{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,4]],"date-time":"2026-03-04T01:14:33Z","timestamp":1772586873828,"version":"3.50.1"},"reference-count":59,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2024,8,5]],"date-time":"2024-08-05T00:00:00Z","timestamp":1722816000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100020206","name":"Health Commission of Shandong Province","doi-asserted-by":"publisher","award":["202313051336"],"award-info":[{"award-number":["202313051336"]}],"id":[{"id":"10.13039\/501100020206","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Jining Medical University","award":["202313051336"],"award-info":[{"award-number":["202313051336"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Dipines are a type of important antihypertensive drug as L-calcium channel blockers, whose core skeleton is the 1,4-dihydropyridine structure. Since the dihydropyridine ring is a key structural factor for biological activity, the thermodynamics of the aromatization dihydropyridine ring is a significant feature parameter for understanding the mechanism and pathways of dipine metabolism in vivo. Herein, 4-substituted-phenyl-2,6-dimethyl-3,5-diethyl-formate-1,4-dihydropyridines are refined as the structurally closest dipine models to investigate the thermodynamic potential of dipine oxidative metabolism. In this work, the thermodynamic cards of dipine models\u2019 aromatization on 21 potential elementary steps in acetonitrile have been established. Based on the thermodynamic cards, the thermodynamic properties of dipine models and related intermediates acting as electrons, hydrides, hydrogen atoms, protons, and two hydrogen ions (atoms) donors are discussed. Moreover, the thermodynamic cards are applied to evaluate the redox properties, and judge or reveal the possible oxidative mechanism of dipine models.<\/jats:p>","DOI":"10.3390\/molecules29153706","type":"journal-article","created":{"date-parts":[[2024,8,5]],"date-time":"2024-08-05T13:57:28Z","timestamp":1722866248000},"page":"3706","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Establishing the Thermodynamic Cards of Dipine Models\u2019 Oxidative Metabolism on 21 Potential Elementary Steps"],"prefix":"10.3390","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0449-7301","authenticated-orcid":false,"given":"Guang-Bin","family":"Shen","sequence":"first","affiliation":[{"name":"College of Medical Engineering, Jining Medical University, Jining 272000, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shun-Hang","family":"Gao","sequence":"additional","affiliation":[{"name":"College of Medical Engineering, Jining Medical University, Jining 272000, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yan-Wei","family":"Jia","sequence":"additional","affiliation":[{"name":"College of Medical Engineering, Jining Medical University, Jining 272000, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Xiao-Qing","family":"Zhu","sequence":"additional","affiliation":[{"name":"The State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Bao-Chen","family":"Qian","sequence":"additional","affiliation":[{"name":"College of Medical Engineering, Jining Medical University, Jining 272000, China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,8,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3131","DOI":"10.1002\/anie.202011793","article-title":"Structural Basis of the Modulation of the Voltage-gated Calcium Ion Channel Cav1.1 by Dihydropyridine Compounds","volume":"60","author":"Gao","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2906","DOI":"10.1021\/jm000028l","article-title":"Permanently Charged Chiral 1,4-Dihydropyridines:\u2009 Molecular Probes of L-Type Calcium Channels. Synthesis and Pharmacological Characterization of Methyl (\u03c9-Trimethylalkylammonium) 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5- pyridinedicarboxylate Iodide, Calcium Channel Antagonists","volume":"43","author":"Peri","year":"2000","journal-title":"J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"810","DOI":"10.1002\/cmdc.201900036","article-title":"Towards Second Generation Cardiomyogenic and Anticardiofibrotic 1,4-Dihydropyridine-Class of TGF\u03b2 Inhibitors","volume":"14","author":"Werner","year":"2019","journal-title":"ChemMedChem"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2455","DOI":"10.1021\/acs.molpharmaceut.8b00308","article-title":"Co-Stabilization of Amorphous Pharmaceuticals\u2014The Case of Nifedipine and Nimodipine","volume":"15","author":"Tu","year":"2018","journal-title":"Mol. Pharm."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Pan, X., Li, R., Guo, H., Zhang, W., Xu, X., Chen, X., and Ding, L. (2021). Dihydropyridine Calcium Channel Blockers Suppress the Transcription of PD-L1 by Inhibiting the Activation of STAT1. Front. Pharmacol., 11.","DOI":"10.3389\/fphar.2020.539261"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"348","DOI":"10.1021\/mp050027v","article-title":"QSAR and Classification Study of 1,4-Dihydropyridine Calcium Channel Antagonists Based on Least Squares Support Vector Machines","volume":"2","author":"Yao","year":"2005","journal-title":"Mol. Pharm."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Christen, D.P. (2007). Dihydropyridine Calcium Channel Blockers for Hypertension. Art Drug Synth., 159\u2013167.","DOI":"10.1002\/9780470134979.ch11"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1021\/ci010117m","article-title":"Comparison between Neural Networks (NN) and Principal Component Analysis (PCA):\u2009 Structure Activity Relationships of 1,4-Dihydropyridine Calcium Channel Antagonists (Nifedipine Analogues)","volume":"43","author":"Takahata","year":"2003","journal-title":"J. Chem. Inf. Com. Sci."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1021\/tx0502591","article-title":"The L-type Calcium Channel Blockers, Hantzsch 1,4-Dihydropyridines, Are Not Peroxyl Radical-Trapping, Chain Breaking Antioxidants","volume":"19","author":"Mulder","year":"2006","journal-title":"Chem. Res. Toxicol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"23621","DOI":"10.1021\/acsomega.1c03872","article-title":"Quantitative Estimation of the Hydrogen-Atom-Donating Ability of 4-Substituted Hantzsch Ester Radical Cations","volume":"6","author":"Shen","year":"2021","journal-title":"ACS Omega"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"9418","DOI":"10.1021\/acscatal.1c02017","article-title":"An Overview of Cytochrome P450 Immobilization Strategies for Drug Metabolism Studies, Biosensing, and Biocatalytic Applications: Challenges and Opportunities","volume":"11","author":"Valikhani","year":"2021","journal-title":"ACS Catal."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"5504","DOI":"10.1021\/jacs.9b00242","article-title":"Reduction Potentials of P450 Compounds I and II: Insight into the Thermodynamics of C-H Bond Activation","volume":"141","author":"Mittra","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"416","DOI":"10.1126\/science.adk8464","article-title":"Asymmetric Photoenzymatic Incorporation of Fluorinated Motifs into Olefins","volume":"385","author":"Li","year":"2024","journal-title":"Science"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1446","DOI":"10.1021\/acs.accounts.4c00129","article-title":"From Ground-State to Excited-State Activation Modes: Flavin-Dependent \u201cEne\u201d-Reductases Catalyzed Non-natural Radical Reactions","volume":"57","author":"Fu","year":"2024","journal-title":"Acc. Chem. Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"16318","DOI":"10.1021\/acscatal.3c03451","article-title":"Computational Exploration of Enzyme Promiscuity: Mechanisms of O2 and NO Reduction Activities of the Desulfovibrio gigas Flavodiiron Protein","volume":"13","author":"Deng","year":"2023","journal-title":"ACS Catal."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"13","DOI":"10.1021\/acscentsci.8b00698","article-title":"Heme and Nonheme High-Valent Iron and Manganese Oxo Cores in Biological and Abiological Oxidation Reactions","volume":"5","author":"Guo","year":"2019","journal-title":"ACS Cent. Sci."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"250","DOI":"10.1021\/jacs.3c08559","article-title":"Electronic Structure and Reactivity of Mononuclear Nonheme Iron\u2013Peroxo Complexes as a Biomimetic Model of Rieske Oxygenases: Ring Size Effects of Macrocyclic Ligands","volume":"146","author":"Zhu","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"13942","DOI":"10.1021\/ja507807v","article-title":"Status of Reactive Non-Heme Metal-Oxygen Intermediates in Chemical and Enzymatic Reactions","volume":"136","author":"Ray","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"3175","DOI":"10.1021\/acs.accounts.3c00449","article-title":"Dioxygen Reduction and Bioinspired Oxidations by Non-heme Iron(II)\u2212\u03b1-Hydroxy Acid Complexes","volume":"56","author":"Chatterjee","year":"2023","journal-title":"Acc. Chem. Res."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"9293","DOI":"10.1021\/ja110190t","article-title":"Calcium Binding and Transport by Coenzyme Q","volume":"133","author":"Bogeski","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Wada, O.Z., Rashid, N., Wijten, P., Thornalley, P., Mckay, G., and Mackey, H.R. (2024). Evaluation of Cell Disruption Methods for Protein and Coenzyme Q10 Quantification in Purple Non-Sulfur Bacteria. Front. Microbiol., 15.","DOI":"10.3389\/fmicb.2024.1324099"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"7747","DOI":"10.1021\/acs.inorgchem.6b01220","article-title":"Catalytic Formation of Hydrogen Peroxide from Coenzyme NADH and Dioxygen with a Water-Soluble Iridium Complex and a Ubiquinone Coenzyme Analogue","volume":"55","author":"Suenobu","year":"2016","journal-title":"Inorg. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2966","DOI":"10.1021\/acs.molpharmaceut.3c00017","article-title":"Influence of Pore Size and Surface Functionalization of Mesoporous Silica Nanoparticles on the Solubility and Antioxidant Activity of Confined Coenzyme Q10","volume":"20","author":"Meka","year":"2023","journal-title":"Mol. Pharm."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"e202310238","DOI":"10.1002\/anie.202310238","article-title":"NADH Photosynthesis System with Affordable Electron Supply and Inhibited NADH Oxidation","volume":"62","author":"Chen","year":"2023","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"5927","DOI":"10.1021\/acs.jpcc.4c00832","article-title":"Synergy Between Metal and Molecular Catalysts for (Photo)electrocatalytic 1,4-NADH Regeneration","volume":"128","author":"Liu","year":"2024","journal-title":"J. Phys. Chem. C"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"18817","DOI":"10.1021\/jacs.4c04725","article-title":"Mechanoresponsive Protein Crystals for NADH Recycling in Multicycle Enzyme Reactions","volume":"146","author":"Yekta","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"6001","DOI":"10.1039\/D2QO01310J","article-title":"Thermodynamics of the Elementary Steps of Organic Hydride Chemistry Determined in Acetonitrile and their Applications","volume":"9","author":"Shen","year":"2022","journal-title":"Org. Chem. Front."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1021\/acs.chemrev.1c00521","article-title":"Free Energies of Proton-Coupled Electron Transfer Reagents and Their Applications","volume":"122","author":"Agarwal","year":"2022","journal-title":"Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"6961","DOI":"10.1021\/cr100085k","article-title":"Thermochemistry of Proton-Coupled Electron Transfer Reagents and its Implications","volume":"110","author":"Warren","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1596","DOI":"10.1021\/jm00159a007","article-title":"Oxidation of 4-Aryl- and 4-Alkyl-Substituted 2,6-Dimethyl-3,5-bis(alkoxycarbony1)-1,4-dihydropyridines by Human Liver Microsomes and Immunochemical Evidence for the Involvement of a Form of Cytochrome P-450","volume":"29","author":"Guengerich","year":"1986","journal-title":"J. Med. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"12535","DOI":"10.1021\/acs.joc.0c01726","article-title":"Thermodynamic Network Cards of Hantzsch Ester, Benzothiazoline, and Dihydrophenanthridine Releasing Two Hydrogen Atoms or Ions on 20 Elementary Steps","volume":"85","author":"Shen","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2809","DOI":"10.1039\/C7CS00171A","article-title":"Thermodynamic and kinetic hydricities of metal-free hydrides","volume":"47","author":"Ilic","year":"2018","journal-title":"Chem. Soc. Rev."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"4569","DOI":"10.1021\/jacs.7b13526","article-title":"Thermodynamic Hydricities of Biomimetic Organic Hydride Donors","volume":"140","author":"Ilic","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"14114","DOI":"10.1021\/jacs.5b07777","article-title":"Solvation Effects on Transition Metal Hydricity","volume":"137","author":"Tsay","year":"2015","journal-title":"J. Am. Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"4671","DOI":"10.1021\/jo980120d","article-title":"Hydride Affinities of Arylcarbenium Ions and Iminium Ions in Dimethyl Sulfoxide and Acetonitrile","volume":"63","author":"Zhang","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"6071","DOI":"10.1039\/c3ob40831k","article-title":"A Classical but New Kinetic Equation for Hydride Transfer Reactions","volume":"11","author":"Zhu","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"9357","DOI":"10.1021\/acs.joc.2c01149","article-title":"Discovering and Evaluating the Reducing Abilities of Polar Alkanes and Related Family Members as Organic Reductants Using Thermodynamics","volume":"87","author":"Shen","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"789","DOI":"10.1021\/jo902332n","article-title":"Hydride, Hydrogen, Proton, and Electron Affinities of Imines and Their Reaction Intermediates in Acetonitrile and Construction of Thermodynamic Characteristic Graphs (TCGs) of Imines as a \u201cMolecule ID Card.\u201d","volume":"75","author":"Zhu","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"31984","DOI":"10.1021\/acsomega.3c03804","article-title":"Thermodynamic Evaluations of Amines as Hydrides or Two Hydrogen Ions Reductants, and Imines as Protons or Two Hydrogen Ions Acceptors, as well as Their Application in Hydrogenation Reactions","volume":"8","author":"Shen","year":"2023","journal-title":"ACS Omega"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"19282","DOI":"10.1002\/anie.202008528","article-title":"Holistic prediction of pKa in diverse solvents based on machine learning approach","volume":"59","author":"Yang","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"8655","DOI":"10.1021\/acs.chemrev.6b00168","article-title":"Thermodynamic Hydricity of Transition Metal Hydrides","volume":"116","author":"Wiedner","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1039\/D3RA08022F","article-title":"Thermodynamic Evaluations on the Acceptorless Dehydrogenation and Hydrogenation of Pre-Aromatic and Aromatic N-Heterocycles in Acetonitrile","volume":"14","author":"Qian","year":"2024","journal-title":"RSC Adv."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"6833","DOI":"10.1039\/D2QO01605B","article-title":"Thermodynamics Regulated Organic Hydride\/Acid Pairs as Novel Organic Hydrogen Reductants","volume":"9","author":"Shen","year":"2022","journal-title":"Org. Chem. Front."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1407","DOI":"10.1002\/ejoc.202001649","article-title":"Strengths of Acids in Acetonitrile","volume":"2021","author":"Tshepelevitsh","year":"2021","journal-title":"Eur. J. Org. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"6735","DOI":"10.1002\/ejoc.201900956","article-title":"On the Basicity of Organic Bases in Different Media","volume":"2019","author":"Tshepelevitsh","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2853","DOI":"10.1021\/jacs.1c12723","article-title":"A Powerful Chiral Super Br\u00f8nsted C-H Acid for Asymmetric Catalysis","volume":"144","author":"Peng","year":"2022","journal-title":"J. Am. Chem. Soc."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1518","DOI":"10.1016\/j.chempr.2023.02.020","article-title":"Data Science Enables the Development of a New Class of Chiral Phosphoric Acid Catalysts","volume":"9","author":"Liles","year":"2023","journal-title":"Chem"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"9047","DOI":"10.1021\/cr5001496","article-title":"Complete Field Guide to Asymmetric BINOL-Phosphate Derived Br\u00f8nsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Br\u00f8nsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates","volume":"114","author":"Parmar","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"11569","DOI":"10.1002\/anie.201303605","article-title":"On the Acidity and Reactivity of Highly Effective Chiral Br\u00f8nsted Acid Catalysts: Establishment of an Acidity Scale","volume":"52","author":"Kaupmees","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"7007","DOI":"10.1021\/jo061145c","article-title":"Negative Kinetic Temperature Effect on the Hydride Transfer from NADH Analogue BNAH to the Radical Cation of N-Benzylphenothiazine in Acetonitrile","volume":"71","author":"Zhu","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Chen, B.-L., Yan, S.-Y., and Zhu, X.-Q. (2023). A Mechanism Study of Redox Reactions of the Ruthenium-oxo-polypyridyl Complex. Molecules, 28.","DOI":"10.3390\/molecules28114401"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"14794","DOI":"10.1021\/jp2067974","article-title":"What Are the Differences between Ascorbic Acid and NADH as Hydride and Electron Sources in Vivo on Thermodynamics, Kinetics, and Mechanism?","volume":"115","author":"Zhu","year":"2011","journal-title":"J. Phys. Chem. B"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"e202204789","DOI":"10.1002\/slct.202204789","article-title":"Thermodynamic and Kinetic Studies of the Activities of Aldehydic C-H Bonds toward Their H-Atom Transfer Reactions","volume":"8","author":"Fu","year":"2023","journal-title":"ChemistrySelect"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"26708","DOI":"10.1021\/acsomega.4c04209","article-title":"Thermodynamic H-Abstraction Abilities of Nitrogen Centered Radical Cations as Potential HAT Catalysts in Y-H Bond Functionalization","volume":"9","author":"Zhao","year":"2024","journal-title":"ACS Omega"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"31425","DOI":"10.1039\/D0RA06745H","article-title":"Theoretical Investigation on the Nature of 4-Substituted Hantzsch Esters as Alkylation Agents","volume":"10","author":"Shen","year":"2020","journal-title":"RSC Adv."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2498","DOI":"10.1039\/c1cs15268h","article-title":"Transfer Hydrogenation with Hantzsch Esters and Related Organic Hydride Donors","volume":"41","author":"Zheng","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1327","DOI":"10.1021\/ar7001864","article-title":"Enantioselective Organocatalytic Transfer Hydrogenation Reactions Using Hantzsch Esters","volume":"40","author":"Ouellet","year":"2007","journal-title":"Acc. Chem. Res."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1084","DOI":"10.1039\/c1gc15027h","article-title":"Advances in Catalytic Metal-Free Reductions: From Bioinspired Concepts to Applications in the Organocatalytic Synthesis of Pharmaceuticals and Natural Products","volume":"13","author":"Rueping","year":"2011","journal-title":"Green Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1021\/acs.chemrestox.1c00340","article-title":"Pyrroloquinoline Quinone Chemistry, Biology, and Biosynthesis","volume":"35","author":"Cordell","year":"2022","journal-title":"Chem. Res. Toxicol."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/15\/3706\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T15:30:20Z","timestamp":1760110220000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/15\/3706"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,8,5]]},"references-count":59,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2024,8]]}},"alternative-id":["molecules29153706"],"URL":"https:\/\/doi.org\/10.3390\/molecules29153706","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,8,5]]}}}