Nano-confined squaraine dye assemblies: New photoacoustic and near-infrared fluorescence dual-modular imaging probes in vivo

Bioconjugate Chemistry

Volumn 25, Issue 11, 2014, Pages 2021-2029

  Zhang, Di ^a   Zhao, Ying Xi ^a,b   Qiao, Zeng Ying ^a   Mayerhöffer, Ulrich ^c   Spenst, Peter ^c   Li, Xiao Jun ^b   Würthner, Frank ^c   Wang, Hao ^a  

^a NATIONAL CENTER FOR NANOSCIENCE AND TECHNOLOGY   (China)

^b HEBEI UNIVERSITY OF TECHNOLOGY   (China)

^c UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BLOOD VESSELS; CYTOLOGY; FLUORESCENCE IMAGING; INFRARED DEVICES; PHOSPHOLIPIDS; PHOTOBLEACHING; SELF ASSEMBLY; TUMORS;

BI-LAYER; FLUORESCENCE TOMOGRAPHY; IMAGING PROBE; IN-VIVO; MODULARS; NEAR-INFRARED FLUORESCENCE; SQUARAINE DYES; SQUARAINES; TISSUE PENETRATIONS; TUMOUR TISSUE;

LIPOSOMES;

FLUORESCENT DYE; LIPOSOME; PHOSPHOLIPID; SQUARAINE; UNCLASSIFIED DRUG; CYCLOBUTANE DERIVATIVE; NANOMATERIAL; PHENOL DERIVATIVE;

ANIMAL EXPERIMENT; ARTICLE; BILAYER MEMBRANE; BLEACHING; BLOOD VESSEL; CONTROLLED STUDY; CYTOPLASM; DRUG DELIVERY SYSTEM; FEMALE; FLUORESCENCE; HYDROPHOBICITY; IN VITRO STUDY; IN VIVO STUDY; MCF 7 CELL LINE; MOUSE; NEAR INFRARED FLUORESCENCE; NONHUMAN; PHOSPHOLIPID BILAYER; PHOTOACOUSTIC TOMOGRAPHY; SOLID TUMOR; THERMOSTABILITY; ANIMAL; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; FLUORESCENCE IMAGING; HUMAN; INFRARED RADIATION; LIGHT RELATED PHENOMENA; MAMMARY NEOPLASMS, EXPERIMENTAL; PHOTOACOUSTICS; PROCEDURES; THREE DIMENSIONAL IMAGING;

ANIMALS; CYCLOBUTANES; FEMALE; FLUORESCENT DYES; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IMAGING, THREE-DIMENSIONAL; INFRARED RAYS; LIPOSOMES; MAMMARY NEOPLASMS, EXPERIMENTAL; MCF-7 CELLS; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NANOSTRUCTURES; OPTICAL IMAGING; OPTICAL PROCESSES; PHENOLS; PHOSPHOLIPIDS; PHOTOACOUSTIC TECHNIQUES;

EID: 84913526894     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc5003983     Document Type: Article

References (51)

1. Frangioni, J. V. (2003) In vivo near-infrared fluorescence imaging Curr. Opin. Chem. Biol. 7, 626-634
2. Sun, H. T., Hosokawa, A., Miwa, Y., Shimaoka, F., Fujii, M., Mizuhata, M., Hayashi, S., and Deki, S. (2009) Strong ultra-broadband near-infrared photoluminescence from bismuth-embedded zeolites and their derivatives Adv. Mater. 21, 3694-3698
3. Chen, J., Tao, J., Ban, D., Helander, M. G., Wang, Z., Qiu, J., and Lu, Z. (2012) Hybrid organic/inorganic optical up-converter for pixel-less near-infrared imaging Adv. Mater. 24, 3138-3142
4. Zhang, Z., Wang, J., and Chen, C. (2013) Near-infrared light-mediated nanoplatforms for cancer thermo-chemotherapy and optical imaging Adv. Mater. 25, 3869-3880
5. Luo, S., Zhang, E., Su, Y., Cheng, T., and Shi, C. (2011) A review of NIR dyes in cancer targeting and imaging Biomaterials 32, 7127-7138
6. Hilderbrand, S. A. and Weissleder, R. (2010) Near-infrared fluorescence: application to in vivo molecular imaging Curr. Opin. Chem. Biol. 14, 71-79
7. Feng, L., Wu, L., and Qu, X. (2013) New horizons for diagnostics and therapeutic applications of graphene and graphene oxide Adv. Mater. 25, 168-186
8. Wang, L. V. and Hu, S. (2012) Photoacoustic tomography: in vivo imaging from organelles to organs Science 335, 1458-1462
9. Zerda, A. D. L., Zavaleta, C., Keren, S., Vaithilingam, S., Bodapati, S., Liu, Z., Levi, J., Smith, B. R., Ma, T. J., Oralkan, O., Cheng, Z., Chen, X., Dai, H., Khuri Yakub, B. T., and Gambhir, S. S. (2008) Carbon nanotubes as photoacoustic molecular imaging agents in living mice Nat. Nanotechnol. 3, 557-562
10. Xu, M. H. and Wang, L. V. (2006) Photoacoustic imaging in biomedicine Rev. Sci. Instrum. 77, 041101-041122
11. Dragulescu Andrasi, A., Kothapalli, S. R., Tikhomirov, G. A., Rao, J., and Gambhir, S. S. (2013) Activatable oligomerizable imaging agents for photoacoustic imaging of furin-like activity in living subjects J. Am. Chem. Soc. 135, 11015-11022
12. Lovell, J. F., Jin, C. S., Huynh, E., Jin, H., Kim, C., Rubinstein, J. L., Chan, W. C. W., Cao, W., Wang, L. V., and Zheng, G. (2011) Porphysome nanovesicles generated by porphyrin bilayers for use as multimodal biophotonic contrast agents Nat. Mater. 10, 324-332
13. Akers, W. J., Kim, C., Berezin, M., Guo, K., Fuhrhop, R., Lanza, G. M., Fischer, G. M., Daltrozzo, E., Zumbusch, A., Cai, X., Wang, L. V., and Achilefu, S. (2011) Noninvasive photoacoustic and fluorescence sentinel lymph node identification using dye-loaded perfluorocarbon nanoparticles ACS Nano 5, 173-182
14. de la Zerda, A., Bodapati, S., Teed, R., May, S. Y., Tabakman, S. M., Liu, Z., Khuri-Yakub, B. T., Chen, X., Dai, H., and Gambhir, S. S. (2012) Family of enhanced photoacoustic imaging agents for high-sensitivity and multiplexing studies in living mice ACS Nano 6, 4694-4701
15. Cook, J. R., Frey, W., and Emelianov, S. (2013) Quantitative photoacoustic imaging of nanoparticles in cells and tissues ACS Nano 7, 1272-1280
16. Hannah, A., Luke, G., Wilson, K., Homan, K., and Emelianov, S. (2013) Indocyanine green-loaded photoacoustic nanodroplets: dual contrast nanoconstructs for enhanced photoacoustic and ultrasound imaging ACS Nano 8, 250-259
17. Nie, L., Chen, M., Sun, X., Rong, P., Zheng, N., and Chen, X. (2014) Palladium nanosheets as highly stable and effective contrast agents for in vivo photoacoustic molecular imaging Nanoscale 6, 1271-1276
18. Cheng, L., Liu, J., Gu, X., Gong, H., Shi, X., Liu, T., Wang, C., Wang, X., Liu, G., Xing, H., Bu, W., Sun, B., and Liu, Z. (2014) PEGylated WS2 nanosheets as a multifunctional theranostic agent for in vivo dual-modal CT/photoacoustic imaging guided photothermal therapy Adv. Mater. 26, 1886-1893
19. Homan, K. A., Souza, M., Truby, R., Luke, G. P., Green, C., Vreeland, E., and Emelianov, S. (2011) Silver nanoplate contrast agents for in vivo molecular photoacoustic imaging ACS Nano 6, 641-650
20. Ku, G., Zhou, M., Song, S., Huang, Q., Hazle, J., and Li, C. (2012) Copper sulfide nanoparticles as a new class of photoacoustic contrast agent for deep tissue imaging at 1064 nm ACS Nano 6, 7489-7496
21. Jokerst, J. V., Cole, A. J., Van de Sompel, D., and Gambhir, S. S. (2012) Gold nanorods for ovarian cancer detection with photoacoustic imaging and resection guidance via raman imaging in living mice ACS Nano 6, 10366-10377
22. Huynh, E., Jin, C. S., Wilson, B. C., and Zheng, G. (2014) Aggregate enhanced trimodal porphyrin shell microbubbles for ultrasound, photoacoustic, and fluorescence imaging Bioconjugate Chem. 25, 796-801
23. Ng, K. K., Shakiba, M., Huynh, E., Weersink, R. A., Roxin, á., Wilson, B. C., and Zheng, G. (2014) Stimuli-responsive photoacoustic nanoswitch for in vivo sensing applications ACS Nano 8, 8363-8373
24. Mayerhöffer, U., Gsänger, M., Stolte, M., Fimmel, B., and Würthner, F. (2013) Synthesis and molecular properties of acceptor-substituted squaraine dyes Chem.-Eur. J. 19, 218-232
25. Mayerhöffer, U., Fimmel, B., and Würthner, F. (2012) Bright near-infrared fluorophores based on squaraines by unexpected halogen effects Angew. Chem., Int. Ed. 124, 168-171
26. Arun, K. T., Epe, B., and Ramaiah, D. (2002) Aggregation behavior of halogenated squaraine dyes in buffer, electrolytes, organized media, and DNA J. Phys. Chem. B 106, 11622-11627
27. Jyothish, K., Hariharan, M., and Ramaiah, D. (2007) Chiral supramolecular assemblies of a squaraine dye in solution and thin films: concentration-, temperature-, and solvent-induced chirality inversion Chem.-Eur. J. 13, 5944-5951
28. Ajayaghosh, A., Chithra, P., Varghese, R., and Divya, K. P. (2008) Controlled self-assembly of squaraines to 1D supramolecular architectures with high molar absorptivity Chem. Commun. 969-971
29. Chithra, P., Varghese, R., Divya, K. P., and Ajayaghosh, A. (2008) Solvent-induced aggregation and cation-controlled self-assembly of tripodal squaraine dyes: optical, chiroptical and morphological properties Chem.-Asian J. 3, 1365-1373
30. Mayerhöffer, U., Deing, K., Gruß, K., Braunschweig, H., Meerholz, K., and Würthner, F. (2009) Outstanding short-circuit currents in BHJ solar cells based on NIR-absorbing acceptor-substituted squaraines Angew. Chem., Int. Ed. 48, 8776-8779
31. Wang, L., Li, L. L., Fan, Y. S., and Wang, H. (2013) Host-guest supramolecular nanosystems for cancer diagnostics and therapeutics Adv. Mater. 25, 3888-3898
32. Wang, L., Li, L. L., Ma, H. L., and Wang, H. (2013) Recent advances in biocompatible supramolecular assemblies for biomolecular detection and delivery Chin. Chem. Lett. 24, 351-358
33. Xu, J. H., Gao, F. P., Liu, X. F., Zeng, Q., Guo, S. S., Tang, Z. Y., Zhao, X. Z., and Wang, H. (2013) Supramolecular gelatin nanoparticles as matrix metalloproteinase responsive cancer cell imaging probes Chem. Commun. 49, 4462-4464
34. Wang, H., Wang, S., Su, H., Chen, K. J., Armijo, A. L., Lin, W. Y., Wang, Y., Sun, J., Kamei, K. I., Czernin, J., Radu, C. G., and Tseng, H. R. (2009) A supramolecular approach for preparation of size-controlled nanoparticles Angew. Chem., Int. Ed. 48, 4344-4348
35. Chen, K. J., Wolahan, S. M., Wang, H., Hsu, C. H., Chang, H. W., Durazo, A., Hwang, L. P., Garcia, M. A., Jiang, Z. K., Wu, L., Lin, Y. Y., and Tseng, H. R. (2011) A small MRI contrast agent library of gadolinium(III)-encapsulated supramolecular nanoparticles for improved relaxivity and sensitivity Biomaterials 32, 2160-2165
36. Zhang, D., Zhao, Y. X., Gao, Y. J., Gao, F. P., Fan, Y. S., Li, X. J., Duan, Z. Y., and Wang, H. (2013) Anti-bacterial and in vivo tumor treatment by reactive oxygen species generated by magnetic nanoparticles J. Mater. Chem. B 1, 5100-5107
37. Wang, S., Chen, K. J., Wu, T. H., Wang, H., Lin, W. Y., Ohashi, M., Chiou, P. Y., and Tseng, H. R. (2010) Photothermal effects of supramolecularly assembled gold nanoparticles for the targeted treatment of cancer cells Angew. Chem., Int. Ed. 49, 3777-3781
38. Fan, K., Cao, C., Pan, Y., Lu, D., Yang, D., Feng, J., Song, L., Liang, M., and Yan, X. (2012) Magnetoferritin nanoparticles for targeting and visualizing tumour tissues Nat. Nanotechnol. 7, 459-464
39. Barreto, J. A., O'Malley, W., Kubeil, M., Graham, B., Stephan, H., and Spiccia, L. (2011) Nanomaterials: applications in cancer imaging and therapy Adv. Mater. 23, H18-H40
40. Gabizon, A. and Papahadjopoulos, D. (1988) Liposome formulations with prolonged circulation time in blood and enhanced uptake by tumors Proc. Natl. Acad. Sci. U.S.A. 85, 6949-6953
41. Mayerhöffer, U. and Würthner, F. (2012) Halogen-arene interactions assist in self-assembly of dyes Angew. Chem., Int. Ed. 51, 5615-5619
42. Szoka, F. and Papahadjopoulos, D. (1978) Procedure for preparation of liposomes with large internal aqueous space and high capture by reverse-phase evaporation Proc. Natl. Acad. Sci. U.S.A. 75, 4194-4198
43. Szoka, F. and Papahadjopoulos, D. (1980) Comparative properties and methods of preparation of lipid vesicles (liposomes) Annu. Rev. Biophy. Bioeng. 9, 467-508
44. Gao, F. P., Lin, Y. X., Li, L. L., Liu, Y., Mayerhöffer, U., Spenst, P., Su, J. G., Li, J. Y., Würthner, F., and Wang, H. (2014) Supramolecular adducts of squaraine and protein for noninvasive tumor imaging and photothermal therapy in vivo Biomaterials 35, 1004-1014
45. Danielli, A., Favazza, C. P., Maslov, K., and Wang, L. V. (2010) Picosecond absorption relaxation measured with nanosecond laser photoacoustics Appl. Phys. Lett. 97, 163701
46. Zeng, J., Goldfeld, D., and Xia, Y. (2013) A plasmon-assisted optofluidic (PAOF) system for measuring the photothermal conversion efficiencies of gold nanostructures and controlling an electrical switch Angew. Chem., Int. Ed. 52, 4169-4173
47. Tian, Q., Jiang, F., Zou, R., Liu, Q., Chen, Z., Zhu, M., Yang, S., Wang, J., Wang, J., and Hu, J. (2011) Hydrophilic Cu9S5 nanocrystals: A photothermal agent with a 25.7% heat conversion efficiency for photothermal ablation of cancer cells in vivo ACS Nano 5, 9761-9771
48. Berlier, J. E., Rothe, A., Buller, G., Bradford, J., Gray, D. R., Filanoski, B. J., Telford, W. G., Yue, S., Liu, J., Cheung, C. Y., Chang, W., Hirsch, J. D., Haugland, R. P., Beechem, J. M., and Haugland, R. P. (2003) Quantitative comparison of long-wavelength Alexa Fluor dyes to Cy dyes: fluorescence of the dyes and their bioconjugates J. Histochem. Cytochem. 51, 1699-1712
49. Lee, N., Choi, S. H., and Hyeon, T. (2013) Nano-sized CT contrast agents Adv. Mater. 25, 2641-2660
50. Hume, D. A. (2006) The mononuclear phagocyte system Curr. Opin. Immunol. 18, 49-53
51. Ji, X., Dong, S., Wei, P., Xia, D., and Huang, F. (2013) A novel diblock copolymer with a supramolecular polymer block and a traditional polymer block: preparation, controllable self-assembly in water, and application in controlled release Adv. Mater. 25, 5725-5729