Self-assembled multicolor nanoparticles based on functionalized twistacene dendrimer for cell fluorescent imaging
Source abstract
Abstract
A series of twistacene-functionalized dendrimers were successfully synthesized and characterized. The model molecule DBPy has a twisted configuration with a torsional angle of 27.69° between pyrene and naphthalene units. The resulting compounds TPPh, TTPy, OTPy and TOPhP can self-assemble into organic nanoparticles through re-precipitation method and emit strong blue, cyan, green and red fluorescence in water, respectively. Additionally, the obtained multicolor nanoparticles showed low cytotoxicity and good photostability that selectively flow into the membrane and cytoplasm of HeLa cells, indicating the feasibility and efficiency in fluorescence imaging. This study might be a new avenue for the design of three-dimensional branched conjugated molecule and specific location imaging in living cell. Chinese researchers have developed a three-dimensional probe with tunable fluorescence emissions for improved imaging of living cells. Dendrimers are emerging polymer materials that grow into globular spheres through a branching process. Jinchong Xiao from the Hebei University and Shu Wang from the Beijing National Laboratory for Molecular Sciences and co-workers conjectured that combining the soft material properties of dendrimers with ‘twistacenes’ — a series of fused benzene rings that controllably emit light — could generate versatile imaging probes with greater affinity for intracellular positions. By tweaking molecular structures and self-assembling the dendrimers into larger organic nanoparticles in water, the researchers synthesized different probes with strong blue, cyan, green and red fluorescence emissions. Cell-based experiments revealed that the team's conjecture was correct: multicoloured nanoparticles were imaged as selectively entering HeLa cell membranes and cytoplasms while displaying minimal cytotoxic side-effects. A series of twistacene-functionalized dendrimers were successfully synthesized and characterized. They can self-assemble into organic nanoparticles through re-precipitation method and emit blue, cyan, green and red fluorescence in water. These multicolor nanoparticles showed low cytotoxicity and good photostability, which could be used for fluorescence imaging of living cells.
Source: openalex_inverted_index · Quality: baseline
Research context
OpenAlex topics: Supramolecular Self-Assembly in Materials · Luminescence and Fluorescent Materials · Dendrimers and Hyperbranched Polymers
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (59)
Show source-provided references
1. Hoeben, F. J. M., Jonkheijm, P., Meijer, E. W. & Schenning, A. P. H. About supramolecular assemblies of π-conjugated systems. Chem. Rev. 105, 1491–1546 (2005).10.1021/cr030070z ↗
2. Babu, S. S., Praveen, V. K. & Ajayaghosh, A. Functional π-gelators and their applications. Chem. Rev. 114, 1973–2129 (2014).10.1021/cr400195e ↗
3. Li, Y., Liu, T., Liu, H., Tian, M. & Li, Y. Self-assembly of intramolecular charge-transfer compounds into functional molecular systems. Acc. Chem. Res. 47, 1186–1198 (2014).10.1021/ar400264e ↗
4. Zheng, H., Li, Y., Liu, H., Yin, X. & Li, Y. Construction of heterostructure materials toward functionality. Chem. Soc. Rev. 40, 4506–4524 (2011).10.1039/c0cs00222d ↗
5. Liu, H., Xu, J., Li, Y. & Li, Y. Aggregate nanostructures of organic molecular materials. Acc. Chem. Res. 43, 1496–1508 (2010).10.1021/ar100084y ↗
6. Xiao, J., Xiao, X., Zhao, Y., Wu, B., Liu, Z., Zhang, X., Wang, S., Zhao, X., Liu, L. & Jiang, L. Synthesis, physical properties and self-assembly behavior of azole-fused pyrene derivatives. Nanoscale 5, 5420–5425 (2013).10.1039/c3nr00523b ↗
7. Pho, T. V., Toma, F. M., Chabinyc, M. L. & Wudl, F. Self-assembling decacyclene triimides prepared through a regioselective hextuple friedel–crafts carbamylation. Angew. Chem. Int. Ed. 52, 1446–1451 (2013).10.1002/anie.201207608 ↗
8. Xiao, J., Yin, Z., Li, H., Zhang, Q., Boey, F., Zhang, H. & Zhang, Q. Postchemistry of organic particles: When TTF microparticles meet TCNQ microstructures in aqueous solution. J. Am. Chem. Soc. 132, 6926–6928 (2010).10.1021/ja102154b ↗
9. Ortony, J. H., Chatterjee, T., Garner, L. E., Chworos, A., Mikhailovsky, A., Kramer, E. J. & Bazan, G. C. Self-assembly of an optically active conjugated oligoelectrolyte. J. Am. Chem. Soc. 133, 8380–8387 (2011).10.1021/ja202776b ↗
10. Feng, L., Zhu, C., Yuan, H., Liu, L., Lv, F. & Wang, S. Conjugated polymer nanoparticles: preparation, properties, functionalization and biological applications. Chem. Soc. Rev. 42, 6620–6633 (2013).10.1039/c3cs60036j ↗
11. Wu, C. & Chiu, D. T. Highly fluorescent semiconducting polymer dots for biology and medicine. Angew. Chem. Int. Ed. 52, 3086–3109 (2013).10.1002/anie.201205133 ↗
12. Wang, F., Liu, Z., Wang, B., Feng, L., Liu, L., Lv, F., Wang, Y. & Wang, S. Multi-colored fibers by self-assembly of DNA, histone proteins, and cationic conjugated polymers. Angew. Chem. Int. Ed. 53, 424–428 (2014).10.1002/anie.201308795 ↗
13. Wu, C., Schneider, T., Zeigler, M., Yu, J., Schiro, P G., Burnham, D. R., McNeill, J. D. & Chiu, D. T. Bioconjugation of ultrabright semiconducting polymer dots for specific cellular targeting. J. Am. Chem. Soc. 132, 15410–15417 (2010).10.1021/ja107196s ↗
14. Feng, G., Li, K., Liu, J., Ding, D. & Liu, B. Bright single-chain conjugated polymer dots embedded nanoparticles for long-term cell tracing and imaging. Small 10, 1212–1219 (2014).10.1002/smll.201302161 ↗
15. Anees, P., Sreejith, S. & Ajayaghosh, A. Self-assembled near-infrared dye nanoparticles as a selective protein sensor by activation of a dormant fluorophore. J. Am. Chem. Soc. 136, 13233–13239 (2014).10.1021/ja503850b ↗
16. Gill, M. R., Lara-Garcia, J., Foster, S. J., Smythe, C., Battaglia, G. & Thomas, J. A. A ruthenium(II) polypyridyl complex for direct imaging of DNA structure in living cells. Nat. Chem. 1, 662–667 (2009).10.1038/nchem.406 ↗
17. Chan, Y. S., Ye, F., Gallina, M. E., Zhang, X., Jin, Y., Wu, I. C. & Chiu, D. T. Hybrid semiconducting polymer dot–quantum dot with narrow-band emission, near-infrared fluorescence, and high brightness. J. Am. Chem. Soc. 134, 7309–7312 (2012).10.1021/ja3022973 ↗
18. Zeigler, M. B., Sun, W., Rong, Y. & Chiu, D. T. Hybrid semiconducting polymer nanoparticles as polarization-sensitive fluorescent probes. J. Am. Chem. Soc. 135, 11453–11456 (2013).10.1021/ja404719f ↗
19. Thomas, A. W., Henson, Z. B., Du, J., Vandenberg, C. A. & Bazan, G. C. Synthesis, characterization, and biological affinity of a near-infrared-emitting conjugated oligoelectrolyte. J. Am. Chem. Soc. 136, 3736–3739 (2014).10.1021/ja412695w ↗
20. Kim, H. J., Heo, C. H. & Kim, H. M. Benzimidazole-based ratiometric two-photon fluorescent probes for acidic pH in live cells and tissues. J. Am. Chem. Soc. 135, 17969–17977 (2013).10.1021/ja409971k ↗
21. Li, M., Feng, L., Lu, H., Wang, S. & Chen, C. Tetrahydro[5]helicene-based nanoparticles for structure-dependent cell fluorescent imaging. Adv. Funct. Mater. 24, 4405–4412 (2014).10.1002/adfm.201400199 ↗
22. Pu, K., Li, K., Zhang, X. & Liu, B. Conjugated oligoelectrolyte harnessed polyhedral oligomeric silsesquioxane as light-up hybrid nanodot for two-photon fluorescence imaging of cellular nucleus. Adv. Mater. 22, 4186–4189 (2010).10.1002/adma.201001544 ↗
23. Depan, D. & Misra, R. D. K. Structural and physicochemical aspects of silica encapsulated ZnO quantum dots with high quantum yield and their natural uptake in HeLa cells. J. Biomed. Mater. Res. Part A 102A, 2934–2941 (2014).10.1002/jbm.a.34963 ↗
24. Jia, Z. & Misra, R. D. K. Tunable ZnO quantum dots for bioimaging: synthesis and photoluminescence. Mater. Tech. Adv. Perf. Mater. 28, 221–227 (2013).
25. Chandrasekaran, S. & Misra, R. D. K. Phtonic antioxidant ZnS (Cd) nanorod synthesis for drug carrier and bioimaging. Mater. Tech. Adv. Perf. Mater. 28, 228–232 (2013).
26. Clar, E. Polycyclic Hydrocarbons, (Academic Press, London, UK, 1964).10.1007/978-3-662-01665-7 ↗
27. Bendikov, M., Wudl, F. & Perepichka, D. Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: the brick and mortar of organic electronics. Chem. Rev. 104, 4891–4946 (2004).10.1021/cr030666m ↗
28. Kaur, I., Jazdzyk, M., Stein, N. N., Prusevich, P. & Miller, G. P. Design, synthesis, and characterization of a persistent nonacene derivative. J. Am. Chem. Soc. 132, 1261–1263 (2010).10.1021/ja9095472 ↗
29. Purushothaman, B., Bruzek, M., Parkin, S. R., Miller, A. F. & Anthony, J. E. Synthesis and structural characterization of crystalline nonacenes. Angew. Chem. Int. Ed. 50, 7013–7017 (2011).10.1002/anie.201102671 ↗
30. Parkhurst, R. R. & Swager, T. M. Synthesis and optical properties of phenylene-containing oligoacene. J. Am. Chem. Soc. 134, 15351–15356 (2012).10.1021/ja3043883 ↗
31. Watanabe, M., Chang, Y. J., Liu, S. W., Chao, T. H., Goto, K., Islam, M. M., Yuan, C. H., Tao, Y. T., Shinmyozu, T. & Chow, T. J. The synthesis, crystal structure and charge-transport properties of hexacene. Nat. Chem. 4, 574–578 (2012).10.1038/nchem.1381 ↗
32. Pascal, R. A. Jr Twisted acenes. Chem. Rev. 106, 4809–4819 (2006).10.1021/cr050550l ↗
33. Xiao, J., Liu, Z., Zhang, X., Wu, W., Ren, T., Lv, B., Jiang, L., Wang, X., Chen, H., Su, W. & Zhao, J. Substituent effects in twisted dibenzotetracene derivatives: blue emitting materials for organic light-emitting diodes. Dyes Pigments 112, 176–182 (2015).10.1016/j.dyepig.2014.07.007 ↗
34. Li, J. & Zhang, Q. Mono- and oligocyclic aromatic ynes and diynes as building blocks to approach larger acenes, heteroacenes, and twistacenes. Synlett 24, 686–696 (2013).10.1055/s-0032-1318157 ↗
35. Xiao, J., Duong, H. M., Liu, Y., Shi, W., Ji, L., Li, G., Li, S., Liu, X., Ma, J., Wudl, F. & Zhang, Q. Synthesis and structure characterization of a stable nonatwistacene. Angew. Chem. Int. Ed. 51, 6094–6098 (2012).10.1002/anie.201200949 ↗
36. Xiao, J., Liu, S., Liu, Y., Ji, L., Liu, X., Zhang, H., Sun, X. & Zhang, Q. Synthesis, structure, and physical properties of 5,7,14,16-tetraphenyl-8:9,12:13-bisbenzo-hexatwistacene. Chem. Asian J. 7, 561–564 (2012).10.1002/asia.201100733 ↗
37. Xiao, J., Malliakas, C. D., Liu, Y., Zhou, F., Li, G., Su, H., Kanatzidis, M. G., Wudl, F. & Zhang, Q. “Clean reaction” strategy to approach a stable, green heptatwistacene containing a single terminal pyrene unit. Chem. Asian J. 7, 672–675 (2012).10.1002/asia.201100910 ↗
38. Xiao, J., Divayana, Y., Zhang, Q., Doung, H. M., Zhang, H., Boey, F., Sun, X. & Wudl, F. Synthesis, structure, and optoelectronic properties of a new twistacene 1,2,3,4,6,13-hexaphenyl-7:8,11:12-bisbenzo-pentacene. J. Mater. Chem. 20, 8167–8170 (2010).10.1039/c0jm01460e ↗
39. Zhang, Q., Divayana, Y., Xiao, J., Wang, Z., Tiekink, E. R. T., Doung, H.M., Zhang, H., Boey, F., Sun, X. & Wudl, F. Synthesis, characterization, and bipolar transporting behavior of a new twisted polycyclic aromatic hydrocarbon: 1’,4’-diphenyl-naphtho-(2’.3’:1.2)-pyrene-6’-nitro-7’-methyl carboxylate. Chem. Eur. J. 16, 7422–7426 (2010).10.1002/chem.201000026 ↗
40. Liu, Z., Wang, W., Wu, W., Chen, H., Zhang, X., Ren, T., Wang, X., Zhao, J. & Xiao, J. Synthesis, characterization and photocurrent behavior of asymmetrical heterotwistacenes. Dyes Pigments 115, 143–148 (2015).10.1016/j.dyepig.2014.12.025 ↗
41. Weil, T., Vosch, T., Hofkens, J., Peneva, K. & Müllen, K. The rylene colorant family—tailored nanoemitters for photonics research and applications. Angew. Chem. Int. Ed. 49, 9068–9093 (2010).10.1002/anie.200902532 ↗
42. Qin, T., Zhou, G., Scheiber, H., Bauer, R. E., Baumgarten, M., Anson, C. E., List, E. J. W. & Müllen, K. Polytriphenylene dendrimers: a unique design for blue-light-emitting materials. Angew. Chem. Int. Ed. 47, 8292–8296 (2008).10.1002/anie.200802854 ↗
43. Qin, T., Wiedemair, W., Nau, S., Trattnig, R., Sax, S., Winkler, S., Vollmer, A., Koch, N., Baumgarten, M., List, E. J. W. & Müllen, K Core, shell, and surface-optimized dendrimers for blue light-emitting diodes. J. Am. Chem. Soc. 133, 1301–1303 (2011).10.1021/ja109734e ↗
44. Wang, J., Yan, J., Tang, Z., Xiao, Q., Ma, Y. & Pei, J. Gradient shape-persistent π-conjugated dendrimers for light-harvesting: synthesis, photophysical properties, and energy funneling. J. Am. Chem. Soc. 130, 9952–9962 (2008).10.1021/ja803109r ↗
45. Wang, J., Luo, J., Liu, L., Zhou, Q, Ma, Y. & Pei, J. Nanosized gradient π-conjugated thienylethynylene dendrimers for light harvesting: synthesis and properties. Org. Lett. 8, 2281–2284 (2006).10.1021/ol0605427 ↗
46. Wang, J., Tang, Z., Xiao, Q., Ma, Y. & Pei, J. Star-shaped D-π-A conjugated molecules: synthesis and broad absorption bands. Org. Lett. 11, 863–866 (2009).10.1021/ol802845w ↗
47. Liu, Z., Xiao, J., Fu, Q., Feng, H., Zhang, X., Ren, T., Wang, S., Ma, D., Wang, X. & Chen, H. Synthesis and physical properties of the conjugated dendrons bearing twisted acenes used in solution processing of organic light-emitting diodes. ACS Appl. Mater. Interfaces 5, 11136–11141 (2013).10.1021/am403394k ↗
48. Schwab, M. G., Qin, T., Pisula, W., Mavrinskiy, A., Feng, X., Baumgarten, M., Kim, H., Laquai, F., Schub, S., Trattnig, R., List, E. J. W. & Müllen, K. Molecular triangles: synthesis, self-assembly, and blue emission of cyclo-7,10-tris-triphenylenyl macrocycles. Chem. Asian J. 6, 3001–3011 (2011).10.1002/asia.201100258 ↗
49. Hammer, B. A. G., Baumqarten, M. & Müllen, K. Covalent attachment and release of small molecules from functional polyphenylene dendrimers. Chem. Commun. 50, 2034–2036 (2014).10.1039/C3CC48741E ↗
50. Hofkens, J., Vosch, T., Maus, M., Köhn, F., Cotlet, M., Weil, T., Herrmann, A., Müllen, K. & De Schryver, F. C. Conformational rearrangements in and twisting of a single molecule. Chem. Phys. Lett. 333, 255–263 (2001).10.1016/S0009-2614(00)01349-X ↗
51. Hu, J., Zhang, D. & Harris, F. W. Ruthenium(III) chloride catalyzed oxidation of pyrene and 2,7-disubstitued pyrenes: an efficient, one-step synthesis of pyrene-4,5-diones and pyrene-4,5,9,10-tetraones. J. Org. Chem. 70, 707–708 (2005).10.1021/jo048509q ↗
52. Tao, Z., Hong, G., Shinji, C., Chen, C., Diao, S., Antaris, A. L., Zhang, B., Zou, Y. & Dai, H. Biological imaging using nanoparticles of small organic molecules with fluorescence emission at wavelengths longer than 1000 nm. Angew. Chem. Int. Ed. 52, 13002–13006 (2013).10.1002/anie.201307346 ↗
53. Wu, C., Szymanski, C. & McNeill, J. Preparation and encapsulation of highly fluorescence conjugated polymer nanoparticles. Langmuir 22, 2956–2960 (2006).10.1021/la060188l ↗
54. Zhang, H., Hong, X., Ba, X., Yu, B., Wen, X., Wang, S., Wang, X., Liu, L. & Xiao, J. Synthesis, physical properties, and photocurrent behavior of strongly emissive boron-chelate heterochrysene derivatives. Asian J. Org. Chem. 3, 1168–1172 (2014).10.1002/ajoc.201402131 ↗
55. Xiao, J., Xu, J., Cui, S., Liu, H., Wang, S. & Li, Y. Supramolecula helix of an amphiphilic pyrene derivatives induced by chiral tryptophan through electrostatic interactions. Org. Lett. 10, 645–648 (2008).10.1021/ol7030087 ↗
56. Balakrishnan, K., Datar, A., Naddo, T., Huang, J., Oitker, R., Yen, M., Zhao, J. & Zang, L. Effect of side-chain substituents on self-assembly of perylene diimide molecules: morphology control. J. Am. Chem. Soc. 128, 7390–7398 (2006).10.1021/ja061810z ↗
57. Gong, X., Milic, T., Xu, C., Battas, J. D. & Drain, C. M. Preparation and characterization of porphyrin nanoparticles. J. Am. Chem. Soc. 124, 14290–14291 (2002).10.1021/ja027405z ↗
58. Vijayakumar, C., Sugiyasu, K. & Takeuchi, M. Oligofluorene-based electrophoretic nanoparticles in aqueous medium as a donor scaffold for fluorescence resonance energy transfer and white-light emission. Chem. Sci. 2, 291–294 (2011).10.1039/C0SC00343C ↗
59. Wang, Y., Jones, E. M., Tang, Y., Ji, E., Lopez, G. P., Chi, E. Y., Schanze, K. S. & Whitten, DG Effect of polymer chain length on membrane perturbation activity of cationic phenylene ethynylene oligomers and polymers. Langmuir 27, 10770–10775 (2011).10.1021/la201820k ↗