A review of NIR dyes in cancer targeting and imaging

Biomaterials

Volumn 32, Issue 29, 2011, Pages 7127-7138

  Luo, Shenglin ^a   Zhang, Erlong ^a   Su, Yongping ^a   Cheng, Tianmin ^a   Shi, Chunmeng ^a  

^a THIRD MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Cancer targeting; Imaging; Multifunctional agents; Near infrared dyes

Indexed keywords

BIOMEDICAL IMAGING; CANCER-TARGETING; CLINICAL USE; DESIGN STRATEGIES; DETECTION SENSITIVITY; INDOCYANINE GREEN; MOLECULAR IMAGING; MOLECULAR PROBES; MULTIFUNCTIONAL AGENTS; NEAR INFRARED DYES; NEAR-INFRARED FLUORESCENCE; NIR DYES; NIR SPECTRUM; OPTICAL IMAGING; ORGANIC DYE; PHOTO-STABILITY; POTENTIAL APPLICATIONS; SIGNIFICANT IMPACTS; SMALL MOLECULES; TARGETED IMAGING; TISSUE AUTOFLUORESCENCE; TUMOR CELLS; TUMOR TARGETING; TUMOR-SPECIFIC LIGANDS;

ANTIBODIES; CHEMICAL DETECTION; DISEASES; LIGANDS; MEDICAL IMAGING; QUANTUM YIELD; TUMORS;

INFRARED DEVICES;

BORONDIPYRROMETHANE; CY3 DYE; CY5.5 DYE; CY7 DYE; CYANINE DYE; DYE; FLUORESCEIN ISOTHIOCYANATE; FLUORESCENT DYE; IODIDE; IR 780; LIPOSOME; METHYLENE BLUE; PHTHALOCYANINE; PORPHYRIN DERIVATIVE; SILICON DIOXIDE; SQUARAINE DERIVATIVE; TEMOPORFIN; UNCLASSIFIED DRUG; ZINC PORPHYRIN POLYMER;

DRUG ABSORPTION; DRUG STRUCTURE; DRUG TARGETING; FLUORESCENCE IMAGING; HUMAN; MOLECULAR IMAGING; NANOENCAPSULATION; NEAR INFRARED FLUORESCENCE IMAGING; NONHUMAN; PRIORITY JOURNAL; REVIEW;

ANIMALS; DIAGNOSTIC IMAGING; FLUORESCENT DYES; HUMANS; MOLECULAR IMAGING; MOLECULAR STRUCTURE; NANOPARTICLES; NEOPLASMS; SENSITIVITY AND SPECIFICITY; SPECTROSCOPY, NEAR-INFRARED;

EID: 79960835810     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2011.06.024     Document Type: Review

References (178)

1. Jemal A., Siegel R., Xu J., Ward E. Cancer statistics, 2010. CA-Cancer J Clin 2010, 60(5):277-300.
2. Greenlee R.T., Murray T., Bolden S., Wingo P.A. Cancer statistics, 2000. CA-Cancer J Clin 2000, 50(1):7-33.
3. Fass L. Imaging and cancer: a review. Mol Oncol 2008, 2(2):115-152.
4. Choy G., Choyke P., Libutti S.K. Current advances in molecular imaging: noninvasive in vivo bioluminescent and fluorescent optical imaging in cancer research. Mol Imaging 2003, 2(4):303-312.
5. Hilderbrand S.A., Weissleder R. Near-infrared fluorescence: application to in vivo molecular imaging. Curr Opin Chem Biol 2010, 14(1):71-79.
6. Pysz M.A., Gambhir S.S., Willmann J.K. Molecular imaging: current status and emerging strategies. Clin Radiol 2010, 65(7):500-516.
7. Frangioni J.V. In vivo near-infrared fluorescence imaging. Curr Opin Chem Biol 2003, 7(5):626-634.
8. Wang Y., Chen L. Quantum dots, lighting up the research and development of nanomedicine. Nanomed Nanotech Biol Med 2011, 10.1016/j.nano.2010.12.006.
9. Bharali D.J., Mousa S.A. Emerging nanomedicines for early cancer detection and improved treatment: current perspective and future promise. Pharmacol Ther 2010, 128(2):324-335.
10. Nurunnabi M., Cho K.J., Choi J.S., Huh K.M., Lee Y.K. Targeted near-IR QDs-loaded micelles for cancer therapy and imaging. Biomaterials 2010, 31(20):5436-5444.
11. Wang H., Huff T.B., Zweifel D.A., He W., Low P.S., Wei A., et al. In vitro and in vivo two-photon luminescence imaging of single gold nanorods. P Natl Acad Sci U S A 2005, 102(44):15752-15756.
12. Janib S.M., Moses A.S., MacKay J.A. Imaging and drug delivery using theranostic nanoparticles. Adv Drug Deliver Rev 2010, 62(11):1052-1063.
13. He X., Wang K., Cheng Z. In vivo near-infrared fluorescence imaging of cancer with nanoparticle-based probes. Wiley Interdiscip Rev Nanomed Nanobiotechnol 2010, 2(4):349-366.
14. He X., Gao J., Gambhir S.S., Cheng Z. Near-infrared fluorescent nanoprobes for cancer molecular imaging: status and challenges. Tredns Mol Med 2010, 16(12):574-583.
15. Nel A., Xia T., Mädler L., Li N. Toxic potential of materials at the nanolevel. Science 2006, 311(5761):622-627.
16. Moore M.N. Do nanoparticles present ecotoxicological risks for the health of the aquatic environment?. Environ Int 2006, 32(8):967-976.
17. Mancini M.C., Kairdolf B.A., Smith A.M., Nie S. Oxidative quenching and degradation of polymer-encapsulated quantum dots: new insights into the long-term fate and toxicity of nanocrystals in vivo. J Am Chem Soc 2008, 130(33):10836-10837.
18. Hoshino A., Hanada S., Yamamoto K. Toxicity of nanocrystal quantum dots: the relevance of surface modifications. Arch Toxicol 2011, 1-14.
19. Alkilany A.M., Nagaria P.K., Hexel C.R., Shaw T.J., Murphy C.J., Wyatt M.D. Cellular uptake and cytotoxicity of gold nanorods: molecular origin of cytotoxicity and surface effects. Small 2009, 5(6):701-708.
20. Nikoobakht B., El-Sayed M.A. Preparation and growth mechanism of gold nanorods (NRs) using seed-mediated growth method. Chem Mater 2003, 15(10):1957-1962.
21. Tsung C.K., Kou X., Shi Q., Zhang J., Yeung M.H., Wang J., et al. Selective shortening of single-crystalline gold nanorods by mild oxidation. J Am Chem Soc 2006, 128(16):5352-5353.
22. Resch-Genger U., Grabolle M., Cavaliere-Jaricot S., Nitschke R., Nann T. Quantum dots versus organic dyes as fluorescent labels. Nat Methods 2008, 5(9):763-775.
23. Escobedo J.O., Rusin O., Lim S., Strongin R.M. NIR dyes for bioimaging applications. Curr Opin Chem Biol 2010, 14(1):64-70.
24. Fischer G.M., Isomäki-Krondahl M., Göttker-Schnetmann I., Daltrozzo E., Zumbusch A. Pyrrolopyrrole cyanine dyes: a new class of near-infrared dyes and fluorophores. Chem - Eur J 2009, 15(19):4857-4864.
25. Gonçalves M.S.T. Fluorescent labeling of biomolecules with organic probes. Chem Rev 2008, 109(1):190-212.
26. Pleijhuis R.G., Langhout G.C., Helfrich W., Themelis G., Sarantopoulos A., Crane L.M., et al. Near-infrared fluorescence (NIRF) imaging in breast-conserving surgery: assessing intraoperative techniques in tissue-simulating breast phantoms. EJSO-Eur J Surg Onc 2011, 37(1):32-39.
27. Pauli J., Vag T., Haag R., Spieles M., Wenzel M., Kaiser W.A., et al. An in vitro characterization study of new near infrared dyes for molecular imaging. Eur J Med Chem 2009, 44(9):3496-3503.
28. Tromberg B.J., Pogue B.W., Paulsen K.D., Yodh A.G., Boas D.A., Cerussi A.E. Assessing the future of diffuse optical imaging technologies for breast cancer management. Med Phys 2008, 35(6):2443-2451.
29. von Burstin J., Eser S., Seidler B., Meining A., Bajbouj M., Mages J., et al. Highly sensitive detection of early-stage pancreatic cancer by multimodal near-infrared molecular imaging in living mice. Int J Cancer 2008, 123(9):2138-2147.
30. Tagaya N., Yamazaki R., Nakagawa A., Abe A., Hamada K., Kubota K., et al. Intraoperative identification of sentinel lymph nodes by near-infrared fluorescence imaging in patients with breast cancer. Am J Surg 2008, 195(6):850-853.
31. Xu H., Eck P.K., Baidoo K.E., Choyke P.L., Brechbiel M.W. Toward preparation of antibody-based imaging probe libraries for dual-modality positron emission tomography and fluorescence imaging. Bioorg Med Chem 2009, 17(4):5176-5181.
32. Mishra A., Behera R.K., Behera P.K., Mishra B.K., Behera G.B. Cyanines during the 1990s: a review. Chem Rev 2000, 100(6):1973-2012.
33. Ballou B., Ernst L.A., Waggoner A.S. Fluorescence imaging of tumors in vivo. Curr Med Chem 2005, 12(7):795-805.
34. Lavis L.D., Raines R.T. Bright ideas for chemical biology. ACS Chem Biol 2008, 3(3):142-155.
35. Kusano M., Tajima Y., Yamazaki K., Kato M., Watanabe M., Miwa M. Sentinel node mapping guided by indocyanine green fluorescence imaging: a new method for sentinel node navigation surgery in gastrointestinal cancer. Dig Surg 2008, 25(2):103-108.
36. Ishizawa T., Fukushima N., Shibahara J., Masuda K., Tamura S., Aoki T., et al. Real-time identification of liver cancers by using indocyanine green fluorescent imaging. Cancer 2009, 115(11):2491-2504.
37. Ishizawa T., Bandai Y., Harada N., Muraoka A., Ijichi M., Kusaka K., et al. Indocyanine green-fluorescent imaging of hepatocellular carcinoma during laparoscopic hepatectomy: an initial experience. Asian J Endosco Surg 2010, 3(1):42-45.
38. Landsman M.L., Kwant G., Mook G.A., Zijlstra W.G. Light-absorbing properties, stability, and spectral stabilization of indocyanine green. J Appl Phys 1976, 40(4):575-583.
39. Haughland R.P. Molecular probes. handbook of fluorescent probes and research chemicals 2002, Molecular Probes Inc, Eugene, OR. 9th ed.
40. Górecki T., Patonay G., Strekowski L., Chin R., Salazar N. Synthesis of novel near-infrared cyanine dyes for metal ion determination. J Heterocyclic Chem 1996, 33(6):1871-1876.
41. Patonay G., Antoine M.D., Devanathan S., Strekowski L. Near-infrared probe for determination of solvent hydrophobicity. Appl Spectrosc 1991, 45(3):457-461.
42. Strekowski L. Heterocyclic polymethine fyes: dynthesis, properties and applications 2008, Springer, Berlin/Heidelberg.
43. Chen X., Peng X., Cui A., Wang B., Wang L., Zhang R. Photostabilities of novel heptamethine 3H-indolenine cyanine dyes with different N-substituents. J Photoch Photobio A 2006, 181(1):79-85.
44. Song F., Peng X., Lu E., Zhang R., Chen X., Song B. Syntheses, spectral properties and photostabilities of novel water-soluble near-infrared cyanine dyes. J Photoch Photobio A 2004, 168(1-2):53-57.
45. Kovalska V.B., Volkova K.D., Losytskyy M.Y., Tolmachev O.I., Balanda A.O., Yarmoluk S.M. 6,6'-Disubstituted benzothiazole trimethine cyanines-new fluorescent dyes for DNA detection. Spectrochim Acta A Mol Biomol Spectrosc 2006, 65(2):271-277.
46. Yarmoluk S.M., Kovalska V.B., Lukashov S.S., Slominskii Y.L. Interaction of cyanine dyes with nucleic acids. XII.[beta]-substituted carbocyanines as possible fluorescent probes for nucleic acids detection. Bioorg Med Chem Lett 1999, 9(12):1677-1678.
47. Peng X., Song F., Lu E., Wang Y., Zhou W., Fan J., et al. Heptamethine cyanine dyes with a large stokes shift and strong fluorescence: a paradigm for excited-state intramolecular charge transfer. J Am Chem Soc 2005, 127(12):4170-4171.
48. Zhou L.C., Zhao G.J., Liu J.F., Han K.L., Wu Y.K., Peng X.J., et al. The charge transfer mechanism and spectral properties of a near-infrared heptamethine cyanine dye in alcoholic and aprotic solvents. J Photoch Photobio A 2007, 187(2-3):305-310.
49. Kim J.S., Kodagahally R., Strekowski L., Patonay G. A study of intramolecular H-complexes of novel bis(heptamethine cyanine) dyes. Talanta 2005, 67(5):947-954.
50. Gragg J.L. Synthesis of near-infrared heptamethine cyanine dyes. Chem Theses 2010, 28.
51. Volkova K.D., Kovalska V.B., Tatarets A.L., Patsenker D.V., Kryvorotenko L.D., Yarmoluk S.M. Spectroscopic study of squaraines as protein-sensitive fluorescent dyes. Dyes Pigm 2007, 72(3):285-292.
52. Oswald B., Lehmann F., Simon L., Terpetschnig E., Wolfbeis O.S. Red laser-induced fluorescence energy transfer in an immunosystem. Anal Biochem 2000, 280(2):272-277.
53. Gross S., Piwnica-Worms D. Molecular imaging strategies for drug discovery and development. Curr Opin Chem Biol 2006, 10(4):334-342.
54. Keller P.J., Pampaloni F., Stelzer E.H. Life sciences require the third dimension. Curr Opin Cell Biol 2006, 18(1):117-124.
55. Gayathri Devi D., Cibin T.R., Ramaiah D., Abraham A. Bis(3,5-diiodo-2,4,6-trihydroxyphenyl) squaraine: a novel candidate in photodynamic therapy for skin cancer models in vivo. J Photochem Photobiol B.Biol 2008, 92(3):153-159.
56. Dilek G., Akkaya E.U. Novel squaraine signalling Zn(II) ions: three-state fluorescence response to a single input. Tetrahedron Lett 2000, 41(19):3721-3724.
57. Lee H., Mason J.C., Achilefu S. Heptamethine cyanine dyes with a robust C-C bond at the central position of the chromophore. J Org Chem 2006, 71(20):7862-7865.
58. Hilderbrand S.A., Kelly K.A., Weissleder R., Tung C.H. Monofunctional near-infrared fluorochromes for imaging applications. Bioconjug Chem 2005, 16(5):1275-1281.
59. Saxena V., Sadoqi M., Shao J. Degradation kinetics of indocyanine green in aqueous solution. J Pharma Sci - US 2003, 92(10):2090-2097.
60. Umezawa K., Citterio D., Suzuki K. Water-soluble NIR fluorescent probes based on squaraine and their application for protein labeling. Anal Sci 2008, 24(2):213-217.
61. Nakazumi H., Ohta T., Etoh H., Uno T., Colyer C.L., Hyodo Y., et al. Near-infrared luminescent bis-squaraine dyes linked by a thiophene or pyrene spacer for noncovalent protein labeling. Synth Met 2005, 153(1-3):33-36.
62. Gassensmith J.J., Baumes J.M., Smith B.D. Discovery and early development of squaraine rotaxanes. Chem Commun 2009, 42:6329-6338.
63. de la Torre G., Claessens C.G., Torres T. Phthalocyanines: old dyes, new materials. putting color in nanotechnology. Chem Commun 2007, 20:2000-2015.
64. Chen Y., Su W., Bai M., Jiang J., Li X., Liu Y., et al. High performance organic field-effect transistors based on amphiphilic tris(phthalocyaninato) rare earth triple-decker complexes. J Am Chem Soc 2005, 127(45):15700-15701.
65. Kimura M., Ueki H., Ohta K., Shirai H., Kobayashi N. Self-organization of low-symmetry adjacent-type metallophthalocyanines having branched alkyl chains. Langmuir 2006, 22(11):5051-5056.
66. de la Torre G., Vázquez P., Agulló-López F., Torres T. Role of structural cactors in the nonlinear optical properties of phthalocyanines and related compounds. Chem Rev 2004, 104(9):3723-3750.
67. Cammidge A.N., Gopee H. Macrodiscotic triphenylenophthalocyanines. Chem Commun 2002, 9:966-967.
68. Huang Z. A review of progress in clinical photodynamic therapy. Technol Cancer Res T 2005, 4(3):283-293.
69. Kralova J., Briza T., Moserova I., Dolensky B., Vasek P., Pouckova P., et al. Glycol porphyrin derivatives as potent photodynamic inducers of apoptosis in tumor cells. J Med Chem 2008, 51(19):5964-5973.
70. Kralova J., Koivukorpi J., Kejik Z., Pouckova P., Sievanen E., Kolehmainen E., et al. Porphyrin-bile acid conjugates: from saccharide recognition in the solution to the selective cancer cell fluorescence detection. Org Biomol Chem 2008, 6(9):1548-1552.
71. Kralova J., Synytsya A., Pouckova P., Koc M., Dvorak M., Kral V. Novel porphyrin conjugates with a potent photodynamic antitumor effect: differential efficacy of mono- and bis-beta-cyclodextrin derivatives in vitro and in vivo. Photochem Photobiol 2006, 82(2):432-438.
72. Zaruba K., Kralova J., Rezanka P., Pouckova P., Veverkova L., Kral V. Modified porphyrin-brucine conjugated to gold nanoparticles and their application in photodynamic therapy. Org Biomol Chem 2010, 8(14):3202-3206.
73. Tanaka Y., Shin J.-Y., Osuka A. Facile synthesis of large meso-pentafluorophenyl-substituted expanded porphyrins. Eur J Org Chem 2008, 2008(8):1341-1349.
74. Srinivasan A., Ishizuka T., Osuka A., Furuta H. Doubly N-confused hexaphyrin: a novel aromatic expanded porphyrin that complexes bis-metals in the core. J Am Chem Soc 2003, 125(4):878-879.
75. Xie Y.S., Yamaguchi K., Toganoh M., Uno H., Suzuki M., Mori S., et al. Triply N-confused hexaphyrins: near-infrared luminescent dyes with a triangular shape. Angew Chem Int Edit 2009, 48(30):5496-5499.
76. Kuimova M.K., Collins H.A., Balaz M., Dahlstedt E., Levitt J.A., Sergent N., et al. Photophysical properties and intracellular imaging of water-soluble porphyrin dimers for two-photon excited photodynamic therapy. Org Biomol Chem 2009, 7(5):889-896.
77. Brinas R.P., Troxler T., Hochstrasser R.M., Vinogradov S.A. Phosphorescent oxygen sensor with dendritic protection and two-photon absorbing antenna. J Am Chem Soc 2005, 127(33):11851-11862.
78. Martos V., Castreño P., Valero J., de Mendoza J. Binding to protein surfaces by supramolecular multivalent scaffolds. Curr Opin Chem Biol 2008, 12(6):698-706.
79. Kasuga K., Matsuura N., Inoue K., Handa M., Sugimori T., Isa K., et al. Unusual absorption spectra found for some phthalocyaninatozinc(II) complexes bearing dendritic substituents at α Positions. Chem Lett 2002, 31(3):352-353.
80. Jang W.-D., Nishiyama N., Kataoka K. Supramolecular assembly of photofunctional dendrimers for biomedical nano-devices. Supramol Chem 2007, 19(4):309-314.
81. Nishiyama N., Jang W.-D., Kataoka K. Supramolecular nanocarriers integrated with dendrimers encapsulating photosensitizers for effective photodynamic therapy and photochemical gene delivery. New J Chem 2007, 31(7):1074-1082.
82. Celli J.P., Spring B.Q., Rizvi I., Evans C.L., Samkoe K.S., Verma S., et al. Imaging and photodynamic therapy: mechanisms, monitoring, and optimization. Chem Rev 2010, 110(5):2795-2838.
83. Li W.-S., Aida T. Dendrimer porphyrins and phthalocyanines. Chem Rev 2009, 109(11):6047-6076.
84. Brown S.B., Brown E.A., Walker I. The present and future role of photodynamic therapy in cancer treatment. Lancet Oncol 2004, 5(8):497-508.
85. Detty M.R., Gibson S.L., Wagner S.J. Current clinical and preclinical photosensitizers for use in photodynamic therapy. J Med Chem 2004, 47(16):3897-3915.
86. Allison R.R., Downie G.H., Cuenca R., Hu X.-H., Childs C.J.H., Sibata C.H. Photosensitizers in clinical PDT. Photodiagnosis and Photodynam 2004, 1(1):27-42.
87. Hu M., Brasseur N., Yildiz S.Z., van Lier J.E., Leznoff C.C. Hydroxyphthalocyanines as potential photodynamic agents for cancer therapy. J Med Chem 1998, 41(11):1789-1802.
88. 2-chelated tetraarylazadipyrromethene as an intrinsic dual chemosensor in the 650-850 nm spectral range. New J Chem 2008, 32(3):483-489.
89. Palma A., Tasior M., Frimannsson D.O., Vu T.T., Mećallet-Renault R., O'Shea D.F. New on-bead near-infrared fluorophores and fluorescent sensor constructs. Org Lett 2009, 11(16):3638-3641.
90. Rickert E.L., Oriana S., Hartman-Frey C., Long X., Webb T.T., Nephew K.P., et al. Synthesis and characterization of fluorescent 4-hydroxytamoxifen conjugates with unique antiestrogenic properties. Bioconjug Chem 2010, 21(5):903-910.
91. Hama Y., Urano Y., Koyama Y., Choyke P.L., Kobayashi H. Activatable fluorescent molecular imaging of peritoneal metastases following pretargeting with a biotinylated monoclonal antibody. Cancer Res 2007, 67(8):3809-3817.
92. Ogawa M., Kosaka N., Choyke P.L., Kobayashi H. Tumor-specific detection of an optically targeted antibody combined with a quencher-conjugated neutravidin "quencher-chaser": a dual "quench and chase" strategy to improve target to nontarget ratios for molecular imaging of cancer. Bioconjug Chem 2008, 20(1):147-154.
93. Donuru V.R., Zhu S., Green S., Liu H. Near-infrared emissive BODIPY polymeric and copolymeric dyes. Polymer 2010, 51(23):5359-5368.
94. Loudet A., Burgess K. BODIPY dyes and their derivatives: syntheses and spectroscopic properties. Chem Rev 2007, 107(11):4891-4932.
95. Rurack K., Kollmannsberger M., Daub J. A highly efficient sensor molecule emitting in the near infrared (NIR): 3,5-distyryl-8-(p-dimethylaminophenyl)difluoroboradiaza-s-indacene. New J Chem 2001, 25(2):289-292.
96. Burghart A., Kim H., Welch M.B., Thoresen L.H., Reibenspies J., Burgess K., et al. 3,5-Diaryl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes: synthesis, spectroscopic, electrochemical, and structural properties. J Org Chem 1999, 64(21):7813-7819.
97. Umezawa K., Matsui A., Nakamura Y., Citterio D., Suzuki K. Bright, color-tunable fluorescent dyes in the vis/NIR region: establishment of new "tailor-made" multicolor fluorophores based on borondipyrromethene. Chem - Eur J 2009, 15(5):1096-1106.
98. Umezawa K., Nakamura Y., Makino H., Citterio D., Suzuki K. Bright, color-tunable fluorescent dyes in the visible-near-infrared region. J Am Chem Soc 2008, 130(5):1550-1551.
99. 2 chelates of tetraarylazadipyrromethenes and evidence for their photodynamic therapeutic behavior. Chem Commun 2002, 17:1862-1863.
100. Loudet A., Bandichhor R., Burgess K., Palma A., McDonnell S.O., Hall M.J., et al. B, O-chelated azadipyrromethenes as near-IR probes. Org Lett 2008, 10(21):4771-4774.
101. Maeda H., Bharate G.Y., Daruwalla J. Polymeric drugs for efficient tumor-targeted drug delivery based on EPR-effect. Eur J Pharm Biopharm 2009, 71(3):409-419.
102. Iyer A.K., Khaled G., Fang J., Maeda H. Exploiting the enhanced permeability and retention effect for tumor targeting. Drug Discov Today 2006, 11(17-18):812-818.
103. Hüttemann M., Lee I., Pecinova A., Pecina P., Przyklenk K., Doan J.W. Regulation of oxidative phosphorylation, the mitochondrial membrane potential, and their role in human disease. J Bioenerg Biomembr 2008, 40(5):445-456.
104. Duncan R., Ringsdorf H., Satchi-Fainaro R. Polymer therapeutics: polymers as drugs, drug and protein conjugates and gene delivery systems: past, present and future opportunities. Springer Berlin / Heidelberg 2006, 1-8.
105. Liu T., Wu L.Y., Hopkins M.R., Choi J.K., Berkman C.E. A targeted low molecular weight near-infrared fluorescent probe for prostate cancer. Bioorg Med Chem Lett 2010, 20(23):7124-7126.
106. Chen Y., Dhara S., Banerjee S.R., Byun Y., Pullambhatla M., Mease R.C., et al. A low molecular weight PSMA-based fluorescent imaging agent for cancer. Biochem Biophys Res Commun 2009, 390(3):624-629.
107. Levi J., Cheng Z., Gheysens O., Patel M., Chan C.T., Wang Y., et al. Fluorescent fructose derivatives for imaging breast cancer cells. Bioconjug Chem 2007, 18(3):628-634.
108. Dasari M., Lee S., Sy J., Kim D., Lee S., Brown M., et al. Hoechst-IR: an imaging agent that detects necrotic tissue in vivo by binding extracellular DNA. Org Lett 2010, 12(15):3300-3303.
109. Tung C.-H., Lin Y., Moon W.K., Weissleder R. A receptor-targeted near-infrared fluorescence probe for in vivo tumor imaging. ChemBioChem 2002, 3(8):784-786.
110. Wang W., Ke S., Kwon S., Yallampalli S., Cameron A.G., Adams K.E., et al. A new optical and nuclear dual-labeled imaging agent targeting interleukin 11 receptor alpha-chain. Bioconjug Chem 2007, 18(2):397-402.
111. 3 in mice using multivalent or monovalent cRGD targeting vectors. Mol Cancer 2007, 6:41.
112. Carpenter R.D., Andrei M., Aina O.H., Lau E.Y., Lightstone F.C., Liu R., et al. Selectively targeting T- and B-cell lymphomas: a benzothiazole antagonist of α4β1 integrin. J Med Chem 2008, 52(1):14-19.
113. Garanger E., Boturyn D., Jin Z., Dumy P., Favrot M.C., Coll J.L. New multifunctional molecular conjugate vector for targeting, imaging, and therapy of tumors. Mol Ther 2005, 12(6):1168-1175.
114. Achilefu S., Dorshow R.B., Bugaj J.E., Rajagopalan R. Novel receptor-targeted fluorescent contrast agents for in vivo tumor imaging. Invest Radiol 2000, 35(8):479-485.
115. Becker A., Hessenius C., Licha K., Ebert B., Sukowski U., Semmler W., et al. Receptor-targeted optical imaging of tumors with near-infrared fluorescent ligands. Nat Biotechnol 2001, 19(4):327-331.
116. Pham W., Medarova Z., Moore A. Synthesis and application of a water-soluble near-infrared dye for cancer detection using optical imaging. Bioconjug Chem 2005, 16(3):735-740.
117. Citrin D., Lee A.K., Scott T., Sproull M., Ménard C., Tofilon P.J., et al. In vivo tumor imaging in mice with near-infrared labeled endostatin. Mol Cancer Ther 2004, 3(4):481-488.
118. Ke S., Wen X., Gurfinkel M., Charnsangavej C., Wallace S., Sevick-Muraca E.M., et al. Near-infrared optical imaging of epidermal growth factor receptor in breast cancer xenografts. Cancer Res 2003, 63(22):7870-7875.
119. Becker A., Riefke B., Ebert B., Sukowski U., Rinneberg H., Semmler W., et al. Macromolecular contrast agents for optical imaging of tumors: comparison of indotricarbocyanine-labeled human serum albumin and transferrin. Photochem Photobiol 2000, 72(2):234-241.
120. Petrovsky A., Schellenberger E., Josephson L., Weissleder R., Bogdanov A. Near-infrared fluorescent imaging of tumor apoptosis. Cancer Res 2003, 63(8):1936-1942.
121. Folli S., Westermann P., Braichotte D., Pelegrin A., Wagnieres G., van den Bergh H., et al. Antibody-indocyanin conjugates for immunophotodetection of human squamous cell carcinoma in nude mice. Cancer Res 1994, 54(10):2643-2649.
122. Ballou B., Fisher G.W., Waggoner A.S., Farkas D.L., Reiland J.M., Jaffe R., et al. Tumor labeling in vivo using cyanine-conjugated monoclonal antibodies. Cancer Immunol Immunther 1995, 41(4):257-263.
123. Soukos N.S., Hamblin M.R., Keel S., Fabian R.L., Deutsch T.F., Hasan T. Epidermal growth factor receptor-targeted immunophotodiagnosis and photoimmunotherapy of oral precancer in vivo. Cancer Res 2001, 61(11):4490-4496.
124. Rosenthal E.L., Kulbersh B.D., King T., Chaudhuri T.R., Zinn K.R. Use of fluorescent labeled anti-epidermal growth factor receptor antibody to image head and neck squamous cell carcinoma xenografts. Mol Cancer Ther 2007, 6(4):1230-1238.
125. Ramjiawan B., Maiti P., Aftanas A., Kaplan H., Fast D., Mantsch H.H., et al. Noninvasive localization of tumors by immunofluorescence imaging using a single chain Fv fragment of a human monoclonal antibody with broad cancer specificity. Cancer 2000, 89(5):1134-1144.
126. Ogawa M., Kosaka N., Choyke P.L., Kobayashi H. In vivo molecular imaging of cancer with a quenching near-infrared fluorescent probe using conjugates of monoclonal antibodies and indocyanine green. Cancer Res 2009, 69(4):1268-1272.
127. Louie A. Multimodality imaging probes: design and challenges. Chem Rev 2010, 110(5):3146-3195.
128. He X., Chen J., Wang K., Qin D., Tan W. Preparation of luminescent Cy5 doped core-shell SFNPs and its application as a near-infrared fluorescent marker. Talanta 2007, 72(4):1519-1526.
129. Lee C.H., Cheng S.H., Wang Y.J., Chen Y.C., Chen N.T., Souris J., et al. Near-infrared mesoporous Silica nanoparticles for optical imaging: characterization and in vivo biodistribution. Adv Funct Mater 2009, 19(2):215-222.
130. He X., Wu X., Wang K., Shi B., Hai L. Methylene blue-encapsulated phosphonate-terminated silica nanoparticles for simultaneous in vivo imaging and photodynamic therapy. Biomaterials 2009, 30(29):5601-5609.
131. Bendsoe N., Persson L., Johansson A., Axelsson J., Svensson J., Grafe S., et al. Fluorescence monitoring of a topically applied liposomal Temoporfin formulation and photodynamic therapy of nonpigmented skin malignancies. J Environ Pathol Toxicol Oncol 2007, 26(2):117-126.
132. Derycke A.S.L., Kamuhabwa A., Gijsens A., Roskams T., De Vos D., Kasran A., et al. Transferrin-conjugated liposome targeting of photosensitizer AlPcS4 to rat bladder carcinoma cells. J Natl Cancer 2004, 96(21):1620-1630.
133. Meerovich I.G., Smirnova Z.S., Oborotova N.A., Luk'yanets E.A., Meerovich G.A., Derkacheva V.M., et al. Hydroxyaluminium tetra-3-phenylthiophthalocyanine is a new effective photosensitizer for photodynamic therapy and fluorescent diagnosis. Bull Exp Biol Med 2005, 139(4):427-430.
134. Rahmanzadeh R., Rai P., Celli J.P., Rizvi I., Baron-Luhr B., Gerdes J., et al. Ki-67 as a molecular target for therapy in an in vitro three-dimensional model for ovarian cancer. Cancer Res 2010, 70(22):9234-9242.
135. Lee S., Ryu J.H., Park K., Lee A., Lee S.Y., Youn I.C., et al. Polymeric nanoparticle-based activatable near-infrared nanosensor for protease determination in vivo. Nano Lett 2009, 9(12):4412-4416.
136. Kim K., Kim J.H., Park H., Kim Y.S., Park K., Nam H., et al. Tumor-homing multifunctional nanoparticles for cancer theragnosis: simultaneous diagnosis, drug delivery, and therapeutic monitoring. J Control Release 2010, 146(2):219-227.
137. Masotti A., Vicennati P., Boschi F., Calderan L., Sbarbati A., Ortaggi G. A novel near-infrared indocyanine dye-polyethylenimine conjugate allows DNA delivery imaging in vivo. Bioconjug Chem 2008, 19(5):983-987.
138. Ghoroghchian P.P., Frail P.R., Susumu K., Blessington D., Brannan A.K., Chance B., et al. Near-infrared-emissive polymersomes: self-assembled soft matter for in vivo optical imaging. Proc Natl Acad Sci USA 2005, 102:2922-2927.
139. Altinoǧlu E.I., Russin T.J., Kaiser J.M., Barth B.M., Eklund P.C., Kester M., et al. Near-infrared emitting cluorophore-doped calcium phosphate nanoparticles for in vivo imaging of human breast cancer. ACS Nano 2008, 2(10):2075-2084.
140. Rao J. Shedding light on tumors using nanoparticles. ACS Nano 2008, 2(10):1984-1986.
141. Backer M.V., Gaynutdinov T.I., Patel V., Bandyopadhyaya A.K., Thirumamagal B.T.S., Tjarks W., et al. Vascular endothelial growth factor selectively targets boronated dendrimers to tumor vasculature. Mol Cancer Ther 2005, 4(9):1423-1429.
142. Song L., Li H., Sunar U., Chen J., Corbin I., Yodh A.G., et al. Naphthalocyanine-reconstituted LDL nanoparticles for in vivo cancer imaging and treatment. Int J Nanomedicine 2007, 2(4):767-774.
143. Zheng G., Li H., Yang K., Blessington D., Licha K., Lund-Katz S., et al. Tricarbocyanine cholesteryl laurates labeled LDL: new near infrared fluorescent probes (NIRFs) for monitoring tumors and gene therapy of familial hypercholesterolemia. Bioorg Med Chem Lett 2002, 12(11):1485-1488.
144. Li H., Zhang Z., Blessington D., Nelson D.S., Zhou R., Lund-Katz S., et al. Carbocyanine labeled LDL for optical imaging of tumors1. Acad Radiol 2004, 11(6):669-677.
145. Chen J., Corbin I.R., Li H., Cao W., Glickson J.D., Zheng G. Ligand conjugated low-density lipoprotein nanoparticles for enhanced optical cancer imaging in vivo. J Am Chem Soc 2007, 129(18):5798-5799.
146. Rao J., Dragulescu-Andrasi A., Yao H. Fluorescence imaging in vivo: recent advances. Curr Opin Biotechnol 2007, 18(1):17-25.
147. Funovics M., Weissleder R., Tung C.H. Protease sensors for bioimaging. Anal Bioanal Chem 2003, 377(6):956-963.
148. Weissleder R., Tung C.H., Mahmood U., Bogdanov A. In vivo imaging of tumors with protease-activated near-infrared fluorescent probes. Nat Biotechnol 1999, 17(4):375-378.
149. Tung C.H. Fluorescent peptide probes for in vivo diagnostic imaging. Pept Sci 2004, 76(5):391-403.
150. Bremer C., Tung C.H., Weissleder R. In vivo molecular target assessment of matrix metalloproteinase inhibition. Nat Med 2001, 7(6):743-748.
151. Tung C.-H., Mahmood U., Bredow S., Weissleder R. In vivo imaging of proteolytic enzyme activity using a novel molecular reporter. Cancer Res 2000, 60(17):4953-4958.
152. Jaffer F.A., Kim D.-E., Quinti L., Tung C.-H., Aikawa E., Pande A.N., et al. Optical visualization of cathepsin K activity in atherosclerosis with a novel, protease-activatable fluorescence sensor. Circulation 2007, 115(17):2292-2298.
153. Messerli S.M., Prabhakar S., Tang Y., Shah K., Cortes M.L., Murthy V., et al. A novel method for imaging apoptosis using a caspase-1 near-infrared fluorescent probe. Neoplasia 2004, 6(2):95-105.
154. Kobayashi H., Ogawa M., Alford R., Choyke P.L., Urano Y. New strategies for fluorescent probe design in medical diagnostic imaging. Chem Rev 2009, 110(5):2620-2640.
155. Wang R., Yu C., Yu F., Chen L. Molecular fluorescent probes for monitoring pH changes in living cells. Trac-Trend Anal Chem 2010, 29(9):1004-1013.
156. Urano Y., Asanuma D., Hama Y., Koyama Y., Barrett T., Kamiya M., et al. Selective molecular imaging of viable cancer cells with pH-activatable fluorescence probes. Nat Med 2009, 15(1):104-109.
157. Povrozin Y.A., Markova L.I., Tatarets A.L., Sidorov V.I., Terpetschnig E.A., Patsenker L.D. Near-infrared, dual-ratiometric fluorescent label for measurement of pH. Anal Biochem 2009, 390(2):136-140.
158. Tang B., Yu F., Li P., Tong L., Duan X., Xie T., et al. A near-infrared neutral pH fluorescent probe for monitoring minor pH changes: imaging in living HepG2 and HL-7702 cells. J Am Chem Soc 2009, 131(8):3016-3023.
159. Tang B., Liu X., Xu K., Huang H., Yang G., An L. A dual near-infrared pH fluorescent probe and its application in imaging of HepG2 cells. Chem Commun 2007, 36:3726-3728.
160. Lee H., Akers W., Bhushan K., Bloch S., Sudlow G., Tang R., et al. Near-infrared pH-activatable fluorescent probes for imaging primary and mtastatic breast tumors. Bioconjug Chem 2011, 22(4):777-784.
161. Jain R.K. Barriers to drug delivery in solid tumors. Sci Am 1994, 271(1):58-65.
162. Goldsmith S.J. Receptor imaging: Competitive or complementary to antibody imaging?. Semin Nucl Med 1997, 27(2):85-93.
163. Nie S. Understanding and overcoming major barriers in cancer nanomedicine. Nanomedicine-UK 2010, 5(1):523-528.
164. Trivedi E.R., Harney A.S., Olive M.B., Podgorski I., Moin K., Sloane B.F., et al. Chiral porphyrazine near-IR optical imaging agent exhibiting preferential tumor accumulation. Proc Natl Acad Sci U S A 2010, 107(4):1284-1288.
165. Yang X., Shi C., Tong R., Qian W., Zhau H.E., Wang R., et al. Near IR heptamethine cyanine dye-mediated cancer imaging. Clin Cancer Res 2010, 16(10):2833-2844.
166. Zhang C., Liu T., Su Y., Luo S., Zhu Y., Tan X., et al. A near-infrared fluorescent heptamethine indocyanine dye with preferential tumor accumulation for in vivo imaging. Biomaterials 2010, 31(25):6612-6617.
167. Zhang C., Wang S., Xiao J., Tan X., Zhu Y., Su Y., et al. Sentinel lymph node mapping by a near-infrared fluorescent heptamethine dye. Biomaterials 2010, 31(7):1911-1917.
168. Shi C., Zhang C., Su Y., Cheng T. Cyanine dyes in optical imaging of tumours. Lancet Oncol 2010, 11(9):815-816.
169. Chen L.B. Mitochondrial membrane potential in living cells. Annu Rev Cell Biol 1988, 4:155-181.
170. Zhang E., Zhang C., Su Y., Cheng T., Shi C. Newly developed strategies for multifunctional mitochondria-targeted agents in cancer therapy. Drug Discov Today 2011, 16(3-4):140-146.
171. Marzolini Catia, Tirona R.G., Kim R.B. Pharmacogenomics of the OATP and OAT families. Pharmacogenomics 2004, 5(3):273-282.
172. Trivedi E.R., Lee S., Zong H., Blumenfeld C.M., Barrett A.G.M., Hoffman B.M. Synthesis of heteroatom substituted naphthoporphyrazine derivatives with near-infrared absorption and emission. J Org Chem 2010, 75(5):1799-1802.
173. Song Y., Zong H., Trivedi E.R., Vesper B.J., Waters E.A., Barrett A.G.M., et al. Synthesis and characterization of new porphyrazine-Gd(III) conjugates as multimodal MR contrast agents. Bioconjug Chem 2010, 21(12):2267-2275.
174. Josephson L., Kircher M.F., Mahmood U., Tang Y., Weissleder R. Near-infrared fluorescent nanoparticles as combined MR/optical imaging probes. Bioconjug Chem 2002, 13(3):554-560.
175. Cai W., Chen K., Li Z.B., Gambhir S.S., Chen X. Dual-function probe for PET and near-infrared fluorescence imaging of tumor vasculature. J Nucl Med 2007, 48(11):1862-1870.
176. McCann C.M., Waterman P., Figueiredo J.L., Aikawa E., Weissleder R., Chen J.W. Combined magnetic resonance and fluorescence imaging of the living mouse brain reveals glioma response to chemotherapy. Neuroimage 2009, 45(2):360-369.
177. Lampidis T.J., Salet C., Moreno G., Chen L.B. Effects of the mitochondrial probe rhodamine 123 and related analogs on the function and viability of pulsating myocardial cells in culture. Inflamm Res 1984, 14(5):751-757.
178. Mojzisova H., Bonneau S., Brault D. Structural and physico-chemical determinants of the interactions of macrocyclic photosensitizers with cells. Eur Biophys J 2007, 36(8):943-953.