The DOI matches its Crossref record; 67 of the 67 references it cites were found in a registry or an index.
Multifunctional Compact Zwitterionic Ligands for Preparing Robust Biocompatible Semiconductor Quantum Dots and Gold Nanoparticles
Abstract
We describe the synthesis of a series of four different ligands which are used to prepare hydrophilic, biocompatible luminescent quantum dots (QDs) and gold nanoparticles (AuNPs). Overall, the ligands are designed to be compact while still imparting a zwitterionic character to the NPs. Ligands are synthesized appended to a bidentate dihydrolipoic acid- (DHLA) anchor group, allowing for high-affinity NP attachment, and simultaneously incorporate tertiary amines along with carboxyl and/or hydroxyl groups. These are placed in close proximity within the ligand structure and their capacity for joint ionization imparts the requisite zwitterionic nature to the nanocrystal. QDs functionalized with the four different compact ligands were subjected to extensive physical characterization including surface charge, wettability, hydrodynamic size, and tolerance to a wide pH range or high salt concentration over time. The utility of the compact ligand coated QDs was further examined by testing of direct conjugation to polyhistidine-appended protein and peptides, aqueous covalent-coupling chemistry, and the ability to engage in Förster resonance energy transfer (FRET). Conjugating cell penetrating peptides to the compact ligand coated QD series facilitated their rapid and efficient cellular uptake, while subsequent cytotoxicity tests showed no apparent decreases in cell viability. In vivo biocompatibility was also demonstrated by microinjecting the compact ligand coated QDs into cells and monitoring their stability over time. Inherent benefits of the ligand design could be extended beyond QDs as AuNPs functionalized with the same compact ligand series showed similar colloidal properties. The strong potential of these ligands to expand NP capabilities in many biological applications is highlighted.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Daniel, M.-C., & Astruc, D. (2004) · Chemical Reviews · doi:10.1021/cr030698+ · Cited by 12,446
Quantum dot bioconjugates for imaging, labelling and sensing
Medintz, I. L., Uyeda, H. T., Goldman, E. R., & Mattoussi, H. (2005) · Nature Materials · doi:10.1038/nmat1390 · Cited by 6,229
Self-citationRenal clearance of quantum dots
Soo Choi, H., Liu, W., Misra, P., Tanaka, E., Zimmer, J. P., Itty Ipe, B., Bawendi, M. G., & Frangioni, J. V. (2007) · Nature Biotechnology · doi:10.1038/nbt1340 · Cited by 4,476
Gold nanoparticles in nanomedicine: preparations, imaging, diagnostics, therapies and toxicity
Boisselier, E., & Astruc, D. (2009) · Chemical Society Reviews · doi:10.1039/b806051g · Cited by 2,842
Self-Assembly of CdSe−ZnS Quantum Dot Bioconjugates Using an Engineered Recombinant Protein
Mattoussi, H., Mauro, J. M., Goldman, E. R., Anderson, G. P., Sundar, V. C., Mikulec, F. V., & Bawendi, M. G. (2000) · Journal of the American Chemical Society · doi:10.1021/ja002535y · Cited by 1,681
Self-assembled nanoscale biosensors based on quantum dot FRET donors
Medintz, I. L., Clapp, A. R., Mattoussi, H., Goldman, E. R., Fisher, B., & Mauro, J. M. (2003) · Nature Materials · doi:10.1038/nmat961 · Cited by 1,601
Self-citationLi, J. J., Wang, Y. A., Guo, W., Keay, J. C., Mishima, T. D., Johnson, M. B., & Peng, X. (2003) · Journal of the American Chemical Society · doi:10.1021/ja0363563 · Cited by 1,566
(2008) · Elsevier eBooks · doi:10.1016/b978-0-12-370501-3.x0001-x · Cited by 1,367
Fluorescence Resonance Energy Transfer Between Quantum Dot Donors and Dye-Labeled Protein Acceptors
Clapp, A. R., Medintz, I. L., Mauro, J. M., Fisher, B. R., Bawendi, M. G., & Mattoussi, H. (2004) · Journal of the American Chemical Society · doi:10.1021/ja037088b · Cited by 1,302
Self-citationHochuli, E., Döbeli, H., & Schacher, A. (1987) · Journal of Chromatography A · doi:10.1016/s0021-9673(00)93969-4 · Cited by 1,112
Designing multifunctional quantum dots for bioimaging, detection, and drug delivery
Zrazhevskiy, P., Sena, M., & Gao, X. (2010) · Chemical Society Reviews · doi:10.1039/b915139g · Cited by 997
Semiconductor Quantum Dots for Bioanalysis
Gill, R., Zayats, M., & Willner, I. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200800169 · Cited by 902
Correlation of the Base Strengths of Amines1
Hall, H. K. (1957) · Journal of the American Chemical Society · doi:10.1021/ja01577a030 · Cited by 807
Design considerations for tumour-targeted nanoparticles
Choi, H. S., Liu, W., Liu, F., Nasr, K., Misra, P., Bawendi, M. G., & Frangioni, J. V. (2010) · Nature Nanotechnology · doi:10.1038/nnano.2009.314 · Cited by 754
Functionalisation of nanoparticles for biomedical applications
Thanh, N. T. K., & Green, L. A. W. (2010) · Nano Today · doi:10.1016/j.nantod.2010.05.003 · Cited by 705
Compact Biocompatible Quantum Dots Functionalized for Cellular Imaging
Liu, W., Howarth, M., Greytak, A. B., Zheng, Y., Nocera, D. G., Ting, A. Y., & Bawendi, M. G. (2008) · Journal of the American Chemical Society · doi:10.1021/ja076069p · Cited by 612
Quantum dot-based resonance energy transfer and its growing application in biology
Medintz, I. L., & Mattoussi, H. (2009) · Phys. Chem. Chem. Phys. · doi:10.1039/b813919a · Cited by 569
Self-citationSynthesis of Compact Multidentate Ligands to Prepare Stable Hydrophilic Quantum Dot Fluorophores
Uyeda, H. T., Medintz, I. L., Jaiswal, J. K., Simon, S. M., & Mattoussi, H. (2005) · Journal of the American Chemical Society · doi:10.1021/ja044031w · Cited by 555
Self-citationBiocompatible Quantum Dots for Biological Applications
Rosenthal, S. J., Chang, J. C., Kovtun, O., McBride, J. R., & Tomlinson, I. D. (2011) · Chemistry & Biology · doi:10.1016/j.chembiol.2010.11.013 · Cited by 532
Susumu, K., Uyeda, H. T., Medintz, I. L., Pons, T., Delehanty, J. B., & Mattoussi, H. (2007) · Journal of the American Chemical Society · doi:10.1021/ja0749744 · Cited by 517
Self-citationAlgar, W. R., Tavares, A. J., & Krull, U. J. (2010) · Analytica Chimica Acta · doi:10.1016/j.aca.2010.05.026 · Cited by 511
Self-citationSmith, A. M., Duan, H., Rhyner, M. N., Ruan, G., & Nie, S. (2006) · Physical Chemistry Chemical Physics · doi:10.1039/b606572b · Cited by 462
Current and prospective applications of metal ion–protein binding
Ueda, E. K. M., Gout, P. W., & Morganti, L. (2003) · Journal of Chromatography A · doi:10.1016/s0021-9673(02)02057-5 · Cited by 456
Cell-Penetrating Quantum Dots Based on Multivalent and Endosome-Disrupting Surface Coatings
Duan, H., & Nie, S. (2007) · Journal of the American Chemical Society · doi:10.1021/ja068158s · Cited by 450
Cell-penetrating and cell-targeting peptides in drug delivery
Vivès, E., Schmidt, J., & Pèlegrin, A. (2008) · Biochimica et Biophysica Acta (BBA) - Reviews on Cancer · doi:10.1016/j.bbcan.2008.03.001 · Cited by 441
Vella, F. (1993) · Biochemical Education · doi:10.1016/0307-4412(93)90158-v · Cited by 434
Compact Cysteine-Coated CdSe(ZnCdS) Quantum Dots for in Vivo Applications
Liu, W., Choi, H. S., Zimmer, J. P., Tanaka, E., Frangioni, J. V., & Bawendi, M. (2007) · Journal of the American Chemical Society · doi:10.1021/ja073790m · Cited by 415
Pathway for Polyarginine Entry into Mammalian Cells
Fuchs, S. M., & Raines, R. T. (2004) · Biochemistry · doi:10.1021/bi035933x · Cited by 374
Biju, V., Itoh, T., & Ishikawa, M. (2010) · Chemical Society Reviews · doi:10.1039/b926512k · Cited by 372
Synthesis and Cell‐Imaging Applications of Glutathione‐Capped CdTe Quantum Dots
Zheng, Y., Gao, S., & Ying, J. Y. (2007) · Advanced Materials · doi:10.1002/adma.200600342 · Cited by 343
Delivering quantum dots into cells: strategies, progress and remaining issues
Delehanty, J. B., Mattoussi, H., & Medintz, I. L. (2009) · Analytical and Bioanalytical Chemistry · doi:10.1007/s00216-008-2410-4 · Cited by 328
Self-citationHydrodynamic Dimensions, Electrophoretic Mobility, and Stability of Hydrophilic Quantum Dots
Pons, T., Uyeda, H. T., Medintz, I. L., & Mattoussi, H. (2006) · The Journal of Physical Chemistry B · doi:10.1021/jp065041h · Cited by 302
Self-citationSolution-Phase Single Quantum Dot Fluorescence Resonance Energy Transfer
Pons, T., Medintz, I. L., Wang, X., English, D. S., & Mattoussi, H. (2006) · Journal of the American Chemical Society · doi:10.1021/ja0657253 · Cited by 282
Self-citationSapsford, K. E., Pons, T., Medintz, I. L., Higashiya, S., Brunel, F. M., Dawson, P. E., & Mattoussi, H. (2007) · The Journal of Physical Chemistry C · doi:10.1021/jp073550t · Cited by 276
Self-citationSelf-Assembled Quantum Dot−Peptide Bioconjugates for Selective Intracellular Delivery
Delehanty, J. B., Medintz, I. L., Pons, T., Brunel, F. M., Dawson, P. E., & Mattoussi, H. (2006) · Bioconjugate Chemistry · doi:10.1021/bc060044i · Cited by 264
Self-citationCapping of CdSe–ZnS quantum dots with DHLA and subsequent conjugation with proteins
Clapp, A. R., Goldman, E. R., & Mattoussi, H. (2006) · Nature Protocols · doi:10.1038/nprot.2006.184 · Cited by 260
Small and Stable Sulfobetaine Zwitterionic Quantum Dots for Functional Live-Cell Imaging
Muro, E., Pons, T., Lequeux, N., Fragola, A., Sanson, N., Lenkei, Z., & Dubertret, B. (2010) · Journal of the American Chemical Society · doi:10.1021/ja1005493 · Cited by 247
Tietz Textbook of Clinical Chemistry
Eckfeldt, J. H. (1999) · Transfusion · doi:10.1046/j.1537-2995.1999.39070794.x · Cited by 228
Gold Nanoparticle Size Controlled by Polymeric Au(I) Thiolate Precursor Size
Briñas, R. P., Hu, M., Qian, L., Lymar, E. S., & Hainfeld, J. F. (2008) · Journal of the American Chemical Society · doi:10.1021/ja076333e · Cited by 223
Mei, B. C., Susumu, K., Medintz, I. L., Delehanty, J. B., Mountziaris, T. J., & Mattoussi, H. (2008) · Journal of Materials Chemistry · doi:10.1039/b810488c · Cited by 210
Self-citationStewart, M. H., Susumu, K., Mei, B. C., Medintz, I. L., Delehanty, J. B., Blanco-Canosa, J. B., Dawson, P. E., & Mattoussi, H. (2010) · Journal of the American Chemical Society · doi:10.1021/ja102898d · Cited by 203
Self-citationMei, B. C., Susumu, K., Medintz, I. L., & Mattoussi, H. (2009) · Nature Protocols · doi:10.1038/nprot.2008.243 · Cited by 202
Self-citationSusumu, K., Mei, B. C., & Mattoussi, H. (2009) · Nature Protocols · doi:10.1038/nprot.2008.247 · Cited by 201
Self-citationWhispering‐Gallery‐Mode Lasing from a Semiconductor Nanocrystal/Microsphere Resonator Composite
Snee, P. T., Chan, Y., Nocera, D. G., & Bawendi, M. G. (2005) · Advanced Materials · doi:10.1002/adma.200401571 · Cited by 197
A Reactive Peptidic Linker for Self-Assembling Hybrid Quantum Dot−DNA Bioconjugates
Medintz, I. L., Berti, L., Pons, T., Grimes, A. F., English, D. S., Alessandrini, A., Facci, P., & Mattoussi, H. (2007) · Nano Letters · doi:10.1021/nl070782v · Cited by 196
Self-citationYong, K.-T., Roy, I., Swihart, M. T., & Prasad, P. N. (2009) · Journal of Materials Chemistry · doi:10.1039/b817667c · Cited by 190
Oh, E., Susumu, K., Goswami, R., & Mattoussi, H. (2010) · Langmuir · doi:10.1021/la904438s · Cited by 173
Self-citationTan, S. J., Jana, N. R., Gao, S., Patra, P. K., & Ying, J. Y. (2010) · Chemistry of Materials · doi:10.1021/cm902989f · Cited by 168
Zwitterionic Biocompatible Quantum Dots for Wide pH Stability and Weak Nonspecific Binding to Cells
Breus, V. V., Heyes, C. D., Tron, K., & Nienhaus, G. U. (2009) · ACS Nano · doi:10.1021/nn900600w · Cited by 163
Park, J., Nam, J., Won, N., Jin, H., Jung, S., Jung, S., Cho, S., & Kim, S. (2011) · Advanced Functional Materials · doi:10.1002/adfm.201001924 · Cited by 161
Quantum Dot Peptide Biosensors for Monitoring Caspase 3 Proteolysis and Calcium Ions
Prasuhn, D. E., Feltz, A., Blanco‐Canosa, J. B., Susumu, K., Stewart, M. H., Mei, B. C., Yakovlev, A. V., Loukou, C., Mallet, J., Oheim, M., et al. (2010) · ACS Nano · doi:10.1021/nn1016132 · Cited by 156
Self-citationMei, B. C., Oh, E., Susumu, K., Farrell, D. F., Mountziaris, T. J., & Mattoussi, H. M. (2009) · Langmuir · doi:10.1021/la901423z · Cited by 152
Self-citationSelf-Assembled Quantum Dot-Sensitized Multivalent DNA Photonic Wires
Boeneman, K., Prasuhn, D. E., Blanco‐Canosa, J. B., Dawson, P. E., Melinger, J. S., Ancona, M. G., Stewart, M. H., Susumu, K., Huston, A. L., & Medintz, I. L. (2010) · Journal of the American Chemical Society · doi:10.1021/ja106465x · Cited by 133
Self-citationLu, H., Schöps, O., Woggon, U., & Niemeyer, C. M. (2008) · Journal of the American Chemical Society · doi:10.1021/ja078243f · Cited by 130
Delehanty, J. B., Bradburne, C. E., Boeneman, K., Susumu, K., Farrell, D. F., Mei, B. C., Blanco‐Canosa, J. B., Dawson, G., Dawson, P. E., Mattoussi, H. M., et al. (2010) · Integrative Biology · doi:10.1039/c0ib00002g · Cited by 130
Self-citationBlackman, B., Battaglia, D. M., & Peng, X. (2008) · Chemistry of Materials · doi:10.1021/cm8000688 · Cited by 118
Blackman, B., Battaglia, D. M., Mıshıma, T. D., Johnson, M. B., & Peng, X. (2007) · Chemistry of Materials · doi:10.1021/cm0704682 · Cited by 112
A Reliable and Efficient First Principles-Based Method for Predicting pKa Values. 2. Organic Acids
Zhang, S.-M., Baker, J., & Pulay, P. (2009) · The Journal of Physical Chemistry A · doi:10.1021/jp9067087 · Cited by 103
Dennis, A. M., Sotto, D. C., Mei, B. C., Medintz, I. L., Mattoussi, H. M., & Bao, G. (2010) · Bioconjugate Chemistry · doi:10.1021/bc900500m · Cited by 101
Self-citationPrasuhn, D. E., Blanco‐Canosa, J. B., Vora, G. J., Delehanty, J. B., Susumu, K., Mei, B. C., Dawson, P. E., & Medintz, I. L. (2010) · ACS Nano · doi:10.1021/nn901393v · Cited by 95
Self-citationGrowing and stability of gold nanoparticles and their functionalization by cysteine
Majzik, A., Patakfalvi, R., Hornok, V., & Dékány, I. (2009) · Gold bulletin · doi:10.1007/bf03214921 · Cited by 85
Dif, A., Boulmedais, F., Pinot, M., Roullier, V., Baudy-Floc’h, M., Coquelle, F. M., Clarke, S. J., Neveu, P. A., Vignaux, F., Borgne, R. L., et al. (2009) · Journal of the American Chemical Society · doi:10.1021/ja902743u · Cited by 77
Design and development of quantum dots and other nanoparticles based cellular imaging probe
Jana, N. R. (2010) · Physical Chemistry Chemical Physics · doi:10.1039/c0cp00726a · Cited by 74
Dithiocarbamates as Capping Ligands for Water-Soluble Quantum Dots
Zhang, Y., Schnoes, A. M., & Clapp, A. R. (2010) · ACS Applied Materials & Interfaces · doi:10.1021/am100996g · Cited by 65
Surface modification of colloidal CdX-based quantum dots for biomedical applications
Oh, J. K. (2010) · Journal of Materials Chemistry · doi:10.1039/c0jm01084g · Cited by 64
Synthesis, structure and spectroscopic characterization of water-soluble CdS nanoparticles
Barglik-Chory, C., Buchold, D. H. M., Schmitt, M. P., Kiefer, W., Heske, C., Kumpf, C., Fuchs, O., Weinhardt, L., Stahl, A. D., Umbach, E., et al. (2003) · Chemical Physics Letters · doi:10.1016/j.cplett.2003.08.068 · Cited by 64
Duan, H., Kuang, M., & Wang, Y. A. (2010) · Chemistry of Materials · doi:10.1021/cm100442x · Cited by 52
Cited by
Meta-analysis of cellular toxicity for cadmium-containing quantum dots
Oh, E., Liu, R., Nel, A., Gemill, K. B., Bilal, M., Cohen, Y., & Medintz, I. L. (2016) · Nature Nanotechnology · doi:10.1038/nnano.2015.338 · Cited by 502
Self-citationQuantum dots as a platform for nanoparticle drug delivery vehicle design
Probst, C. E., Zrazhevskiy, P., Bagalkot, V., & Gao, X. (2013) · Advanced Drug Delivery Reviews · doi:10.1016/j.addr.2012.09.036 · Cited by 466
Metadata
- Authors
- Susumu, K., Oh, E., Delehanty, J. B., Blanco-Canosa, J. B., Johnson, B. J., Jain, V., Hervey, W. J., Algar, W. R., Boeneman, K., Dawson, P. E., & Medintz, I. L.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-05-25
- Volume
- 133
- Issue
- 24
- Pages
- 9480-9496
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2316703007
- Cited by
- 293
- References
- 67
- FWCI
- 11.62
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
