Chirality最新文献

Exploring Naproxen Cocrystals Through Solid-State Vibrational Circular Dichroism

IF 2.8 4区化学

Chirality Pub Date : 2025-02-17 DOI: 10.1002/chir.70027

Adam Sklenář, Anne Zehnacker-Rentien, Jakub Kaminský, Jan Rohlíček, Petr Bouř

{"title":"Exploring Naproxen Cocrystals Through Solid-State Vibrational Circular Dichroism","authors":"Adam Sklenář, Anne Zehnacker-Rentien, Jakub Kaminský, Jan Rohlíček, Petr Bouř","doi":"10.1002/chir.70027","DOIUrl":"https://doi.org/10.1002/chir.70027","url":null,"abstract":"Vibrational circular dichroism (VCD) spectroscopy appears as a useful method for characterizing optically active substances in the solid state. This is particularly important for active pharmaceutical ingredients. However, measurement and interpretation of the spectra bring about many difficulties. To assess the experimental and computational methodologies, we explore an anti-inflammatory drug, naproxen. Infrared (IR) and VCD spectra of the pure compound and its cocrystals with alanine and proline were recorded, and the data were interpreted by quantum chemical simulations based on a cluster model and density functional theory. Although unpolarized IR spectroscopy can already distinguish pure ingredients from cocrystals or a mixture, the VCD technique is much more sensitive. For example, the naproxen carboxyl group strongly interacts with the zwitterionic alanine in the cocrystal via two strong hydrogen bonds, which results in a rather rigid structure crystallizing in the chiral P212121 Sohncke group and its VCD is relatively strong. In contrast, the d-proline and (S)-naproxen cocrystal (P21 group) involves a single hydrogen bond between the subunits, which together with a limited motion of the proline ring gives a weaker signal. Solid-state VCD spectroscopy thus appears useful for exploring composite crystal structures and interactions within them, including studies of pharmaceutical compounds.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70027","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143431509","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

A Novel, Simple, Isocratic HPLC-UV Method for Determination of Chiral Purity for Dibenzoyl-L-Tartaric Acid (L-DBTA)

IF 2.8 4区化学

Chirality Pub Date : 2025-02-17 DOI: 10.1002/chir.70028

Pradeep Kumar Gollapudi, Padmaja Nimmagadda, Kranthi Kumar Gollapudi

{"title":"A Novel, Simple, Isocratic HPLC-UV Method for Determination of Chiral Purity for Dibenzoyl-L-Tartaric Acid (L-DBTA)","authors":"Pradeep Kumar Gollapudi, Padmaja Nimmagadda, Kranthi Kumar Gollapudi","doi":"10.1002/chir.70028","DOIUrl":"https://doi.org/10.1002/chir.70028","url":null,"abstract":"<div>\u0000 \u0000 Dibenzoyl-L-tartaric acid (L-DBTA) is a crucial compound in the synthesis of chiral molecules, particularly within the pharmaceutical industry. Ensuring the enantiomeric purity of L-DBTA is essential for regulatory compliance, quality control, and process optimization. To achieve this, a high-performance liquid chromatography (HPLC) method was developed and validated for determining the D-DBTA content in L-DBTA. The method validation adhered to ICH Q2(R2) guidelines, covering parameters such as system suitability, solution stability, robustness, linearity, range, limit of detection (LOD), limit of quantification (LOQ), accuracy, and precision. HPLC separation was performed using a Chiral PAK IA column (250 × 4.6 mm, 5.0 μm) with an isocratic mobile phase consisting of n-heptane, isopropanol (IPA), and trifluoroacetic acid (900:100:1 v/v/v). The column temperature was maintained at 40°C, and the sample cooler was kept at ambient conditions. Detection was carried out at 230 nm, achieving a resolution greater than 1.5 between L-DBTA and D-DBTA. The method demonstrated excellent linearity over a range of 30%–200% of the specification limit, with accuracy and range established from the LOQ level to 200%. Solution stability was confirmed for 1 day at room temperature, and precision was validated at both the LOQ and 100% levels. All validation parameters met the acceptance criteria, confirming the method's suitability for routine testing and batch release at quality control sites. This HPLC method is both sensitive and selective, ensuring the reliable determination of chiral purity in L-DBTA and its impurities.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143423817","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

Development of Acid-Functionalized Molecularly Imprinted Phenolic Resin for Chiral Recognition of S-Venlafaxine

IF 2.8 4区化学

Chirality Pub Date : 2025-02-17 DOI: 10.1002/chir.70023

Rua B. Alnoman

{"title":"Development of Acid-Functionalized Molecularly Imprinted Phenolic Resin for Chiral Recognition of S-Venlafaxine","authors":"Rua B. Alnoman","doi":"10.1002/chir.70023","DOIUrl":"https://doi.org/10.1002/chir.70023","url":null,"abstract":"<div>\u0000 \u0000 This article reports the synthesis of a molecularly imprinted phenolic formaldehyde resin for the selective recognition of the cationic S-enantiomer of venlafaxine. The resin was developed through the condensation polymerization of p-hydroxybenzoic acid (4-HBA) and 4-nitrophenol (4-NP) with formaldehyde in an acidic medium. The resultant polymer was reduced to introduce amino groups into the polymer to obtain a dual-functional resin with amino and carboxylic groups (CA-P). After the uptake of S-VF, glutaraldehyde cross-linking stabilized the resin and formed its enantioselective cavities. Adsorption studies showed that optimum conditions occurred at pH 7, whereas the maximum adsorption capacity was 420 mg/g according to the Langmuir isotherm. The selectivity coefficient of S-VF-IP was 13 times that of NIP, confirming that the imprinting process indeed occurred. Chiral separation experiments using the SV-imprinted polymer (S-VF-IP) column resulted in 98% enantiomeric excess for R-VF, whereas the respective NIP did not provide any enantioselectivity. These results show a great possibility of the developed resin in efficient enantioselective separation and offer a promising method for the purification of chiral drugs from racemic mixtures in pharmaceutical applications.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 3","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143431510","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 (Im)possible Interplays Between Natural and Magnetic Optical Activity in Chiral Samples

IF 2.8 4区化学

Chirality Pub Date : 2025-02-13 DOI: 10.1002/chir.70024

Francesco Zinna

引用次数: 0

Chirooptical 2,2′-Dimethoxybiphenyl Crystals Generated From Suzuki–Miyaura Coupling Reaction Catalyzed by Pd-Loaded Chiral Silica

IF 2.8 4区化学

Chirality Pub Date : 2025-02-11 DOI: 10.1002/chir.70026

Shunpei Yoshimori, Ren-Hua Jin

{"title":"Chirooptical 2,2′-Dimethoxybiphenyl Crystals Generated From Suzuki–Miyaura Coupling Reaction Catalyzed by Pd-Loaded Chiral Silica","authors":"Shunpei Yoshimori, Ren-Hua Jin","doi":"10.1002/chir.70026","DOIUrl":"https://doi.org/10.1002/chir.70026","url":null,"abstract":"In this work, we report a one-pot approach that combines crystal ripening with the Suzuki–Miyaura coupling reaction. We investigated the reaction between 2-methoxyphenyl bromide and 2-methoxyphenylboronic acid, catalyzed by a series of Pd-loaded chiral optical (D- or L-) and racemic (DL-) silica/polyethyleneimine (PEI) systems, which produced crystalline 2,2′-dimethoxybiphenyl (DMB). The silica used as a catalyst was prepared using our previously established method, in which chirality was imparted to the silica through catalytic templates composed of polyethyleneimine (PEI) and tartaric acid. Both enantiopure (D- or L-; 100% ee) and racemic (DL-; 0% ee) tartaric acid-mediated silica, after tartaric acid removal and palladium (Pd) loading, exhibited similar catalytic activities, leading to the quantitative precipitation of 2,2′-dimethoxybiphenyl in a water/ethanol (1:1 by volume) medium. Interestingly, the 2,2′-dimethoxybiphenyl crystals formed and ripened in the presence of Pd-loaded chiral D- and L-silica/PEI exhibited octahedral morphology and displayed remarkable chiroptical activity with a mirror-image relationship. This represents a novel example of using chiral Pd-loaded silica to synthesize axially chiral biphenyl in crystalline form.","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.70026","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389141","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

Voltammetric Sensor for Naproxen Enantiomers Based on a Paste Electrode Modified With a Chiral Nickel(II) Complex

IF 2.8 4区化学

Chirality Pub Date : 2025-02-10 DOI: 10.1002/chir.70025

Rufina A. Zilberg, Julia B. Teres, Ivan V. Vakulin, Elena O. Bulysheva, Genghiskhan R. Mukhametdinov, Maria A. Sycheva, Anastasia А. Volkova, Aleksei A. Titov, Victor I. Maleev, Vladimir A. Larionov

{"title":"Voltammetric Sensor for Naproxen Enantiomers Based on a Paste Electrode Modified With a Chiral Nickel(II) Complex","authors":"Rufina A. Zilberg, Julia B. Teres, Ivan V. Vakulin, Elena O. Bulysheva, Genghiskhan R. Mukhametdinov, Maria A. Sycheva, Anastasia А. Volkova, Aleksei A. Titov, Victor I. Maleev, Vladimir A. Larionov","doi":"10.1002/chir.70025","DOIUrl":"https://doi.org/10.1002/chir.70025","url":null,"abstract":"<div>\u0000 \u0000 An enantioselective voltammetric sensor (EVS) comprising a paste electrode made of graphitized thermal Carboblack C (CBPE) modified with a Ni(II) complex based on (S)-(2-aminomethyl)pyrrolidine and 3,5-di-tert-butylsalicylaldehyde was developed for the recognition and determination of naproxen (Nap) enantiomers. The proposed sensor was characterized by scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDS-SEM), Fourier-transform infrared spectroscopy (FT-IR), molecular dynamics and quantum chemical simulations, electrochemical impedance spectroscopy (EIS), and cyclic voltammetry (CV) methods. Using the differential pulse voltammetry (DPV), the CBPE@(S)-Ni sensor was found to have good selectivity for Nap enantiomers (ip1S/ip1R = 1.43, ip2S/ip2R = 1.27 for the first/second peaks, respectively). The sensor demonstrates the highest sensitivity to (S)-Nap (6.44 and 6.90 μA/mM for the first and second peaks). The linear concentration range is from 5.0 × 10−5 to 1 × 10−3 M and from 2.0 × 10−4 to 1 × 10−3 M for (S)- and (R)-Nap, respectively, where the detection limits for the first and second peaks are 5.31 × 10−7 M and 4.96 × 10−7 M for (S)-Nap and 7.40 × 10−7 and 6.79 × 10−7 for (R)-Nap. The suggested sensor was successfully tested for the determination of Nap enantiomers in mixtures, in biological fluids, and in medicinal drug forms. In all the cases, the relative standard deviation (RSD) does not exceed 4.7%; the recovery percentage is in the range of 99.2%–101.3%.\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"37 2","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143380300","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

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, Sharath Babu Haridasyam, Narasimha S. Lakka, Chandrasekar Kuppan, Poornima Ravinathan, Sanjeeva R. Chinnakadoori","doi":"10.1002/chir.70017","DOIUrl":"https://doi.org/10.1002/chir.70017","url":null,"abstract":"<div>\u0000 \u0000 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.\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, Anuruddha Rajaram Chabukswar, Kunal Ganesh Raut, Pooja Tanaji Giri","doi":"10.1002/chir.70021","DOIUrl":"10.1002/chir.70021","url":null,"abstract":"<div>\u0000 \u0000 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.\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

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, William M. Coleman III, Weston J. Umstead","doi":"10.1002/chir.70020","DOIUrl":"10.1002/chir.70020","url":null,"abstract":"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 (R) 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 R 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.","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