{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,22]],"date-time":"2026-01-22T17:33:53Z","timestamp":1769103233032,"version":"3.49.0"},"reference-count":59,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2023,9,12]],"date-time":"2023-09-12T00:00:00Z","timestamp":1694476800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["21971160"],"award-info":[{"award-number":["21971160"]}]},{"name":"National Natural Science Foundation of China","award":["22271183"],"award-info":[{"award-number":["22271183"]}]},{"name":"National Natural Science Foundation of China","award":["TP2019039"],"award-info":[{"award-number":["TP2019039"]}]},{"name":"Program for Professor of Special Appointment at Shanghai Institutions of Higher Learning","award":["21971160"],"award-info":[{"award-number":["21971160"]}]},{"name":"Program for Professor of Special Appointment at Shanghai Institutions of Higher Learning","award":["22271183"],"award-info":[{"award-number":["22271183"]}]},{"name":"Program for Professor of Special Appointment at Shanghai Institutions of Higher Learning","award":["TP2019039"],"award-info":[{"award-number":["TP2019039"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Supramolecular assembly of amphiphilic molecules in aqueous solutions to form stimuli-responsive entities is attractive for developing intelligent supramolecular materials for bioapplications. Here we report on the supramolecular chiral assembly of amphiphilic dendronized tetraphenylethylenes (TPEs) in aqueous solutions. Hydrophobic TPE moieties were connected to the hydrophilic three-fold dendritic oligoethylene glycols (OEGs) through a tripeptide proline\u2013hydroxyproline\u2013glycol (POG) to afford the characteristic topological structural effects of dendritic OEGs and the peptide linker. Both ethoxyl- and methoxyl-terminated dendritic OEGs were used to modulate the overall hydrophilicity of the dendronized TPEs. Their supramolecular aggregates exhibited thermoresponsive behavior that originated from the dehydration and collapse of the dendritic OEGs, and their cloud point temperatures (Tcps) were tailored by solution pH conditions. Furthermore, aggregation-induced fluorescent emission (AIE) from TPE moieties was used as an indicator to follow the assembly, which was reversibly tuned by temperature variation at different pH conditions. Supramolecular assemblies from these dendronized amphiphiles exhibited enhanced supramolecular chirality, which was dominated mainly by the interaction balance between TPE with dendritic OEG and TPE with POG moieties and was modulated through different solvation by changing solution temperature or pH conditions. More interestingly, ethoxyl-terminated dendritic OEG provided a much stronger shielding effect than its methoxyl-terminated counterpart to prevent amino groups within the peptide from protonation, even in strong acidic conditions, resulting in different responsive behavior to the solution temperature and pH conditions for these supramolecular aggregates.<\/jats:p>","DOI":"10.3390\/molecules28186580","type":"journal-article","created":{"date-parts":[[2023,9,12]],"date-time":"2023-09-12T21:41:12Z","timestamp":1694554872000},"page":"6580","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Dual-Responsive Supramolecular Chiral Assemblies from Amphiphilic Dendronized Tetraphenylethylenes"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6989-7923","authenticated-orcid":false,"given":"Jianan","family":"Zhang","sequence":"first","affiliation":[{"name":"International Joint Laboratory of Biomimetic and Smart Polymers, School of Materials Science and Engineering, Shanghai University, Nanchen Street 333, Shanghai 200444, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-5005-3657","authenticated-orcid":false,"given":"Xueting","family":"Lu","sequence":"additional","affiliation":[{"name":"International Joint Laboratory of Biomimetic and Smart Polymers, School of Materials Science and Engineering, Shanghai University, Nanchen Street 333, Shanghai 200444, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3851-7406","authenticated-orcid":false,"given":"Wen","family":"Li","sequence":"additional","affiliation":[{"name":"International Joint Laboratory of Biomimetic and Smart Polymers, School of Materials Science and Engineering, Shanghai University, Nanchen Street 333, Shanghai 200444, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0078-3223","authenticated-orcid":false,"given":"Afang","family":"Zhang","sequence":"additional","affiliation":[{"name":"International Joint Laboratory of Biomimetic and Smart Polymers, School of Materials Science and Engineering, Shanghai University, Nanchen Street 333, Shanghai 200444, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,9,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1039\/B919678C","article-title":"Supramolecular Amphiphiles","volume":"40","author":"Zhang","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2576","DOI":"10.1039\/b807500j","article-title":"Hierarchical Construction of Self-Assembled Low Dimensional Molecular Architectures Observed by Using Scanning Tunneling Microscopy","volume":"38","author":"Yang","year":"2009","journal-title":"Chem. Soc. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"5589","DOI":"10.1039\/C6CS00176A","article-title":"Peptide Self-Assembly: Thermodynamics and Kinetics","volume":"45","author":"Wang","year":"2016","journal-title":"Chem. Soc. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"813","DOI":"10.1126\/science.1205962","article-title":"Functional Supramolecular Polymers","volume":"335","author":"Aida","year":"2012","journal-title":"Science"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1396","DOI":"10.1126\/science.aav4677","article-title":"The Construction of Supramolecular Systems","volume":"363","author":"Vantomme","year":"2019","journal-title":"Science"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"5604","DOI":"10.1021\/acs.chemrev.1c00815","article-title":"Supramolecular Adhesive Hydrogels for Tissue Engineering Applications","volume":"122","author":"Zhao","year":"2022","journal-title":"Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"12515","DOI":"10.1021\/ja9627656","article-title":"Self-Assembling Amphiphiles for Construction of Protein Molecular Architecture","volume":"118","author":"Yu","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5352","DOI":"10.1021\/la010223i","article-title":"Self-Assembly of Model Collagen Peptide Amphiphiles","volume":"17","author":"Gore","year":"2001","journal-title":"Langmuir"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"9021","DOI":"10.1039\/c1sm06008b","article-title":"Self-Organization of Amide Dendrons with Focal Dipeptide Units","volume":"7","author":"Lee","year":"2011","journal-title":"Soft Matter"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"8443","DOI":"10.1039\/c3ob40532j","article-title":"The Self-Assembly of Cystine-Bridged \u03b3-Peptide-Based Cyclic Peptide-Dendron Hybrids","volume":"11","author":"Lin","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"104201","DOI":"10.1039\/C6RA21261A","article-title":"Effects of Temperature, pH and Counterions on the Stability of Peptide Amphiphile Nanofiber Structures","volume":"6","author":"Ozkan","year":"2016","journal-title":"RSC Adv."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2525","DOI":"10.1002\/anie.200805010","article-title":"Controllable Peptide-Dendron Self-Assembly: Interconversion of Nanotubes and Fibrillar Nanostructures","volume":"48","author":"Shao","year":"2009","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"664","DOI":"10.1039\/b609047h","article-title":"Designing Peptide Based Nanomaterials","volume":"37","author":"Ulijn","year":"2008","journal-title":"Chem. Soc. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2195","DOI":"10.1039\/C2CC16609G","article-title":"Tripeptide Self-Assembled Hydrogels: Unexpected Twists of Chirality","volume":"48","author":"Marchesan","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"5495","DOI":"10.1002\/anie.201100807","article-title":"Direct Observation of Time-Resolved Polymorphic States in the Self-Assembly of End-Capped Heptapeptides","volume":"50","author":"Adamcik","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2885","DOI":"10.1021\/la504757c","article-title":"Electrostatic and Aromatic Interaction-Directed Supramolecular Self-Assembly of a Designed Fmoc-Tripeptide into Helical Nanoribbons","volume":"31","author":"Xie","year":"2015","journal-title":"Langmuir"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1554","DOI":"10.1021\/nn405790x","article-title":"\u201cSingle-Single\u201d Amphiphilic Janus Dendrimers Self-Assemble into Uniform Dendrimersomes with Predictable Size","volume":"8","author":"Zhang","year":"2014","journal-title":"ACS Nano"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"707","DOI":"10.1016\/j.ijpharm.2018.07.030","article-title":"Dendrimers: A Versatile Nanocarrier for Drug Delivery and Targeting","volume":"548","author":"Sherje","year":"2018","journal-title":"Int. J. Pharm."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/bip.21328","article-title":"Self-Assembly of Peptide Amphiphiles: From Molecules to Nanostructures to Biomaterials","volume":"94","author":"Cui","year":"2010","journal-title":"Biopolymers"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"6389","DOI":"10.1002\/chem.201003049","article-title":"Hierarchical Self-Assembly of Amphiphilic Peptide Dendrons: Evolution of Diverse Chiral Nanostructures through Hydrogel Formation over a Wide pH Range","volume":"17","author":"Duan","year":"2011","journal-title":"Chem. Eur. J."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"11663","DOI":"10.1021\/ja063408q","article-title":"Understanding the Mechanism of Gelation and Stimuli-Responsive Nature of a Class of Metallo-Supramolecular Gels","volume":"128","author":"Weng","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6807","DOI":"10.1002\/anie.200702136","article-title":"Self-Assembly of T-Shaped Aromatic Amphiphiles into Stimulus- Responsive Nanofibers","volume":"46","author":"Moon","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1971","DOI":"10.1021\/ar500033n","article-title":"Stimuli-Responsive Supramolecular Polymers in Aqueous Solution","volume":"47","author":"Ma","year":"2014","journal-title":"Acc. Chem. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1900577","DOI":"10.1002\/advs.201900577","article-title":"Steering the Self-Assembly Outcome of a Single NDI Monomer into Three Morphologically Distinct Supramolecular Assemblies, with Concomitant Change in Supramolecular Polymerization Mechanism","volume":"6","author":"Markiewicz","year":"2019","journal-title":"Adv. Sci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"7189","DOI":"10.1021\/jacs.1c02983","article-title":"Spin Filtering in Supramolecular Polymers Assembled from Achiral Monomers Mediated by Chiral Solvents","volume":"143","author":"Mondal","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"32140","DOI":"10.1021\/acsomega.0c04919","article-title":"Phototriggered Supramolecular Assembly","volume":"5","author":"Mukherjee","year":"2002","journal-title":"ACS Omega"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2600","DOI":"10.1021\/acs.accounts.0c00434","article-title":"Molecular Photoswitching in Confined Spaces","volume":"53","author":"Grommet","year":"2020","journal-title":"Acc. Chem. Res."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2204413","DOI":"10.1002\/adma.202204413","article-title":"Photoresponsive Supramolecular Polymers: From Light-Controlled Small Molecules to Smart Materials","volume":"35","author":"Xu","year":"2023","journal-title":"Adv. Mater."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"651","DOI":"10.1038\/nature11839","article-title":"Responsive biomimetic networks from polyisocyanopeptide hydrogels","volume":"493","author":"Kouwer","year":"2013","journal-title":"Nature"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"448","DOI":"10.1021\/jacs.9b11290","article-title":"Assembly Pattern of Supramolecular Hydrogel Induced by Lower Critical Solution Temperature Behavior of Low-Molecular-Weight Gelator","volume":"142","author":"Wu","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1022","DOI":"10.1021\/la404784e","article-title":"Morphology Control Between Twisted Ribbon, Helical Ribbon, and Nanotube Self-Assemblies with His-Containing Helical Peptides in Response to pH Change","volume":"30","author":"Uesaka","year":"2014","journal-title":"Langmuir"},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1700999","DOI":"10.1002\/smll.201700999","article-title":"Reconfigurable Chiral Self-Assembly of Peptides through Control of Terminal Charges","volume":"13","author":"Xie","year":"2017","journal-title":"Small"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"7304","DOI":"10.1021\/cr500671p","article-title":"Supramolecular Chirality in Self-Assembled Systems","volume":"115","author":"Liu","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1696","DOI":"10.1038\/s41467-023-37412-0","article-title":"Four Distinct Network Patterns of Supramolecular\/Polymer Composite Hydrogels Controlled by Formation Kinetics and Interfiber Interactions","volume":"14","author":"Nakamura","year":"2023","journal-title":"Nat. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3084","DOI":"10.1038\/s41467-023-38948-x","article-title":"Mechanosensitive Non-Equilibrium Supramolecular Polymerization in Closed Chemical Systems","volume":"14","author":"Lang","year":"2023","journal-title":"Nat. Commun."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"318","DOI":"10.1038\/nmat4483","article-title":"Stress-Stiffening-Mediated Stem-Cell Commitment Switch in Soft Responsive Hydrogels","volume":"15","author":"Das","year":"2016","journal-title":"Nat. Mater."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"13308","DOI":"10.1021\/jacs.8b07697","article-title":"Polymorphism in Benzene-1,3,5-tricarboxamide Supramolecular Assemblies in Water: A Subtle Trade-off between Structure and Dynamics","volume":"140","author":"Matsumoto","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4993","DOI":"10.1038\/s41467-021-25299-8","article-title":"Light-Fueled Transient SupraMolecular Assemblies in Water as Fluorescence Modulators","volume":"12","author":"Chen","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4182","DOI":"10.1021\/jacs.8b12777","article-title":"Substrate-Driven Transient Self-Assembly and Spontaneous Disassembly Directed by Chemical Reaction with Product Release","volume":"141","author":"Wang","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"10361","DOI":"10.1021\/acs.langmuir.0c01338","article-title":"Self-Assembly of Peptide Chiral Nanostructures with Sequence-encoded Enantioseparation Capability","volume":"36","author":"Fan","year":"2020","journal-title":"Langmuir"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"360","DOI":"10.1038\/s41586-018-0034-1","article-title":"Amino Acid and Peptide Directed Synthesis of Chiral Plasmonic Gold Nanoparticles","volume":"556","author":"Lee","year":"2018","journal-title":"Nature"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"12697","DOI":"10.1021\/jacs.9b05329","article-title":"Helical Sulfono-\u03b3-AA Peptides with Aggregation-Induced Emission and Circularly Polarized Luminescence","volume":"141","author":"Shi","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"23726","DOI":"10.1039\/c2jm31949g","article-title":"Tetraphenylethene: A Versatile AIE Building Block for The Construction of Efficient Luminescent Materials for Organic Light-Emitting Diodes","volume":"22","author":"Zhao","year":"2012","journal-title":"J. Mater. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2491","DOI":"10.1039\/c3cc00010a","article-title":"From Tetraphenylethene to Tetranaphthylethene: Structural Evolution in AIE Luminogen Continues","volume":"49","author":"Zhou","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2300746","DOI":"10.1002\/adfm.202300746","article-title":"Development of Sulfonamide-Functionalized Charge-Reversal AIE Photosensitizers for Precise Photodynamic Therapy in the Acidic Tumor Microenvironment","volume":"33","author":"Yang","year":"2023","journal-title":"Adv. Funct. Mater."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"12895","DOI":"10.1021\/acsnano.3c04971","article-title":"Ultralong Room-Temperature Phosphorescence with Second-level Lifetime in Water Based on Cyclodextrin Supramolecular Assembly","volume":"17","author":"Li","year":"2023","journal-title":"ACS Nano"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1845","DOI":"10.1021\/acsnano.2c10826","article-title":"Aggregation-Induced Emission-Active Nanostructures: Beyond Biomedical Applications","volume":"17","author":"Chua","year":"2023","journal-title":"ACS Nano"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3618","DOI":"10.1021\/acsnano.9b00218","article-title":"Real-Time Monitoring of Hierarchical Self-Assembly and Induction of Circularly Polarized Luminescence from Achiral Luminogens","volume":"13","author":"Zhang","year":"2019","journal-title":"ACS Nano"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"839","DOI":"10.1021\/acsnano.8b08358","article-title":"Visualizing the Initial Step of Self-Assembly and the Phase Transition by Stereogenic Amphiphiles with Aggregation-Induced Emission","volume":"13","author":"Peng","year":"2019","journal-title":"ACS Nano"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"20067","DOI":"10.1021\/acsnano.1c07764","article-title":"Thermoresponsive supramolecular assemblies from dendronized amphiphiles to form fluorescent spheres with tunable chirality","volume":"15","author":"Liu","year":"2021","journal-title":"ACS Nano"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"12221","DOI":"10.1039\/C4CC03119A","article-title":"Dendronized Supramolecular Polymers","volume":"50","author":"Yan","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2000325","DOI":"10.1002\/marc.202000325","article-title":"Confined Microenvironments from Thermoresponsive Dendronized Polymers","volume":"41","author":"Xu","year":"2020","journal-title":"Macromol. Rapid Commun."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"12780","DOI":"10.1039\/D1CC05358B","article-title":"Dendronized Polydiacetylenes via Photo-Polymerization of Supramolecular Assemblies Showing Thermally Tunable Chirality","volume":"57","author":"Liu","year":"2021","journal-title":"Chem. Commun."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"5683","DOI":"10.1002\/anie.201001469","article-title":"EPR Spectroscopic Characterization of Local Nanoscopic Heterogeneities during the Thermal Collapse of Thermoresponsive Dendronized Polymers","volume":"49","author":"Junk","year":"2010","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3931","DOI":"10.1021\/acs.macromol.3c00581","article-title":"Thermoresponsive Dendronized Microgels through In Situ Cross-Linking Polymerization to Exhibit Enhanced Confinement for Solvatochromic Dyes","volume":"56","author":"Zhang","year":"2023","journal-title":"Macromolecules"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"5377","DOI":"10.1021\/acsabm.2c00755","article-title":"Thermo-Gelling Dendronized Chitosans for Modulating Protein Activity","volume":"5","author":"Yao","year":"2022","journal-title":"ACS Appl. Bio Mater."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"11848","DOI":"10.1039\/D2CP01286C","article-title":"Thermoresponsive Dendritic Oligoethylene Glycols","volume":"24","author":"Xu","year":"2022","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"281","DOI":"10.1016\/j.polymer.2016.07.027","article-title":"OEGylated Collagen Mimetic Polypeptides with Enhanced Supramolecular Assembly","volume":"99","author":"Zhao","year":"2016","journal-title":"Polymer"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1701","DOI":"10.1002\/marc.201300605","article-title":"Thermoresponsive Dendronized Polyprolines via the \u201cGrafting to\u201d Route","volume":"34","author":"Zhang","year":"2013","journal-title":"Macromol. Rapid Commun."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/18\/6580\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:49:33Z","timestamp":1760129373000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/18\/6580"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,9,12]]},"references-count":59,"journal-issue":{"issue":"18","published-online":{"date-parts":[[2023,9]]}},"alternative-id":["molecules28186580"],"URL":"https:\/\/doi.org\/10.3390\/molecules28186580","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,9,12]]}}}