Abstract
Fluorescent-labelled nanoparticles conjugate the SPR of nanomaterials as well as the fluorescence properties of the capping dye. In this work, we report a study on the synthesis of fluorescent l-tyrosine (l-Tyr) and fluorescein (Fluo)-capped silver nanoparticles (AgNPs) carried out by a fine-tuning of the analytical concentration of the reagents. The AgNPs have been characterized by TEM, UV–Vis, ATR–FTIR, and photoluminescence (PL) spectroscopy and DLS. The adsorption of cysteine and homocysteine on the surface of the nanoparticles has been studied to evaluate their overall evolution in solution and their possible interactions with more complex systems, such as proteins. Opposed to homocysteine, cysteine induces aggregation either of tyrosine- and fluorescein-capped nanoparticles, which are therefore promising systems for the discrimination of biothiols. Furthermore, tyrosine-capped AgNPs, in spite of the better coordinating characteristics of this amino acid with respect to fluorescein, show aggregation abilities with cysteine greater than the fluorescein-capped ones that are unexpectedly more stable and thus less prone to aggregation phenomena.
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Alderighi L, Gans P, Ienco A et al (1999) Hyperquad simulation and speciation (HySS): a utility program for the investigation of equilibria involving soluble and partially soluble species. Coord Chem Rev 184:311–318. https://doi.org/10.1016/S0010-8545(98)00260-4
Alies B, Renaglia E, Rózga M et al (2013) Cu(II) affinity for the Alzheimer’s peptide: tyrosine fluorescence studies revisited. Anal Chem 85:1501–1508. https://doi.org/10.1021/ac302629u
Aran Terol P, Kumita JR, Hook SC et al (2015) Solvent exposure of Tyr10 as a probe of structural differences between monomeric and aggregated forms of the amyloid-β peptide. Biochem Biophys Res Commun 468:696–701. https://doi.org/10.1016/j.bbrc.2015.11.018
Aryal S, Remant RB, Bhattarai N et al (2006) Study of electrolyte induced aggregation of gold nanoparticles capped by amino acids. J Colloid Interface Sci 299:191–197. https://doi.org/10.1016/j.jcis.2006.01.045
Austin LA, Mackey MA (2014) The optical, photothermal, and facile surface chemical properties of gold and silver nanoparticles in biodiagnostics, therapy, and drug delivery. Arch Toxicol 88:1391–1417. https://doi.org/10.1007/s00204-014-1245-3
Chakraborty A, Boer JC, Selomulya C, Plebanski M (2018) Amino acid functionalized inorganic nanoparticles as cutting-edge therapeutic and diagnostic agents. Bioconjug Chem 29:657–671. https://doi.org/10.1021/acs.bioconjchem.7b00455
Chen J, Liu M, Huang Q et al (2018) A novel light-induced ATRP for the preparation of water dispersible fluorescent nanodiamonds and their biological imaging applications. Ceram Int 44:9907–9914. https://doi.org/10.1016/j.ceramint.2018.03.011
Cherukula K, Lekshmi KM, Uthaman S et al (2016) Multifunctional inorganic nanoparticles: recent progress in thermal therapy and imaging. Nanomaterials 6:76. https://doi.org/10.3390/nano6040076
Chinen AB, Guan CM, Ferrer JR, Barnaby SN, Merkel TJ, Mirkin CA (2015) Nanoparticle probes for the detection of cancer biomarkers, cells, and tissues by fluorescence. Chem Rev 115:10530. https://doi.org/10.1016/j.physbeh.2017.03.040
Combs JA, Denicola GM (2019) The non-essential amino acid cysteine becomes essential for tumor proliferation and survival. Cancers (Basel). https://doi.org/10.3390/cancers11050678
Conde J, Baptista PV (2012) Nanophotonics for molecular diagnostics and therapy applications. Int J Photoenergy. https://doi.org/10.1155/2012/619530
Contino A, Maccarrone G, Zimbone M et al (2014) The pivotal role of copper(II) in the enantiorecognition of tryptophan and histidine by gold nanoparticles. Anal Bioanal Chem 406:481–491. https://doi.org/10.1007/s00216-013-7466-0
Contino A, Maccarrone G, Zimbone M et al (2015) Fine tuning the pH triggers the enantiorecognition of underivatized amino acids by silver nanoparticles: a novel approach based on the focused use of solution equilibria. J Colloid Interface Sci 443:30–35. https://doi.org/10.1016/j.jcis.2014.11.067
Contino A, Maccarrone G, Zimbone M et al (2016) Tyrosine capped silver nanoparticles: a new fluorescent sensor for the quantitative determination of copper(II) and cobalt(II) ions. J Colloid Interface Sci 462:216–222. https://doi.org/10.1016/j.jcis.2015.10.008
Contino A, Maccarrone G, Fragalà ME et al (2017) Conjugated Gold–porphyrin monolayers assembled on inorganic surfaces. Chem - A Eur J 23:14937–14943. https://doi.org/10.1002/chem.201703523
Csapó E, Patakfalvi R, Hornok V et al (2012) Effect of pH on stability and plasmonic properties of cysteine-functionalized silver nanoparticle dispersion. Colloids Surf B Biointerfaces 98:43–49. https://doi.org/10.1016/j.colsurfb.2012.03.036
Dahan I, Sorrentino S, Boujemaa-Paterski R, Medalia O (2018) Tiopronin-protected gold nanoparticles as a potential marker for cryo-EM and tomography. Structure. https://doi.org/10.1016/j.str.2018.06.009
Davies M, Jones RL (1954) Infra-red absorptions and molecular structures of phenol, phenolphthalein, fluorescein, and some alkali derivatives. J Chem Soc 1954:120–125. https://doi.org/10.1039/jr9540000120
Del Pino P, Pelaz B, Zhang Q et al (2014) Protein corona formation around nanoparticles—from the past to the future. Mater Horizons 1:301–313. https://doi.org/10.1039/c3mh00106g
Díez I, Ras RHA (2011) Fluorescent silver nanoclusters. Nanoscale 3:1963–1970. https://doi.org/10.1039/c1nr00006c
Espinosa A, Curcio A, Cabana S et al (2018) Intracellular biodegradation of Ag nanoparticles, storage in ferritin, and protection by a Au shell for enhanced photothermal therapy. ACS Nano 12:6523–6535. https://doi.org/10.1021/acsnano.8b00482
Fulton LA, Zhang P, Seitz WR et al (2018) Dynamic aggregation of poly-N-isopropylacrylamide characterized using second-order scattering. Appl Spectrosc 72:1341–1348. https://doi.org/10.1177/0003702818778601
Galletto P, Brevet PF, Girault HH, Antoine R, Girault HG (1999) Enhancement of the second harmonic response by adsorbates on gold colloids: the effect of aggregation. J Phys Chem 103:8706–8710. https://doi.org/10.1021/jp991937t
Gibbs GM, Roelants K, O’Bryan MK (2008) The CAP superfamily: cysteine-rich secretory proteins, antigen 5, and pathogenesis-related 1 proteins—roles in reproduction, cancer, and immune defense. Endocr Rev 29:865–897. https://doi.org/10.1210/er.2008-0032
Greish K (2007) Enhanced permeability and retention of macromolecular drugs in solid tumors: a royal gate for targeted anticancer nanomedicines. J Drug Target 15:457–464. https://doi.org/10.1080/10611860701539584
Holcomb IN, Kabakoff RC, Chan B et al (2000) FIZZ1, a novel cysteine-rich secreted protein associated with pulmonary inflammation, defines a new gene family. EMBO J 19:4046–4055. https://doi.org/10.1093/emboj/19.15.4046
Hu M, Qian L, Briñas RP et al (2008) Gold nanoparticle–protein arrays improve resolution for cryo-electron microscopy. J Struct Biol. https://doi.org/10.1016/j.jsb.2007.09.023
Ihs A, Liedberg B, Uvdal K et al (1990) Infrared and photoelectron spectroscopy of amino acids on copper: glycine, l-alanine and β-alanine. J Colloid Interface Sci 140:192–206. https://doi.org/10.1016/0021-9797(90)90335-L
Jares-Erijman EA, Jovin TM (2003) FRET imaging. Nat Biotechnol 21:1387–1395. https://doi.org/10.1038/nbt896
Kang KA, Wang J, Jasinski JB, Achilefu S (2011) Fluorescence manipulation by gold nanoparticles: from complete quenching to extensive enhancement. J Nanobiotechnology 9:1–13. https://doi.org/10.1186/1477-3155-9-16
Kästner C, Böhmert L, Braeuning A et al (2018) Fate of fluorescence labels—their adsorption and desorption kinetics to silver nanoparticles. Langmuir 34:7153–7160. https://doi.org/10.1021/acs.langmuir.8b01305
Khazanov E, Yavin E, Pascal A et al (2012) Detecting a secreted gastric cancer biomarker molecule by targeted nanoparticles for real-time diagnostics. Pharm Res 29:983–993. https://doi.org/10.1007/s11095-011-0638-8
Kukulski W, Schorb M, Welsch S et al (2011) Correlated fluorescence and 3D electron microscopy with high sensitivity and spatial precision. J Cell Biol 192:111–119. https://doi.org/10.1083/jcb.201009037
Lakowicz JR (2006) Principles of fluorescence spectroscopy. Springer Science & Business Media, Berlin
Lee SH, Jun B (2019) Silver nanoparticles : synthesis and application for nanomedicine. Int J Mol Sci 20:865. https://doi.org/10.3390/ijms20040865
Li A, Song Z (2014) Study of silver nanoparticles sensitized fluorescence and second-order scattering of terbium(III)-pefloxacin mesylate complex and determination of pefloxacin mesylate. Sci World J. https://doi.org/10.1155/2014/742935
Lin J, Lee H-I, Song Y, Cook NR, Selhub J, Manson JAE, Buring JE, Zhang SM (2010) Plasma homocysteine and cysteine and risk of breast cancer in women. Cancer Res 70:2397–2405. https://doi.org/10.1158/0008-5472
Liu X, Shan G, Yu J et al (2017) Laser heating of metallic nanoparticles for photothermal ablation applications. AIP Adv. https://doi.org/10.1063/1.4977554
Liu SG, Li N, Han L et al (2018) Size-dependent modulation of fluorescence and light scattering: a new strategy for development of ratiometric sensing. Mater Horizons 5:454–460. https://doi.org/10.1039/c7mh00872d
Lu C, Zu Y (2007) Specific detection of cysteine and homocysteine: recognizing one methylene difference using fluorosurfactant-capped gold nanoparticles. Chem Commun. https://doi.org/10.1039/b708603b
Mandyla SP, Tsogas GZ, Vlessidis AG, Giokas DL (2017) Determination of gold nanoparticles in environmental water samples by second-order optical scattering using dithiotreitol-functionalized CdS quantum dots after cloud point extraction. J Hazard Mater 323:67–74. https://doi.org/10.1016/j.jhazmat.2016.03.039
Margulies D, Melman G, Shanzer A (2005) Fluorescein as a model molecular calculator with reset capability. Nat Mater 4:768–771. https://doi.org/10.1038/nmat1469
Markuszewski R, Diehl H (1980) The infrared spectra and structures of the three solid forms of fluorescein and related compounds. Talanta 27:937–946. https://doi.org/10.1016/0039-9140(80)80125-1
Mirzahosseini A, Noszála B (2014) The species- and site-specific acid–base properties of biological thiols and their homodisulfides. J Pharmac Biomed Anal 95:184–192. https://doi.org/10.1016/j.jpba.2014.02.023
Mudunkotuwa IA, Grassian VH (2014) Histidine adsorption on TiO2 nanoparticles: an integrated spectroscopic, thermodynamic, and molecular-based approach toward understanding nano–bio interactions. Langmuir 30:8751–8760. https://doi.org/10.1021/la500722n
Mulfinger L, Solomon SD, Bahadory M et al (2007) Synthesis and study of silver nanoparticles. J Chem Educ 84:322. https://doi.org/10.1021/ed084p322
Murphy G, Fan JH, Mark SD et al (2011) Prospective study of serum cysteine levels and oesophageal and gastric cancers in China. Gut 60:618–623. https://doi.org/10.1136/gut.2010.225854
Neelgund GM, Oki A (2018) Photothermal effect of Ag nanoparticles deposited over poly(amidoamine) grafted carbon nanotubes. J Photochem Photobiol A Chem 364:309–315. https://doi.org/10.1016/j.jphotochem.2018.06.007
Nunes SC, Ramos C, Lopes-Coelho F et al (2018) Cysteine allows ovarian cancer cells to adapt to hypoxia and to escape from carboplatin cytotoxicity. Sci Rep 8:1–17. https://doi.org/10.1038/s41598-018-27753-y
Paramelle D, Sadovoy A, Gorelik S et al (2014) A rapid method to estimate the concentration of citrate capped silver nanoparticles from UV-visible light spectra. Analyst 139:4855–4861. https://doi.org/10.1039/c4an00978a
Penkowa M (2006) Metallothioneins are multipurpose neuroprotectants during brain pathology. FEBS J 273:1857–1870. https://doi.org/10.1111/j.1742-4658.2006.05207.x
Perween S, Chandanshive B, Kotamarthi HC, Khushalani D (2013) Single amino acid based self-assembled structure. Soft Matter 9:10141–10145. https://doi.org/10.1039/c3sm51054a
Preston GW, Phillips DH (2016) Quantification of a peptide standard using the intrinsic fluorescence of tyrosine. Anal Bioanal Chem 408:2187–2193. https://doi.org/10.1007/s00216-016-9334-1
Qian H, Zhu M, Wu Z, Jin R (2012) Quantum sized gold nanoclusters with atomic precision. Acc Chem Res 45:1470–1479. https://doi.org/10.1021/ar200331z
ReactLABTM Equilibria (2019) Jplus Consulting Pty Ltd. http://jplusconsulting.com/products/reactlab-equilibria/. Accessed June 2019
Riley RS, Day ES (2017) Gold nanoparticle-mediated photothermal therapy: applications and opportunities for multimodal cancer treatment. Wires Nanomed Nanobi 9:1449. https://doi.org/10.1002/wnan.1449
Rouillat MH, Antoine R, Benichou E, Brevet P (2001) Resonant hyper Rayleigh scattering of single and aggregated gold nanoparticle. Anal Sci 17:i235–i238. https://doi.org/10.14891/analscisp.17icas.0.i235.0
Slistan-Grijalva A, Herrera-Urbina R, Rivas-Silva JF et al (2005) Classical theoretical characterization of the surface plasmon absorption band for silver spherical nanoparticles suspended in water and ethylene glycol. Phys E Low-Dimensional Syst Nanostruct 27:104–112. https://doi.org/10.1016/j.physe.2004.10.014
Socrates G (2004) Infrared and Raman characteristic group frequencies: tables and charts. Wiley, Hoboken
Soo Choi H, Liu W, Misra P et al (2007) Renal clearance of quantum dots. Nat Biotechnol 25:1165–1170. https://doi.org/10.1038/nbt1340
Sperling RA, Parak WJ (2010) Surface modification, functionalization and bioconjugation of colloidal inorganic nanoparticles. Phil Trans R Soc A 368:1333–1383. https://doi.org/10.1098/rsta.2009.0273
Tam F, Goodrich GP, Johnson BR, Halas NJ (2007) Plasmonic enhancement of molecular fluorescence. Nano Lett 7:496–501. https://doi.org/10.1021/nl062901x
Walkey CD, Chan WCW (2012) Understanding and controlling the interaction of nanomaterials with proteins in a physiological environment. Chem Soc Rev 41:2780–2799. https://doi.org/10.1039/c1cs15233e
Wang L, Roitberg A, Meuse C, Gaigalas AK (2001) Raman and FTIR spectroscopies of fluorescein in solutions. Spectrochim Acta Part A Mol Biomol Spectrosc 57:1781–1791. https://doi.org/10.1016/S1386-1425(01)00408-5
Wei L, Lu J, Xu H et al (2015) Silver nanoparticles: synthesis, properties, and therapeutic applications. Drug Discov Today 20:595–601. https://doi.org/10.1016/j.drudis.2014.11.014
Wolfbeis OS (2015) An overview of nanoparticles commonly used in fluorescent bioimaging. Chem Soc Rev 44:4743–4768. https://doi.org/10.1039/c4cs00392f
Xie Y, Yang X, Pu J et al (2010) Homogeneous competitive assay of ligand affinities based on quenching fluorescence of tyrosine/tryptophan residues in a protein via Frster-resonance-energy-transfer. Spectrochim Acta Part A Mol Biomol Spectrosc 77:869–876. https://doi.org/10.1016/j.saa.2010.08.021
Zarei M, Aalaie J (2019) Profiling of nanoparticle—protein interactions by electrophoresis techniques. Anal Bioanal Chem 411:79–96. https://doi.org/10.1007/s00216-018-1401-3
Zhang Y, Ren W, Fan YZ et al (2019) A facile and label-free ratiometric optical sensor for selective detection of norepinephrine by combining second-order scattering and fluorescence signals. Anal Bioanal Chem 411:3081–3089. https://doi.org/10.1007/s00216-019-01762-w
Acknowledgements
We thank Salvatore Pannitteri (CNR-IMM, Catania, Italy) for technical assistance and Università di Catania (Piano per la Ricerca di Ateneo Linea di Intervento 2) for financial support. We specially thank Prof. Vincenzo Cucinotta (University of Catania) for helpful discussion.
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Scollo, F., Seggio, M., Torrisi, R.L. et al. New fluorescent-labelled nanoparticles: synthesis, characterization and interactions with cysteine and homocysteine to evaluate their stability in aqueous solution. Appl Nanosci 10, 1157–1172 (2020). https://doi.org/10.1007/s13204-019-01241-9
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DOI: https://doi.org/10.1007/s13204-019-01241-9