{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,19]],"date-time":"2026-10-19T19:43:41Z","timestamp":1792439021987,"version":"4.5.0"},"reference-count":66,"publisher":"American Chemical Society (ACS)","issue":"43","license":[{"start":{"date-parts":[[2015,10,15]],"date-time":"2015-10-15T00:00:00Z","timestamp":1444867200000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000110","name":"Nanotechnology Initiative","doi-asserted-by":"publisher","award":["IGERT NSF DGE-0903715"],"award-info":[{"award-number":["IGERT NSF DGE-0903715"]}],"id":[{"id":"10.13039\/100000110","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000272","name":"National Institute for Health Research","doi-asserted-by":"publisher","award":["R33CA155586"],"award-info":[{"award-number":["R33CA155586"]}],"id":[{"id":"10.13039\/501100000272","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000272","name":"National Institute for Health Research","doi-asserted-by":"publisher","award":["U01CA151650"],"award-info":[{"award-number":["U01CA151650"]}],"id":[{"id":"10.13039\/501100000272","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2014,11,4]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>N-Hydroxysuccinimide (NHS) ester terminal groups are commonly used to covalently couple amine-containing biomolecules (e.g., proteins and peptides) to surfaces via amide linkages. This one-step aminolysis is often performed in buffered aqueous solutions near physiological pH (pH 6 to pH 9). Under these conditions, the hydrolysis of the ester group competes with the amidization process, potentially degrading the efficiency of the coupling chemistry. The work herein examines the efficiency of covalent protein immobilization in borate buffer (50 mM, pH 8.50) using the thiolate monolayer formed by the chemisorption of dithiobis (succinimidyl propionate) (DSP) on gold films. The structure and reactivity of these adlayers are assessed via infrared spectroscopy (IR), X-ray photoelectron spectroscopy (XPS), electrochemical reductive desorption, and contact angle measurements. The hydrolysis of the DSP-based monolayer is proposed to follow a reaction mechanism with an initial nucleation step, in contrast to a simple pseudo first-order reaction rate law for the entire reaction, indicating a strong dependence of the interfacial reaction on the packing and presence of defects in the adlayer. This interpretation is used in the subsequent analysis of IR-ERS kinetic plots which give a heterogeneous aminolysis rate constant, ka, that is over 3 orders of magnitude lower than that of the heterogeneous hydrolysis rate constant, kh. More importantly, a projection of these heterogeneous kinetic rates to protein immobilization suggests that under coupling conditions in which low protein concentrations and buffers of near physiological pH are used, proteins are more likely physically adsorbed rather than covalently linked. This result is paramount for biosensors that use NHS chemistry for protein immobilization due to effects that may arise from noncovalently linked proteins.<\/jats:p>","DOI":"10.1021\/la503439g","type":"journal-article","created":{"date-parts":[[2014,10,15]],"date-time":"2014-10-15T16:37:39Z","timestamp":1413391059000},"page":"12868-12878","source":"Crossref","is-referenced-by-count":160,"title":["Succinimidyl Ester Surface Chemistry: Implications\nof the Competition between Aminolysis and Hydrolysis on Covalent Protein\nImmobilization"],"prefix":"10.1021","volume":"30","author":[{"given":"China Y.","family":"Lim","sequence":"first","affiliation":[{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicholas A.","family":"Owens","sequence":"additional","affiliation":[{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ronald D.","family":"Wampler","sequence":"additional","affiliation":[{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yixin","family":"Ying","sequence":"additional","affiliation":[{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jennifer H.","family":"Granger","sequence":"additional","affiliation":[{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marc D.","family":"Porter","sequence":"additional","affiliation":[{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]},{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]},{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]},{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]},{"name":"University of Utah , and the, , , ,","place":["Salt Lake City, Utah, United States, 84112"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Makoto","family":"Takahashi","sequence":"additional","affiliation":[{"name":"Hokkaido University , , ,","place":["Sapporo, Japan, 060-0810"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katsuaki","family":"Shimazu","sequence":"additional","affiliation":[{"name":"Hokkaido University , , ,","place":["Sapporo, Japan, 060-0810"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,10,15]]},"reference":[{"key":"2026090315013465100_cit1","doi-asserted-by":"crossref","first-page":"9618","DOI":"10.1002\/anie.200801711","article-title":"Chemical Strategies\nfor Generating Protein Biochips","volume":"47","author":"Jonkheijm","year":"2008","journal-title":"Angew. Chem.,\nInt. 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J."},{"key":"2026090315013465100_cit6","doi-asserted-by":"crossref","first-page":"1001","DOI":"10.1039\/b708461g","article-title":"SERS as a\nbioassay platform: fundamentals, design, and applications","volume":"37","author":"Porter","year":"2008","journal-title":"Chem. Soc. Rev."},{"key":"2026090315013465100_cit7","doi-asserted-by":"crossref","first-page":"2811","DOI":"10.1039\/c0an00354a","article-title":"Competitive surface-enhanced\nRaman scattering assay for the 1,25-dihydroxy metabolite of vitamin\nD3","volume":"135","author":"Dufek","year":"2010","journal-title":"Analyst"},{"key":"2026090315013465100_cit8","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1016\/0022-2836(76)90011-5","article-title":"Chemical probes of extended biological\nstructures:\nSynthesis and properties of the cleavable protein cross-linking reagent\n[35S]dithiobis(succinimidyl propionate)","volume":"104","author":"Lomant","year":"1976","journal-title":"J. Mol. 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Protein Res."},{"key":"2026090315013465100_cit15","doi-asserted-by":"crossref","first-page":"547","DOI":"10.1016\/S0956-5663(03)00274-4","article-title":"Novel biosensor\nchip for simultaneous detection of DNA-carcinogen adducts with low-temperature\nfluorescence","volume":"19","author":"Grubor","year":"2004","journal-title":"Biosens. Bioelectron."},{"key":"2026090315013465100_cit16","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1021\/la202967t","article-title":"Nanomolar Hydrogen Peroxide Detection Using Horseradish\nPeroxidase Covalently Linked to Undoped Nanocrystalline Diamond Surfaces","volume":"28","author":"Wang","year":"2012","journal-title":"Langmuir"},{"key":"2026090315013465100_cit17","doi-asserted-by":"crossref","first-page":"5530","DOI":"10.1021\/ac990759x","article-title":"Dithiobissuccinimidyl\nPropionate as an Anchor for Assembling Peroxidases at Electrodes Surfaces\nand Its Application in a H2O2 Biosensor","volume":"71","author":"Darder","year":"1999","journal-title":"Anal. 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