Convergent synthesis and evaluation of 18F-labeled azulenic COX2 probes for cancer imaging

Frontiers in Oncology

Volumn 2 JAN, Issue , 2013, Pages

  Nolting, Donald D ^a   Nickels, Michael ^a   Tantawy, Mohammed N ^a   Yu, James Y H ^a   Xie, Jingping ^a   Peterson, Todd E ^a   Crews, Brenda C ^a,b   Marnett, Larry ^a,b,c   Gore, John C ^a,b,c,d   Pham, Wellington ^a,b,c,d  

^a VANDERBILT UNIVERSITY   (United States)

^b VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c VANDERBILT INGRAM CANCER CENTER   (United States)

^d VANDERBILT UNIVERSITY   (United States)

Author keywords

Azulene; Breast cancer; Convergence synthesis; COx2; Ct; Molecular imaging; Pet

Indexed keywords

(2 METHYL 3 ((4 METHYLTHIAZOL 2 YL)METHYL)AZULEN 1 YL) (4 NITROPHENYL)METHANONE; (2 METHYLAZULEN 1 YL)(4 METHYLTHIAZOL 2 YL) METHANOL; 2 METHYL AZULENE; 2 METHYLAZULENE 1 CARBALDEHYDE; 4 METHYL 2 ((2 METHYLAZULEN 1 YL)METHYL)THIAZOLE; AZULENE DERIVATIVE; CYCLOOXYGENASE 2 INHIBITOR; FLUORINE 18; POTASSIUM CARBONATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL LABELING; COMPUTER ASSISTED TOMOGRAPHY; CONTROLLED STUDY; CONVERGENT EVOLUTION; DIAGNOSTIC IMAGING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IC 50; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REAL TIME POLYMERASE CHAIN REACTION; ROOM TEMPERATURE; SYNTHESIS; THIN LAYER CHROMATOGRAPHY; WESTERN BLOTTING;

EID: 84890718865     PISSN: None     EISSN: 2234943X     Source Type: Journal    
DOI: 10.3389/fonc.2012.00207     Document Type: Article

References (33)

1. Chan, T. A., Morin, P. J., Vogelstein, B., and Kinzler, K. W. (1998). Mechanisms underlying nonsteroidal antiinflammatory drug-mediated apoptosis. Proc. Natl. Acad. Sci. U.S.A. 95, 681-686.
2. Dubois, R. N., Abramson, S. B., Crofford, L., Gupta, R. A., Simon, L. S., Van De Putte, L. B., et al. (1998). Cyclooxygenase in biology, and disease. FASEB J. 12, 1063-1073.
3. Fueger, B. J., Czernin, J., Hildebrandt, I., Tran, C., Halpern, B. S., Stout, D., et al. (2006). Impact of animal handling on the results of 18F-FDG PET studies in mice. J. Nucl. Med. 47, 999-1006.
4. Fujita, T., Matsui, M., Takaku, K., Uetake, H., Ichikawa, W., Taketo, M. M., et al. (1998). Size-, and invasion-dependent increase in cyclooxygenase 2 levels in human colorectal carcinomas. Cancer Res. 58, 4823-4826.
5. Glynn, S. A., Prueitt, R. L., Ridnour, L. A., Boersma, B. J., Dorsey, T. M., Wink, D. A., et al. (2010). COX-2 activation is associated with Akt phosphorylation and poor survival in ER-negative, HER2-positive breast cancer. BMC Cancer 10:626. doi: 10.1186/1471-2407-10-626
6. Harizi, H., Juzan, M., Pitard, V., Moreau, J. F., and Gualde, N. (2002). Cyclooxygenase-2-issued prostaglandin e(2) enhances the production of endogenous IL-10, which down-regulates dendritic cell functions. J. Immunol. 168, 2255-2263.
7. Harmey, J. H., Bucana, C. D., Lu, W., Byrne, A. M., McDonnell, S., Lynch, C., et al. (2002). Lipopolysaccharide-induced metastatic growth is associated with increased angiogenesis, vascular permeability and tumor cell invasion. Int. J. Cancer 101, 415-422.
8. Hida, T., Yatabe, Y., Achiwa, H., Muramatsu, H., Kozaki, K., Nakamura, S., et al. (1998). Increased expression of cyclooxygenase 2 occurs frequently in human lung cancers, specifically in adenocarcinomas. Cancer Res. 58, 3761-3764.
9. Hill, R., Li, Y., Tran, L. M., Dry, S., Calvopina, J. H., Garcia, A., et al. (2012). Cell intrinsic role of Cox-2 in pancreatic cancer development. Mol. Cancer Ther. doi: 10.1158/1535-7163 [Epub ahead of print].
10. Jalilian, A. R., Tabatabai, S. A., Shafiee, A., Afarideh, H., Najafi, R., and Bineshmarvasti, M. (2000). One-step, no-carrier-added synthesis of a 18F-labeled benzodiazepine receptor ligand. J. Labelled Comp. Radiopharm. 43, 545-555.
11. Kobukai, S., Kremers, G. J., Cobb, J. G., Baheza, R., Xie, J., Kuley, A., et al. (2011). Induction of antitumor immunity by dendritic cells loaded with MPA11P-conjugated mucin-1 peptide antigen. Transl. Oncol. 4, 1-8.
12. Loening, A. M., and Gambhir, S. S. (2003). AMIDE: a free software tool for multimodality medical image analysis. Mol. Imaging 2, 131-137.
13. McCarthy, T. J., Sheriff, A. U., Graneto, M. J., Talley, J. J., and Welch, M. J. (2002). Radiosynthesis, in vitro validation, and in vivo evaluation of 18F-labeled COX-1 and COX-2 inhibitors. J. Nucl. Med. 43, 117-124.
14. Moore, B. C., and Simmons, D. L. (2000). COX-2 Inhibition, apoptosis, and chemoprevention by nonsteroidal anti-inflammatory drugs. Curr. Med. Chem. 7, 1131-1144.
15. Mueller, K., Faeh, C., and Diederich, F. (2007). Fluorine in pharmaceuticals: looking beyond intuition. Science 317, 1881-1886.
16. Murata, H., Kawano, S., Tsuji, S., Tsuji, M., Sawaoka, H., Kimura, Y., et al. (1999). Cyclooxygenase-2 overexpression enhances lymphatic invasion and metastasis in human gastric carcinoma. Am. J. Gastroenterol. 94, 451-455.
17. Muthuswamy, R., Mueller-Berghaus, J., Haberkorn, U., Reinhart, T. A., Schadendorf, D., and Kalinski, P. (2010). PGE(2) transiently enhances DC expression of CCR7 but inhibits the ability of DCs to produce CCL19 and attract naive T cells. Blood 116, 1454-1459.
18. Nagler, C., Hardt, C., Zanker, K. S., and Dittmar, T. (2011). Co-cultivation of murine BMDCs with 67NR mouse mammary carcinoma cells give rise to highly drug resistant cells. Cancer Cell Int. 11, 21.
19. Nasir, A., Lopez, A., Boulware, D., Malafa, M., and Coppola, D. (2011). Correlation between COX-2, and APC expression in left versus right-sided human colon cancer. Anticancer Res. 31, 2191-2195.
20. Nolting, D. D., Nickels, M., Price, R., Gore, J. C., and Pham, W. (2009). Synthesis of bicyclo[5.3.0]azulene derivatives. Nat. Protoc. 4, 1113-1117.
21. Pham, W., Weissleder, R., and Tung, C. H. (2002). An azulene dimer as a near-infrared quencher. Angew. Chem. Int. Ed. Engl. 41, 3659-3662, 3519.
22. Prabhakaran, J., Majo, V. J., Simpson, N. R., van Heertum, R. L., Mann, J. J., and Kumar, J. S. (2005). Synthesis of [11C]celecoxib: a potential PET probe for imaging COX-2 expression. J. Labelled Comp. Radiopharm. 48, 887-895.
23. Rouzer, C. A., and Marnett, L. J. (2009). Cyclooxygenases: structural, and functional insights. J. Lipid Res. 50(Suppl.), S29-S34.
24. Shimada, K., Anai, S., Marco, D. A., Fujimoto, K., and Konishi, N. (2011). Cyclooxygenase 2-dependent and independent activation of Akt through casein kinase 2alpha contributes to human bladder cancer cell survival. BMC Urol. 11:8. doi: 10.1186/1471-2490-11-8
25. Singh, B., Cook, K. R., Vincent, L., Hall, C. S., Martin, C., and Lucci, A. (2011). Role of COX-2 in tumorospheres derived from a breast cancer cell line. J. Surg. Res. 168, e39-e49.
26. Sobolewski, C., Cerella, C., Dicato, M., Ghibelli, L., and Diederich, M. (2010). The role of cyclooxygenase-2 in cell proliferation and cell death in human malignancies. Int. J. Cell Biol. 215158.
27. Stolina, M., Sharma, S., Lin, Y., Dohadwala, M., Gardner, B., Luo, J., et al. (2000). Specific inhibition of cyclooxygenase 2 restores antitumor reactivity by altering the balance of IL-10 and IL-12 synthesis. J. Immunol. 164, 361-370.
28. Tomiyama, T., Tomiyama, I., and Yokota, M. (1999). Preparation of azulene derivatives as COX-2 inhibitors. JP 11302266:JP 1998-115303.
29. Uddin, M. J., Crews, B. C., Blobaum, A. L., Kingsley, P. J., Gorden, D. L., McIntyre, J. O., et al. (2010). Selective visualization of cyclooxygenase-2 in inflammation and cancer by targeted fluorescent imaging agents. Cancer Res. 70, 3618-3627.
30. Uddin, M. J., Crews, B. C., Ghebreselasie, K., Huda, I., Kingsley, P. J., Ansari, M. S., et al. (2011). Fluorinated cyclooxygnase-2 inhibitors as agents in PET imaging of inflammation and cancer. Cancer Prev. Res. 4, 1536-1545.
31. van Ryn, J., Trummlitz, G., and Pairet, M. (2000). COX-2 selectivity, and inflammatory processes. Curr. Med. Chem. 7, 1145-1161.
32. Xie, W. L., Chipman, J. G., Robertson, D. L., Erikson, R. L., and Simmons, D. L. (1991). Expression of a mitogen-responsive gene encoding prostaglandin synthase is regulated by mRNA splicing. Proc. Natl. Acad. Sci. U.S.A. 88, 2692-2696.
33. Yokota, K., Kusaka, M., Ohshima, T., Yamamoto, S., Kurihara, N., Yoshino, T., et al. (1986). Stimulation of prostaglandin E2 synthesis in cloned osteoblastic cells of mouse (MC3T3-E1) by epidermal growth factor. J. Biol. Chem. 26115410-15415.