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Each human serum albumin (HSA) carrier bears multiple nitroxides conjugated via homocysteine thiolactones. These molecular conjugates retain important physical and biological properties of their HSA component, and the resistance of their nitroxide groups to bioreduction was retained or enhanced. The relaxivities are similar for these four conjugates and are much greater than those of their individual components: the HSA or the small nitroxide molecules. This new family of conjugates has excellent prospects for optimization as ORCAs.<\/jats:p>","DOI":"10.3390\/molecules25071709","type":"journal-article","created":{"date-parts":[[2020,4,10]],"date-time":"2020-04-10T05:31:16Z","timestamp":1586496676000},"page":"1709","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":32,"title":["Human Serum Albumin Labelled with Sterically-Hindered Nitroxides as Potential MRI Contrast Agents"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3486-0335","authenticated-orcid":false,"given":"Sergey","family":"Dobrynin","sequence":"first","affiliation":[{"name":"N.N. 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Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"639","DOI":"10.4155\/fmc-2017-0215","article-title":"Gadolinium as an MRI contrast agent","volume":"10","author":"Kim","year":"2018","journal-title":"Future Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"17025","DOI":"10.1021\/jacs.9b09149","article-title":"Molecular MR Imaging with Gd(III)-based Agents: Challenges and Key Advances","volume":"141","author":"Li","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2264","DOI":"10.1021\/acs.bioconjchem.9b00499","article-title":"The Transition from Metal-Based to Metal-Free Contrast Agents for T1 Magnetic Resonance Imaging Enhancement","volume":"30","author":"Akakuru","year":"2019","journal-title":"Bioconjug. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1007\/s00330-012-2597-9","article-title":"Nephrogenic systemic fibrosis and gadolinium-based contrast media: Updated ESUR Contrast Medium Safety Committee guidelines","volume":"23","author":"Thomsen","year":"2013","journal-title":"Eur. Radiol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"229","DOI":"10.1007\/s40263-018-0500-1","article-title":"Gadolinium-Based Contrast Agent-Related Toxicities","volume":"32","author":"Pasquini","year":"2018","journal-title":"CNS Drugs"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1016\/j.mric.2017.06.007","article-title":"Gadolinium Deposition and Chronic Toxicity","volume":"25","author":"Ramalho","year":"2017","journal-title":"Magn. Reson. Imaging Clin. N. Am."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"s1","DOI":"10.5301\/jva.5000713","article-title":"Gadolinium contrast agents \u2013 are they really safe?","volume":"18","author":"Malikova","year":"2017","journal-title":"J. Vasc. Access"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"720","DOI":"10.1056\/NEJMc070248","article-title":"Nephrogenic systemic fibrosis, gadolinium, and iron mobilization","volume":"357","author":"Swaminathan","year":"2007","journal-title":"N. Engl. J. Med."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/jbt.22225","article-title":"Toxicity of iron oxide nanoparticles: Size and coating effects","volume":"32","author":"Abakumov","year":"2018","journal-title":"J. Biochem. Mol. Toxicol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"5358","DOI":"10.3402\/nano.v1i0.5358","article-title":"Potential toxicity of superparamagnetic iron oxide nanoparticles (SPION)","volume":"1","author":"Singh","year":"2010","journal-title":"Nano Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s13205-018-1286-z","article-title":"Recent advances and future prospects of iron oxide nanoparticles in biomedicine and diagnostics","volume":"8","author":"Vallabani","year":"2018","journal-title":"3 Biotech"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1106","DOI":"10.1021\/cr500286d","article-title":"19F Magnetic Resonance Imaging (MRI): From Design of Materials to Clinical Applications","volume":"115","author":"Tirotta","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1007\/s10334-018-0724-6","article-title":"Fluorine polymer probes for magnetic resonance imaging: Quo vadis?","volume":"32","author":"Jirak","year":"2019","journal-title":"Magn. Reson. Mater. Physics Biol. Med."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"800","DOI":"10.1021\/acscentsci.7b00253","article-title":"Nitroxide-Based Macromolecular Contrast Agents with Unprecedented Transverse Relaxivity and Stability for Magnetic Resonance Imaging of Tumors","volume":"3","author":"Nguyen","year":"2017","journal-title":"ACS Cent. Sci."},{"key":"ref_16","first-page":"139","article-title":"Nitroxyl Modified Tobacco Mosaic Virus as a Metal-Free High- Relaxivity MRI and EPR Active Superoxide Sensor","volume":"176","author":"Dharmarwardana","year":"2017","journal-title":"Physiol. Behav."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"8898","DOI":"10.1021\/la5007296","article-title":"Nitroxide-loaded hexosomes provide MRI contrast in vivo","volume":"30","author":"Bye","year":"2014","journal-title":"Langmuir"},{"key":"ref_18","first-page":"347","article-title":"Nitroxides as Cancer Imaging Agents","volume":"11","year":"2012","journal-title":"Anti-Cancer Agents Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"11343","DOI":"10.1021\/acsnano.8b06160","article-title":"Triply Loaded Nitroxide Brush-Arm Star Polymers Enable Metal-Free Millimetric Tumor Detection by Magnetic Resonance Imaging","volume":"12","author":"Nguyen","year":"2018","journal-title":"ACS Nano"},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Soikkeli, M., Horkka, K., Moilanen, J.O., Timonen, M., Kavakka, J., and Heikkinen, S. (2018). Synthesis, stability and relaxivity of teepo-met: An organic radical as a potential tumour targeting contrast agent for magnetic resonance imaging. Molecules, 23.","DOI":"10.3390\/molecules23051034"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"15507","DOI":"10.1039\/C4RA11455H","article-title":"Synthesis and in vitro phantom NMR and MRI studies of fully organic free radicals, TEEPO-glucose and TEMPO-glucose, potential contrast agents for MRI","volume":"5","author":"Soikkeli","year":"2015","journal-title":"RSC Adv."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1021\/bc00001a004","article-title":"Potential of Albumin Labeled with Nitroxides as a Contrast Agent for Magnetic Resonance Imaging and Spectroscopy","volume":"1","author":"Chan","year":"1990","journal-title":"Bioconjug. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Lee, H., Shahrivarkevishahi, A., Lumata, J.L., Luzuriaga, M.A., Hagge, L.M., Benjamin, C.E., Brohlin, O.R., Parish, C.R., Firouzi, H.R., and Nielsen, S.O. (2020). Chemical Science enhancement of metal-free magnetic resonance imaging contrast agents. Chem. Sci.","DOI":"10.26434\/chemrxiv.9640862"},{"key":"ref_24","unstructured":"Kocherginsky, N., and Swartz, H.M. (1995). Metabolism and Distribution of Nitroxides In Vivo. Nitroxide Spin Labels: Reactions in Biology and Chemistry, CRC Press."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/s41598-019-49370-z","article-title":"A new perspective on membrane-embedded Bax oligomers using DEER and bioresistant orthogonal spin labels","volume":"9","author":"Teucher","year":"2019","journal-title":"Sci. Rep."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"5322","DOI":"10.1021\/ol302506f","article-title":"Synthesis and reduction kinetics of sterically shielded pyrrolidine nitroxides","volume":"14","author":"Paletta","year":"2012","journal-title":"Org. Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"8016","DOI":"10.1021\/jo301235j","article-title":"Synthesis of 2,5-bis(spirocyclohexane)-substituted nitroxides of pyrroline and pyrrolidine series, including thiol-specific spin label: An analogue of MTSSL with long relaxation time","volume":"77","author":"Kirilyuk","year":"2012","journal-title":"J. Org. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1632","DOI":"10.1016\/j.freeradbiomed.2007.02.030","article-title":"The chemistry and biology of nitroxide compounds","volume":"42","author":"Soule","year":"2007","journal-title":"Free Radic. Biol. Med."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"15724","DOI":"10.1021\/ja3079829","article-title":"Organic Radical Contrast Agents for Magnetic Resonance Imaging","volume":"134","author":"Rajca","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"5249","DOI":"10.1039\/C4NR07591A","article-title":"Core-shell hybrid upconversion nanoparticles carrying stable nitroxide radicals as potential multifunctional nanoprobes for upconversion luminescence and magnetic resonance dual-modality imaging","volume":"7","author":"Chen","year":"2015","journal-title":"Nanoscale"},{"key":"ref_31","first-page":"139","article-title":"Polyoxazoline-Based Bottlebrush and Brush-Arm Star Polymers via ROMP: Syntheses and Applications as Organic Radical Contrast Agents","volume":"176","author":"Alvaradejo","year":"2017","journal-title":"Physiol. Behav."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5526","DOI":"10.1016\/j.bbagen.2013.04.023","article-title":"Albumin as a versatile platform for drug half-life extension","volume":"1830","author":"Sleep","year":"2013","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"511","DOI":"10.4155\/tde-2017-0038","article-title":"Albumin-based drug delivery using cysteine 34 chemical conjugates \u2013 important considerations and requirements","volume":"8","author":"Caspersen","year":"2017","journal-title":"Ther. Deliv"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/chem.201904587","article-title":"A Methanethiosulfonate Derivative of OX063 Trityl: A Promising and Efficient Reagent for SDSL of Proteins","volume":"26","author":"Tormyshev","year":"2020","journal-title":"Chem. A Eur. J."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"13271","DOI":"10.1002\/anie.201904152","article-title":"Triplet Fullerenes as Prospective Spin Labels for Nanoscale Distance Measurements by Pulsed Dipolar EPR","volume":"58","author":"Krumkacheva","year":"2019","journal-title":"Angew. Chemie Int. Ed."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/ncomms5740","article-title":"Selective chemical protein modification","volume":"5","author":"Spicer","year":"2014","journal-title":"Nat. Commun."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"4004","DOI":"10.1021\/jacs.7b12874","article-title":"Chemo- and Regioselective Lysine Modification on Native Proteins","volume":"140","author":"Matos","year":"2018","journal-title":"J. Am. Chem. Soc."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"11783","DOI":"10.1002\/anie.201405924","article-title":"Site-selective labeling of a lysine residue in human serum albumin","volume":"53","author":"Asano","year":"2014","journal-title":"Angew. Chemie Int. Ed."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4050","DOI":"10.1016\/j.bmcl.2011.04.119","article-title":"Synthesis and characterization of fluorinated homocysteine derivatives as potential molecular probes for 19F magnetic resonance spectroscopy and imaging","volume":"21","author":"Chubarov","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"3925","DOI":"10.1016\/j.bmcl.2017.05.084","article-title":"Multifunctional human serum albumin-therapeutic nucleotide conjugate with redox and pH-sensitive drug release mechanism for cancer theranostics","volume":"27","author":"Lisitskiy","year":"2017","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1007\/s00726-013-1617-7","article-title":"Identification of N-homocysteinylation sites in plasma proteins","volume":"46","author":"Sikora","year":"2014","journal-title":"Amino Acids"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"967","DOI":"10.1016\/j.jprot.2011.01.021","article-title":"Analysis of site-specific N-homocysteinylation of human serum albumin in vitro and in vivo using MALDI-ToF and LC-MS\/MS mass spectrometry","volume":"74","author":"Marczak","year":"2011","journal-title":"J. Proteomics"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"132","DOI":"10.1016\/j.ab.2010.04.034","article-title":"Direct monitoring of albumin lysine-525 N-homocysteinylation in human serum by liquid chromatography\/mass spectrometry","volume":"405","author":"Sikora","year":"2010","journal-title":"Anal. Biochem."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Pr\u00e4bst, K., Engelhardt, H., Ringgeler, S., and H\u00fcbner, H. (2017). Basic Colorimetric Proliferation Assays: MTT, WST, and Resazurin. Cell Viability Assays. Methods in Molecular Biology, Humana Press.","DOI":"10.1007\/978-1-4939-6960-9_1"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"55","DOI":"10.1016\/0022-1759(83)90303-4","article-title":"Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays","volume":"65","author":"Mosmann","year":"1983","journal-title":"J. Immunol. Methods"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"470","DOI":"10.1007\/s00018-003-3204-7","article-title":"Molecular basis of homocysteine toxicity in humans","volume":"61","author":"Jakubowski","year":"2004","journal-title":"Cell. Mol. Life Sci."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"6943","DOI":"10.1016\/j.bmc.2015.09.043","article-title":"Design of protein homocystamides with enhanced tumor uptake properties for 19F magnetic resonance imaging","volume":"23","author":"Chubarov","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"551","DOI":"10.1073\/pnas.0909737107","article-title":"Homocystamides promote free-radical and oxidative damage to proteins","volume":"107","author":"Escobedo","year":"2010","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Frank, D., Espeel, P., Claessens, S., Mes, E., and Du Prez, F.E. (2016). Synthesis of thiolactone building blocks as potential precursors for sustainable functional materials. Tetrahedron, 6\u201315.","DOI":"10.1016\/j.tet.2016.08.076"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1007\/12_2014_304","article-title":"One-pot double modification of polymers based on thiolactone chemistry","volume":"269","author":"Espeel","year":"2015","journal-title":"Adv. Polym. Sci."},{"key":"ref_51","unstructured":"Dobrynin, S.A., Khoroshunova, Y.V., and Kirilyuk, I.A. (2019). Synthesis of 2,2,5,5-tetraethyl-3-carboxypyrrolidine 1-oxyl. (2,702,331), RU. Patent No."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1877","DOI":"10.1055\/s-2008-1078526","article-title":"A novel method for the synthesis of N-alkoxyamines starting from nitroxide radicals and ketones","volume":"2008","author":"Dichtl","year":"2008","journal-title":"Synlett"},{"key":"ref_53","first-page":"3","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"5392","DOI":"10.1021\/acs.joc.8b00085","article-title":"Synthesis of 3,4-Bis(hydroxymethyl)-2,2,5,5-tetraethylpyrrolidin-1-oxyl via 1,3-Dipolar Cycloaddition of Azomethine Ylide to Activated Alkene","volume":"83","author":"Dobrynin","year":"2018","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3655","DOI":"10.1055\/s-0032-1317516","article-title":"Synthesis of nitroxide-annulated carbocycles and heterocycles","volume":"44","author":"Zsolnai","year":"2012","journal-title":"Synthesis"},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Kalai, T., Balog, M., Jek\u0151, J., and Hideg, K. (1999). Synthesis and reactions of a symmetric paramagnetic pyrrolidine diene. Synthesis, 973\u2013980.","DOI":"10.1055\/s-1999-3502"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"3612","DOI":"10.1016\/S0021-9258(19)34184-5","article-title":"The heterogeneity of bovine albumin with respect to sulfhydryl and dimer content","volume":"243","author":"Janatova","year":"1968","journal-title":"J. Biol. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1178","DOI":"10.1007\/s13361-011-0116-x","article-title":"Protein conformation and supercharging with DMSO from aqueous solution","volume":"22","author":"Sterling","year":"2011","journal-title":"J. Am. Soc. Mass Spectrom."},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"De Abreu Costa, L., Ottoni, M.H.F., Dos Santos, M.G., Meireles, A.B., De Almeida, V.G., De F\u00e1tima Pereira, W., De Avelar-Freitas, B.A., and Brito-Melo, G.E.A. (2017). Dimethyl sulfoxide (DMSO) decreases cell proliferation and TNF-\u03b1, IFN-, and IL-2 cytokines production in cultures of peripheral blood lymphocytes. Molecules, 22.","DOI":"10.3390\/molecules22111789"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"3246","DOI":"10.1021\/jo01046a528","article-title":"Oxidation of Thiols by Dimethyl Sulfoxide","volume":"28","author":"Yiannios","year":"1963","journal-title":"J. Org. Chem."},{"key":"ref_61","first-page":"11","article-title":"Interaction of L-cysteine with dimethyl sulfoxide in mild conditions","volume":"2","author":"Papanyan","year":"2013","journal-title":"Proc. Yerevan State Univ."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"561","DOI":"10.1007\/s00726-006-0432-9","article-title":"Mechanisms of homocysteine toxicity in humans","volume":"32","author":"Twardowski","year":"2007","journal-title":"Amino Acids"},{"key":"ref_63","doi-asserted-by":"crossref","unstructured":"Jakubowski, H. (2013). Homocysteine in Protein Structure\/Function and Human Disease, Springer.","DOI":"10.1007\/978-3-7091-1410-0"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1093\/protein\/4.6.669","article-title":"Convex constraint analysis: A natural deconvolution of circular dichroism curves of proteins","volume":"4","author":"Perczel","year":"1991","journal-title":"Protein Eng."},{"key":"ref_65","first-page":"218","article-title":"Assimilation, accommodation, and overaccommodation: An examination of information processing styles in female victims of adolescent and adult sexual assault","volume":"1","author":"Varkovitzky","year":"2012","journal-title":"ProQuest Diss. Theses"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"889","DOI":"10.1016\/j.jmb.2010.05.039","article-title":"Protein N-homocysteinylation induces the formation of toxic amyloid-like protofibrils","volume":"400","author":"Paoli","year":"2010","journal-title":"J. Mol. Biol."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"3316","DOI":"10.1093\/nar\/gkg565","article-title":"VADAR: A web server for quantitative evaluation of protein structure quality","volume":"31","author":"Willard","year":"2003","journal-title":"Nucleic Acids Res."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1021\/ct100578z","article-title":"PROPKA3: Consistent Treatment of Internal and Surface Residues in Empirical pKa Predictions","volume":"7","author":"Olsson","year":"2011","journal-title":"J. Chem. Theory Comput."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"2284","DOI":"10.1021\/ct200133y","article-title":"Improved treatment of ligands and coupling effects in empirical calculation and rationalization of pKa values","volume":"7","author":"Olsson","year":"2011","journal-title":"J. Chem. Theory Comput."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1088","DOI":"10.1126\/science.2160734","article-title":"Transmembrane protein structure: Spin labeling of bacteriorhodopsin mutants","volume":"248","author":"Altenbach","year":"1990","journal-title":"Science"},{"key":"ref_71","first-page":"299","article-title":"Easyspin: Simulating CW ESR spectra","volume":"27","author":"Stoll","year":"2007","journal-title":"Biol. Magn. Reson."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1016\/j.jmr.2005.08.013","article-title":"EasySpin, a comprehensive software package for spectral simulation and analysis in EPR","volume":"178","author":"Stoll","year":"2006","journal-title":"J. Magn. Reson."},{"key":"ref_73","doi-asserted-by":"crossref","unstructured":"Zhurko, I.F., Dobrynin, S., Gorodetskii, A.A., Glazachev, Y.I., Rybalova, T.V., Chernyak, E.I., Asanbaeva, N., Bagryanskaya, E.G., and Kirilyuk, I.A. (2020). 2-Butyl-2-tert-butyl-5,5-diethylpyrrolidine-1-oxyls: Synthesis and properties. Molecules, 25.","DOI":"10.3390\/molecules25040845"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"78","DOI":"10.3109\/10715762.2014.979409","article-title":"Sterically shielded spin labels for in-cell EPR spectroscopy: Analysis of stability in reducing environment","volume":"49","author":"Jagtap","year":"2015","journal-title":"Free Radic. Res."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"789","DOI":"10.1021\/ja028190w","article-title":"The role of oxoammonium cation in the SOD-mimic activity of cyclic nitroxides","volume":"125","author":"Goldstein","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"5460","DOI":"10.1038\/ncomms6460","article-title":"Redox-responsive branched-bottlebrush polymers for in vivo MRI and fluorescence imaging Molly","volume":"5","author":"Sowers","year":"2014","journal-title":"Nat Commun."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1016\/j.bmcl.2017.12.061","article-title":"Biotin-decorated anti-cancer nucleotide theranostic conjugate of human serum albumin: Where the seed meets the soil?","volume":"28","author":"Popova","year":"2018","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/s40591-016-0048-8","article-title":"Albumin-based drug delivery: Harnessing nature to cure disease","volume":"4","author":"Larsen","year":"2016","journal-title":"Mol. Cell. Ther."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"229","DOI":"10.2147\/IJGM.S102819","article-title":"Human serum albumin homeostasis: A new look at the roles of synthesis, catabolism, renal and gastrointestinal excretion, and the clinical value of serum albumin measurements","volume":"9","author":"Levitt","year":"2016","journal-title":"Int. J. Gen. Med."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/7\/1709\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T09:16:35Z","timestamp":1760174195000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/7\/1709"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,4,8]]},"references-count":79,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2020,4]]}},"alternative-id":["molecules25071709"],"URL":"https:\/\/doi.org\/10.3390\/molecules25071709","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,4,8]]}}}