Charge and hydrophobicity effects of NIR fluorophores on bone-specific imaging

Theranostics

Volumn 5, Issue 6, 2015, Pages 609-617

  Bao, Kai ^a,b   Nasr, Khaled A ^a,c   Hyun, Hoon ^a   Lee, Jeong Heon ^a   Gravier, Julien ^a   Gibbs, Summer L ^d   Choi, Hak Soo ^a  

^a BETH ISRAEL DEACONESS MEDICAL CENTER   (United States)

^b SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^c UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^d Oregon Health and Science University Department of Biomedical Engineering   (United States)

Author keywords

Bone targeting; Charge and hydrophobicity; Microcalcification; Near infrared fluorophores; Zwitterionic fluorophores

Indexed keywords

CALCIUM SALT; FLUORESCENT DYE; HYDROXYAPATITE; PAMIDRONATE CW 800; PAMIDRONATE ZW 800 1; PAMIDRONATE ZW 800 3A; PAMIDRONIC ACID; UNCLASSIFIED DRUG; BISPHOSPHONIC ACID DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BONE EXAMINATION; BONE IMAGING; CONTROLLED STUDY; DRUG BINDING; DRUG CLEARANCE; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG HALF LIFE; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE IMAGING; HYDROPHOBICITY; IMAGING; IN VIVO STUDY; MALE; MOUSE; NEAR INFRARED IMAGING SYSTEM; NONHUMAN; PHYSICAL CHEMISTRY; PLASMA CLEARANCE; ANIMAL; BONE; CALCINOSIS; CHEMICAL PHENOMENA; CHEMISTRY; FEMALE; NEAR INFRARED SPECTROSCOPY; PATHOLOGY; PROCEDURES; STATIC ELECTRICITY; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; BONE AND BONES; CALCINOSIS; DIPHOSPHONATES; FEMALE; FLUORESCENT DYES; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MICE; SPECTROSCOPY, NEAR-INFRARED; STATIC ELECTRICITY; TISSUE DISTRIBUTION;

EID: 84930650858     PISSN: None     EISSN: 18387640     Source Type: Journal    
DOI: 10.7150/thno.11222     Document Type: Article

References (38)

1. Jung A, Bisaz S, Fleisch H. The binding of pyrophosphate and two diphosphonates by hydroxyapatite crystals. Calcified tissue research. 1973; 11:269-80.
2. Fleisch H. Bisphosphonates--history and experimental basis. Bone. 1987; 8 Suppl 1: S23-8.
3. van Beek ER, Lowik CW, Ebetino FH, Papapoulos SE. Binding and antiresorptive properties of heterocycle-containing bisphosphonate analogs:structure-activity relationships. Bone. 1998; 23: 437-42.
4. Lipton A, Theriault RL, Hortobagyi GN, Simeone J, Knight RD, Mellars K, et al. Pamidronate prevents skeletal complications and is effective palliative treatment in women with breast carcinoma and osteolytic bone metastases:long term follow-up of two randomized, placebo-controlled trials. Cancer. 2000; 88: 1082-90.
5. Ogawa K, Mukai T, Arano Y, Ono M, Hanaoka H, Ishino S, et al. Development of a rhenium-186-labeled MAG3-conjugated bisphosphonate for the palliation of metastatic bone pain based on the concept of bifunctional radiopharmaceuticals. Bioconjugate chemistry. 2005; 16: 751-7.
6. Lam MG, de Klerk JM, van Rijk PP, Zonnenberg BA. Bone seeking radiopharmaceuticals for palliation of pain in cancer patients with osseous metastases. Anti-cancer agents in medicinal chemistry. 2007; 7: 381-97.
7. Vitha T, Kubicek V, Hermann P, Kolar ZI, Wolterbeek HT, Peters JA, et al. Complexes of DOTA-bisphosphonate conjugates: probes for determination of adsorption capacity and affinity constants of hydroxyapatite. Langmuir : the ACS journal of surfaces and colloids. 2008; 24: 1952-8.
8. Qiu L, Cheng W, Lin J, Luo S, Xue L, Pan J. Synthesis and biological evaluation of novel (99m)Tc-labelled bisphosphonates as superior bone imaging agents. Molecules. 2011; 16: 6165-78.
9. Ogawa K, Washiyama K. Bone target radiotracers for palliative therapy of bone metastases. Current medicinal chemistry. 2012; 19: 3290-300.
10. Rasulova N, Lyubshin V, Arybzhanov D, Sagdullaev S, Krylov V, Khodjibekov M. Optimal timing of bisphosphonate administration in combination with samarium-153 oxabifore in the treatment of painful metastatic bone disease. World journal of nuclear medicine. 2013; 12: 14-8.
11. Park MH, Hyun H, Ashitate Y, Wada H, Park G, Lee JH, et al. Prototype nerve-specific near-infrared fluorophores. Theranostics. 2014; 4: 823-33.
12. Choi HS, Nasr K, Alyabyev S, Feith D, Lee JH, Kim SH, et al. Synthesis and in vivo fate of zwitterionic near-infrared fluorophores. Angew Chem Int Ed Engl. 2011; 50: 6258-63.
13. Hyun H, Bordo MW, Nasr K, Feith D, Lee JH, Kim SH, et al. cGMP-Compatible preparative scale synthesis of near-infrared fluorophores. Contrast Media Mol Imaging. 2012; 7: 516-24.
14. Ashitate Y, Vooght CS, Hutteman M, Oketokoun R, Choi HS, Frangioni JV. Simultaneous assessment of luminal integrity and vascular perfusion of the gastrointestinal tract using dual-channel near-infrared fluorescence. Mol Imaging. 2012; 11: 301-8.
15. Ashitate Y, Lee BT, Ngo LH, Laurence RG, Hutteman M, Oketokoun R, et al. Quantitative assessment of nipple perfusion with near-infrared fluorescence imaging. Ann Plast Surg. 2013; 70: 149-53.
16. Tanaka E, Choi HS, Fujii H, Bawendi MG, Frangioni JV. Image-guided oncologic surgery using invisible light: completed pre-clinical development for sentinel lymph node mapping. Ann Surg Oncol. 2006; 13: 1671-81.
17. Mieog JS, Troyan SL, Hutteman M, Donohoe KJ, van der Vorst JR, Stockdale A, et al. Toward optimization of imaging system and lymphatic tracer for near-infrared fluorescent sentinel lymph node mapping in breast cancer. Ann Surg Oncol. 2011; 18: 2483-91.
18. Liu F, Lunsford EP, Tong J, Ashitate Y, Gibbs SL, Yu J, et al. Real-time monitoring of tumorigenesis, dissemination, & drug response in a preclinical model of lymphangioleiomyomatosis/tuberous sclerosis complex. PLoS One. 2012; 7: e38589.
19. Ashitate Y, Hyun H, Kim SH, Lee JH, Henary M, Frangioni JV, et al. Simultaneous mapping of pan and sentinel lymph nodes for real-time image-guided surgery. Theranostics. 2014; 4: 693-700.
20. Tanaka E, Ohnishi S, Laurence RG, Choi HS, Humblet V, Frangioni JV. Real-time intraoperative ureteral guidance using invisible near-infrared fluorescence. J Urol. 2007; 178: 2197-202.
21. Matsui A, Tanaka E, Choi HS, Kianzad V, Gioux S, Lomnes SJ, et al. Real-time, near-infrared, fluorescence-guided identification of the ureters using methylene blue. Surgery. 2010; 148: 78-86.
22. Verbeek FP, van der Vorst JR, Tummers QR, Boonstra MC, de Rooij KE, Lowik CW, et al. Near-Infrared Fluorescence Imaging of Both Colorectal Cancer and Ureters Using a Low-Dose Integrin Targeted Probe. Ann Surg Oncol. 2014.
23. Matsui A, Tanaka E, Choi HS, Winer JH, Kianzad V, Gioux S, et al. Real-time intra-operative near-infrared fluorescence identification of the extrahepatic bile ducts using clinically available contrast agents. Surgery. 2010; 148: 87-95.
24. Ashitate Y, Stockdale A, Choi HS, Laurence RG, Frangioni JV. Real-time simultaneous near-infrared fluorescence imaging of bile duct and arterial anatomy. J Surg Res. 2012; 176: 7-13.
25. Choi HS, Gibbs SL, Lee JH, Kim SH, Ashitate Y, Liu F, et al. Targeted zwitterionic near-infrared fluorophores for improved optical imaging. Nat Biotechnol. 2013; 31: 148-53.
26. Hutteman M, Choi HS, Mieog JS, van der Vorst JR, Ashitate Y, Kuppen PJ, et al. Clinical translation of ex vivo sentinel lymph node mapping for colorectal cancer using invisible near-infrared fluorescence light. Ann Surg Oncol. 2011; 18: 1006-14.
27. Lee JH, Park G, Hong GH, Choi J, Choi HS. Design considerations for targeted optical contrast agents. Quant Imaging Med Surg. 2012; 2: 266-73.
28. Choi HS, Liu W, Liu F, Nasr K, Misra P, Bawendi MG, et al. Design considerations for tumour-targeted nanoparticles. Nat Nanotechnol. 2010; 5:42-7.
29. Frangioni JV. In vivo near-infrared fluorescence imaging. Curr Opin Chem Biol. 2003; 7: 626-34.
30. Zaheer A, Lenkinski RE, Mahmood A, Jones AG, Cantley LC, Frangioni JV. In vivo near-infrared fluorescence imaging of osteoblastic activity. Nat Biotechnol. 2001; 19: 1148-54.
31. Bhushan KR, Misra P, Liu F, Mathur S, Lenkinski RE, Frangioni JV. Detection of breast cancer microcalcifications using a dual-modality SPECT/NIR fluorescent probe. J Am Chem Soc. 2008; 130: 17648-9.
32. Bhushan KR, Tanaka E, Frangioni JV. Synthesis of conjugatable bisphosphonates for molecular imaging of large animals. Angew Chem Int Ed Engl. 2007; 46: 7969-71.
33. Choi HS, Frangioni JV. Nanoparticles for biomedical imaging: fundamentals of clinical translation. Mol Imaging. 2010; 9: 291-310.
34. Choi HS, Ipe BI, Misra P, Lee JH, Bawendi MG, Frangioni JV. Tissue-and organ-selective biodistribution of NIR fluorescent quantum dots. Nano Lett. 2009; 9: 2354-9.
35. Choi HS, Liu W, Misra P, Tanaka E, Zimmer JP, Itty Ipe B, et al. Renal clearance of quantum dots. Nat Biotechnol. 2007; 25: 1165-70.
36. Moriguchi T, Yano K, Nakagawa S, Kaji F. Elucidation of adsorption mechanism of bone-staining agent alizarin red S on hydroxyapatite by FT-IR microspectroscopy. Journal of colloid and interface science. 2003; 260: 19-25.
37. Hyun H, Wada H, Bao K, Gravier J, Yadav Y, Laramie M, et al. Phosphonated near-infrared fluorophores for biomedical imaging of bone. Angew Chem Int Ed Engl. 2014; 53: 10668-72.
38. Freedman JD, Lusic H, Snyder BD, Grinstaff MW. Tantalum oxide nanoparticles for the imaging of articular cartilage using x-ray computed tomography: visualization of ex vivo/in vivo murine tibia and ex vivo human index finger cartilage. Angew Chem Int Ed Engl. 2014; 53: 8406-10.