{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,16]],"date-time":"2026-03-16T03:06:12Z","timestamp":1773630372603,"version":"3.50.1"},"reference-count":59,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2024,10,29]],"date-time":"2024-10-29T00:00:00Z","timestamp":1730160000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["22-13-00293"],"award-info":[{"award-number":["22-13-00293"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Antibodies"],"abstract":"<jats:p>When developing immunochemical test systems, it is necessary to obtain specific antibodies. Their quality depends, among other things, on the immunogen used. When preparing hapten\u2013protein conjugates to obtain antibodies for low-molecular-weight compounds, the key factors are the structure of the hapten itself, the presence of a spacer, the size of the carrier protein and the degree of its modification by hapten molecules. This work shows that one additional factor\u2014the conditions for obtaining the hapten\u2013protein conjugate\u2014is overlooked. In this work, we have synthesized conjugates of bisphenol A derivative 4,4-bis(hydroxyphenyl)valeric acid (BVA), the protein carrier soybean trypsin inhibitor (STI), and bovine serum albumin (BSA) in reaction media combining water with two organic solvents: dimethylformamide (DMF) or dimethyl sulfoxide (DMSO). Namely, BSADMF\u2013BVA, STIDMF\u2013BVA, BSADMSO\u2013BVA and STIDMSO\u2013BVA conjugates were obtained. Rabbit polyclonal antibodies against the BSADMF\u2013BVA conjugate demonstrated basically different interactions in the developed ELISA systems using either STIDMF\u2013BVA or STIDMSO\u2013BVA conjugates. The use of the STIDMF\u2013BVA conjugate demonstrated the absence of competition in combination with antisera obtained from BSADMF\u2013BVA in an ELISA. A competitive interaction was observed only with the use of the STIDMSO\u2013BVA conjugate. Under the selected conditions, the detection limit of bisphenol A was 8.3 ng\/mL, and the working range of determined concentrations was 18.5\u2013290.3 ng\/mL. The obtained data demonstrate the possibility of achieving sensitive immunoassays by simply varying the reaction media for the hapten\u2013protein conjugation, which could provide an additional tool in the development of immunoassays for other low-molecular-weight compounds.<\/jats:p>","DOI":"10.3390\/antib13040089","type":"journal-article","created":{"date-parts":[[2024,10,29]],"date-time":"2024-10-29T06:29:57Z","timestamp":1730183397000},"page":"89","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Comparison of Conjugates Obtained Using DMSO and DMF as Solvents in the Production of Polyclonal Antibodies and ELISA Development: A Case Study on Bisphenol A"],"prefix":"10.3390","volume":"13","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3761-7472","authenticated-orcid":false,"given":"Anna N.","family":"Berlina","sequence":"first","affiliation":[{"name":"A.N. Bach Institute of Biochemistry, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect 33, 119071 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nadezhda S.","family":"Komova","sequence":"additional","affiliation":[{"name":"A.N. Bach Institute of Biochemistry, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect 33, 119071 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kseniya V.","family":"Serebrennikova","sequence":"additional","affiliation":[{"name":"A.N. Bach Institute of Biochemistry, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect 33, 119071 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3008-2839","authenticated-orcid":false,"given":"Anatoly V.","family":"Zherdev","sequence":"additional","affiliation":[{"name":"A.N. Bach Institute of Biochemistry, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect 33, 119071 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4008-4918","authenticated-orcid":false,"given":"Boris B.","family":"Dzantiev","sequence":"additional","affiliation":[{"name":"A.N. Bach Institute of Biochemistry, Research Center of Biotechnology of the Russian Academy of Sciences, Leninsky Prospect 33, 119071 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,10,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"10944","DOI":"10.1021\/acs.jafc.0c04333","article-title":"Influence of small molecular property on antibody response","volume":"68","author":"Wen","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Berlina, A.N., Komova, N.S., Serebrennikova, K.V., Zherdev, A.V., and Dzantiev, B.B. (2024). Determination of Nonylphenol in a Highly Sensitive Chemiluminescent Immunoenzyme Assay of Natural Waters. Appl. Sci., 14.","DOI":"10.3390\/app14051685"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"268","DOI":"10.1080\/09540105.2019.1707171","article-title":"Current advances in immunoassays for the detection of antibiotics residues: A review","volume":"31","author":"Ahmed","year":"2020","journal-title":"Food Agric. Immunol."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"116087","DOI":"10.1016\/j.trac.2020.116087","article-title":"Recent advances of lateral flow immunoassay for mycotoxins detection","volume":"133","author":"Xing","year":"2020","journal-title":"TrAC Trends Anal. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1016\/j.tifs.2021.02.045","article-title":"Developmental trend of immunoassays for monitoring hazards in food samples: A review","volume":"111","author":"Xiao","year":"2021","journal-title":"Trends Food Sci. Technol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2000267","DOI":"10.1002\/pmic.202000267","article-title":"Drug hapten-specific T-cell activation: Current status and unanswered questions","volume":"21","author":"Adair","year":"2021","journal-title":"Proteomics"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1111\/imr.12889","article-title":"Modulation of immune responses using adjuvants to facilitate therapeutic vaccination","volume":"296","author":"Schijns","year":"2020","journal-title":"Immunol. Rev."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"956","DOI":"10.1021\/acs.bioconjchem.0c00099","article-title":"Click chemistry-assisted bioconjugates for hapten immunodiagnostics","volume":"31","author":"Mercader","year":"2020","journal-title":"Bioconj. Chem."},{"key":"ref_9","unstructured":"Hermanson, G.T. (2008). Bioconjugate Techniques, Academic Press. [2nd ed.]."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1002\/ieam.4611","article-title":"An overview of the occurrence, fate, and human risks of the bisphenol-A present in plastic materials, components, and products","volume":"19","author":"Hahladakis","year":"2023","journal-title":"Integr. Environ. Assess. Manag."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Nagarajan, M., Maadurshni, G.B., and Manivannan, J. (2023). Exposure to low dose of Bisphenol A (BPA) intensifies kidney oxidative stress, inflammatory factors expression and modulates Angiotensin II signaling under hypertensive milieu. J. Biochem. Mol. Toxicol., 38.","DOI":"10.1002\/jbt.23533"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1439","DOI":"10.1002\/etc.5633","article-title":"Studies of Endocrine Disruptors: Nonylphenol and Isomers in Biological Models","volume":"42","year":"2023","journal-title":"Environ. Toxicol. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"132","DOI":"10.1016\/j.reprotox.2013.08.008","article-title":"Bisphenol A and human health: A review of the literature","volume":"42","author":"Rochester","year":"2013","journal-title":"Reprod. Toxicol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/j.aca.2004.06.066","article-title":"Biosensor immunoassays for the detection of bisphenol A","volume":"528","author":"Marchesini","year":"2005","journal-title":"Anal. Chim. Acta"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1570","DOI":"10.1039\/c3ay26220k","article-title":"An indirect competitive enzyme-linked immunosorbent assay for bisphenol-A based on the synthesis of a poly-l-lysine\u2013hapten conjugate as a coating antigen","volume":"5","author":"Zhou","year":"2013","journal-title":"Anal. Methods"},{"key":"ref_16","first-page":"509","article-title":"Development of monoclonal antibody-based immunoassays for the analysis of bisphenol A in canned vegetables","volume":"46","author":"Moreno","year":"2011","journal-title":"J. Environ. Sci. Health Part B"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Sun, Y., Zhang, H., Shi, J., Zhang, Z., and Gong, R. (2017). Identification of a novel inhibitor against Middle East respiratory syndrome coronavirus. Viruses, 9.","DOI":"10.3390\/v9090255"},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Berlina, A.N., Ragozina, M.Y., Gusev, D.I., Zherdev, A.V., and Dzantiev, B.B. (2023). Development of Chemiluminescent ELISA for Detection of Diisobutyl Phthalate in Water, Lettuce and Aquatic Organisms. Chemosensors, 11.","DOI":"10.3390\/chemosensors11070393"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"9826","DOI":"10.1016\/S0021-9258(19)68702-8","article-title":"Amino acid sequence adjacent to a sulfhydryl group exposed on illumination of bovine rhodopsin","volume":"256","author":"Khatami","year":"1981","journal-title":"J. Biol. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"328","DOI":"10.1016\/0003-2697(66)90275-2","article-title":"Determination of free amino groups in proteins by trinitrobenzenesulfonic acid","volume":"14","author":"Habeeb","year":"1966","journal-title":"Anal. Biochem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1278","DOI":"10.1107\/S0907444912027047","article-title":"Structures of bovine, equine and leporine serum albumin","volume":"68","author":"Bujacz","year":"2012","journal-title":"Acta Crystallogr. Sect. D Biol. Crystallogr."},{"key":"ref_22","unstructured":"PDB. Protein Data Bank (2024, October 23). Crystal Structure of a Potato Sti-Kunitz Bifunctional Inhibitor of Serine and Aspartic Proteases in Space Group P4322 AND PH 7.4. Available online: https:\/\/www.rcsb.org\/sequence\/5G00#A."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"880","DOI":"10.1016\/j.ijbiomac.2020.05.260","article-title":"Comparative study of the protein denaturing ability of different organic cosolvents","volume":"160","author":"Magsumov","year":"2020","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1177\/1087057105284218","article-title":"DMSO-related effects in protein characterization","volume":"11","author":"Tjernberg","year":"2006","journal-title":"SLAS Discov."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"54","DOI":"10.1016\/j.carbon.2016.09.064","article-title":"Diamond\/carbon nanotube composites: Raman, FTIR and XPS spectroscopic studies","volume":"111","author":"Varga","year":"2017","journal-title":"Carbon"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1016\/j.jim.2008.10.011","article-title":"Preparation and characterization of bisphenol A-cationized bovine serum albumin","volume":"340","author":"Feng","year":"2009","journal-title":"J. Immunol. Methods"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1111\/j.1745-7270.2007.00320.x","article-title":"Fourier transform infrared spectroscopic analysis of protein secondary structures","volume":"39","author":"Kong","year":"2007","journal-title":"Acta Biochim. Biophys. Sin."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3575","DOI":"10.1016\/j.watres.2009.05.010","article-title":"UV-VIS and FTIR spectroscopic analyses of inclusion complexes of nonylphenol and nonylphenol ethoxylate with \u03b2-cyclodextrin","volume":"43","author":"Bonenfant","year":"2009","journal-title":"Water Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1222","DOI":"10.1016\/j.jlumin.2011.02.009","article-title":"Complexes between CI Acid Orange 6 and human serum albumin, a multi-spectroscopic approach to investigate the binding behavior","volume":"131","author":"Zhou","year":"2011","journal-title":"J. Lumin."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1021\/bm1011568","article-title":"Phenotypic characterization of the binding of tetracycline to human serum albumin","volume":"12","author":"Chi","year":"2011","journal-title":"Biomacromolecules"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"4201","DOI":"10.1529\/biophysj.106.093187","article-title":"Resurrecting abandoned proteins with pure water: CD and NMR studies of protein fragments solubilized in salt-free water","volume":"91","author":"Li","year":"2006","journal-title":"Biophys. J."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2745","DOI":"10.1529\/biophysj.105.074401","article-title":"Kinetics and thermodynamics of type VIII \u03b2-turn formation: A CD, NMR, and microsecond explicit molecular dynamics study of the GDNP tetrapeptide","volume":"90","author":"Fuchs","year":"2006","journal-title":"Biophys. J."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"111590","DOI":"10.1016\/j.msec.2020.111590","article-title":"Thermoresponsive BSA hydrogels with phase tunability","volume":"119","author":"Khanna","year":"2021","journal-title":"Mater. Sci. Eng. C"},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Borzova, V.A., Markossian, K.A., Chebotareva, N.A., Kleymenov, S.Y., Poliansky, N.B., Muranov, K.O., Stein-Margolina, V.A., Shubin, V.V., Markov, D.I., and Kurganov, B.I. (2016). Kinetics of thermal denaturation and aggregation of bovine serum albumin. PLoS ONE, 11.","DOI":"10.1371\/journal.pone.0153495"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"5394","DOI":"10.1016\/j.bbagen.2013.05.017","article-title":"Binding, unfolding and refolding dynamics of serum albumins","volume":"1830","author":"Anand","year":"2013","journal-title":"Biochim. Biophys. Acta (BBA)-Gen. Subj."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"2716","DOI":"10.1016\/j.jlumin.2011.07.011","article-title":"Fluorescence spectrometric studies on the binding of puerarin to human serum albumin using warfarin, ibuprofen and digitoxin as site markers with the aid of chemometrics","volume":"131","author":"Zhang","year":"2011","journal-title":"J. Lumin."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1016\/j.tca.2012.08.016","article-title":"Spectroscopic and isothermal titration calorimetry studies of binding interaction of ferulic acid with bovine serum albumin","volume":"548","author":"Ojha","year":"2012","journal-title":"Thermochim. Acta"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1016\/j.ijbiomac.2021.02.112","article-title":"Heat-induced self-assembling of BSA at the isoelectric point","volume":"177","author":"Comez","year":"2021","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Zhang, Y., Liu, R., Li, H., Li, Y., and Liu, X. (2023). Interactions between Soybean Trypsin Inhibitor and Chitosan in an Aqueous Solution. Polymers, 15.","DOI":"10.3390\/polym15071594"},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Luo, S., Chen, T., Liu, C., Zou, C., and Chen, C. (2011, January 10\u201312). Structural and immunogenic effect of complete antigen linked by different spacer arm. Proceedings of the 2011 5th International Conference on Bioinformatics and Biomedical Engineering, Wuhan, China.","DOI":"10.1109\/icbbe.2011.5781532"},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Kumar, D., Oberoi, H.S., Singh, H., Shrivastav, T.G., Bhukya, P.L., Kumari, M., Koner, B.C., and Sonkar, S.C. (2023). Development and optimization of an in-house heterologous ELISA for detection of prednisolone drug in enzyme conjugates using spacers. Front. Immunol., 14.","DOI":"10.3389\/fimmu.2023.1200328"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"4246","DOI":"10.1039\/C5AY00818B","article-title":"A fluorescence polarization immunoassay method for detection of the bisphenol A residue in environmental water samples based on a monoclonal antibody and 4\u2032-(aminomethyl) fluorescein","volume":"7","author":"Huang","year":"2015","journal-title":"Anal. Methods"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1108\/PRT-03-2017-0022","article-title":"A highly sensitive and quantitative detection method for bisphenol A (BPA) by competitive immunoassay based on surface-enhanced Raman spectroscopy","volume":"47","author":"Lei","year":"2018","journal-title":"Pigment Resin Technol."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Raysyan, A., Zwigart, S.D., Eremin, S.A., and Schneider, R.J. (2023). BPA Endocrine Disruptor Detection at the Cutting Edge: FPIA and ELISA Immunoassays. Biosensors, 13.","DOI":"10.3390\/bios13060664"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Sotnikov, D.V., Zherdev, A.V., Zvereva, E.A., Eremin, S.A., and Dzantiev, B.B. (2021). Changing cross-reactivity for different immunoassays using the same antibodies: Theoretical description and experimental confirmation. Appl. Sci., 11.","DOI":"10.3390\/app11146581"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"520","DOI":"10.1021\/jf970438r","article-title":"Development of immunoassays for type II synthetic pyrethroids. 1. Hapten design and application to heterologous and homologous assays","volume":"46","author":"Lee","year":"1998","journal-title":"J. Agric. Food Chem."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"8296","DOI":"10.1021\/ac5017437","article-title":"Heterologous antigen selection of camelid heavy chain single domain antibodies against tetrabromobisphenol A","volume":"86","author":"Wang","year":"2014","journal-title":"Anal. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","unstructured":"Burkin, M.A., Galvidis, I.A., and Eremin, S.A. (2019). Specific and generic immunorecognition of glycopeptide antibiotics promoted by unique and multiple orientations of hapten. Biosensors, 9.","DOI":"10.3390\/bios9020052"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"5718","DOI":"10.1039\/C8AN01771A","article-title":"Combined heterologies for monoclonal antibody-based immunoanalysis of fluxapyroxad","volume":"143","author":"Mercader","year":"2018","journal-title":"Analyst"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/S0003-2670(98)00826-5","article-title":"Effect of competitor design on immunoassay specificity: Development and evaluation of an enzyme-linked immunosorbent assay for 2,4-dinitrophenol","volume":"387","author":"Marco","year":"1999","journal-title":"Anal. Chim. Acta"},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Wang, J., Shen, X., Zhong, P., Li, Z., Tang, Q., Huang, X., Zherdev, A.V., Dzantiev, B.B., Eremin, S.A., and Xiao, Z. (2021). Heterologous immunoassay strategy for enhancing detection sensitivity of banned dye rhodamine B in fraudulent food. Chem. Biol. Technol. Agric., 8.","DOI":"10.1186\/s40538-021-00211-0"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"7616","DOI":"10.1016\/j.tet.2009.06.109","article-title":"Formation of DMSO and DMF radicals with minute amounts of base","volume":"65","author":"Sliwka","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1007\/s00894-016-3022-0","article-title":"Cooperativity of intermolecular hydrogen bonds in microsolvated DMSO and DMF clusters: A DFT, AIM, and NCI analysis","volume":"22","author":"Venkataramanan","year":"2016","journal-title":"J. Mol. Model."},{"key":"ref_54","doi-asserted-by":"crossref","unstructured":"Zou, Z., Dai, L., Liu, D., and Du, W. (2021). Research Progress in Enzymatic Synthesis of Vitamin E Ester Derivatives. Catalysts, 11.","DOI":"10.3390\/catal11060739"},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Yuan, P., Xiang, J.-C., and Wu, A.-X. (2024). Recent Achievements in Organic Reactions in DMSO. Green Solvents in Organic Synthesis, Wiley.","DOI":"10.1002\/9783527841943.ch4"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"11664","DOI":"10.1021\/ja9045839","article-title":"Catalytic Asymmetric Synthesis of Chiral Tertiary Organoboronic Esters through Conjugate Boration of \u03b2-Substituted Cyclic Enones","volume":"131","author":"Chen","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1060","DOI":"10.31635\/ccschem.023.202302999","article-title":"Synthesis of unprotected \u03b1-tertiary amines and 1, 2-amino alcohols from vinyl azides by light induced denitrogenative alkylarylation\/dialkylation","volume":"6","author":"Li","year":"2024","journal-title":"CCS Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"3312","DOI":"10.1039\/D1GC00604E","article-title":"Replacing DMF in solid-phase peptide synthesis: Varying the composition of green binary solvent mixtures as a tool to mitigate common side-reactions","volume":"23","author":"Jadhav","year":"2021","journal-title":"Green Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"5927","DOI":"10.1007\/s00216-014-8035-x","article-title":"Characterization and optimization of heroin hapten-BSA conjugates: Method development for the synthesis of reproducible hapten-based vaccines","volume":"406","author":"Torres","year":"2014","journal-title":"Anal. Bioanal. Chem."}],"container-title":["Antibodies"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/2073-4468\/13\/4\/89\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:22:52Z","timestamp":1760113372000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/2073-4468\/13\/4\/89"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,10,29]]},"references-count":59,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2024,12]]}},"alternative-id":["antib13040089"],"URL":"https:\/\/doi.org\/10.3390\/antib13040089","relation":{},"ISSN":["2073-4468"],"issn-type":[{"value":"2073-4468","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,10,29]]}}}