Chirality最新文献

{"title":"Expanding the Role of Chiral Drugs and Chiral Nanomaterials as a Potential Therapeutic Tool","authors":"Sourabh Satapathy,&nbsp;Shivam Kumar,&nbsp;Balak Das Kurmi,&nbsp;Ghanshyam Das Gupta,&nbsp;Preeti Patel","doi":"10.1002/chir.23698","DOIUrl":"10.1002/chir.23698","url":null,"abstract":"<div>\u0000 \u0000 <p>Chirality, the property of molecules having mirror-image forms, plays a crucial role in pharmaceutical and biomedical research. This review highlights its growing importance, emphasizing how chiral drugs and nanomaterials impact drug effectiveness, safety, and diagnostics. Chiral molecules serve as precise diagnostic tools, aiding in accurate disease detection through unique biomolecule interactions. The article extensively covers chiral drug applications in treating cardiovascular diseases, CNS disorders, local anesthesia, anti-inflammatories, antimicrobials, and anticancer drugs. Additionally, it explores the emerging field of chiral nanomaterials, highlighting their suitability for biomedical applications in diagnostics and therapeutics, enhancing medical treatments.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 7","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141497268","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}

{"title":"Induced Chirality in Sulfasalazine by Complexation With Albumins: Theoretical and Experimental Study","authors":"Giulia Saneti Grandini,&nbsp;Valdecir Farias Ximenes,&nbsp;Nelson Henrique Morgon,&nbsp;Aguinaldo Robinson de Souza","doi":"10.1002/chir.23696","DOIUrl":"10.1002/chir.23696","url":null,"abstract":"<p>Through molecular recognition, drugs can interact and complex with macromolecules circulating in the body. The serum albumin transport protein, found in several mammals, has several interaction sites where these molecules can be located. The drug sulfasalazine (SSZ) is known in the literature to complex at drug site 1 (DS1) in human serum (HSA) and bovine serum (BSA) proteins. This complexation can be studied using various spectroscopic techniques. With the techniques used in this work, absorption in the ultraviolet and visible regions (UV–Vis) and electronic circular dichroism (ECD), a significant difference was observed in the results involving HSA and BSA. The application of theoretical methodologies, such as TD-DFT and molecular docking, suggests that the conformation that SSZ assumes in DS1 of the two proteins is different, which exposes it to different amino acid residues and different hydrophobicities. This difference in conformation may be related to the location of DS1 where the drug interacts or to the possibility of SSZ moving in the BSA site, due to its larger size, and moving less freely in HSA.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 7","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141533747","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}

{"title":"Self-Assembled Chiral Film Based on Melanin Polymers","authors":"Massimiliano Gaeta,&nbsp;Gabriele Travagliante,&nbsp;Matteo Barcellona,&nbsp;Maria Elena Fragalà,&nbsp;Roberto Purrello,&nbsp;Alessandro D'Urso","doi":"10.1002/chir.23695","DOIUrl":"10.1002/chir.23695","url":null,"abstract":"<div>\u0000 \u0000 <p>Chirality plays a fundamental role in natural phenomena, yet its manifestation on solid surfaces remains relatively unexplored. In this study, we investigate the formation of chiroptical melanin-based self-assembled films on quartz substrates, leveraging mussel-inspired surface chemistry. Water-soluble porphyrins serve as molecular synthons, facilitating the spontaneous formation of hetero-aggregates in phosphate-buffered saline containing L- or D-DOPA. Spectroscopic analysis reveals chiral transfer from DOPA enantiomers to porphyrin hetero-aggregates, followed by the disruption of these latter and subsequent generation of chiral melanin structures in solution. Quartz substrates inserted into these solutions spontaneously accumulate homogeneous melanin-like films over days, demonstrating the feasibility of self-assembly. The resulting films exhibit characteristic UV/Vis and CD spectra, with distinct signals indicating successful chiral induction. Interestingly, the AFM characterizations reveal a distinct surface morphology, and in addition, some thermal and mechanical properties have been taken into account. Overall, this study sheds light on the formation, stability, and chiroptical properties of melanin-based films, paving the way for their application in various fields.</p>\u0000 </div>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 6","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141418121","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}

{"title":"Graph-theoretical chirality measure and chirality–property relations for chemical structures with multiscale mirror asymmetries","authors":"Minjeong Cha,&nbsp;Jessica Ma,&nbsp;Ji-Young Kim,&nbsp;Emine Sumeyra Turali Emre,&nbsp;Nicholas A. Kotov","doi":"10.1002/chir.23678","DOIUrl":"10.1002/chir.23678","url":null,"abstract":"<p>Chirality is an essential geometric property unifying small molecules, biological macromolecules, inorganic nanomaterials, biological microparticles, and many other chemical structures. Numerous chirality measures have attempted to quantify this geometric property of mirror asymmetry and to correlate these measures with physical and chemical properties. However, their utility has been widely limited because these correlations have been largely notional. Furthermore, chirality measures also require prohibitively demanding computations, especially for chiral structures comprised of thousands of atoms. Acknowledging the fundamental problems with quantification of mirror asymmetry, including the ambiguity of sign-variable pseudoscalar chirality measures, we revisit this subject because of the significance of quantifying chirality for quantitative biomimetics and describing the chirality of nanoscale materials that display chirality continuum and scale-dependent mirror asymmetry. We apply the concept of torsion within the framework of differential geometry to the graph theoretical representation of chiral molecules and nanostructures to address some of the fundamental problems and practical limitations of other chirality measures. Chiral gold clusters and other chiral structures are used as models to elaborate a graph-theoretical chirality (GTC) measure, demonstrating its applicability to chiral materials with different degrees of chirality at different scales. For specific cases, we show that GTC provides an adequate description of both the sign and magnitude of mirror asymmetry. The direct correlations with macroscopic properties, such as chiroptical spectra, are enhanced by using the hybrid chirality measures combining parameters from discrete mathematics and physics. Taking molecular helices as an example, we established a direct relation between GTC and optical activity, indicating that this chirality measure can be applied to chiral metamaterials and complex chiral constructs.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 6","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23678","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141300158","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}

{"title":"Determination of N-centered stereochemistry in N22-methylated chlorophyll-a derivatives and their epimer-dependent optical spectra","authors":"Riko Ataka,&nbsp;Tohru Taniguchi,&nbsp;Kenji Monde,&nbsp;Hitoshi Tamiaki","doi":"10.1002/chir.23681","DOIUrl":"10.1002/chir.23681","url":null,"abstract":"<p>An <i>N</i>-centered epimeric mixture of chlorophyll-<i>a</i> derivatives methylated at the inner nitrogen atom was separated by reverse-phase high-performance liquid chromatography. Circular dichroism (CD) spectroscopic analyses of the epimerically pure N22-methyl-chlorins revealed that the minor first-eluted and major second-eluted stereoisomers were (22<i>S</i>)- and (22<i>R</i>)-configurations, respectively. Their visible absorption and CD spectra in solution were dependent on the N22-stereochemistry. The epimer-dependent spectral changes were independent of the substituents at the peripheral 3-position of the core chlorin chromophore.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 6","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-06-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23681","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141260549","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}

{"title":"Enantioselective liquid–liquid extraction of 2-cyclohexylmandelic acid enantiomers using chiral ionic liquids","authors":"Yachun Luo,&nbsp;Xiaoyu Deng,&nbsp;Yan Zhang,&nbsp;Genlin Sun,&nbsp;Zhihong Yan","doi":"10.1002/chir.23682","DOIUrl":"10.1002/chir.23682","url":null,"abstract":"<p>Obtaining optically pure compounds in an eco-friendly and cost-efficient manner plays an important role in human health and pharmaceutical industry. Racemic separation using multistage stereoselective liquid–liquid extraction has become one of the most practical and effective approach to access homochiral enantiomers. Currently, chiral ionic liquids (CILs) with structural designability have become a promising chiral additive and enable them as adjustable candidates for racemic separation. Herein, a high-effective stereoselective liquid–liquid extraction process composed of imidazolium cations and amino acid-derived anions as the chiral additive was established for racemic 2-cyclohexylmandelic acid (CHMA) separation. We have systematically investigated the choice of organic solvent, concentration of CIL, extraction temperature, and the pH of aqueous phase. For three-stage stereoselective extraction, the maximum enantiomeric excess (<i>e.e</i>.) for CHMA was reached up to 40.6%. Furthermore, the mechanism of steric effect and stereoselective capacity between the CILs and racemic CHMA was discussed and simulated. We envision that the work will facilitate the development of CILs in multistage liquid–liquid extraction and promote the large-scale production of optically pure enantiomers.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 6","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141160988","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}

{"title":"Counting the truxillines—11 or more, the question is now","authors":"Tomislav Portada,&nbsp;Zlatko Brkljača","doi":"10.1002/chir.23680","DOIUrl":"10.1002/chir.23680","url":null,"abstract":"<p>Truxillines are a group of tropane alkaloids present in coca leaves that are formed by photochemical dimerization of cinnamoylcocaine(s). Proportion of different truxilline forms present in cocaine serves as its geographical, manufacture, and storage “fingerprint”; thus, the quantitative determination of truxilline content represents one of the powerful methods of analysis and characterization of cocaine samples. Contrary to the statements repeatedly presented in the literature, namely, that there exist exactly 11 truxillines and that every single truxilline is diastereomer of any other, here we show that, in fact, a total of 15 truxillines exist, which can be divided in two structurally isomeric groups—five mutually diastereomeric truxillates and 10 mutually diastereomeric truxinates.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 6","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141070413","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}

{"title":"Chirality in electromagnetic radiation from relativistic electrons","authors":"Masahiro Katoh,&nbsp;Masaki Fujimoto,&nbsp;Elham Salehi,&nbsp;Masahito Hosaka,&nbsp;Hideki Kawaguchi","doi":"10.1002/chir.23677","DOIUrl":"10.1002/chir.23677","url":null,"abstract":"<p>Electrons in circular motion emit electromagnetic radiation and lose their energy and angular momentum, both of which are carried away by the radiation field. Electromagnetic radiation from such electrons is not only circularly polarized but also, in general, possessing helical phase structure, the former of which corresponds to spin angular momentum and the latter orbital angular momentum. Based on the classical electrodynamics, we show that the chiral topological property related to the orbital angular momentum arises from deformation of the electromagnetic field due to the relativistic effect.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23677","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140944226","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}

{"title":"Exploring a Lux® i-Amylose-3 column in normal phase and polar-organic mode for chiral separation of cathinone derivatives and pyrovalerones using high-performance liquid chromatography","authors":"Elisabeth Seibert,&nbsp;Katharina Götz,&nbsp;Martin G. Schmid","doi":"10.1002/chir.23679","DOIUrl":"10.1002/chir.23679","url":null,"abstract":"<p>Each year, new psychoactive substances appear on the global drug market leading to constant changes. Most of these compounds with stimulating effect possess a chiral center, thus leading to two enantiomers with presumably different pharmacological properties. Among them, synthetic cathinones, often misleadingly traded as “bath salts,” play an important role. There is little knowledge about the distinct effect of the enantiomers. The aim of this study was to test a commercially available Lux® i-Amylose-3 column by HPLC-UV for enantiorecognition of cathinone derivatives. Overall, 80 compounds were tested in normal phase mode, where 75 substances were separated under initial conditions. After method optimization, at least partial separation was achieved for the remaining compounds. The same set of substances was measured in polar-organic mode, where 63 analytes were resolved into their enantiomers under initial conditions with very short retention times. Both modes showed complementary results for the individual compounds. Furthermore, the tested methods proved to be suitable for differentiation of positional isomers, which can be useful for drug checking programs. All measurements were carried out under isocratic conditions, and intraday and interday repeatability tests were performed.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/chir.23679","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140944230","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}

{"title":"The stereoselective pharmacokinetics of the desmethyl-phencynonate hydrochloride in beagle dogs","authors":"Jinglai Li,&nbsp;Lan Yin,&nbsp;Yuexin Li,&nbsp;Junying Sun,&nbsp;Xiaoying Wang,&nbsp;Zhenqing Zhang,&nbsp;Shan Xiong","doi":"10.1002/chir.23669","DOIUrl":"10.1002/chir.23669","url":null,"abstract":"<p>The aim of this study was to investigate the chiral inversion and the stereoselective pharmacokinetic profiles of desmethyl-phencynonate hydrochloride after administration of the single isomer and its racemate to beagle dogs. A liquid chromatography with tandem mass spectrometry (LC–MS/MS) method was established for determination of the stereoisomers on chiral columns in beagle dog plasma, which met all the requirements. The chiral inversion in dogs of the desmethyl-phencynonate hydrochloride were studied after administration of the single isomer or the racemic modification. The stereoselective pharmacokinetic profiles of the desmethyl-phencynonate hydrochloride were studied by assays for simultaneous isomers after administration of the racemic modification. The results showed that the absorption of the <i>R</i>­configuration dosed as the single isomer was higher than it dosed as the racemic modification. The <i>AUC</i>_(0-t), <i>AUC</i>_(0-∞), and <i>C</i>_max of the <i>S</i>­configuration were much higher than those of <i>R</i>­configuration after oral administration of the racemic desmethyl-phencynonate hydrochloride. The chiral inversion of desmethyl-phencynonate isomers could not occur in dogs after administration of the <i>R</i>­configuration.</p>","PeriodicalId":10170,"journal":{"name":"Chirality","volume":"36 5","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140920708","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}