Gold nanoparticles coated with carbosilane dendrons in protein sample preparation

Abstract

The feasibility of using carbosilane dendronized gold nanoparticles (GNPs) for protein sample preparation was evaluated. Three different dendrons with three different generations (1G, 2G, and 3G) were employed to modify the GNPs, viz. sulfonate terminated (STC-GNPs), carboxylate terminated (CTC-GNPs), and trimethylammonium terminated (ATC-GNPs) dendrons. The synthesis of the CTC-GNP is described. The other dendronized GNPs were synthesized using previously described routes. Bovine serum albumin, lysozyme, and myoglobin were employed to study the potential of GNPs to interact with proteins. The interaction between the GNPs and the proteins was evaluated using fluorescence spectroscopy and polyacrylamide gel electrophoresis. The CTC-GNPs and STC-GNPs under acidic and neutral conditions, respectively, promoted the establishment of electrostatic interactions with positively charged proteins. Proteins from 10 to 75 kDa molecular weights interacted with GNPs at protein: nanoparticle ratios of 1:0.25. The GNPs were applied to the extraction of proteins from a peach seed. In the authors’ perception, the method is a clean alternative to established extraction methods based on the use of organic or polluting chemicals.

Schematic representation of the interaction of peach seeds proteins and carbosilane dendron coated gold nanoparticles, and the electrophoretic profiles of extracted proteins.

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References

  1. 1.

    Brust M, Walker M, Bethell D, Schiffrin DJ, Whyman R (1994) Synthesis of thiol-derivatised gold nanoparticles in a two-phase liquid–liquid system. J Chem Soc Chem Commun 0:801–802. https://doi.org/10.1039/C39940000801

    CAS  Article  Google Scholar 

  2. 2.

    Elbert KC, Lee JD, Wu Y, Murray CB (2018) Improved chemical and colloidal stability of gold nanoparticles through dendron capping. Langmuir 34:13333–13338. https://doi.org/10.1021/acs.langmuir.8b02960

    CAS  Article  PubMed  Google Scholar 

  3. 3.

    Newkome GR, Moorefield CN, Vögtle F (2001) Dendrimers and dendrons: concepts, synthesis, applications. Willey-VCH, Weinheim

    Google Scholar 

  4. 4.

    Kalhapure RS, Kathiravan MK, Akamanchi KG, Govender T (2015) Dendrimers-from organic synthesis to pharmaceutical applications: an update. Pharm Dev Technol 20:22–40. https://doi.org/10.3109/10837450.2013.862264

    CAS  Article  PubMed  Google Scholar 

  5. 5.

    Malik N, Wiwattanapatapee R, Klopsch R, Lorenz K, Frey H, Weener J, Meijer EW, Paulus W, Duncan R (2000) Dendrimers: relationship between structure and biocompatibility in vitro, and preliminary studies on the biodistribution of 125I-labelled polyamidoamine dendrimers in vivo. J Control Release 65:133–148. https://doi.org/10.1016/S0168-3659(99)00246-1

    CAS  Article  PubMed  Google Scholar 

  6. 6.

    Lee JH, Cha KE, Kim MS, Hong HW, Chung DJ, Ryu G, Myung H (2009) Nanosized polyamidoamine (PAMAM) dendrimer-induced apoptosis mediated by mitochondrial dysfunction. Toxicol Lett 190:202–207. https://doi.org/10.1016/j.toxlet.2009.07.018

    CAS  Article  PubMed  Google Scholar 

  7. 7.

    Labieniec-Watala M, Karolczak K, Siewiera K, Watala C (2013) The janus face of PAMAM dendrimers used to potentially cure nonenzymatic modifications of biomacromolecules in metabolic disorders—a critical review of the pros and cons. Molecules 18:13769–13811. https://doi.org/10.3390/molecules181113769

    CAS  Article  PubMed  PubMed Central  Google Scholar 

  8. 8.

    Hatano K, Matsuoka K, Terunuma D (2013) Carbosilane glycodendrimers. Chem Soc Rev 42:4574–4598. https://doi.org/10.1039/C2CS35421G

    CAS  Article  PubMed  Google Scholar 

  9. 9.

    Arnáiz E, Doucede LI, García-Gallego S, Urbiola K, Gómez R, Tros de Ilarduya C, de la Mata FJ (2012) Synthesis of cationic carbosilane dendrimers via click chemistry and their use as effective carriers for DNA transfection into cancerous cells. Mol Pharm 9:433–447. https://doi.org/10.1021/mp200542

    Article  PubMed  Google Scholar 

  10. 10.

    Gras R, Relloso M, García MI, de la Mata FJ, Gómez R, López-Fernández LA, Muñoz-Fernández MA (2012) The inhibition of Th17 immune response in vitro and in vivo by the carbosilane dendrimer 2G-NN16. Biomaterials 33:4002–4009. https://doi.org/10.1016/j.biomaterials.2012.02.018

    CAS  Article  PubMed  Google Scholar 

  11. 11.

    Sánchez-Milla M, Pastor I, Maly M, Serramía MJ, Gómez R, Sánchez-Nieves J, Ritort F, Muñoz-Fernández MÁ, de la Mata FJ (2018) Study of non-covalent interactions on dendriplex formation: influence of hydrophobic, electrostatic and hydrogen bonds interactions. Colloids Surf B Biointerfaces 162:380–388. https://doi.org/10.1016/j.colsurfb.2017.12.009

    CAS  Article  PubMed  Google Scholar 

  12. 12.

    González-García E, Maly M, de la Mata FJ, Gómez R, Marina ML, García MC (2017) Factors affecting interactions between sulphonate-terminated dendrimers and proteins: a three case study. Colloids Surf B 149:196–205. https://doi.org/10.1016/j.colsurfb.2016.10.020

    CAS  Article  Google Scholar 

  13. 13.

    González-García E, Maly M, de la Mata FJ, Gómez R, Marina ML, García MC (2016) Proof of concept of a greener protein purification/enrichment method bases on carboxylate-terminated carbosilane dendrimer-protein interactions. Anal Bioanal Chem 408:7679–7687. https://doi.org/10.1007/s00216-016-9864-6

    CAS  Article  PubMed  Google Scholar 

  14. 14.

    González-García E, Gutiérrez Ulloa CE, de la Mata FJ, Marina ML, García MC (2017) Sulphonate-terminated carbosilane dendron-coated nanotubes: a greener point of view in protein sample preparation. Anal Bioanal Chem 409:5337–5348. https://doi.org/10.1007/s00216-017-0479-3

    CAS  Article  PubMed  Google Scholar 

  15. 15.

    Shcharbin D, Pedziwiatr-Werbicka E, Serchenya T, Cyboran-Mikolajczyk S, Prakhira L, Abashkin V, Dzmitruk V, Ionov M, Loznikova S, Shyrochyna I, Sviridov O, Peña-González CE, Gumiel AB, Gómez R, de la Mata FJ, Bryszewska M (2018) Role of cationic carbosilane dendrons and metallic core of functionalized gold nanoparticles in their interaction with human serum albumin. Int J Biol Macromol 118:1773–1780. https://doi.org/10.1016/j.ijbiomac.2018.07.023

    CAS  Article  PubMed  Google Scholar 

  16. 16.

    Moerz ST, Huber P (2014) Protein adsorption into Mesopores: a combination of electrostatic interaction, counterion release, and van der Waals forces. Langmuir 30:2729–2737. https://doi.org/10.1021/la404947j

    CAS  Article  PubMed  Google Scholar 

  17. 17.

    Jin B, Bao WJ, Wu ZQ, Xia XH (2012) In situ monitoring of protein adsorption on a nanoparticulated gold film by attenuated total reflection surface-enhanced infrared absorption spectroscopy. Langmuir 28:9460–9465. https://doi.org/10.1021/la300819u

    CAS  Article  PubMed  Google Scholar 

  18. 18.

    Kim Y, Ko SM, Nam JM (2016) Protein-nanoparticle interaction-induced changes in protein structure and aggregation. Chem Asian J 11:1869–1877. https://doi.org/10.1002/asia.201600236

    CAS  Article  PubMed  Google Scholar 

  19. 19.

    Peña-González CE, García-Broncano P, Ottaviani MF, Cangiotti M, Fattori A, Hierro-Oliva M, González-Martín ML, Pérez-Serrano J, Gómez R, Muñoz-Fernández MA, Sánchez-Nieves J, de la Mata FJ (2016) Dendronized anionic gold nanoparticles: synthesis. Characterization, and antiviral activity. Chem Eur J 22:2987–2999. https://doi.org/10.1002/chem.201504262

    CAS  Article  PubMed  Google Scholar 

  20. 20.

    Peña-González CE, Pedziwiatr-Werbicka E, Martín-Pérez T, Szewczyk EM, Copa-Patiño JL, Soliveri J, Pérez-Serrano J, Gómez R, Bryszewska M, Sánchez-Nieves J, de la Mata FJ (2017) Antibacterial and antifungal properties of dendronized silver and gold nanoparticles with cationic carbosilane dendrons. Int J Pharm 528:55–61. https://doi.org/10.1016/j.ijpharm.2017.05.067

    CAS  Article  PubMed  Google Scholar 

  21. 21.

    Fuentes-Paniagua E, Peña-González CE, Galán M, Gómez R, de la Mata FJ, Sánchez-Nieves J (2013) Thiol-Ene synthesis of cationic Carbosilane Dendrons: a new family of Synthons. Organometallics 32:1789–1796. https://doi.org/10.1021/om301217g

    CAS  Article  Google Scholar 

  22. 22.

    Vásquez-Villanueva R, Marina ML, García MC (2015) Revalorization of a peach (Prunus persica (L.) Batsch) byproduct: extraction and characterization of ACE-inhibitory peptides from peach stones. J Funct Foods 18:137–146. https://doi.org/10.1016/j.jff.2015.06.056

    CAS  Article  Google Scholar 

  23. 23.

    Bradford MM (1976) Rapid and sensitive method for quantitation of microgram quantities of protein utilizing principle of protein-dye binding. Anal Biochem 72:248–254. https://doi.org/10.1016/0003-2697(76)90527-3

    CAS  Article  PubMed  Google Scholar 

  24. 24.

    Hanus LH, Ploehn HJ (1999) Conversion of intensity-averaged photon correlation spectroscopy measurements to number-averaged particle size distributions. 1. Theoretical development. Langmuir 15:3091–3100. https://doi.org/10.1021/la980958w

    CAS  Article  Google Scholar 

  25. 25.

    Eftink MR (1994) The use of fluorescence methods to monitor unfolding transitions in proteins. Biophys J 66:482–501

    CAS  Article  Google Scholar 

  26. 26.

    Volden S, Lystvet SM, Halskau Ø, Glomm WR (2012) Generally applicable procedure for in situ formation of fluorescence protein gold nanostructures. RSC Adv 2:11704–11711. https://doi.org/10.1039/C2RA21931J

    CAS  Article  Google Scholar 

  27. 27.

    Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer, New York

    Google Scholar 

  28. 28.

    Treuel L, Malissek M, Grass S, Diendorf J, Mahl D, Meyer-Zaika W, Epple M (2012) Quantifying the influence of polymer coatings on the serum albumin corona formation around silver and gold nanoparticles. J Nanopart Res 14:1–12. https://doi.org/10.1007/s11051-012-1102-3

    CAS  Article  Google Scholar 

Download references

Acknowledgements

This work was supported by the Spanish Ministry of Economy and Competitiveness (ref. AGL2016-79010-R and CTQ2017-86224-P). R.V.-V thanks the University of Alcalá for the pre-doctoral contract. 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 la Salud Carlos III with assistance from the European Regional Development Fund.

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Correspondence to M. Concepción García.

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Electronic Supplementary Material

ESM 1

Complete description of the preparation of first to third generation carboxylate terminated carbosilane dendrons. Figures of scheme of synthesis and structures of carboxylate dendrons, NMR spectra of dendrons. Gel corresponding to the protein that interacted 1G STC-GNP. Table of Mw, isoelectric point (pI), net charge at different pHs, and number of Trp residues for BSA, Myo, and Lyz. (DOCX 709 kb)

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Vásquez-Villanueva, R., Peña-González, C.E., Sánchez-Nieves, J. et al. Gold nanoparticles coated with carbosilane dendrons in protein sample preparation. Microchim Acta 186, 508 (2019). https://doi.org/10.1007/s00604-019-3587-2

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Keywords

  • Dendrimer
  • Interaction
  • Protein extraction
  • Nanomaterial
  • Sustainability