Boron Difluoride Complexes Bearing Polyethylene Glycol Chains 含聚乙二醇链的轴向手性席夫碱二氟化硼配合物圆偏振发光的控制符号和大小。
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-14 DOI: 10.1002/chir.70014
Masahiro Ikeshita, Miku Ichinose, Daiya Suzuki, Jungo Ono, Yoshitane Imai, Takashi Tsuno
{"title":"Controlling Sign and Magnitude of Circularly Polarized Luminescence of Axially Chiral Schiff-Base Boron Difluoride Complexes Bearing Polyethylene Glycol Chains","authors":"Masahiro Ikeshita,&nbsp;Miku Ichinose,&nbsp;Daiya Suzuki,&nbsp;Jungo Ono,&nbsp;Yoshitane Imai,&nbsp;Takashi Tsuno","doi":"10.1002/chir.70014","DOIUrl":"10.1002/chir.70014","url":null,"abstract":"<div>\u0000 \u0000 <p>The synthesis, structure, and circularly polarized luminescence (CPL) properties of axially chiral boron difluoride complexes are described. A series of optically pure bis (boron difluoride) complexes were prepared in 5 steps from commercially available (<i>S</i>)- or (<i>R</i>)-BINOL as starting materials. The complexes were found to exhibit similar yellow photoluminescence in solution, regardless of the type of substituents on the nitrogen atoms. Notably, for the complex with polyethylene glycol chains, homogeneous and transparent films were formed by the drop-cast method, showing intense CPL with a different sign from that of the solution state. Density functional theory (DFT) calculations were performed to understand their photophysical behavior including configuration-dependent CPL properties.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142977632","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Proceedings From 19th International Conference on Chiroptical Spectroscopy, Hiroshima, Japan 第十九届国际光谱学会议论文集，日本广岛。
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-14 DOI: 10.1002/chir.70015
Koichi Matsuo, Tatsuo Nehira, Nina Berova, Gennaro Pescitelli, Oliver Trapp, Simona Collina
{"title":"Proceedings From 19th International Conference on Chiroptical Spectroscopy, Hiroshima, Japan","authors":"Koichi Matsuo,&nbsp;Tatsuo Nehira,&nbsp;Nina Berova,&nbsp;Gennaro Pescitelli,&nbsp;Oliver Trapp,&nbsp;Simona Collina","doi":"10.1002/chir.70015","DOIUrl":"10.1002/chir.70015","url":null,"abstract":"","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142977635","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Construction of a Vibrational Circular Dichroism Instrument Equipped With a Thermoelectrically Cooled Detector for Prolonged Measurements 带热电冷却探测器的振动圆二色仪的研制。
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-14 DOI: 10.1002/chir.70019
Hisako Sato, Masaru Shimizu, Keisuke Watanabe, Jun Koshoubu
{"title":"Construction of a Vibrational Circular Dichroism Instrument Equipped With a Thermoelectrically Cooled Detector for Prolonged Measurements","authors":"Hisako Sato,&nbsp;Masaru Shimizu,&nbsp;Keisuke Watanabe,&nbsp;Jun Koshoubu","doi":"10.1002/chir.70019","DOIUrl":"10.1002/chir.70019","url":null,"abstract":"<div>\u0000 \u0000 <p>A vibrational circular dichroism (VCD) instrument having a thermoelectrically cooled detector (denoted as a TEC unit) was constructed in this study. An electronic device, instead of liquid nitrogen, was employed in the instrument to cool the detector. The feasibility of the system was examined by recording the VCD spectra of liquid pinenes and insect wings. VCD signals were obtained at a constant baseline that was stable for more than 40 h. The spectrometer equipped with a TEC unit exhibited potential for performing measurements for prolonged time periods.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142977628","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enantioselective Degradation and Processing Factors of Seven Chiral Pesticides During the Processing of Wine and Rice Wine 7种手性农药在酒和黄酒加工过程中的对映选择性降解及加工因素
IF 2.8 4区 化学
Chirality Pub Date : 2025-01-12 DOI: 10.1002/chir.70018
Yuting Tan, Nuanhui Wen, Zhiqiang Lu, Wenjie Wei, Haiyan Shi, Minghua Wang
{"title":"Enantioselective Degradation and Processing Factors of Seven Chiral Pesticides During the Processing of Wine and Rice Wine","authors":"Yuting Tan,&nbsp;Nuanhui Wen,&nbsp;Zhiqiang Lu,&nbsp;Wenjie Wei,&nbsp;Haiyan Shi,&nbsp;Minghua Wang","doi":"10.1002/chir.70018","DOIUrl":"10.1002/chir.70018","url":null,"abstract":"<div>\u0000 \u0000 <p>Chiral pesticides often undergo enantioselective degradation during food fermentation. In this study, the enantioselective fates of seven chiral pesticides during processing of wine and rice wine were investigated. The results revealed that <i>R</i>-metalaxyl, <i>R</i>-mefentrifluconazole and <i>S</i>-hexaconazole were preferentially degraded during wine processing with EF values of 0.57, 0.78, and 0.43, respectively, whereas <i>S</i>-metalaxyl and <i>R</i>-hexaconazole were preferentially degraded during rice wine processing with EF values of 0.44 and 0.54, respectively. Stereoselectivity was attributed to fermentative bacterial activity. The processing factor (PF) values for the five pesticides ranged from 0.04 to 0.34 during wine processing and from 0.02 to 0.29 during rice wine processing, suggesting that fermentation can mitigate pesticide exposure risks and ensure food safety. This study enhances our understanding of enantioselective fate of chiral pesticides during fermented food processing, provides guidance for the application of chiral pesticides, and enables the dietary risk of chiral pesticides in processed products to be assessed more accurately.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142969866","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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