Skip to main content
SpringerLink
Log in

Smart 0D nanomaterials assembled by green luminescent terbium hybrids for the detection of tryptophan

  • Research Paper
  • Published:
Journal of Nanoparticle Research Aims and scope Submit manuscript

Abstract

A new class of terbium hybrids within the silica framework has been synthesized using modified silylated derivatives of aromatic acids. These organic–inorganic materials have very homogenous spherical shapes (diameter around 60 nm) and exhibit characteristic green emissions in DMSO/H2O (1:1). Significantly, they present highly selective and rapid (1–2 s) emission quenching effects with respect to tryptophan compared to other essential amino acids for human. In addition, enhanced thermal stabilities can be achieved in these hybrid materials.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  • Alegre E, López AS, González A (2005) Tryptophan metabolites interfere with the Ehrlich reaction used for the measurement of kynurenine. Anal Biochem 339:188–189

    Article  CAS  Google Scholar 

  • Bao ZJ, Sun SN, Li J, Chen XQ, Dong SY, Ma HM (2006) Direct identification of tryptophan in a mixture of amino acids by the naked eye. Angew Chem Int Ed 45:6723–6725

    Article  CAS  Google Scholar 

  • Botting NP (1995) Chemistry and neurochemistry of the kynurenine pathway of tryptophan metabolism. Chem Soc Rev 24:401–412

    Article  CAS  Google Scholar 

  • Bunzli JCG (2010) Lanthanide luminescence for biomedical analyses and imaging. Chem Rev 110:2729–2755

    Article  Google Scholar 

  • Bunzli JCG, Piguet C (2005) Taking advantage of luminescent lanthanide ions. Chem Soc Rev 34:1048–1077

    Article  Google Scholar 

  • Fan Y, Liu JH, Lu HT, Zhang Q (2011) Electrochemistry and voltammetric determination of l-tryptophan and l-tyrosine using a glassy carbon electrode modified with a Nafion/TiO2-graphene composite film. Microchim Acta 173:241–247

    Article  CAS  Google Scholar 

  • Goncalves MC, Bermudez VD, Ferreira RAS, Carlos LD, Ostrovskii D, Rocha J (2004) Optically functional di-urethanesil nanohybrids containing Eu3+ ions. Chem Mater 16:2530–2543

    Article  CAS  Google Scholar 

  • Gunnlaugsson T, Glynn M, Tocci GM, Kruger PE, Pfeffer FM (2006) Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors. Coord Chem Rev 250:3094–3117

    Article  CAS  Google Scholar 

  • Guo L, Fu LS, Ferreira RAS, Carlos LD, Li QP, Yan B (2011) Novel lanthanide luminescent materials based on multifunctional complexes of 2-sulfanylpyridine-3-carboxylic acid and silica/titania hosts. J Mater Chem 21:15600–15607

    Article  CAS  Google Scholar 

  • Guo XM, Canet JL, Boyer D, Gautier A, Mahiou R (2012) Sol–gel emulsion synthesis of biphotonic core–shell nanoparticles based on lanthanide doped organic–inorganic hybrid materials. J Mater Chem 22:6117–6122

    Article  CAS  Google Scholar 

  • Herr JK, Smith JE, Medley CD, Shangguan DH, Tan WH (2006) Aptamer-conjugated nanoparticles for selective collection and detection of cancer cells. Anal Chem 78:2918–2924

    Article  CAS  Google Scholar 

  • Ho JA, Chang HC, Su WT (2012) DOPA-mediated reduction allows the facile synthesis of fluorescent gold nanoclusters for use as sensing probes for ferric ions. Anal Chem 84:3246–3253

    Article  Google Scholar 

  • Horacek J, Zavesicka L, Tintera J, Dockery C, Platilova V, Kopecek M, Spaniel F, Bubenikova V, Hoschl C (2005) The effect of tryptophan depletion on brain activation measured by functional magnetic resonance imaging during the stroop test in healthy subjects. Physiol Res 54:235–244

    CAS  Google Scholar 

  • Lakowicz JR (2006) Principles of fluorescence spectroscopy. Springer, Berlin, pp 536–538

    Book  Google Scholar 

  • Lu LH, Liu FY, Sun GY, Zhang HJ, Xi SQ, Wang HS (2004) In situ synthesis of monodisperse luminescent terbium complex-silica nanocomposites. J Mater Chem 14:2760–2762

    Article  CAS  Google Scholar 

  • Michinobu T, Shinoda S, Nakanishi T, Hill JP, Fujii K, Player TN, Tsukube H, Ariga K (2006) Mechanical control of enantioselectivity of amino acid recognition by cholesterol-armed cyclen monolayer at the air–water interface. J Am Chem Soc 128:14478–14479

    Article  CAS  Google Scholar 

  • Montalti M, Prodi L, Zaccheroni N, Charbonnière L, Douce L, Ziessel R (2001) A luminescent anion sensor based on a europium hybrid complex. J Am Chem Soc 123:12694–12695

    Article  CAS  Google Scholar 

  • Ouyang RZ, Lei JP, Ju HX, Xue YD (2007) A molecularly imprinted copolymer designed for enantioselective recognition of glutamic acid. Adv Funct Mater 17:3223–3230

    Article  CAS  Google Scholar 

  • Pagnot T, Audebert P, Tribillon G (2000) Metal dispersed activated carbon fibers and their application for removal of SO x . Chem Phys Lett 322:572–578

    Article  CAS  Google Scholar 

  • Parker D (2000) Luminescent lanthanide sensors for pH, pO2 and selected anions. Coord Chem Rev 205:109–130

    Article  CAS  Google Scholar 

  • Pinho SLC, Faneca H, Geraldes CFGC, Rocha J, Carlos LD, Delville MH (2012) Silica nanoparticles for bimodal MRI-optical imaging by grafting Gd3+ and Eu3+/Tb3+ complexes. Eur J Inorg Chem 16:2828–2837

    Article  Google Scholar 

  • Potesil D, Petrlova J, Adam V, Vacek J, Klejdus B, Zehnalek J, Trnkova L, Havel L, Kizek R (2005) Simultaneous femtomole determination of cysteine, reduced and oxidized glutathione, and phytochelatin in maize (Zea mays L.) kernels using high-performance liquid chromatography with electrochemical detection. J Chromatogr A 1084:134–144

    Article  CAS  Google Scholar 

  • Rosse RB, Schwartz BL, Zlotolow S, Banay-Schwartz M, Trinidad AC, Peace TD, Deutsch SL (1992) Effect of a low-tryptophan diet as an adjuvant to conventional neuroleptic therapy in schizophrenia. Clin Neuropharmacol 15:129–141

    Article  CAS  Google Scholar 

  • Sasaki S, Hashizume A, Citterio D, Fujii E, Suzuki K (2002) Trifluoroacetophenone derivatives as amino acid selective ionophores for the potentiometric determination of phenylalanine. Angew Chem Int Ed 114:3131–3133

    Article  Google Scholar 

  • Sato Y, Iwata T, Tokutomi S, Kandori H (2005) Reactive cysteine is protonated in the triplet excited state of the LOV2 domain in adiantum phytochrome3. J Am Chem Soc 127:1088–1089

    Article  CAS  Google Scholar 

  • Shao N, Jin JY, Cheung SM, Yang RH, Chan WH, Mo T (2006) A spiropyran-based ensemble for visual recognition and quantification of cysteine and homocysteine at physiological levels. Angew Chem Int Ed 45:4944–4948

    Article  CAS  Google Scholar 

  • Shinoda S, Tsukube H (2011) Luminescent lanthanide complexes as analytical tools in anion sensing, pH indication and protein recognition. Analyst 136:431–435

    Article  CAS  Google Scholar 

  • Shinoda S, Yano K, Tsukube H (2010) Combinatorial screening of a lanthanide complex library for luminescence sensing of amino acids. Chem Commun 46:3110–3112

    Article  CAS  Google Scholar 

  • Stich MIJ, Schaeferling M, Wolfbeis OS (2009) Multicolor fluorescent and permeation-selective microbeads enable simultaneous sensing of pH, oxygen, and temperature. Adv Mater 21:2216–2220

    Article  CAS  Google Scholar 

  • Tan CL, Wang QM (2011) Reversible terbium luminescent polyelectrolyte hydrogels for detection of H2PO4 − and HSO4 − in water. Inorg Chem 50:2953–2957

    Article  CAS  Google Scholar 

  • Tsukube H, Hosokubo M, Wada M, Shinoda S, Tamiaki H (2001) Specific recognition of chiral amino alcohols via lanthanide coordination chemistry: structural optimization of lanthanide tris(beta-diketonates) toward effective circular dichroism/fluorescence probing. Inorg Chem 40:740–745

    Article  CAS  Google Scholar 

  • Wang QM, Yan B (2004) Novel luminescent terbium molecular-based hybrids with modified m-aminobenzoic acid covalently bonded with silica. J Mater Chem 14:2450–2454

    Article  CAS  Google Scholar 

  • Wang QM, Yan B (2006) Designing a family of luminescent hybrid materials by 3-(triethoxysilyl)-propyl isocyanate grafted 2-hydroxynicotinic acid bridge molecules. J Organomet Chem 691:3567–3573

    Article  CAS  Google Scholar 

  • Wang QM, Tan CL, Chen HY, Tamiaki H (2010) A new fluoride luminescence quencher based on a nanostructured covalently bonded terbium hybrid material. J Phys Chem C 114:13879–13883

    Article  CAS  Google Scholar 

  • Wang XH, Wang XY, Wang YQ, Guo ZJ (2011) Terbium (III) complex as a luminescent sensor for human serum albumin in aqueous solution. Chem Commun 47:8127–8129

    Article  CAS  Google Scholar 

  • Williamson BL, Klarskov K, Tomlinson AJ, Gleich GJ, Naylor S (1998) Problems with over-the-counter 5-hydroxy-l-tryptophan. Nat Med 4:983–984

    Article  CAS  Google Scholar 

  • Yan B, Wang QM (2007) Organization of luminescent molecular-scale hybrids with double strong chemical bonds from modification of a functional bridge. J Optoclectron Adv Mater 9:3907–3911

    CAS  Google Scholar 

  • Zhang HJ, Yan B, Wang SB, Ni JZ (1997) The photophysical properties of binary and ternary complexes of rare earths with conjugated carboxylic acids and 1,10-phenanthroline. J Photochem Photobiol A 109:223–228

    Article  CAS  Google Scholar 

  • Zhang R, Yu XJ, Ye ZQ, Wang GL, Zhang WZ, Yuan LJ (2010) Turn-on luminescent probe for cysteine/homocysteine based on a ruthenium (II) complex. Inorg Chem 49:7898–7903

    Article  CAS  Google Scholar 

  • Zhao C, Song YJ, Qu KG, Ren JS, Qu XG (2010) Luminescent rare-earth complex covalently modified single-walled carbon nanotubes: design, synthesis, and DNA sequence-dependent red luminescence enhancement. Chem Mater 22:5718–5724

    Article  CAS  Google Scholar 

Download references

Acknowledgments

S. T. thanks the research fund of innovative project supported by South China Normal University for undergraduate students (2012). Q. M. appreciates support from the National Natural Science Foundation of China (No. 21002035).

Author information

Authors and Affiliations

  1. Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, School of Chemistry and Environment, South China Normal University, Guangzhou, 510006, People’s Republic of China

    Qianming Wang

  2. School of Chemistry and Environment, South China Normal University, Guangzhou, 510006, People’s Republic of China

    Shuting Pang, Zhan Zhou & Qianming Wang

Authors
  1. Shuting Pang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhan Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Qianming Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Qianming Wang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2548 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pang, S., Zhou, Z. & Wang, Q. Smart 0D nanomaterials assembled by green luminescent terbium hybrids for the detection of tryptophan. J Nanopart Res 15, 1495 (2013). https://doi.org/10.1007/s11051-013-1495-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s11051-013-1495-7

Keywords

Search

Navigation