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Molecules 2017, 22(11), 1970; doi:10.3390/molecules22111970

Design, Synthesis, and Use of Peptides Derived from Human Papillomavirus L1 Protein for the Modification of Gold Electrode Surfaces by Self-Assembled Monolayers

1
Department of Pharmacy, Universidad Nacional de Colombia, Carrera 45 No 26-85, Building 450, Office 213, 11321 Bogotá, Colombia
2
Department of Chemistry, Universidad Nacional de Colombia, Carrera 45 No 26-85, Building 450, Office 334, 11321 Bogotá, Colombia
3
Department of Research, Centro de Investigación y Desarrollo Tecnológico en Electroquímica, S.C., Parque Tecnológico Querétaro, Sanfandila, Pedro Escobedo, 76703 Querétaro, Mexico
*
Author to whom correspondence should be addressed.
Received: 29 October 2017 / Revised: 10 November 2017 / Accepted: 10 November 2017 / Published: 14 November 2017
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Abstract

In order to obtain gold electrode surfaces modified with Human Papillomavirus L1 protein (HPV L1)-derived peptides, two sequences, SPINNTKPHEAR and YIK, were chosen. Both have been recognized by means of sera from patients infected with HPV. The molecules, Fc-Ahx-SPINNTKPHEAR, Ac–C–Ahx-(Fc)KSPINNTKPHEAR, Ac–C–Ahx-SPINNTKPHEAR(Fc)K, C–Ahx–SPINNTKPHEAR, and (YIK)2Ahx–C, were designed, synthesized, and characterized. Our results suggest that peptides derived from the SPINNTKPHEAR sequence, containing ferrocene and cysteine residues, are not stable and not adequate for electrode surface modification. The surface of polycrystalline gold electrodes was modified with the peptides C-Ahx-SPINNTKPHEAR or (YIK)2-Ahx-C through self-assembly. The modified polycrystalline gold electrodes were characterized via infrared spectroscopy and electrochemical measurements. The thermodynamic parameters, surface coverage factor, and medium pH effect were determined for these surfaces. The results indicate that surface modification depends on the peptide sequence (length, amino acid composition, polyvalence, etc.). The influence of antipeptide antibodies on the voltammetric response of the modified electrode was evaluated by comparing results obtained with pre-immune and post-immune serum samples. View Full-Text
Keywords: modified gold electrodes; self-assembled monolayer; synthetic peptides; ferrocene motif modified gold electrodes; self-assembled monolayer; synthetic peptides; ferrocene motif
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Lara Carrillo, J.A.; Fierro Medina, R.; Manríquez Rocha, J.; Bustos Bustos, E.; Insuasty Cepeda, D.S.; García Castañeda, J.E.; Rivera Monroy, Z.J. Design, Synthesis, and Use of Peptides Derived from Human Papillomavirus L1 Protein for the Modification of Gold Electrode Surfaces by Self-Assembled Monolayers. Molecules 2017, 22, 1970.

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