Comparative studies of potential cancer biomarkers carbon-11 labeled MMP inhibitors (S)-2-(4′-[11C]methoxybiphenyl-4-sulfonylamino)-3- methylbutyric acid and N-hydroxy-(R)-2-[[(4′-[11C] methoxyphenyl)sulfonyl]benzylamino]-3-methylbutanamide

Nuclear Medicine and Biology

Volumn 31, Issue 1, 2004, Pages 77-85

  Zheng, Qi Huang ^a   Fei, Xiangshu ^a   Liu, Xuan ^a   Wang, Ji Quan ^a   Stone, K Lee ^a   Martinez, Tanya D ^a   Gay, Dawn J ^a   Baity, Winston L ^a   Miller, Kathy D ^a   Sledge, George W ^a   Hutchins, Gary D ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

(S) 2 (4 11C methoxybiphenyl 4 sulfonylamino) 3 methylbutyric acid; Cancer biomarkers; Carbon 11; Matrix metalloproteinase inhibitor; Positron emission tomography

Indexed keywords

2 (4' HYDROXYBIPHENYL 4 SULFONYLAMINO) 3 METHYLBUTYRIC ACID TERT BUTYL ESTER; 2 (4' METHOXYBIPHENYL 4 SULFONYLAMINO) 3 METHYLBUTYRIC ACID C 11; 2 (N BENZYL 4 METHOXYBENZENESULFONAMIDO) N HYDROXY 3 METHYLBUTANAMIDE; 2 [[(4' METHOXYPHENYL)SULFONYL]BENZYLAMINO] 3 METHYLBUTANAMIDE C 11; BIOLOGICAL MARKER; BIPHENYL DERIVATIVE; CARBON 11; CARBON DIOXIDE; CGS 25966 C 11; ESTER DERIVATIVE; INTERLEUKIN 1ALPHA; MATRIX METALLOPROTEINASE INHIBITOR C 11; PHENOL DERIVATIVE; RADIOPHARMACEUTICAL AGENT; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; VALINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG SYNTHESIS; HYDROLYSIS; METHYLATION; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; SOLID PHASE EXTRACTION;

EID: 1642451807     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0969-8051(03)00111-2     Document Type: Article

References (35)

1. Afzal S., Lalani el-N., Foulkes W.D., Boyce B., Tickle S., Cardillo M.R., Baker T., Pignatelli M., Stamp G.W. Matrix metalloproteinase-2 and tissue inhibitor of metalloproteinase-2 expression and synthetic matrix metalloproteinase-2 inhibitor binding in ovarian carcinomas and tumor cell lines. Lab Invest. 74:1996;406-421.
2. Bremer C., Tung C.-H., Weissleder R. In vivo molecular target assessment of matrix metalloproteinase inhibition. Nat Med. 7:2001;743-748.
3. Brown P.D. Matrix metalloproteinase inhibitors. Breast Cancer Res Treat. 52:1998;125-136.
4. 11C] methyl-CGS 27023A and its analogs, new potential PET breast cancer imaging agents. J Labelled Cpd Radiopharm. 45:2002;449-470.
5. 11C]CGS 25966, a new potential PET tumor imaging agent. J Labelled Cpd Radiopharm. 46:2003;343-351.
6. Furumoto S., Iwata R., Ido T. Design and synthesis of fluorine-18 labeled matrix metalloproteinase inhibitor for cancer imaging. J Labelled Cpd Radiopharm. 45:2002;975-986.
7. 18F-labeled matrix metalloproteinase-2 inhibitor for cancer imaging by PET. J Nucl Med. 43:(Suppl 5):2002;1462.
8. Greenwald R.A., Zucker S., Golub L.M. Inhibition of matrix metalloproteinases, therapeutic applications. Ann NY Acad Sci. 878:1999;1-761.
9. Ha H.Y., Moon H.B., Nam M.S., Lee J.W., Ryoo Z.Y., Lee T.H., Lee K.K., So B.J., Sato H., Seiki M., Yu D.Y. Overexpression of membrane-type matrix metalloproteinase-1 gene induces mammary gland abnormalities and adenocarcinoma in transgenic mice. Cancer Res. 61:2001;984-990.
10. Hagmann W.K., Lark M.W., Becker J.W. Inhibition of matrix metalloproteinases. Bristol J.A. Ann Rep Med Chem, Vol. 31. 1996;231-240 Academic Press, New York.
11. Hahnel E., Harvey J.M., Joyce R., Robbins P.D., Sterrett G.F., Hahnel R. Stromelysin-3 expression in breast cancer biopsies clinico-pathological correlations . Int J Cancer. 55:1993;771-774.
12. Hanessian S., MacKay D.B., Moitessier N. Design and synthesis of matrix metalloproteinase inhibitors guided by molecular modeling. Picking the S(1) pocket using conformationally constrained inhibitors. J Med Chem. 44:2001;3074-3082.
13. Hutchins G.D., Rouze N., Stone K.L., Krishnamurthi G., Liang Y. Initial imaging experience with IndyPET II. J Nucl Med. 43:(Suppl):2002;59P.
14. Jeng A.Y., Chou M., Parker D.T. Sulfonamide-based hydroxamic acids as potent inhibitors of mouse macrophage metalloelastase. Bioorg Med Chem Lett. 8:1998;897-902.
15. 11C]methyl triflate. Appl Radiat Isot. 43:1992;1383-1385.
16. Jiang Y., Goldberg I.D., Shi Y.E. Complex roles of tissue inhibitors of metalloproteinases in cancer. Oncogene. 21:2002;2245-2252.
17. MacPherson L.M., Bayburt E.K., Capparelli M.P., Carroll B.J., Goldstein R., Justice M.R., Zhu L., Hu S., Melton R.A., Fryer L., Goldberg R.L., Doughty J.R., Spirito S., Blancuzzi V., Wilson D., O'Byrne E.M., Ganu V., Parker D.T. Discovery of CGS 27023A, a non-peptidic, potent, and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits. J Med Chem. 40:1997;2525-2532.
18. Miyaura N., Yanagi T., Suzuki A. The palladium-catalyzed cross-coupling reaction of phenylboronic acid with haloarenes in the presence of bases. Syn Commun. 11:1981;513-519.
19. 11C]methyl triflate. Nucl Med Biol. 26:1999;467-471.
20. O'Brien P.M., Ortwine D.F., Pavlovsky A.G., Picard J.A., Sliskovic D.R., Roth B.D., Dyer R.D., Johnson L.L., Man C.F., Hallak H. Structure-activity relationships and pharmacokinetic analysis for a series of potent, systemically available biphenylsulfonamide matrix metalloproteinase inhibitors. J Med Chem. 43:2000;156-166.
21. Price A., Shi Q., Morris D., Wilcox M.E., Brasher P.M., Rewcastle N.B., Shalinsky D., Zou H., Appelt K., Johnston R.N., Yong V.W., Edwards D., Forsyth P. Marked inhibition of tumor growth in a malignant glioma tumor model by a novel synthetic matrix metalloproteinase inhibitor AG3340. Clin Cancer Res. 5:1999;845-854.
22. Rasmussen H.S., McCann P.P. Matrix metalloproteinase inhibition as a novel anticancer strategy a review with special focus on batimastat and marimastat . Pharmacol Ther. 75:1997;69-75.
23. Rouze N.C., Hutchins G.D. Design of IndyPET-2, a high-resolution, high-sensitivity dedicated research scanner. J Nucl Med. 42:(Suppl):2001;364P.
24. Scozzafava A., Supuran C.T. Carbonic anhydrase and matrix metalloproteinase inhibitors sulfonylated amino acid hydroxamates with MMP inhibitory properties act as efficient inhibitors of CA isozymes I, II, and IV, and N-hydroxysulfonamides inhibit both these zinc enzymes . J Med Chem. 43:2000;3677-3687.
25. Steward W.P. Marimastat (BB2516) current status of development . Cancer Chemother Pharmacol. 43:(Suppl):1999;S56-60.
26. Summers J.B., Davidsen S.K. Matrix metalloproteinase inhibitors and cancer. Bristol J.A. Ann Rep in Med Chem, Vol 33. 1998;131-140 Academic Press, New York.
27. Vihinen P., Kahari V.M. Matrix metalloproteinases in cancer prognostic markers and therapeutic targets . Int J Cancer. 99:2002;157-166.
28. Whittaker M., Flooyd C.D., Brown P., Gearing A.J.H. Design and therapeutic application of matrix metalloproteinase inhibitors. Chem Rev. 99:1999;2735-2776.
29. 11C]methyl-halo-CGS 27023A analogs, new potential PET breast cancer imaging agents. Nucl Med Biol. 29:2002;761-770.
30. 11C]methyl-CGS 27023A a new PET breast cancer imaging agent . J Labelled Cpd Radiopharm. 44:(Suppl 1):2001;S104-106.
31. 6-alkylguanine-DNA alkyltransferase. J Labelled Cpd Radiopharm. 45:2002;1239-1252.
32. 11C]β-CIT labeled at nitrogen or oxygen positions. Nucl Med Biol. 23:1996;981-986.
33. 11C]Nor-β-CIPPT . J Labelled Cpd Radiopharm. 40:(Suppl 1):1997;551-553.
34. 11C]Choline as a potential PET marker for imaging of breast cancer athymic mice. Nucl Med Biol. 29:2002;803-807.
35. 11C]HE-β-CNT new PET monoamine transporter radiotracers containing polar hydroxyethyl groups, accessible from the corresponding fluoroethyl derivatives . J Labelled Cpd Radiopharm. 40:(Suppl 1):1997;548-550.