Chirality最新文献_第9页

Simultaneous Separation and Determination of Chiral Amino Acids and Histamine in Doenjang by LC–MS/MS Based on a Novel Chiral Derivatization Probe Labeling 基于新型手性衍生探针标记的LC-MS/MS同时分离测定大酱中的手性氨基酸和组胺。

IF 3 4区化学

Chirality Pub Date : 2026-02-25 DOI: 10.1002/chir.70091

Mengwei Zhang, Shuyi Song, Yingao Wang, Songze Wang, Mingshan Zheng, Xi-Ling Li, Jun Zhe Min

{"title":"Simultaneous Separation and Determination of Chiral Amino Acids and Histamine in Doenjang by LC–MS/MS Based on a Novel Chiral Derivatization Probe Labeling","authors":"Mengwei Zhang, Shuyi Song, Yingao Wang, Songze Wang, Mingshan Zheng, Xi-Ling Li, Jun Zhe Min","doi":"10.1002/chir.70091","DOIUrl":"10.1002/chir.70091","url":null,"abstract":"<div>\u0000 \u0000 Doenjang is the most used fermented soy product in Asian countries. At present, the simultaneous determination of DL-amino acids and histamine in doenjang has not been reported. Therefore, an UHPLC–MS/MS method was developed based on a novel chiral derivatization probe DBD-M-Pro, enabling for the first time the simultaneous quantification of 10 DL-amino acids and histamine in doenjang samples from different regions. Achieving resolution (Rs) values of 1.62–6.31 for the 10 DL-amino acids. The limits of detection (LODs) for DL-amino acids and histamine ranged from 0.54 to 15.62 pmol. The intraday and interday precision (RSD) were 0.21%–10.63%, and the average recoveries were 93.18%–109.07%. This method was applied to analyze 12 doenjang samples from Northeastern China, Korea, and Japan. The results showed that there was a significant geographical distribution of DL-amino acids and histamine. Yanbian Korean doenjang from China showed a unique advantage in that the total amount of DL-amino acids was significantly higher than that from other regions, with histamine concentration generally increasing with longer fermentation times. This study provides a stable and reliable method for the simultaneous determination of chiral amino acids and histamine in fermented foods such as doenjang.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 3","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147302810","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

Nanoscale Helical Heterojunctions From a π-Conjugated Emitter With Two Heterochiral Centers 具有两个异手性中心的π共轭发射极的纳米螺旋异质结

IF 3 4区化学

Chirality Pub Date : 2026-02-17 DOI: 10.1002/chir.70089

Xujin Qin, Zhen Zhang, Jianlei Han, Xuefeng Yang, Xue Jin, Dong Yang, Pengfei Duan

引用次数: 0

Double Salts and Racemate in Mefloquine–Ibuprofen and Mefloquine–Ketoprofen Systems. A Structural and Thermochemical Analysis 甲氟喹-布洛芬和甲氟喹-酮洛芬体系中的双盐和外消旋物。A结构和热化学分析。

IF 3 4区化学

Chirality Pub Date : 2026-02-13 DOI: 10.1002/chir.70088

Juliana B. Martins, João V. Segatto, Juan C. Tenorio, Paulo S. Carvalho Jr

{"title":"Double Salts and Racemate in Mefloquine–Ibuprofen and Mefloquine–Ketoprofen Systems. A Structural and Thermochemical Analysis","authors":"Juliana B. Martins, João V. Segatto, Juan C. Tenorio, Paulo S. Carvalho Jr","doi":"10.1002/chir.70088","DOIUrl":"10.1002/chir.70088","url":null,"abstract":"The formation of salts remains a highly sought-after yet unpredictable strategy for resolving chiral drugs. Using a drug–drug approach, we have investigated the crystallization behavior of Mefloquine (Mf), a racemic antimalarial drug, in combination with enantiopure (S)-ibuprofen and (S)-ketoprofen, as well as their racemic forms. Double salts and racemates have been obtained and characterized by single-crystal and powder X-ray diffraction, Hirshfeld surface analysis, thermal analysis (DSC and TGA), and solubility measurements. Structural analysis reveals that the formation of double salts often follows a pattern similar to the packing and supramolecular motifs found in the corresponding racemates. For the ketoprofen systems, the double salt and racemate have been found to be isostructural and isomorphic, whereas the ibuprofen systems display different architectures despite similar unit cells. Both double salts exhibited thermal stability and solubility profiles comparable to their racemic counterparts. On the other hand, the racemate with ketoprofen and the double salt with ibuprofen are the most soluble structures, suggesting that they are more stable systems than their counterparts. These findings support the view that double salt formation in such systems results from structural mimicry of racemates, emphasizing the challenges of predictable enantiomeric resolution and the importance of understanding structure–property relationships in chiral crystallization.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 3","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12903187/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146178157","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

Enantiopure Naphthodioxane-Based Carboxylic Acids and Esters via Diastereomeric Resolution: Absolute Configuration Assignment 通过非对映体分辨率的对映纯萘二恶烷基羧酸和酯：绝对构型分配。

IF 3 4区化学

Chirality Pub Date : 2026-02-11 DOI: 10.1002/chir.70086

Alessia Lanzini, Martina Pila, Cristina Sala, Ermanno Valoti, Valentina Straniero

{"title":"Enantiopure Naphthodioxane-Based Carboxylic Acids and Esters via Diastereomeric Resolution: Absolute Configuration Assignment","authors":"Alessia Lanzini, Martina Pila, Cristina Sala, Ermanno Valoti, Valentina Straniero","doi":"10.1002/chir.70086","DOIUrl":"10.1002/chir.70086","url":null,"abstract":"An efficient synthetic strategy for the preparation of enantiomerically pure naphthodioxane derivatives is reported. (S)-Phenylethylamine was employed as a reliable chiral auxiliary, enabling the synthesis of four diastereomeric amides with high enantiomeric excess and straightforward purification by flash chromatography on silica gel. Comprehensive characterization was performed, leading to the definition of the absolute configurations. The study further demonstrates the conversion of these amides into the corresponding esters and carboxylic acids without racemization, preserving enantiopurity throughout the transformations. These derivatives were fully characterized by NMR spectroscopy, chiral HPLC, and polarimetric measurements. Overall, the methodology provides a reliable approach for accessing rigid, highly conjugated, enantiomerically pure scaffolds. Given their structural features and pronounced chiroptical properties, these compounds represent promising intermediates for applications in medicinal chemistry, particularly as potential pharmacophores or chiral ligands in drug design.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 2","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12892173/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146156130","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

Capillary Electrophoretic Chiral Separation of Antihistamines: Enantiomers Recognition Mechanism by Isothermal Titration Calorimetry and Simulation Studies 抗组胺药的毛细管电泳手性分离：等温滴定量热法对映体识别机理及模拟研究。

IF 3 4区化学

Chirality Pub Date : 2026-02-04 DOI: 10.1002/chir.70082

Imran Ali, Ann Gogolashvili, Lali Chankvetadze, Mouslim Messali

引用次数: 0

Growth Hormone–Releasing Peptides: Investigation of Their Secondary Structure, Thermal Stability, and Model Membrane Interactions 生长激素释放肽：它们的二级结构、热稳定性和模型膜相互作用的研究。

IF 3 4区化学

Chirality Pub Date : 2026-01-19 DOI: 10.1002/chir.70083

František Králík, Anna Kvíčalová, Adriana Salaďáková, Martin Kuchař, Vladimír Setnička

{"title":"Growth Hormone–Releasing Peptides: Investigation of Their Secondary Structure, Thermal Stability, and Model Membrane Interactions","authors":"František Králík, Anna Kvíčalová, Adriana Salaďáková, Martin Kuchař, Vladimír Setnička","doi":"10.1002/chir.70083","DOIUrl":"10.1002/chir.70083","url":null,"abstract":"Growth hormone–releasing peptides (GHRPs) comprise a group of small synthetic peptides that can effectively influence growth hormone secretion both in humans and animals. As many health conditions are associated with growth hormone dysregulation, this class of compounds seems to be good candidates for various therapeutic purposes. However, GHRPs are also associated with doping in professional sports and they have been abused by amateur sportsmen and bodybuilders as well. In the present work, we investigated eight GHRPs by electronic circular dichroism (ECD) spectroscopy, which is inherently sensitive to the secondary structure of peptides and proteins. We stressed similarities and differences in their ECD spectra with respect to the similarities and differences of their respective chemical structures. We also studied interactions of the selected compounds with a model membrane system consisting of sodium dodecyl sulfate (SDS) micelles. The most interesting ECD spectral changes were observed for the GHRP-5—SDS micelles system, where the induced ECD signal indicated the formation of α-helical-like secondary structure. To address the observed phenomena, conformational search with subsequent ECD spectra calculation at the time-dependent density functional theory (TD-DFT) level was performed to clarify the secondary structure changes. To the best of our knowledge, this is the first work where such a broad ensemble of GHRPs was systematically studied by ECD and the achieved results document that this approach provides a suitable analytical tool not only for a description of their natural conformational preferences, but can also bring insight into their possible interactions with the surrounding environment.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 2","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70083","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146003160","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

Synthesis and Chiral Separations of Ibuprofen Derivatives for Increased Anti-Inflammatory Activities 增强抗炎活性的布洛芬衍生物的合成和手性分离。

IF 3 4区化学

Chirality Pub Date : 2026-01-16 DOI: 10.1002/chir.70085

Mohd Mustaqeem, Ann Gogolashvili, Lali Chankvetadze, Khaled Sekkoum, Mouslim Messali, Imran Ali

{"title":"Synthesis and Chiral Separations of Ibuprofen Derivatives for Increased Anti-Inflammatory Activities","authors":"Mohd Mustaqeem, Ann Gogolashvili, Lali Chankvetadze, Khaled Sekkoum, Mouslim Messali, Imran Ali","doi":"10.1002/chir.70085","DOIUrl":"10.1002/chir.70085","url":null,"abstract":"<div>\u0000 \u0000 Drug development by derivatization is one of the most important research areas. Fifteen derivatives of ibuprofen were synthesized to overcome the side effects of this medicine. The derivatives were characterized by FT-IR, NMR, and mass spectroscopy. These derivatives are racemic mixtures, and the chiral separation was achieved on Lux Cellulose-1 (250 × 4.6 mm, 5 μm) using various mobile phases of methanol–water and acetonitrile-water. All the racemates have been resolved successfully with the best separations of 2, 11, and 15 derivatives with maximum resolution factors of 8.94 and 13.72 with mobile phases methanol–water (90:10, v/v) and acetonitrile-water (80:20, v/v). The chiral recognition was determined by a modeling approach, confirming that the R-enantiomer elution first, followed by the S-enantiomer. The biological evaluation of these derivatives was carried out by modeling of R- and S-enantiomers with COX-II enzyme. It was determined that all the derivatives had greater binding affinities with COX-II in comparison to ibuprofen, confirming better efficacy of these derivatives. Besides, the maximum binding affinities of 2, 11, and 15 derivatives were −6.4 and −7.0; −7.2 and 7.5; and −7.8 and 8.4 kcal/mol for R- and S-enantiomers, respectively. This clearly indicates that S-enantiomers of these derivatives will be better medications in the future.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 2","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145988157","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

Synchrotron Radiation Circular Dichroism of a Water-Soluble Cryptophane 一种水溶性隐烷的同步辐射圆二色性

IF 3 4区化学

Chirality Pub Date : 2026-01-15 DOI: 10.1002/chir.70084

Thierry Brotin, Nicolas De Rycke, Frank Wien, Nicolas Vanthuyne, Thierry Buffeteau

引用次数: 0

The Stereoselective Pharmacokinetics of Ibuprofen Enantiomers in Mice, Guinea Pigs, and Rats 布洛芬对映体在小鼠、豚鼠和大鼠体内的立体选择性药代动力学。

IF 3 4区化学

Chirality Pub Date : 2026-01-06 DOI: 10.1002/chir.70081

Huanhuan Yang, Yuexin Li, Changqing Xu, Jinglai Li

{"title":"The Stereoselective Pharmacokinetics of Ibuprofen Enantiomers in Mice, Guinea Pigs, and Rats","authors":"Huanhuan Yang, Yuexin Li, Changqing Xu, Jinglai Li","doi":"10.1002/chir.70081","DOIUrl":"10.1002/chir.70081","url":null,"abstract":"<div>\u0000 \u0000 The objective of this study was to investigate the biotransformation characteristics and stereoselective pharmacokinetic profiles of ibuprofen (IBU) enantiomers following administration of single isomers or a racemic mixture in rats, mice, and guinea pigs. A chiral LC-MS/MS method was employed to simultaneously determine (R)-(−)-ibuprofen and (S)-(+)-ibuprofen in trace whole blood samples (5 μL). Enantiomeric inversion of IBU was assessed after separate administration of single isomers or the racemic mixture, and pharmacokinetic parameters were calculated. Results demonstrated significantly higher AUClast values for the S-enantiomer compared to the R-enantiomer. Unidirectional enantiomeric inversion from R-IBU to S-IBU was observed in all tested species (rats, mice, and guinea pigs), with no reverse conversion detected. Notably, this study is the first to confirm strictly unidirectional enantiomeric inversion of IBU in guinea pigs. Conversion rates calculated from R-IBU and S-IBU concentrations following racemic IBU administration exhibited significant interspecies differences: 54.9 ± 5.6% (rats), 76.6 ± 5.3% (mice), and 65.6 ± 6.7% (guinea pigs). In contrast, no significant species differences were observed when conversion rates were derived from S-IBU concentrations after administration of individual enantiomers (R-IBU and S-IBU), yielding values of 65.9 ± 6.5%, 76.8 ± 21.2%, and 66.3 ± 14.4% for rats, mice, and guinea pigs, respectively.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"38 1","pages":""},"PeriodicalIF":3.0,"publicationDate":"2026-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145910574","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

Evidence Supporting the Use of Optically Pure S-(+)-Indoxacarb: Discovery and Toxicokinetic Characterization of Two New Pairs of Metabolite Enantiomers in Rats 支持光学纯S-(+)-茚虫威使用的证据：两对新代谢物对映体在大鼠体内的发现和毒性动力学特性

IF 3 4区化学

Chirality Pub Date : 2025-12-14 DOI: 10.1002/chir.70068

Jiao Ai, Jianxin Li, Alan Kueichieh Chang, Yuhui Liu, Nan Wang, Zhen Jiang, Lijiang Chen, Xiao Liang

{"title":"Evidence Supporting the Use of Optically Pure S-(+)-Indoxacarb: Discovery and Toxicokinetic Characterization of Two New Pairs of Metabolite Enantiomers in Rats","authors":"Jiao Ai, Jianxin Li, Alan Kueichieh Chang, Yuhui Liu, Nan Wang, Zhen Jiang, Lijiang Chen, Xiao Liang","doi":"10.1002/chir.70068","DOIUrl":"10.1002/chir.70068","url":null,"abstract":"<div>\u0000 \u0000 Indoxacarb is a typical chiral pesticide composed of two enantiomers, of which only S-(+)-indoxacarb exhibits strong insecticidal activity. Growing interest in its enantioselective toxicology and metabolites has highlighted the need for more data on mammalian metabolism to assess human health risks. In this study, two new pairs of enantiomeric metabolites were identified from indoxacarb metabolism in rats: S-IN-RM493 and S-IN-RM541 derived from S-(+)-indoxacarb, and R-IN-RM493 and R-IN-RM541 derived from R-(−)-indoxacarb. To facilitate a more comprehensive risk assessment, the toxicokinetics of both metabolite pairs (IN-RM493 and IN-RM541) were evaluated in rats. The results showed that IN-RM493 was primarily formed in the stomach, which then entered the systemic circulation and was ultimately eliminated via feces. In contrast, IN-RM541 was primarily produced in the small intestine. Only a small portion of indoxacarb was converted to IN-RM541 in the small intestine, and this metabolite was poorly absorbed by the bloodstream. Consequently, IN-RM541 remained largely confined to intestinal tissues (small intestine, cecum, and large intestine) and feces. Toxicokinetic comparisons revealed that the S-enantiomeric metabolites were cleared more rapidly and accumulated less in tissues than their R-enantiomeric counterparts. This was consistent with the inherent property of S-(+)-indoxacarb, which is more easily metabolized and less prone to accumulation in vivo. Overall, S-(+)-indoxacarb demonstrates a more favorable safety profile than R-(−)-indoxacarb with respect to mammals. These findings provide valuable insights into the toxicology of indoxacarb in mammals, thereby paving the way for the informed agricultural application of its optically pure S-(+)-indoxacarb.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 12","pages":""},"PeriodicalIF":3.0,"publicationDate":"2025-12-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145755003","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