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(12) United States Patent (10) Patent No.: US 7,993,927 B2 Frangioni (45) Date of Patent: Aug

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(12) United States Patent (10) Patent No.: US 7,993,927 B2 Frangioni (45) Date of Patent: Aug US007993 927B2 (12) United States Patent (10) Patent No.: US 7,993,927 B2 Frangioni (45) Date of Patent: Aug. 9, 2011 (54) HISTOLOGY METHODS FOREIGN PATENT DOCUMENTS WO WO96, 17628 6, 1996 (75) Inventor: John V. Frangioni, Wayland, MA (US) WO WO98,22146 5, 1998 WO WO98,48838 11, 1998 (73) Assignee: Beth Israel Deaconess Medical Center, WO WO 98.48846 11, 1998 Inc., Boston, MA (US) WO WO O2/O98885 12/2002 OTHER PUBLICATIONS (*) Notice: Subject to any disclaimer, the term of this Parungo et al., “Intraoperative identification of esophageal sentinel patent is extended or adjusted under 35 1ymph nodes with near-infrared fluorescence imaging'.--- - - - - J. Thorac. U.S.C. 154(b) by 1070 days. Cardiovasc. Surg., Apr. 2005; 129: 84.* Kim et al., “Near-infrared fluorescent type II quantum dots for sen (21) Appl. No.: 11/824,915 tinellymph node mapping”. Nature Biotechnology 22,93-97 (Jan. 1, 2004).* (22) Filed: Jul. 3, 2007 gatesBrinkley, with "A Dyes, Brief Haptens, Survey ofand Methods Cross-Linking for Preparing Reagents'. Protein Perspec Conju O O tives in Bioconjugate Chemistry, pp. 59-70, C. Meares (Ed.), ACS (65) Prior Publication Data Publication, Washington, D.C. (1993). US 2008/OO7356.6 A1 Mar 27, 2008 Frangioni, J.V., “In vivo near-infrared fluorescence imaging. Curr. • 1- s Opin. Chem. Biol. 7:626-634 (2003). O O Hilger et al., “Near-infrared fluorescence imaging of HER-2 protein Related U.S. Application Data over-expression in tumour cells'. Eur, Radiol., 14:1124-1129 (2004). Li et al., “Tumor Localization Using Fluorescence of Indocyanine (60) Provisional application No. 60/818,399, filed on Jul. 3, Green (ICG) in rat models”, SPIE, 2389:789-797 (1995). 2006. Licha et al., “Synthesis and characterization of cyanine dyes as con trast agents for near-infrared imaging”, SPIE. 2927: 192-198 (1996). (51) Int. Cl. Lim et al., “Selection of quantum dot wavelengths for biomedical GOIN 33/48 (2006.01) assays and imaging'. Mol. Imaging, 2:50-64 (2003). (52) U.S. Cl. .......... 436/63; 436/164; 436/172; 436/176: (Continued) 436/808; 435/40.5:435/40.52 (58) Field of Classification Search .................... 436/63, Primary Examiner-Jill Warden 436/164, 172,176,808; 435/405, 4052 Assistant Examiner - Monique Cole See application file for complete search history. (74) Attorney, Agent, or Firm — Fish & Richardson P.C. (56) References Cited (57) ABSTRACT Described are methods of visualizing biological samples U.S. PATENT DOCUMENTS using histological staining and invisible light (e.g., infrared or 5.453,505 A 9, 1995 Lee et al. near-infrared) fluorescence. 7,776,529 B2 * 8/2010 Dallwig et al. ................... 435/6 2006, 0083678 A1 4/2006 Frangioni et al. 30 Claims, 1 Drawing Sheet A:::::::: 8:3i *::::::cs:::::::: US 7,993,927 B2 Page 2 OTHER PUBLICATIONS Riefke et al., “In vivo characterization of cyanine dyes as contrast Nakayama et al., “Quantitation of brown adipose tissue perfusion in agents for near-infrared imaging, SPIE. 2927: 199-208 (1996). transgenic mice using near-infrared fluorescence imaging. Mol. Slavik, “Fluorescent Probes in Cellular and Molecular Biology”. Imaging, 2:37-49 (2003). CRC Press, Inc., pp. 1-12 (1994). Ohnishi et al., “Intraoperative detection of cell injury and cell death Xiang et al., “Detection of Myelination Using a Novel Histological with an 800 nm near-infrared fluorescent annexin V derivative'. Am. Probe'. J. Histochemistry & Cytochemistry, 53:1511-1516 (2005). J. Transplant., 6:2321-2331 (2006). Zaheer et al., “IRDye78 Conjugates for Near-Infrared Fluorescence Ohnishi et al., “Organic Alternatives to Quantum Dots for Intraopera Imaging”. Molecular Imaging, 1:354-364 (2002). tive Near-Infrared Fluorescent Sentinel Lymph Node Mapping”. Zaheer et al., “In vivo near-infrared fluorescence imaging of Molecular Imaging, 4:172-181 (2005). osteoblastic activity”. Nat. Biotechnol. 19:1148-1154 (2001). Patonay et al., “Near-Infrared Fluorogenic Labels: New Approach to an Old Problem”, Analytical Chemistry, 63:321A-327A (1991). * cited by examiner U.S. Patent Aug. 9, 2011 US 7,993,927 B2 } posodon, US 7,993,927 B2 1. 2 HISTOLOGY METHODS following the step of contacting the sample with the compo sition that includes an invisible light fluorophore and prior to CROSS-REFERENCE TO RELATED contacting the sample with the histological stain. In some APPLICATIONS embodiments, one or more steps of sample preparation are automated. This application claims priority to U.S. application Ser. In some embodiments, the composition that includes an invisible light (e.g., infrared or near-infrared) fluorophore No. 60/818,399, filed on Jul. 3, 2006, the entire contents of also includes a targeting ligand capable of binding (e.g., which are incorporated by reference herein. directly or indirectly) to a specific component, e.g., a compo TECHNICAL FIELD 10 nent or Suspected component of the sample. Exemplary tar geting ligands include proteins, antibodies, and low molecu This invention relates to methods of visualizing biological lar weight compounds. In some embodiments, the targeting samples using histological stains and invisible light (e.g., ligand includes a member of a binding pair, e.g., a ligand infrared or near-infrared) fluorescence. receptor pair. In some embodiments, the targeting ligand is 15 biotin or an avidin. The invisible light fluorophore can be BACKGROUND linked (e.g., conjugated) to the targeting ligand covalently or non-covalently. Conjugated targeting ligands can be used in Histological stains can be used for the examination of cells immunofluorescence methods, e.g., as a secondary antibody or tissue to determine abnormalities, such as disease states. to detect binding of a primary antibody to an antigen of Hematoxylin and eosin are commonly used to delineate cel interest in the sample. lular structures in biological samples. Visualizing histological staining of the sample can be per formed, e.g., by eye or using a microscope. In some embodi SUMMARY ments, an image of the sample can be captured using a cam era, e.g., using film, or using a charge coupled device. The This disclosure relates to the use of histological staining of 25 capturing of one or more images of one or more samples can cells and tissue in combination with the use of invisible light be automated. (e.g., infrared or near-infrared) fluorophores to enable visu Visualizing invisible light (e.g., infrared or near-infrared) alization of a sample using both visible light and invisible fluorescence of the sample can be performed, e.g., by fluo light fluorescence. Also disclosed, inter alia, are biological rescence microscopy. In some embodiments, an image of the samples containing both histological stains and invisible light 30 sample can be captured using a camera, e.g., using film, or fluorophores and kits for histological staining that include an using a charge coupled device. The capturing of one or more invisible light fluorophore. images of one or more samples can be automated. The invention features methods of visualizing a biological The invention also features biological samples that include sample that include contacting a biological sample with a a histological stain and an invisible light (e.g., infrared or compound that includes an invisible light (e.g., infrared or 35 near-infrared) fluorophore. In some embodiments, the invis near-infrared) fluorophore; contacting the biological sample ible light fluorophore is not a conventional histology dye with one or more histological stains (e.g., dyes Such as hema (e.g., methylene blue). toxylin and eosin and/or chromophoric histochemicals); In further aspects, the invention features kits that include a visualizing the sample under visible light; and visualizing histological stain and an invisible light (e.g., infrared or near invisible light fluorescence of the sample. Visualizing the 40 infrared) fluorophore. The kits can further include instruc sample under visible light and visualizing infrared fluores tions for using the histological stain and the invisible light cence can be performed separately or simultaneously. In fluorophore in a method of visualizing a biological sample. Some embodiments, one or more steps of the method are The new methods allow for concurrent use of histological automated. staining and techniques such as immunofluorescence to In other aspects, the invention features methods of prepar 45 detect specific antigens in biological samples. Since both ing a biological sample that include contacting the biological procedures can be used on one biological sample, colocaliza sample with a compound that includes an invisible light (e.g., tion of components of the sample is simplified. infrared or near-infrared) fluorophore, fixing the sample, and An “invisible light fluorophore' is a compound that emits contacting the sample with one or more histological stains. light at wavelengths above those visible to the human eye, i.e., In some embodiments, the sample includes one or more of 50 above 670 nm, e.g., up to 10,000 nm or up to 100,000 nm. cells, tissues, blood, bone, cartilage, collagen, or other con These invisible light fluorophores do not change the appear nective tissue. The sample can include eukaryotic cells and/or ance of histological stains, and because tissue autofluores prokaryotic cells. In some embodiments, the sample includes cence at these wavelengths is generally low, detection is cancer cells, pre-cancerous cells, or cells suspected to be extremely sensitive. In some embodiments, invisible light cancerous or pre-cancerous. In some embodiments, the 55 fluorophores can also include fluorophores that are visible to sample is an ex vivo or in vitro sample. the naked human eye, as long as they also fluoresce in the In some embodiments, a biological sample is isolated (e.g., invisible light region. biopsied) from a subject, e.g., a human, for further analysis. As used herein, the term “biological sample” refers to Preparation of the sample prior to contacting it with a com isolated, in vitro, and ex vivo cells and/or tissues.
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