Alkylphosphocholine analogs for broad-spectrum cancer imaging and therapy

Science Translational Medicine

Volumn 6, Issue 240, 2014, Pages

  Weichert, Jamey P ^a,b,c   Clark, Paul A ^a   Kandela, Irawati K ^c   Vaccaro, Abram M ^c   Clarke, William ^c   Longino, Marc A ^a,c   Pinchuk, Anatoly N ^a,c   Farhoud, Mohammed ^b   Swanson, Kyle I ^a   Floberg, John M ^a   Grudzinski, Joseph ^a,c   Titz, Benjamin ^c   Traynor, Anne M ^a   Chen, Hong En ^a   Hall, Lance T ^a   Pazoles, Christopher J ^c   Pickhardt, Perry J ^a   Kuo, John S ^a,b  

^a UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

^b UNIVERSITY OF WISCONSIN   (United States)

^c Cellectar   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

18 (4 IODOPHENYL)OCTADECYL PHOSPHOCHOLINE; 18 (4 IODOPHENYL)OCTADECYL PHOSPHOCHOLINE I 124; 18 (4 IODOPHENYL)OCTADECYL PHOSPHOCHOLINE I 125; 18 (4 IODOPHENYL)OCTADECYL PHOSPHOCHOLINE I 131; CHOLINE DERIVATIVE; CLR 1404; CLR 1501; CLR 1502; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; PHOSPHORYLCHOLINE;

ADVANCED CANCER; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BRAIN TISSUE; BREAST CANCER; CANCER CELL LINE; CANCER DIAGNOSIS; CANCER INHIBITION; CANCER PATIENT; CANCER STEM CELL; CANCER SURVIVAL; CANCER THERAPY; CLINICAL TRIAL (TOPIC); COLORECTAL CANCER; COMPUTED TOMOGRAPHY SCANNER; COMPUTER ASSISTED EMISSION TOMOGRAPHY; CONTROLLED STUDY; DRUG EFFICACY; DRUG RETENTION; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; DRUG UPTAKE; FEMALE; FLOW CYTOMETRY; FLUORESCENCE IMAGING; GLIOBLASTOMA; GLIOMA; HUMAN; HUMAN CELL; HUMAN TISSUE; IMMUNOHISTOCHEMISTRY; IN VITRO STUDY; IN VIVO STUDY; ISOTOPE LABELING; KIDNEY CANCER; MALE; MOLECULAR IMAGING; MOUSE; NEURAL STEM CELL; NONHUMAN; OVARY CANCER; PANCREAS CANCER; PERSONALIZED MEDICINE; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; PROSTATE CANCER; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STRUCTURE ACTIVITY RELATION; SURVIVAL TIME; TUMOR XENOGRAFT; UTERUS CANCER; ANALOGS AND DERIVATIVES; ANIMAL; COMPUTER ASSISTED TOMOGRAPHY; DIAGNOSTIC USE; DRUG SCREENING; NEOPLASMS; PROCEDURES; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; FEMALE; HUMANS; MICE; NEOPLASMS; PHOSPHORYLCHOLINE; POSITRON-EMISSION TOMOGRAPHY; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON; TOMOGRAPHY, X-RAY COMPUTED; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 84903208296     PISSN: 19466234     EISSN: 19466242     Source Type: Journal    
DOI: 10.1126/scitranslmed.3007646     Document Type: Article

References (40)

1. G. Ting, C. H. Chang, H. E. Wang, T. W. Lee, Nanotargeted radionuclides for cancer nuclear imaging and internal radiotherapy. J. Biomed. Biotechnol. 2010, 953537 (2010).
2. A. Tedcastle, R. Cawood, Y. Di, K. D. Fisher, L. W. Seymour, Virotherapy-Cancer targeted pharmacology. Drug Discov. Today 17, 215-220 (2012).
3. M. Steiner, D. Neri, Antibody-radionuclide conjugates for cancer therapy: Historical considerations and new trends. Clin. Cancer Res. 17, 6406-6416 (2011).
4. Z. S. Guo, S. H. Thorne, D. L. Bartlett, Oncolytic virotherapy: Molecular targets in tumor-selective replication and carrier cell-mediated delivery of oncolytic viruses. Biochim. Biophys. Acta 1785, 217-231 (2008).
5. S. Kaur, G. Venktaraman, M. Jain, S. Senapati, P. K. Garg, S. K. Batra, Recent trends in antibodybased oncologic imaging. Cancer Lett. 315, 97-111 (2012).
6. A. Fernandez-Fernandez, R. Manchanda, A. J. McGoron, Theranostic applications of nanomaterials in cancer: Drug delivery, image-guided therapy, and multifunctional platforms. Appl. Biochem. Biotechnol. 165, 1628-1651 (2011).
7. M. M. Lin, H. H. Kim, H. Kim, J. Dobson, K. Kim do, Surface activation and targeting strategies of superparamagnetic iron oxide nanoparticles in cancer-oriented diagnosis and therapy. Nanomedicine 5, 109-133 (2010).
8. S. Bhattacharyya, R. A. Kudgus, R. Bhattacharya, P. Mukherjee, Inorganic nanoparticles in cancer therapy. Pharm. Res. 28, 237-259 (2011).
9. S. Bao, Q. Wu, R. E. McLendon, Y. Hao, Q. Shi, A. B. Hjelmeland, M. W. Dewhirst, D. D. Bigner, J. N. Rich, Glioma stem cells promote radioresistance by preferential activation of the DNA damage response. Nature 444, 756-760 (2006).
10. A. Singh, J. Settleman, EMT, cancer stem cells and drug resistance: An emerging axis of evil in the war on cancer. Oncogene 29, 4741-4751 (2010).
11. P. A. Clark, M. Iida, D. M. Treisman, H. Kalluri, S. Ezhilan, M. Zorniak, D. L. Wheeler, J. S. Kuo, Activation of multiple ERBB family receptors mediates glioblastoma cancer stem-like cell resistance to EGFR-targeted inhibition. Neoplasia 14, 420-428 (2012).
12. F. Snyder, M. L. Blank, H. P. Morris, Occurrence and nature of O-alkyl and O-alk-I-enyl moieties of glycerol in lipids of Morris transplanted hepatomas and normal rat liver. Biochim. Biophys. Acta 176, 502-510 (1969).
13. F. Snyder, R. Wood, Alkyl and alk-1-enyl ethers of glycerol in lipids from normal and neoplastic human tissues. Cancer Res. 29, 251-257 (1969).
14. J. F. Soodsma, C. Piantadosi, F. Snyder, The biocleavage of alkyl glyceryl ethers in Morris hepatomas and other transplantable neoplasms. Cancer Res. 30, 309-311 (1970).
15. M. A. Rampy, A. N. Pinchuk, J. P. Weichert, R. W. Skinner, S. J. Fisher, R. L. Wahl, M. D. Gross, R. E. Counsell, Synthesis and biological evaluation of radioiodinated phospholipid ether stereoisomers. J. Med. Chem. 38, 3156-3162 (1995).
16. K. L. Meyer, S. W. Schwendner, R. E. Counsell, Potential tumor or organ-imaging agents. 30. Radioiodinated phospholipid ethers. J. Med. Chem. 32, 2142- 2147 (1989).
17. M. A. Rampy, R. S. Brown, A. N. Pinchuk, J. P. Weichert, R. W. Skinner, S. J. Fisher, R. L. Wahl, M. D. Gross, S. P. Ethier, R. E. Counsell, Biological disposition and imaging of a radioiodinated alkylphosphocholine in two rodent models of breast cancer. J. Nucl. Med. 37, 1540-1545 (1996).
18. A. N. Pinchuk, M. A. Rampy, M. A. Longino, R. W. Skinner, M. D. Gross, J. P. Weichert, R. E. Counsell, Synthesis and structure-activity relationship effects on the tumor avidity of radioiodinated phospholipid ether analogues. J. Med. Chem. 49, 2155-2165 (2006).
19. L. Kuerschner, D. Richter, H. K. Hannibal-Bach, A. Gaebler, A. Shevchenko, C. S. Ejsing, C. Thiele, Exogenous ether lipids predominantly target mitochondria. PLOS One 7, e31342 (2012).
20. W. J. van Blitterswijk, M. Verheij, Anticancer mechanisms and clinical application of alkylphospholipids. Biochim. Biophys. Acta 1831, 663- 674 (2013).
21. A. H. van der Luit, S. R. Vink, J. B. Klarenbeek, D. Perrissoud, E. Solary, M. Verheij,W. J. van Blitterswijk, A new class of anticancer alkylphospholipids uses lipid rafts as membrane gateways to induce apoptosis in lymphoma cells. Mol. Cancer Ther. 6, 2337-2345 (2007).
22. D. Lingwood, K. Simons, Lipid rafts as a membrane-organizing principle. Science 327, 46-50 (2010).
23. Y. C. Li, M. J. Park, S. K. Ye, C. W. Kim, Y. N. Kim, Elevated levels of cholesterol-rich lipid rafts in cancer cells are correlated with apoptosis sensitivity induced by cholesterol-depleting agents. Am. J. Pathol. 168, 1107-1118 (2006).
24. M. Zorniak, P. A. Clark, H. E. Leeper, M. D. Tipping, D. M. Francis, K. R. Kozak, M. S. Salamat, J. S. Kuo, Differential expression of 2?,3?-cyclic-nucleotide 3?-phosphodiesterase and neural lineage markers correlate with glioblastoma xenograft infiltration and patient survival. Clin. Cancer Res. 18, 3628 -3636 (2012).
25. L. Qiang, Y. Yang, Y. J. Ma, F. H. Chen, L. B. Zhang, W. Liu, Q. Qi, N. Lu, L. Tao, X. T. Wang, Q. D. You, Q. L. Guo, Isolation and characterization of cancer stem like cells in human glioblastoma cell lines. Cancer Lett. 279, 13-21 (2009).
26. S. Peickert, J. Waurig, C. Dittfeld, A. Dietrich, Y. Garbe, L. Kabus, M. Baumann, M. Grade, T. Ried, L. A. Kunz-Schughart, Rapid re-expression of CD133 protein in colorectal cancer cell lines in vitro and in vivo. Lab. Invest. 92, 1607-1622 (2012).
27. A. Hackshaw, C. Harmer, U. Mallick, M. Haq, J. A. Franklyn, 131I activity for remnant ablation in patients with differentiated thyroid cancer: A systematic review. J. Clin. Endocrinol. Metab. 92, 28-38 (2007).
28. B. Pohlman, J. Sweetenham, R. M. Macklis, Review of clinical radioimmunotherapy. Expert Rev. Anticancer Ther. 6, 445-461 (2006).
29. R. M. Macklis, B. Pohlman, Radioimmunotherapy for non-Hodgkin 's lymphoma: A review for radiation oncologists. Int. J. Radiat. Oncol. Biol. Phys. 66, 833 -841 (2006).
30. K. Simons, J. L. Sampaio, Membrane organization and lipid rafts. Cold Spring Harb. Perspect. Biol. 3, a004697 (2011).
31. A. Kusumi, T. K. Fujiwara, N. Morone, K. J. Yoshida, R. Chadda, M. Xie, R. S. Kasai, K. G. Suzuki, Membrane mechanisms for signal transduction: The coupling of the meso-scale raft domains to membrane-skeleton-induced compartments and dynamic protein complexes. Semin. Cell Dev. Biol. 23, 126-144 (2012).
32. S. Staubach, F. G. Hanisch, Lipid rafts: Signaling and sorting platforms of cells and their roles in cancer. Expert Rev. Proteomics 8, 263-277 (2011).
33. B. Giebel, D. Corbeil, J. Beckmann, J. Höhn, D. Freund, K. Giesen, J. Fischer, G. Kögler, P. Wernet, Segregation of lipid raft markers including CD133 in polarized human hematopoietic stem and progenitor cells. Blood 104, 2332-2338 (2004).
34. H. Wolburg, S. Noell, P. Fallier-Becker, A. F. Mack, K. Wolburg-Buchholz, The disturbed blood-brain barrier in human glioblastoma. Mol. Aspects Med. 33, 579-589 (2012).
35. T. J. Mangner, J. L. Wu, D. M. Wieland, Solid-phase exchange radioiodination of aryl iodides. Facilitation by ammonium sulfate. J. Organ. Chem. 47, 1484-1488 (1982).
36. C. N. Svendsen, M. G. ter Borg, R. J. Armstrong, A. E. Rosser, S. Chandran, T. Ostenfeld, M. A. Caldwell, A new method for the rapid and long term growth of human neural precursor cells. J. Neurosci. Methods 85, 141-152 (1998).
37. L. S. Liebeskind, J. Srogl, Heteroaromatic thioether-boronic acid cross-coupling under neutral reaction conditions. Org. Lett. 4, 979-981 (2002).
38. E. Peña-Cabrera, A. Aguilar-Aguilar, M. Gonzalez-Domínguez, E. Lager, R. Zamudio-Vazquez, J. Godoy-Vargas, F. Villanueva-García, Simple, general, and efficient synthesis of mesosubstituted borondipyrromethenes from a single platform. Org. Lett. 9, 3985-3988(2007).
39. T. V. Goud, A. Tutar, J. F. Biellmann, Synthesis of 8-heteroatom- substituted 4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene dyes (BODIPY). Tetrahedron 62, 5084-5091 (2006).
40. K. Kemper, M. R. Sprick, M. de Bree, A. Scopelliti, L. Vermeulen, M. Hoek, J. Zeilstra, S. T. Pals, H. Mehmet, G. Stassi, J. P. Medema, The AC133 epitope, but not the CD133 protein, is lost upon cancer stem cell differentiation. Cancer Res. 70, 719-729 (2010).