Abstract
Reduction or removal of solvents and reagents in protein sample preparation is a requirement. Dendrimers can strongly interact with proteins and have great potential as a greener alternative to conventional methods used in protein sample preparation. This work proposes the use of single-walled carbon nanotubes (SWCNTs) functionalized with carbosilane dendrons with sulfonate groups for protein sample preparation and shows the successful application of the proposed methodology to extract proteins from a complex matrix. SEM images of nanotubes and mixtures of nanotubes and proteins were taken. Moreover, intrinsic fluorescence intensity of proteins was monitored to observe the most significant interactions at increasing dendron generations under neutral and basic pHs. Different conditions for the disruption of interactions between proteins and nanotubes after protein extraction and different concentrations of the disrupting reagent and the nanotube were also tried. Compatibility of extraction and disrupting conditions with the enzymatic digestion of proteins for obtaining bioactive peptides was also studied. Finally, sulfonate-terminated carbosilane dendron-coated SWCNTs enabled the extraction of proteins from a complex sample without using non-environmentally friendly solvents that were required so far.
Similar content being viewed by others
References
Armenta S, Garrigues S, de la Guardia M. Green analytical chemistry. Trac-Trends Anal Chem. 2008;27:497–511.
Wang W, Tai F, Chen S. Optimizing protein extraction from plant tissues for enhanced proteomics analysis. J Sep Sci. 2008;31:2032–9.
Ward WW, Swiatek G. Protein purification. Curr Anal Chem. 2009;5:85–105.
Kalhapure RS, Kathiravan MK, Akamanchi KG, Govender T. Dendrimers—from organic synthesis to pharmaceutical applications: an update. Pharm Dev Technol. 2015;20:22–40.
Martinho N, Florindo H, Silva L, Brocchini S, Zloh M, Barata T. Molecular modeling to study dendrimers for biomedical applications. Molecules. 2014;19:20424–67.
Bravo-Osuna I, Vicario-de-la-Torre M, Andrés-Guerrero V, Sánchez-Nieves J, Guzmán-Navarro M, de la Mata FJ, Gómez R, de las Heras B, Argueso P, Ponchel G, Herrero-Vanrell R, Molina-Martínez IT. Novel water-soluble muco adhesive carbosilane dendrimers for ocular administration. Mol Pharm. 2016;13:2966–76.
Hatano K, Matsuoka K, Terunuma D. Carbosilane glycodendrimers. Chem Soc Rev. 2013;42:4574–98.
González-García E, Maly M, de la Mata FJ, Gómez R, Marina ML, García MC. Factors affecting interactions between sulphonate-terminated dendrimers and proteins: a three case study. Colloid Surf B-Biointerfaces. 2017;149:196–205.
González-García E, Maly M, de la Mata FJ, Gómez R, Marina ML, García MC. Proof of concept of a “greener” protein purification/enrichment method based on carboxylate-terminated carbosilane dendrimer–protein interactions. Anal Bioanal Chem. 2016;408:7679–87.
Vichchulada P, Lipscomb LD, Zhang Q, Lay MDJ. Incorporation of single-walled carbon nanotubes into functional sensor applications. Nanosci Nanotechnol. 2009;9:2189–200.
Abdalla S, Al-Marzouki F, Al-Ghamdi AA, Abdel-Daiem A. Different technical applications of carbon nanotubes. Nanoscale Res Lett. 2015;10:358.
Liang F, Chen B. A review on biomedical applications of single-walled carbon nanotubes. Curr Med Chem. 2010;17:10–24.
Li L, Lin R, He H, Sun M, Jiang L, Gao M. Interaction of amidated single-walled carbon nanotubes with protein by multiple spectroscopic methods. J Lumin. 2014;145:125–31.
Morikawa M, Kuboki Y, Akasaka T, Abe S, Takita H, Watari F. Adsorption behavior of albumin and other proteins on carbon nanotubes studied by chromatography. Bioceramics 24. 2013;529-530:615–20.
Horn DW, Tracy K, Easley CJ, Davis VA. Lysozyme dispersed single-walled carbon nanotubes: interaction and activity. J Phys Chem C. 2012;116:10341–8.
Du J, Ge C, Lu Y, Bai R, Li D, Yang Y, Liao L, Chen CJ. The interaction of serum proteins with carbon nanotubes depend on the physicochemical properties of nanotubes. Nanosci Nanotechnol. 2011;11:10102–10.
Kane RS, Stroock AD. Nanobiotechnology: protein–nanomaterial interactions. Biotechnol Prog. 2007;23:316–9.
Mehra NK, Palakurthi S. Interactions between carbon nanotubes and bioactives: a drug delivery perspective. Drug Discov Today. 2016;21:585–97.
Fan Y, Wu G, Su F, Li K, Xu L, Han X, Yan Y. Lipase oriented-immobilized on dendrimer-coated magnetic multi-walled carbon nanotubes toward catalyzing biodiesel production from waste vegetable oil. Fuel. 2016;178:172–8.
Deb AK, Das SC, Saha A, Wayu MB, Marksberry MH, Baltz RJ, Chusuei CC. Ascorbic acid, acetaminophen, and hydrogen peroxide detection using a dendrimer-encapsulated Pt nanoparticle carbon nanotube composite. J Appl Electrochem. 2016;46:289–98.
Alam AKMM, Beg MDH, Yunus RM, Mina MF, Maria KH, Mieno T. Evolution of functionalized multi-walled carbon nanotubes by dendritic polymer coating and their anti-scavenging behavior during curing process. Mater Lett. 2016;167:58–60.
Caminade A, Majoral J. Dendrimers and nanotubes: a fruitful association. Chem Soc Rev. 2010;39:2034–47.
Sridevi S, Vasu KS, Jayaraman N, Asokan S, Sood AK. Optical bio-sensing devices based on etched fiber Bragg gratings coated with carbon nanotubes and graphene oxide along with a specific dendrimer. Sens Actuator B-Chem. 2014;195:150–5.
Xu L, Zhu Y, Yang X, Li C. Amperometric biosensor based on carbon nanotubes coated with polyaniline/dendrimer-encapsulated Pt nanoparticles for glucose detection. Mater Sci Eng C-Mater Biol Appl. 2009;29:1306–10.
Miodek A, Mejri N, Gomgnimbou M, Sola C, Korri-Youssoufi H. E-DNA sensor of mycobacterium tuberculosis based on electrochemical assembly of nanomaterials (MWCNTs/PPy/PAMAM). Anal Chem. 2015;87:9257–64.
Li F, Peng J, Zheng Q, Guo X, Tang H, Yao S. Carbon nanotube-polyamidoamine dendrimer hybrid-modified electrodes for highly sensitive electrochemical detection of microRNA24. Anal Chem. 2015;87:4806–13.
Zhang J, Zhu Y, Chen C, Yang X, Li C. Carbon nanotubes coated with platinum nanoparticles as anode of biofuel cell. Particuology. 2012;10:450–5.
Pan B, Cui D, Xu P, Ozkan C, Feng G, Ozkan M, Huang T, Chu B, Li Q, He R, Hu G. Synthesis and characterization of polyamidoamine dendrimer-coated multi-walled carbon nanotubes and their application in gene delivery systems. Nanotechnology. 2009;20:125101.
González-García E, Marina ML, García MC. Plum (Prunus domestica L.) by-product as a new and cheap source of bioactive peptides: extraction method and peptides characterization. J Funct Food. 2014;11:428–37.
González-García E, Puchalska P, Marina ML, García MC. Fractionation and identification of antioxidant and angiotensin-converting enzyme-inhibitory peptides obtained from plum (Prunus domestica L.) stones. J Funct Food. 2015;19:376–84.
González-García E, Marina ML, García MC, Righetti PG, Fasoli E. Identification of plum and peach seed proteins by nLC-MS/MS via combinatorial peptide ligand libraries. J Proteome. 2016;148:105–12.
Lakshminarayanan PV, Toghiani H, Pittman CU. Nitric acid oxidation of vapor grown carbon nanofibers. Carbon. 2004;42:2433–42.
Bradford MM. Rapid and sensitive method for quantitation of microgram quantities of protein utilizing principle of protein–dye binding. Anal Biochem. 1976;72:248–54.
Li P-S, Lee I-L, Yu W-L, Sun J-S, Jane W-N, Shen H-H. A novel albumin-based tissue scaffold for autogenic tissue engineering applications. Sci Rep. 2014;4:5600.
Eftink MR. The use of fluorescence methods to monitor unfolding transitions in proteins. Biophys J. 1994;66:482–501.
Eftink MR. Fluorescence quenching reactions. Probing biological macromolecular structures. In: Dewey TG, editor. Biophysical and biochemical aspects of fluorescence spectroscopy. US: Springer; 1991. p. 1–41.
Rohiwal SS, Satvekar RK, Tiwari AP, Raut AV, Kumbhar SG, Pawar SH. Investigating the influence of effective parameters on molecular characteristics of bovine serum albumin nanoparticles. Appl Surf Sci. 2015;334:157–64.
Hashimoto S, Fukasaka J, Takeuchi HJ. Structural study on acid-induced unfolding intermediates of myoglobin by using UV resonance Raman scattering from tryptophan residues. Raman Spectrosc. 2001;32:557–63.
Acknowledgements
This work was supported by the Spanish Ministry of Economy and Competitiveness (ref. AGL2012-36362, AGL2016-79010-R, and CTQ-2014-54004-P). E.G.G., M.C.G., and M.L.M. also thank the Comunidad Autónoma of Madrid (Spain) and European funding from FEDER program (project S2013/ABI-3028, AVANSECAL-CM). E.G.-G. thanks the University of Alcalá for her pre-doctoral contract and C.G.U. thanks the Spanish Ministry of Economy and Competitiveness (FPI 2012) for his pre-doctoral contract. The authors thank Jorge Pérez Serrano, chief of the CAI Medicina y Biología de la Universidad de Alcalá, for his kind assistance with scanning electron microscopy and Novozymes Spain for the generous donation of Alcalase enzyme. CIBER-BBN is an initiative funded by the VI National R&D&i Plan 2008–2011, Iniciativa Ingenio 2010, Consolider Program, CIBER Actions and financed by the Instituto de Salud Carlos III with assistance from the European Regional Development Fund.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The authors declare that there is no conflict of interest.
Rights and permissions
About this article
Cite this article
González-García, E., Gutiérrez Ulloa, C.E., de la Mata, F.J. et al. Sulfonate-terminated carbosilane dendron-coated nanotubes: a greener point of view in protein sample preparation. Anal Bioanal Chem 409, 5337–5348 (2017). https://doi.org/10.1007/s00216-017-0479-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00216-017-0479-3