Activatable organic near-infrared fluorescent probes based on a bacteriochlorin platform: Synthesis and multicolor in vivo imaging with a single excitation

Bioconjugate Chemistry

Volumn 25, Issue 2, 2014, Pages 362-369

  Harada, Toshiko ^a   Sano, Kohei ^a   Sato, Kazuhide ^a   Watanabe, Rira ^a   Yu, Zhanqian ^b   Hanaoka, Hirofumi ^a   Nakajima, Takahito ^a   Choyke, Peter L ^a   Ptaszek, Marcin ^b   Kobayashi, Hisataka ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

^b UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIOLOGY; BODY FLUIDS; DISEASES; EMISSION SPECTROSCOPY; FLUORESCENCE IMAGING; FLUORESCENCE QUENCHING; FLUORESCENCE SPECTROSCOPY; FLUOROPHORES; PROBES; PROTEINS;

BACTERIOCHLORINS; FLUORESCENT PROBES; HUMAN SERUM ALBUMINS; IN-VIVO IMAGING; MULTI-COLORS; NEAR-INFRARED; NEAR-INFRARED FLUORESCENT; ORGANICS; OVARIAN CANCERS; SINGLE EXCITATION;

INFRARED DEVICES;

CYANINE DYE; DIAGNOSTIC AGENT; FLUORESCENT DYE; HGSA NMP4; HGSA NMP5; LECTIN; RED FLUORESCENT PROTEIN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL MODEL; ARTICLE; BINDING AFFINITY; CANCER CELL CULTURE; CANCER DIAGNOSIS; CONJUGATION; CONTROLLED STUDY; DIAGNOSTIC IMAGING; DIAGNOSTIC TEST ACCURACY STUDY; DISSEMINATED CANCER; DRUG CONJUGATION; EXCITATION; FLUORESCENCE IMAGING; IN VITRO STUDY; IN VIVO STUDY; INTERNALIZATION; MOLECULAR IMAGING; MOUSE; NONHUMAN; OVARY CANCER; PERITONEUM METASTASIS; SENSITIVITY AND SPECIFICITY; SURFACE PROPERTY;

CELL LINE, TUMOR; FEMALE; FLUORESCENT DYES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PORPHYRINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROSCOPY, NEAR-INFRARED;

EID: 84894443401     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc4005238     Document Type: Article

References (34)

1. Keereweer, S., Kerrebijn, J. D., van Driel, P. B., Xie, B., Kaijzel, E. L., Snoeks, T. J., Que, I., Hutteman, M., van der Vorst, J. R., Mieog, J. S., Vahrmeijer, A. L., van de Velde, C. J., Baatenburg de Jong, R. J., and Lowik, C. W. (2011) Optical image-guided surgery - where do we stand? Mol. Imaging Biol. 13, 199-207
2. van Dam, G. M., Themelis, G., Crane, L. M., Harlaar, N. J., Pleijhuis, R. G., Kelder, W., Sarantopoulos, A., de Jong, J. S., Arts, H. J., van der Zee, A. G., Bart, J., Low, P. S., and Ntziachristos, V. (2011) Intraoperative tumor-specific fluorescence imaging in ovarian cancer by folate receptor-alpha targeting: first in-human results Nat. Med. 17, 1315-1319
3. Kobayashi, H. and Choyke, P. L. (2011) Target-cancer-cell-specific activatable fluorescence imaging probes: rational design and in vivo applications Acc. Chem. Res. 44, 83-90
4. Kobayashi, H., Longmire, M. R., Ogawa, M., and Choyke, P. L. (2011) Rational chemical design of the next generation of molecular imaging probes based on physics and biology: mixing modalities, colors and signals Chem. Soc. Rev. 40, 4626-4648
5. Kobayashi, H., Ogawa, M., Alford, R., Choyke, P. L., and Urano, Y. (2010) New strategies for fluorescent probe design in medical diagnostic imaging Chem. Rev. 110, 2620-2640
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. Weissleder, R. and Pittet, M. J. (2008) Imaging in the era of molecular oncology Nature 452, 580-589
8. Kobayashi, H., Hama, Y., Koyama, Y., Barrett, T., Regino, C. A., Urano, Y., and Choyke, P. L. (2007) Simultaneous multicolor imaging of five different lymphatic basins using quantum dots Nano Lett. 7, 1711-1716
9. Koyama, Y., Barrett, T., Hama, Y., Ravizzini, G., Choyke, P. L., and Kobayashi, H. (2007) In vivo molecular imaging to diagnose and subtype tumors through receptor-targeted optically labeled monoclonal antibodies Neoplasia 9, 1021-1029
10. Kobayashi, H., Ogawa, M., Kosaka, N., Choyke, P. L., and Urano, Y. (2009) Multicolor imaging of lymphatic function with two nanomaterials: quantum dot-labeled cancer cells and dendrimer-based optical agents Nanomedicine 4, 411-419
11. Lindsey, J. S., Mass, O., and Chen, C.-Y. (2011) Tapping the near infrared spectral region with bacteriochlorin arrays New J. Chem. 35, 511-516
12. Grimm, B., Porra, R. J., Rüdiger, W., and Scheer, H. (2006) Chlorophylls and Bacteriochlorophylls. Biochemistry, Biophysics, Function and Applications, in Advances in Photosynthesis and Respiration (Scheer, H., Ed.) Springer, Dodrecht, The Netherlands.
13. Brückner, C., Samankumara, L., and Ogikubo, J. (2012) Syntheses of Bacteriochlorins and Isobacteriochlorins, in Handbook of Porphyrin Sciences, vol 17, (Kadish, K. M., Smith, K. M., and Guilard, R., Eds.) pp 1-112, World Scientific, River Edge, NY.
14. Yang, E., Kirmaier, C., Krayer, M., Taniguchi, M., Kim, H. J., Diers, J. R., Bocian, D. F., Lindsey, J. S., and Holten, D. (2011) Photophysical properties and electronic structure of stable, tunable synthetic bacteriochlorins: extending the features of native photosynthetic pigments J. Phys. Chem. B 115, 10801-10816
15. Taniguchi, M., Cramer, D. L., Bhise, A. D., Kee, H. L., Bocian, D. F., Holten, D., and Lindsey, J. S. (2008) Accessing the near-infrared spectral region with stable, synthetic, wavelength-tunable bacteriochlorins New J. Chem. 32, 947-958
16. Cao, W., Ng, K. K., Corbin, I., Zhang, Z., Ding, L., Chen, J., and Zheng, G. (2009) Synthesis and evaluation of a stable bacteriochlorophyll-analog and its incorporation into high-density lipoprotein nanoparticles for tumor imaging Bioconjugate Chem. 20, 2023-2031
17. Liu, T. W., Chen, J., Burgess, L., Cao, W., Shi, J., Wilson, B. C., and Zheng, G. (2011) Multimodal bacteriochlorophyll theranostic agent Theranostics 1, 354-362
18. Ptaszek, M., Kee, H. L., Muthiah, C., Nothdurft, R., Akers, W., Achilefu, S., Culver, J. P., and Holten, D. (2010) Near-infrared molecular imaging probes based on chlorin-bacteriochlorin dyads Proc. SPIE 7576E, 1-9
19. Lovell, J. F., Jin, C. S., Huynh, E., Jin, H., Kim, C., Rubinstein, J. L., Chan, W. C., 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
20. Yu, Z. and Ptaszek, M. (2013) Near-IR emissive chlorin-bacteriochlorin energy-transfer dyads with a common donor and acceptors with tunable emission wavelength J. Org. Chem. 78, 10678-10691
21. Ogawa, M., Kosaka, N., Choyke, P. L., and Kobayashi, H. (2009) H-type dimer formation of fluorophores: a mechanism for activatable, in vivo optical molecular imaging ACS Chem. Biol. 4, 535-546
22. Ogawa, M., Kosaka, N., Choyke, P. L., and Kobayashi, H. (2009) In vivo molecular imaging of cancer with a quenching near-infrared fluorescent probe using conjugates of monoclonal antibodies and indocyanine green Cancer Res. 69, 1268-1272
23. Sutton, J. M., Clarke, O. J., Fernandez, N., and Boyle, R. W. (2002) Porphyrin, chlorin, and bacteriochlorin isothiocyanates: useful reagents for the synthesis of photoactive bioconjugates Bioconjugate Chem. 13, 249-263
24. Sutton, J. M., Fernandez, N., and Boyle, R. W. (2000) Functionalized diphenylchlorins and bacteriochlorins: their synthesis and bioconjugation for targeted photodynamic therapy and tumor imaging J. Porphyrins Phthalocyanines 4, 655-658
25. Springer, J. W., Parkes-Loach, P. S., Reddy, K. R., Krayer, M., Jiao, J., Lee, G. M., Niedzwiedzki, D. M., Harris, M. A., Kirmaier, C., Bocian, D. F., Lindsey, J. S., Holten, D., and Loach, P. A. (2012) Biohybrid photosynthetic antenna complexes for enhanced light-harvesting J. Am. Chem. Soc. 134, 4589-4599
26. Reddy, K. R., Jiang, J., Krayer, M., Harris, M. A., Springer, J. W., Yang, E., Jiao, J., Niedzwiedzki, D. M., Pandithavidana, D., Parkes-Loach, P. S., Kirmaier, C., Loach, P. A., Bocian, D. F., Holten, D., and Lindsey, J. S. (2013) Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures Chem. Sci. 4, 2036-2053
27. McCarthy, J. R., Bhaumik, J., Merbouh, N., and Weissleder, R. (2009) High-yielding syntheses of hydrophilic conjugatable chlorins and bacteriochlorins Org. Biomol. Chem. 7, 3430-3436
28. Regino, C. A., Ogawa, M., Alford, R., Wong, K. J., Kosaka, N., Williams, M., Feild, B. J., Takahashi, M., Choyke, P. L., and Kobayashi, H. (2010) Two-step synthesis of galactosylated human serum albumin as a targeted optical imaging agent for peritoneal carcinomatosis J. Med. Chem. 53, 1579-1586
29. Hama, Y., Urano, Y., Koyama, Y., Kamiya, M., Bernardo, M., Paik, R. S., Shin, I. S., Paik, C. H., Choyke, P. L., and Kobayashi, H. (2007) A target cell-specific activatable fluorescence probe for in vivo molecular imaging of cancer based on a self-quenched avidin-rhodamine conjugate Cancer Res. 67, 2791-2799
30. Gunn, A. J., Hama, Y., Koyama, Y., Kohn, E. C., Choyke, P. L., and Kobayashi, H. (2007) Targeted optical fluorescence imaging of human ovarian adenocarcinoma using a galactosyl serum albumin-conjugated fluorophore Cancer Sci. 98, 1727-1733
31. Hama, Y., Urano, Y., Koyama, Y., Choyke, P. L., and Kobayashi, H. (2006) Targeted optical imaging of cancer cells using lectin-binding BODIPY conjugated avidin Biochem. Biophys. Res. Commun. 348, 807-813
32. Kosaka, N., Ogawa, M., Paik, D. S., Paik, C. H., Choyke, P. L., and Kobayashi, H. (2010) Semiquantitative assessment of the microdistribution of fluorescence-labeled monoclonal antibody in small peritoneal disseminations of ovarian cancer Cancer Sci 101, 820-825
33. Hama, Y., Urano, Y., Koyama, Y., Choyke, P. L., and Kobayashi, H. (2007) D-galactose receptor-targeted in vivo spectral fluorescence imaging of peritoneal metastasis using galactosamin-conjugated serum albumin-rhodamine green J. Biomed. Opt. 12, 051501
34. Alexander, V. M., Sano, K., Yu, Z., Nakajima, T., Choyke, P. L., Ptaszek, M., and Kobayashi, H. (2012) Galactosyl human serum albumin-NMP1 conjugate: a near infrared (NIR)-activatable fluorescence imaging agent to detect peritoneal ovarian cancer metastases Bioconjugate Chem. 23, 1671-1679