Activity analysis of the carbodiimide-mediated amine coupling reaction on self-assembled monolayers by cyclic voltammetry

Electrochimica Acta

Volumn 89, Issue , 2013, Pages 616-622

  Liu, Lin ^a,b   Deng, Dehua ^a   Xing, Yun ^a   Li, Sujuan ^a   Yuan, Baiqing ^a   Chen, Jing ^a   Xia, Ning ^a,b  

^a ANYANG NORMAL UNIVERSITY   (China)

^b CENTRAL SOUTH UNIVERSITY   (China)

Author keywords

Amine coupling reaction; Carbodiimide; Cyclic voltammetry; N hydroxysulfosuccinimide; Self assembled monolayers

Indexed keywords

11-MERCAPTOUNDECANOIC ACID; ACTIVITY ANALYSIS; ACYLATION REACTIONS; AMINE COUPLING; AMINE GROUPS; AMINOLYSIS; AQUEOUS SYSTEM; CARBODIIMIDES; CARBOXYL GROUPS; COVALENT ATTACHMENT; ELECTRODE SURFACES; ELECTRON TRANSFER; ELECTRON-TRANSFER RESISTANCE; GOLD ELECTRODES; N-HYDROXYSULFOSUCCINIMIDE; NEGATIVELY CHARGED; OXIDATION REACTIONS; POSITIVELY CHARGED; REDOX PROBE; SAMS; SMALL MOLECULES; SOLUTION PH; VERSATILE METHODS;

ACYLATION; BIOSENSORS; CYCLIC VOLTAMMETRY; ELECTRON TRANSITIONS; ESTERIFICATION; ESTERS; NUCLEIC ACIDS; PROBES; SELF ASSEMBLED MONOLAYERS;

REACTION INTERMEDIATES;

EID: 84871387246     PISSN: 00134686     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.electacta.2012.11.049     Document Type: Article

References (34)

1. B.L. Frey, and R.M. Corn Covalent attachment and derivatization of poly(L-lysine) monolayers on gold surfaces as characterized by polarization-modulation FT-IR spectroscopy Analytical Chemistry 68 1996 3187
2. J. Dai, Z. Li, J. Jin, Y. Shi, J. Cheng, J. Kong, and S. Bi Some thoughts on the existence of ion and water channels in highly dense and well-ordered CH3-terminated alkanethiol self-assembled monolayers on gold Biosensors and Bioelectronics 24 2009 1074
3. Z. Li, T. Niu, Z. Zhang, and S. Bi Potential control characteristics of short-chain thiols of thioctic acid and mercaptohexanol self-assembled on gold Electrochimica Acta 55 2010 6907
4. J.C. Love, L.A. Estroff, J.K. Kriebel, R.G. Nuzzo, and G.M. Whitesides Self-assembled monolayers of thiolates on metals as a form of nanotechnology Chemical Reviews 105 2005 1103
5. D. Samanta, and A. Sarkar Immobilization of bio-macromolecules on self-assembled monolayers: methods and sensor applications Chemical Society Reviews 40 2011 2567
6. L. Liu, J. Du, S. Li, B. Yuan, H. Han, M. Jing, and N. Xia Amplified voltammetric detection of dopamine using ferrocene-capped gold nanoparticle/streptavidin conjugates Biosensors and Bioelectronics 2012 10.1016/j.bios.2012.09.061
7. J.C. Sheehan, and J.J. Hlaoka The use of water-soluble and basic carbodiimides in peptide synthesis Journal of Organic Chemistry 21 1956 439
8. N. Nakajima, and Y. Ikada Mechanism of amide formation by carbodiimide for bioconjugation in aqueous media Bioconjugate Chemistry 6 1995 123
9. L. Liu, S. Li, L. Liu, D. Deng, and N. Xia Simple, sensitive and selective detection of dopamine using dithiobis(succinimidylpropionate)-modified gold nanoparticles as colorimetric probes Analyst 137 2012 3794
10. M. Ligaj, J. Jasnowska, W.G. Musiał, and M. Filipiak Covalent attachment of single-stranded DNA to carbon paste electrode modified by activated carboxyl groups Electrochimica Acta 51 2006 5193
11. M.R. Lewis, A. Raubitschek, and J.E. Shively A facile, water-soluble method for modification of proteins with DOTA. Use of elevated temperature and optimized pH to achieve high specific activity and high chelate stability in radiolabeled immunoconjugates Bioconjugate Chemistry 5 1994 565
12. D. Sehgal, and I.K. Vijay A method for the high efficiency of water-soluble carbodiimide-mediated amidation Analytical Biochemistry 218 1994 87
13. J.V. Staros N-Hydroxysulfosuccinimide active esters: Bis(N- hydroxysulfosuccinimide) esters of two dicarboxylic acids are hydrophilic, membrane-impermeant, protein cross-link Biochemistry 21 1982 3950
14. E.J.M. Tournier, J. Wallach, and P. Blond Sulfosuccinimidyl 4-(N-maleimidomethyl)-1-cyclohexane carboxylate as a bifunctional immobilization agent. Optimization of the coupling conditions Analytica Chimica Acta 361 1998 33
15. J.M. Campiña, A. Martins, and F. Silva Immobilization of β-cyclodextrin on gold surfaces by chemical derivatization of an 11-amino-1-undecanthiol self-assembled monolayer Electrochimica Acta 55 2009 90
16. J.F. Cabrita, L.M. Abrantes, and A.S. Viana N-Hydroxysuccinimide- terminated self-assembled monolayers on gold for biomolecules immobilisation Electrochimica Acta 50 2005 2117
17. F. Wei, B. Sun, Y. Guo, and X.S. Zhao Monitoring DNA hybridization on alkyl modified silicon surface through capacitance measurement Biosensors and Bioelectronics 18 2003 1157
18. N. Patel, M.C. Davies, M. Hartshorne, R.J. Heaton, C.J. Roberts, S.J.B. Tendler, and P.M. Williams Immobilization of protein molecules onto homogeneous and mixed carboxylate-terminated self-assembled monolayers Langmuir 13 1997 6485
19. S. Sam, L. Touahir, J. Salvador Andresa, P. Allongue, J.-N. Chazalviel, A.C. Gouget-Laemmel, C. Henry de Villeneuve, A. Moraillon, F. Ozanam, N. Gabouze, and S. Djebbar Semiquantitative study of the EDC/NHS activation of acid terminal groups at modified porous silicon surfaces Langmuir 26 2010 809
20. S.-J. Xiao, S. Brunner, and M. Wieland Reactions of surface amines with heterobifunctional cross-linkers bearing both succinimidyl ester and maleimide for grafting biomolecules Journal of Physical Chemistry B 108 2004 16508
21. S. Herrwerth, T. Rosendahl, C. Feng, J. Fick, W. Eck, M. Himmelhaus, R. Dahint, and M. Grunze Covalent coupling of antibodies to self-assembled monolayers of carboxy-functionalized poly(ethyleneglycol): Protein resistance and specific binding of biomolecules Langmuir 19 2003 1880
22. Z. Pei, H. Anderson, A. Myrskog, G. Dunér, B. Ingemarsson, and T. Aastrup Optimizing immobilization on two-dimensional carboxyl surface: pH dependence of antibody orientation and antigen binding capacity Analytical Biochemistry 398 2010 161
23. J. Lahiri, L. Isaacs, J. Tien, and G.M. Whitesides A strategy for the generation of surfaces presenting ligands for studies of binding based on an active ester as a common reactive intermediate: A surface plasmon resonance study Analytical Chemistry 71 1999 777
24. A.A. Deckert, K.A. Anderson, K.M. Mullaugh, and C. Delaney Comprehensive study of the formation and reaction of a tethered N-hydroxysulfosuccinimidyl ester used to covalently tether proteins to surfaces Journal of Physical Chemistry B 108 2004 15808
25. J.A. Phelps, S. Morisse, M. Hindir, M.-C. Degat, E. Pauthe, and P.R. Van Tassel Nanofilm biomaterials: Localized cross-linking to optimize mechanical rigidity and bioactivity Langmuir 27 2011 1123
26. J. Dai, Z. Bao, L. Sun, S.U. Hong, G.L. Baker, and M.L. Bruening High-capacity binding of proteins by poly(acrylic acid) brushes and their derivatives Langmuir 22 2006 4274
27. G.H. Degenhart, B. Dordi, H. Schönherr, and G.J. Vancso Micro- and nanofabrication of robust reactive arrays based on the covalent coupling of dendrimers to activated monolayers Langmuir 20 2004 6216
28. L. Touahir, P. Allongue, D. Aureau, R. Boukherroub, J.-N. Chazalviel, E. Galopin, A.C. Gouget-Laemmel, C. Henry de Villeneuve, A. Moraillon, J. Niedziółka-Jönsson, F. Ozanam, J. Salvador Andresa, S. Sam, I. Solomon, and S. Szunerits Molecular monolayers on silicon as substrates for biosensors Bioelectrochemistry 80 2010 17
29. A. Moraillon, A.C. Gouget-Laemmel, F. Ozanam, and J.-N. Chazalviel Amidation of monolayers on silicon in physiological buffers: A quantitative IR study Journal of Physical Chemistry C 112 2008 7158
30. C. Wang, Q. Yan, H.-B. Liu, X.-H. Zhou, and S.-J. Xiao Different EDC/NHS activation mechanisms between PAA and PMAA brushes and the following amidation reactions Langmuir 27 2011 12058
31. A.J. Bard, L.R. Faulkner, Electrochemical Methods: Fundamentals and Applications, Wiley, New York, 2001.
32. L.V. Protsailo, and W.R. Fawcett Studies of electron transfer through self-assembled monolayers using impedance spectroscopy Electrochimica Acta 45 2000 3497
33. S.-J. Ding, B.-W. Chang, C.-C. Wu, M.-F. Lai, and H.-C. Chang Electrochemical evaluation of avidin-biotin interaction on self-assembled gold electrodes Electrochimica Acta 50 2005 3660
34. 3+ and ferrocene dimethanol Electrochimica Acta 39 1994 817