Optical imaging of tumors with copper-labeled rhodamine derivatives by targeting mitochondria

Theranostics

Volumn 2, Issue 10, 2012, Pages 988-998

  Yan, Xin ^a   Zhou, Yang ^a   Liu, Shuang ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

CU labeled rhodamine derivatives; Fluorescent probes; Optical imaging

Indexed keywords

2,2',2'' [10 [2 [[5 CARBOXY 5 [3 CARBOXY 4 (6 HYDROXY 3 OXO 3H XANTHEN 9 YL)BENZAMIDO]PENTYL]AMINO] 2 OXOETHYL] 1,4,7,10 TETRAAZACYCLODODECANE 1,4,7 TRIYL]TRIACETIC ACID; 5 [N [1 CARBOXY 5 [2 [4,7,10 TRIS(CARBOXYMETHYL) 1,4,7,10 TETRAAZACYCLODODECAN 1 YL]ACETAMIDO]PENTYL]SULFAMOYL] 2 [6 (DIETHYLAMINO) 3 (DIETHYLIMINIO) 3H XANTHEN 9 YL]BENZENESULFONATE; COPPER 64; FLUORESCENT DYE; N [9 [2 CARBOXY 4 [[1 CARBOXY 5 [2 [4,7,10 TRIS(CARBOXYMETHYL) 1,4,7,10 TETRAAZACYCLODODECAN 1 YL]ACETAMIDO]PENTYL]CARBAMOYL]PHENYL] 6 (DIMETHYLAMINO) 3H XANTHEN 3 YLIDENE] N METHYLMETHANAMINIUM; RHODAMINE; TETRAXETAN; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BREAST TUMOR; CANCER DIAGNOSIS; CONTROLLED STUDY; DIAGNOSTIC ACCURACY; DRUG DISPOSITION; DRUG SCREENING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; FIBROBLAST; FLUORESCENCE; GLIOMA; HUMAN; HUMAN CELL; MITOCHONDRION; MULTIDRUG RESISTANCE; NONHUMAN; STAINING;

EID: 84870557647     PISSN: None     EISSN: 18387640     Source Type: Journal    
DOI: 10.7150/thno.4818     Document Type: Article

References (56)

1. Jemal A, Siegel R, Xu J, Ward E. Cancer statistics, 2010. CA Cancer J Clin 2010; 60, 1-24.
2. Kroemer G, Dallaporta B, Resche-Rigon M. The mitochondrial death/life regulator in apoptosis and necrosis. Annu Rev Physiol 1998; 60, 619-42.
3. Modica-Napolitano JS, Aprille JR. Delocalized lipophilic cations selec-tively target the mitochondria of carcinoma Cells. Adv Drug Deliv Rev 2001; 49, 63-70.
4. Duchen MR. Mitochondria in health and disease, perspectives on a new mitochondrial biology. Mol Aspects Med 2004; 25, 365-451.
5. Mannella CA. The relevance of mitochondrial membrane topology to mitochondrial function. Biochim Biophys Acta 2006; 1762, 140-7.
6. Summerhayes IC, Lampidis TJ, Bernal SD, Nadakavukaren JJ, Nada-kavukaren KK, Shepard EL, Chen LB. Unusual retention of Rhodamine 123 by mitochondria in muscle and carcinoma cells. Proc Natl Acad Sci USA 1982; 77, 990-4.
7. Modica-Napolitano JS, Aprille JR. Basis for the selective cytotoxicity of Rhodamine 123. Cancer Res 1987; 47, 4361-5.
8. Davis S, Weiss MJ, Wong JR, Lampidis TJ, Chen LB. Mitochondrial and plasma membrane potentials cause unusual accumulation and retention of Rhodamine 123 by human breast adenocarcinoma-derived MCF-7 cells. J Biol Chem 1985; 260, 13844-50.
9. Dairkee SH, Hackett AJ. Differential retention of Rhodamine 123 by breast carcinoma and normal human mammary tissue. Breast Cancer Res Treat 1991; 18, 57-61.
10. Modica-Napolitano JS, Singh KK. Mitochondria as targets for detection and treatment of Cancer. Expert Rev Mol Med. 2002; 4, 1-19.
11. Gottlieb E, Thompson CB. Targeting the mitochondria to enhance tumor suppression. Methods Mol Biol 2003; 223, 543-54.
12. Ross MF, Kelso GF, Blaikie FH, James AM, Cocheme HM, Filipovska A, Da Ros T, Hurd TR, Smith RA, Murphy MP. Lipophilic tri-phenylphosphonium cations as tools in mitochondrial bioenergetics and free radical biology. Biochemistry (Mosc) 2005; 70, 222-30.
13. Liu S, Kim YS, Zhai S, Shi J, Hou G. Evaluation of 64Cu(DO3A-xy-TPEP) as a potential PET radiotracer for monitoring tumor multidrug re-sistance. Bioconj Chem 2009; 20, 790-8.
14. Wang J, Yang CT, Kim YS, Sreerama SG, Cao Q, Li ZB, He Z, Chen X, Liu S. 64Cu-Labeled triphenylphosphonium and triphenylarsonium cations as highly tumor-selective imaging agents. J Med Chem 2007; 50, 5057-69.
15. Kim YS, Yang C, Wang J, Sreerama SG, Cao Q, Li Z, He Z, Chen X, Liu S. Effects of targeting moiety, linker, bifunctional chelator, and molecular charge on biological properties of 64Cu-labeled triphenylphosphonium cations. J Med Chem 2008; 51, 2971-84.
16. Yang CT, Kim YS, Wang J, Wang L, Shi J, Li ZB, Chen X, Fan M, Li JJ, Liu S. 64Cu-Labeled 2-(diphenylphosphoryl)ethyldiphenylphosphonium cations as highly selective tumor imaging agents, effects of linkers and chelates on radiotracer biodistribution characteristics. Bioconj Chem 2008; 19, 2008-22.
17. Lichtshtein D, Kaback HR, Blume AJ. Use of a lipophilic cation for de-termination of membrane potential in neuroblastoma-glioma hybrid cell suspensions. Proc Natl Acad Sci USA 1979; 76, 650-4.
18. Hockings PD, Rogers PJ. The Measurement of transmembrane electrical potential with lipophilic cations. Biochim Biophys Acta 1996; 1282, 101-6.
19. Huang SG. Development of a high throughput screening assay for mi-tochondrial membrane potential in living cells. J Biomol Screening 2002; 7, 383-9.
20. Lefevre C, Kang HC, Haugland RP, Malekzadeh N, Arttamangkul S, Haugland RP. Texas Red-X and Rhodamine Red-X, new derivatives of sulforhodamine 101 and Lissamine Rhodamine B with improved label-ing and fluorescence properties. Bioconj Chem 1996; 7, 482-9.
21. Mao C, Kisaalita WS. Determination of resting membrane potential of individual neuroblastoma cells (IMR-32) using a potentiometric dye (TMRM) and confocal microscopy. J Fluoresc 2004; 14, 739-43.
22. Scaduto R. Jr, Grotyohann LW. Measurement of mitochondrial mem-brane potential using fluorescent rhodamine derivatives. Biophys J 1999; 76, 469-77.
23. Licha K, Olbrich C. Optical imaging in drug discovery and diagnostic applications. Adv Drug Deliv Rev 2005; 57, 1087-1108.
24. Jakobs S. High resolution imaging of live mitochondria. Biochim Bio-phys Acta 2006; 1763, 561-75.
25. Lavis LD, Chao TY, Raines RT. Fluorogenic label for biomolecular im-aging. ACS Chem Biol 2006; 1, 252-60.
26. Hama Y, Urano Y, Koyama Y, Kamiya M, Bernardo M, Paik RS, Shin IS, Paik CH, Choyke PL, Kobayashi H. A target cell-specific activatable flu-orescence probe for in vivo molecular imaging of cancer based on a self-quenched Avidin-Rhodamine conjugate. Cancer Res 2007; 67, 2791-9.
27. Glunde K, Foss CA, Takagi T, Wildes F, Bhujwalla ZM. Synthesis of 6'-O-Lissamine-rhodamine B-glucosamine as a novel probe for fluores-cence imaging of lysosomes in breast tumors. Bioconj Chem 2005; 16, 843-51.
28. Longmire MR, Ogawa M, Hama Y, Kosaka N, Regino CA, Choyke PL, Kobayashi H. Determination of optimal rhodamine fluorophore for in vivo optical imaging. Bioconj Chem 2008; 19, 1735-42.
29. Yova D, Atlamazoglou V, Kavantzas N, Loukas S. Development of a fluorescence-based imaging system for colon cancer diagnosis using two novel rhodamine derivatives. Lasers Med Sci 2000; 15, 140-7.
30. 64Cu-labeled Lissa-mine Rhodamine B, a promising PET radiotracer targeting tumor mito-chondria. Mol Pharm 2011; 8, 1198-1208.
31. 64Cu-Labeled phosphonium cation as PET radiotracers for tumor imaging. Bioconj Chem 2011; 22, 1459-72.
32. Massoud TF, Gambhir SS. Molecular imaging in living subjects, seeing fundamental biological processes in a new light. Genes Dev 2003; 17, 545-80.
33. Cheng Z, Levi J, Xiong Z, Gheysens O, Keren S, Chen X, Gambhir SS. Near-infrared fluorescent deoxyglucose analogue for tumor optical im-aging in cell culture and living mice. Bioconj Chem 2006; 17, 662-9.
34. Ntziachristos V, Bremer C, Weissleder R. Fluorescence imaging with near-infrared light, new technological advances that enable in vivo mo-lecular imaging. Eur Radiol 2003; 13, 195-208.
35. Mahmood U, Weissleder R. Near-infrared optical imaging of proteases in cancer. Mol Cancer Ther 2003; 2, 489-96.
36. Achilefu S. Lighting up tumors with receptor-specific optical molecular probes. Technol Cancer Res Treat 2004; 3, 393-409.
37. Sevick-Muraca EM, Houston JP, Gurfinkel M. Fluorescence-enhanced, near-infrared diagnostic imaging with contrast agents. Curr Opin Chem Biol 2002; 6, 642-50.
38. Hawrysz DJ, Sevick-Muraca EM. Developments toward diagnostic breast cancer imaging using near-infrared optical measurements and fluorescent contrast agents. Neoplasia 2000; 2, 388-417.
39. de Graaf AO, van den Heuvel LP, Dijkman HB, de Abreu RA, Birkenkamp KU, de Witte T, van der Reijden BA, Smeitink JA, Jansen JH. Bcl-2 prevents loss of mitochondria in CCCP-induced apoptosis. Exp Cell Res 2004; 299, 533-40.
40. Horton KL, Stewart KM, Fonseca SB, Guo Q, Kelley SO. Mitochon-dria-penetrating peptides. Chem Biol 2008; 15, 375-82.
41. Boswell CA, Sun X, Niu W, Weisman GR, Wong EH, Rheingold AL, Anderson CJ. Comparative in vivo stability of copper-64-labeled cross-bridged and conventional tetraazamacrocyclic complexes. J Med Chem 2004; 47, 1465-74.
42. Boswell CA, McQuade P, Weisman GR, Wong EH, Anderson CJ. Opti-mization of labeling and metabolite analysis of copper-64-labeled azamacrocyclic chelators by radio-LC-MS. Nucl Med Biol 2005; 32, 29-38.
43. Sprague JE, Peng Y, Fiamengo AL, Woodin KS, Southwick EA, Wiseman GR, Wong EH, Golden JA, Rheingold AL, Anderson CJ. Synthesis, characterization and in vivo studies of Cu(II)-64-labeled cross-bridged tetraazamacrocycle-amide complexes as models of peptide conjugate imaging agents. J Med Chem 2007; 50, 2527-35.
44. Ling V. Multidrug resistance, molecular mechanisms and clinical rele-vance. Cancer Chemother Pharmacol 1997; 40, S3-S8.
45. Gros P, Ben Neriah YB, Croop JM, Housman DE. Isolation and expres-sion of a complementary DNA that confers multidrug resistance. Nature 1986; 323, 728-31.
46. Zaman GJ, Flens MJ, Van Leusden MR, de Haas M, Mulder HS, Lan-kelma J, Pinedo HM, Scheper RJ, Baas F, Broxterman HJ, Borst P. The human multidrug resistance-associated-protein MRP is a plasma mem-brane drug-efflux pump. Proc Natl Acad Sci USA 1994; 91, 8822-6.
47. Klein I, Sarkadi B, Varadi A. An inventory of the human ABC proteins. Biochim Biophys Acta 1999; 1461, 237-62.
48. Shapiro AB, Ling V. Reconstitution of drug transport by purified P-glycoprotein. J Biol Chem 1995; 270, 16167-75.
49. Mao Q, Deeley RG, Cole SP. Functional reconstitution of substrate transport by purified multidrug resistance protein MRP1 (ABCC1) in phospholipid vesicles. J Biol Chem 2000; 275, 34166-72.
50. Liu B, Sun D, Xia W, Hung MC, Yu D. Cross-reactivity of C219 an-ti-p170mdr-1 antibody with p185c-erbB2 in breast cancer cells, cautions on evaluating p170mdr-1. J Natl Cancer Inst. 1997; 89, 1524-9.
51. Engel JB, Schally AV, Halmos G, Baker B, Nagy A, Keller G. Targeted cytotoxicity bombesin analog AN-215 effectively inhibits experimental human breast cancers with low induction of multi-drug resistance pro-teins. Endocrine-Related Cancer 2005; 12, 999-1009.
52. Savas B, Kerr PE, Pross HF. Lymphokine-activated killer cell suscepti-bility and adhesion molecule expression of multidrug resistant breast carcinoma. Cancer Cell Int 2006; 6, 24-9.
53. Seelig A. A general pattern for substrate recognition by P-glycoprotein. Eur J Biochem 1998; 251, 252-61.
54. Altenberg GA, Vanoye CG, Horton JK, Reuss L. Unidirectional fluxes of rhodamine 123 in multidrug-resistant cells, evidence against direct drug extrusion from the plasma membrane. Proc Natl Acad Sci USA 1994; 91, 4654-7.
55. Sarkadi B, Müller M. Search for specific inhibitors of multidrug re-sistance in cancer. Semin Cancer Biol 1997; 8, 171-82.
56. Eytan GD, Regev R, Oren G, Hurwitz CD, Assaraf YG. Efficiency of P-glycoprotein-mediated exclusion of rhodamine dyes from multi-drug-resistant cells is determined by their passive transmembrane movement rate. Eur J Biochem 1997; 248, 104-12.