Abstract
In this study, a cyclic disulfide-bonded peptide (ATTO 590-cyclo(2,11)-HCHVH DPLPHLHCH, clyco(ATTO-HCHV) was designed and synthesized. The β-turn design by the dipeptide d-Pro-l-Pro and the intradisulfide bridge using two cysteines make all histidines residues align on one face of the peptide, suggesting less steric hindrance during the self-assembly with quantum dots (QDs) and higher binding affinity than histag. QDs and clyco(ATTO-HCHV) at different molar ratio were sequentially injected into the capillary; strong Förster resonance energy transfer (FRET) signals were observed in both donor and acceptor channels, indicating the efficient binding of the novel cyclic peptide ligand onto the QDs to form clyco(ATTO-HCHV)-QD assembly inside the capillary. Capillary electrophoresis coupled with fluorescence detection (CE-FL) results indicated that the cyclic ligand clyco(ATTO-HCHV) had a much higher binding affinity than that of the linear form peptide ligand ATTO-HCHV. Additionally, the interval time of the injection and the sampling time were also investigated using CE-FL combining with FRET technology. Lastly, the stability of clyco(ATTO-HCHV)-QD was systematically examined in the presence of the imidazole competitor. It is believed that this new in-capillary assay significantly reduced the sample consumption and the analysis time.
Graphical abstract
Similar content being viewed by others
References
Na N, Liu L, Taes YE, Zhang C, Huang B, Liu Y, Ma L, Ouyang J (2010) Direct CdTe quantum-dot-based fluorescence imaging of human serum proteins. Small 6:1589–1592
Michalet X, Pinaud FF, Bentolila LA, Tsay JM, Doose S, Li JJ, Sundaresan G, Wu AM, Gambhir SS, Weiss S (2005) Quantum dots for live cells, in vivo imaging, and diagnostics. Science 307:538–544
Alivisatos P (2004) The use of nanocrystals in biological detection. Nat Biotechnol 22:47–52
Clapp AR, Medintz IL, Mauro JM, Fisher BR, Bawendi MG, Mattoussi H (2004) Fluorescence resonance energy transfer between quantum dot donors anddye-labeled protein acceptors. J Am Chem Soc 126:301–310
Sapsford KE, Pons T, Medintz IL, Higashiya S, Brunel FM, Dawson PE, Mattoussi H (2007) Kinetics of metal-affinity driven self-assembly between proteins or peptides and CdSe-ZnS quantum dots. J Phys Chem C 111:11528–11538
Hainfeld JF, Liu W, Halsey CM, Freimuth P, Powell RD (1999) Ni-NTA-gold clusters target His-tagged proteins. J Struct Biol 127:185–198
Hochuli E, Bannwarth W, Döbeli H, Gentz R, Stüber D (1988) Genetic approach to facilitate purification of recombinant proteins with a novel metal chelate adsorbent. Nat Biotechnol 6:1321–1325
Wang JH, Xia J (2011) Preferential binding of a novel polyhistidine peptide dendrimer ligand on quantum dots probed by capillary electrophoresis. Anal Chem 83:6323–6329
Wang JH, Zhang CC, Liu L, Karunakaran AK, Qiu L, Ding SM, Fu ML, Gao LQ, Jiang PJ (2016) A capillary electrophoresis method to explore the self-assembly of a novel polypeptide ligand with quantum dots. Electrophoresis 37:2156–2162
Wang JH, Li LC, Zhang CC, Fan J, Yang L, Gu YQ, Liu FF, Wang CL, Dong BY, Qiu L, Jiang PJ (2015) In-capillary probing QDs and HAT tag self-assembly and displacement using Förster resonance energy transfer. Electrophoresis 36:2636–2641
Li YQ, Guan LY, Wang JH, Zhang HL, Chen J, Lin S, Chen W, Zhao YD (2010) Simultaneous detection of dual single-base mutations by capillary electrophoresis using quantum dot-molecular beacon probe. Biosens Bioelectron 26:2317–2322
Li YQ, Wang JH, Zhang HL, Yang J, Guan LY, Chen H, Luo QM, Zhao YD (2010) High-sensitivity quantum dot-based fluorescence resonance energy transfer bioanalysis by capillary electrophoresis. Biosens Bioelectron 25:1283–1289
Mendonsa SD, Bowser MT (2003) In vitro evolution of functional DNA usingcapillary electrophoresis. J Am Chem Soc 126:20–21
Mendonsa SD, Bowser MT (2005) In vitro selection of aptamers with affinity forneuropeptide Y using capillary electrophoresis. J Am Chem Soc 127:9382–9383
Mendonsa SD, Bowser MT (2004) In vitro selection of high-affinity DNA ligands forhuman IgE using capillary electrophoresis. Anal Chem 76:5387–5392
Clapp AR, Medintz IL, Mauro JM, Fisher BR, Bawendi MG, Mattoussi H (2004) Fluorescence resonance energy transfer between quantum dot donors anddye-labeled protein acceptors. J Am Chem Soc 126:301–310
Nikiforov T, Beechem JM (2006) Development of homogeneous binding assaysbased on fluorescence resonance energy transfer between quantum dots andAlexa Fluor fluorophores. Anal Biochem 357:68–76
Chang YQ, Cai C, Li LY, Miao JJ, Ucakturk E, Li GY, Ly M, Linhardt RJ (2013) Ultrasensitive detection and quantification of acidic disaccharides using capillary electrophoresis and quantum dot-based fluorescence resonance energy transfer. Anal Chem 85:9356–9362
Hohng S, Ha T (2005) Single-molecule quantum-dot fluorescence resonance energytransfer. ChemPhysChem 6:956–960
Wang JH, Li JY, Li JC, Liu FF, Zhou X, Yao Y, Wang CL, Qiu L, Jiang PJ (2015) In-capillary self-assembly and proteolytic cleavage of polyhistidine peptide capped quantum dots. Anal Chem Acta 895:112–117
Stanisavljevic M, Chomoucka J, Dostalova S, Krizkova S (2014) Interactions between CdTe quantum dots and DNA revealed by capillary electrophoresis with laser-induced fluorescence detection. Electrophoresis 35:2587–2592
John AR (2008) β-Hairpin peptidomimetics: design, structures and biological activities. Acc Chem Res 41:1278–1288
Freeman R, Finder T, Gill R, Willner I (2010) Probing protein kinase (CK2) and alkaline phosphatase with CdSe/ZnS quantum dots. Nano Lett 10:2192–2196
Gao L, Uttamchandani M, Yao SQ (2012) Comparative proteomic profiling of mammalian cell lysates using phosphopeptide microarrays. Chem Commun 48:2240–2242
Gao L, Yu Z, Meng D, Zheng F, Ong YS, Miao P, Lee SS, Wen L (2015) Analogue of melanotan II (MT II): a novel melanotropin with superpotent action on frog skin. Protein Peptide Lett 22:762–766
Gao L, Sun H, Uttamchandani M, Yao SQ (2013) Phosphopeptide microarrays for comparative proteomic profiling of cellular lysates. Methods Mol Biol 1002:233–251
Sun T, Han H, Hudalla GA, Wen Y, Pompano RR, Collier JH (2016) Thermal stability of self-assembled peptide vaccine materials. Acta Biomater 30:62–71
Wang JH, Jiang PJ, Qiu L, Wang CL, Xia J (2015) Resolving antibody-peptide complexes with different ligand stoichiometries reveals a marked affinity enhancement through multivalency. Talanta 115:394–400
Wang JH, Xia J (2012) Capillary electrophoretic studies on displacement and proteolytic cleavage of surface bound oligohistidine peptide on quantum dots. Anal Chim Acta 709:120–127
Lu Y, Wang JP, Wang JH, Wang L, Au SW, Xia J (2012) Genetically encodable design of ligand “bundling” on the surface of nanoparticles. Langmuir 28:13788–13792
Liu WH, Greytak AB, Lee J, Wong CR, Park J, Marshall LF, Jiang W, Curtin PN, Ting AY, Nocera DG, Fukumura D, Jain RK, Bawendi MG (2010) Compact biocompatible quantum dots via raft-mediated synthesis of imidazole-based random copolymer ligand. J Am Chem Soc 132:472–483
Acknowledgements
This work was supported by the National Natural Science Foundation (Grant Number 21602020), the Natural Science Foundation of Jiangsu Province (Grant No. BK20141170), the Project of Jiangsu Province Industry-University-Research joint innovation fund (Grant No. BY2016029-22) and the International Scientific Cooperation Project of Changzhou Scientific Bureau (Grant No. CZ20160015). This work was also supported by the Advanced Catalysis and Green Manufacturing Collaborative Innovation Center of Changzhou University, and the 333 Project of Jiangsu Province.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
Conflict of Interest
The authors declare that they have no conflict of interest.
Human Rights and Participants
This article does not contain any studies with human participants or animals performed by any of the authors.
Additional information
Published in the topical collection Peptide and Protein Analysis with Debby Mangelings and Gerhard K. E. Scriba as editors.
Rights and permissions
About this article
Cite this article
Qiu, L., Zhang, C., Gu, T. et al. De Novo Design of a Cyclic Polyhistidine Peptide for Binding with Quantum Dots: Self-Assembly Investigation Using Capillary Electrophoresis. Chromatographia 81, 41–46 (2018). https://doi.org/10.1007/s10337-017-3319-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10337-017-3319-x