References
- Supuran CT. Carbonic anhydrases: novel therapeutic applications for inhibitors and activators. Nat Rev Drug Discov 2008;7:168–81
- Oosterwijk E, Ruiter DJ, Hoedemaeker PJ, et al. Monoclonal antibody G-250 recognizes a determinant present in renal-cell carcinoma and absent from normal kidney. Int J Cancer 1986;38:489–94
- Ord JJ, Agrawal S, Thamboo TP, et al. An investigation into the prognostic significance of necrosis and hypoxia in high grade and invasive bladder cancer. J Urol 2007;178:677–82
- Hutchison GJ, Valentine HR, Loncaster JA, et al. Hypoxia-inducible factor lot expression as an intrinsic marker of hypoxia: Correlation with tumor oxygen, pimonidazole measurements, and outcome in locally advanced carcinoma of the cervix. Clin Cancer Res 2004;10:8405–12
- Koukourakis MI, Bentzen SM, Giatromanolaki A, et al. Endogenous markers of two separate, hypoxia response pathways (hypoxia inducible factor 2 alpha and carbonic anhydrase 9) are associated with radiotherapy failure in head and neck cancer patients recruited in the CHART randomized trial. J Clin Oncol 2006;24:727–35
- Trastour C, Benizri E, Ettore F, et al. HIF-1 alpha and CA IX staining in invasive breast carcinomas: prognosis and treatment outcome. Int J Cancer 2007;120:1451–8
- Hussain SA, Ganesan R, Reynolds G, et al. Hypoxia-regulated carbonic anhydrase IX expression is associated with poor survival in patients with invasive breast cancer. Brit J Cancer 2007;96:104–9
- Swinson DEB, Jones JL, Richardson D, et al. Carbonic anhydrase IX expression, a novel surrogate marker of tumor hypoxia, is associated with a poor prognosis in non-small-cell lung cancer. J Clin Oncol 2003;21:473–82
- Dorai T, Sawczuk I, Pastorek J, et al. Role of carbonic anhydrases in the progression of renal cell carcinoma subtypes: proposal of a unified hypothesis. Cancer Invest 2006;24:754–79
- Wykoff CC, Beasley NJP, Watson PH, et al. Hypoxia-inducible expression of tumor-associated carbonic anhydrases. Cancer Res 2000;60:7075–83
- Mandriota SJ, Turner KJ, Davies DR, et al. HIF activation identifies early lesions in VHL kidneys: evidence for site-specific tumor suppressor function in the nephron. Cancer Cell 2002;1:459–68
- Ivanov SV, Kuzmin I, Wei MH, et al. Down-regulation of transmembrane carbonic anhydrases in renal cell carcinoma cell lines by wild-type von Hippel-Lindau transgenes. Proc Natl Acad Sci USA 1998;95:12596–601
- Lou Y, McDonald PC, Oloumi A, et al. Targeting tumor hypoxia: suppression of breast tumor growth and metastasis by novel carbonic anhydrase IX inhibitors. Cancer Res 2011;71:3364–76
- Korkeila E, Talvinen K, Jaakkola PM, et al. Expression of carbonic anhydrase IX suggests poor outcome in rectal cancer. Brit J Cancer 2009;100:874–80
- Koukourakis MI, Giatromanolaki A, Sivridis E, et al. Hypoxia-activated tumor pathways of angiogenesis and pH regulation independent of anemia in head-and-neck cancer. Int J Radiat Oncol Biol Phys 2004;59:67–71
- Swietach P, Hulikova A, Vaughan-Jones RD, Harris AL. New insights into the physiological role of carbonic anhydrase IX in tumour pH regulation. Oncogene 2010;29:6509–21
- Svastova E, Hulikova A, Rafajova M, et al. Hypoxia activates the capacity of tumor-associated carbonic anhydrase IX to acidify extracellular pH. FEBS Lett 2004;577:439–45
- Swietach P, Vaughan-Jones RD, Harris AL. Regulation of tumor pH and the role of carbonic anhydrase 9. Cancer Metast Rev 2007;26:299–310
- Kroemer G, Pouyssegur J. Tumor cell metabolism: ancer’s achilles’ heel. Cancer cell 2008;13:472–82
- Stock C, Schwab A. Protons make tumor cells move like clockwork. Pflug Arch Eur J Physiol 2009;458:981–92
- Supuran CT. Indisulam: an anticancer sulfonamide in clinical development. Expert Opin Investig Drugs 2003;12:283–7
- Thiry A, Dogne JM, Masereel B, Supuran CT. Targeting tumor-associated carbonic anhydrase IX in cancer therapy. Trends Pharmacol Sci 2006;27:566–73
- Siebels M, Rohrmann K, Oberneder R, et al. A clinical phase I/II trial with the monoclonal antibody cG250 (RENCAREX®) and interferon-alpha-2a in metastatic renal cell carcinoma patients. World J Urol 2011;29:121–6
- Belldegrun A. Chimeric monoclonal antibody cG250 (Rencarex®) as immunotherapy of renal cell carcinoma: clinical Phase II summary and current adjuvant Phase III trial in non-metastasized RCC after nephrectomy. Ann Oncol 2005;16:18
- Stillebroer AB, Mulders PFA, Boerman OC, et al. Carbonic anhydrase IX in renal cell carcinoma: implications for prognosis, diagnosis, and therapy. Eur Urol 2010;58:75–83
- Brouwers AH, Dorr U, Lang O, et al. 131I-cG250 monoclonal antibody immunoscintigraphy versus [18F]FDG-PET imaging in patients with metastatic renal cell carcinoma: a comparative study. Nucl Med Commun 2002;23:229–36
- Brouwers AH, Buijs WC, Boerman OC, et al. Higher uptake in renal cell carcinoma (RCC) metastases with In-111-labeled chimeric monoclonal antibody G250 (cG250) than with I-131-cG250 in an intra-patient comparison. J Nucl Med 2003;44:171P–2P
- Divgi CR, Pandit-Taskar N, Jungbluth AA, et al. Preoperative characterisation of clear-cell renal carcinoma using iodine-124-labelled antibody chimeric G250 (124I-cG250) and PET in patients with renal masses: a phase I trial. Lancet Oncol 2007;8:304–10
- Hoeben BAW, Kaanders JHAM, Franssen GM, et al. PET of hypoxia with 89Zr-Labeled cG250-F(ab′)2 in head and neck tumors. J Nucl Med 2010;51:1076–83
- Apte SD, Chin FT, Graves EE. Synthesis of a new PET radiotracer targeting carbonic anhydrase IX. J Label Compd Radiopharm 2009;52:S408
- Akurathi V, Dubois L, Lieuwes NG, et al. Synthesis and biological evaluation of a 99mTc-labelled sulfonamide conjugate for in vivo visualization of carbonic anhydrase IX expression in tumor hypoxia. Nucl Med Biol 2010;37:557–64
- Asakawa C, Ogawa M, Kumata K, et al. Radiosynthesis of three [11C]ureido-substituted benzenesulfonamides as PET probes for carbonic anhydrase IX in tumors. Bioorg Med Chem Lett 2011;21:7017–20
- Kolb HC, Walsh JC, Kasi D, et al. Development of molecular imaging probes for carbonic anhydrase-IX using click chemistry. US Patent 0317842; 2010
- Doss M, Alpaugh RK, Yu JQ. Biodistribution and radiation dosimetry of CA-IX PET imaging agent 18F-VM4-037 measured in healthy volunteers. Mol Imaging Biol 2010;12:S124
- Lu G, Hillier SM, Maresca KP, et al. Synthesis and SAR of novel Re/99mTc-labeled benzenesulfonamide carbonic anhydride IX inhibitors for molecular imaging of tumor hypoxia. J Med Chem 2013;56:510--20
- Pacchiano F, Carta F, McDonald PC, et al. Ureido-substituted benzenesulfonamides potently inhibit carbonic anhydrase IX and show antimetastatic activity in a model of breast cancer metastasis. J Med Chem 2011;54:1896–902
- Baker BR, Hurlbut JA. Irreversible enzyme inhibitors. CLIIIProteolytic enzymes 11 Inhibition of guinea pig complement by substituted phenoxyacetamides. J Med Chem 1969;12:415–19
- Carta F, Maresca A, Scozzafava A, Supuran CT. Novel coumarins and 2-thioxo-coumarins as inhibitors of the tumor-associated carbonic anhydrases IX and XII. Bioorg Med Chem 2012;20:2266–73
- Touisni N, Maresca A, McDonald PC, et al. Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors. J Med Chem 2011;54:8271–7
- Wilson AA, Dasilva JN, Houle S. Synthesis of two radiofluorinated cocaine analogs using distilled 2-[18F]fluoroethyl bromide. Appl Radiat Isot 1995;46:765–70
- Gokce B, Gencer N, Arslan O, et al. Evaluation of in vitro effects of some analgesic drugs on erythrocyte and recombinant carbonic anhydrase I and II. J Enzym Inhib Med Chem 2012;27:37–42
- Senturk M, Gulcin I, Beydemir S, et al. In vitro inhibition of human carbonic anhydrase I and II isozymes with natural phenolic compounds. Chem Biol Drug Des 2011;77:494–9
- Guler OO, de Sımone G, Supuran CT. Drug design studies of the novel antitumor targets carbonic anhydrase IX and XII. Curr Med Chem 2010;17:1516–26
- Hendricks JA, Keliher EJ, Marinelli B. In vivo PET imaging of histone deacetylases by 18F-suberoylanilide hydroxamic acid (18F-SAHA). J Med Chem 2011;54:5576–82
- Groves K, Bao B, Zhang J, et al. Synthesis and evaluation of near-infrared fluorescent sulfonamide derivatives for imaging of hypoxia-induced carbonic anhydrase IX expression in tumors. Bioorg Med Chem Lett 2012;22:653–7
- Kim KH, Isin EM, Yun CH, et al. Kinetic deuterium isotope effects for 7-alkoxycoumarin O-dealkylation reactions catalyzed by human cytochromes P450 and in liver microsomes – rate-limiting C--H bond breaking in cytochrome P450 1A2 substrate oxidation. FEBS J 2006;273:2223–31
- Yamazaki H, Inoue K, Mimura M, et al. 7-ethoxycoumarin O-deethylation catalyzed by cytochromes P450 1A2 and 2E1 in human liver microsomes. Biochem Pharmacol 1996;51:313–19
- Tewson TJ, Welch MJ. Preparation and preliminary biodistribution of no carrier added F-18 fluoroethanol. J Nucl Med 1980;21:559–64
- Ling G, Gu J, Genter MB, et al. Regulation of cytochrome P450 gene expression in the olfactory mucosa. Chem Biol Interact 2004;147:247–58