A potent gelatinase inhibitor with anti-tumor-invasive activity and its metabolic disposition

Chemical Biology and Drug Design

Volumn 73, Issue 2, 2009, Pages 189-202

  Lee, Mijoon ^a   Celenza, Giuseppe ^a   Boggess, Bill ^a   Blase, Jennifer ^a   Shi, Qicun ^a   Toth, Marta ^a   Bernardo, M Margarida ^b   Wolter, William R ^a   Suckow, Mark A ^a   Hesek, Dusan ^a   Noll, Bruce C ^a   Fridman, Rafael ^b   Mobashery, Shahriar ^a   Chang, Mayland ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Anti tumor activity; Gelatinase inhibitor; Metabolism

Indexed keywords

4 [4 (THIIRANYLMETHYLSULFONYL)PHENOXY]PHENYLMETHANESULFONATE; ALPHA METHYLENE; CYSTEINE; DRUG METABOLITE; GELATINASE A; GELATINASE B; GELATINASE INHIBITOR; SULFINIC ACID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INVASION; CELL INVASION; CONTROLLED STUDY; CYTOTOXICITY; DOSE RESPONSE; DRUG BLOOD LEVEL; DRUG INHIBITION; DRUG MECHANISM; DRUG METABOLISM; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; FEMALE; FIBROSARCOMA; HUMAN; HUMAN CELL; HYDROXYLATION; METHYLATION; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; REPEATED DRUG DOSE; RING OPENING; SINGLE DRUG DOSE; TUMOR CELL;

ANIMALS; ANTINEOPLASTIC AGENTS; BIPHENYL COMPOUNDS; CELL LINE, TUMOR; COMPUTATIONAL BIOLOGY; FEMALE; GELATINASES; HUMANS; MATRIX METALLOPROTEINASE 2; MATRIX METALLOPROTEINASE 9; MESYLATES; MICE; MICE, INBRED BALB C; NEOPLASM INVASIVENESS;

EID: 58849102666     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2008.00750.x     Document Type: Article

References (27)

1. Chambers A.F., Groom A.C., MacDonald I.C. (2002) Dissemination and growth of cancer cells in metastatic sites. Nat Rev Cancer 2 : 563 572.
2. Sporn M.B. (1996) The war on cancer. Lancet 347 : 1377 1381.
3. Lee M., Fridman R., Mobashery S. (2004) Extracellular proteases as targets for treatment of cancer metastases. Chem Soc Rev 33 : 401 409.
4. Massova I., Kotra L.P., Fridman R., Mobashery S. (1998) Matrix metalloproteinases: structures, evolution, and diversification. FASEB J 12 : 1075 1095.
5. Nagase H., Meng Q., Malinovskii V., Huang W., Chung L., Bode W., Maskos K., Brew K. (1999) Engineering of Selective TIMPs. Inhibition of Matrix Metalloproteinases: Therapeutic Applications. New York : New York Academy of Science p. 1 11
6. Stamenkovic I. (2003) Extracellular matrix remodelling: the role of matrix metalloproteinases. J Pathol 200 : 448 464.
7. Sternlicht M.D., Werb Z. (2001) How matrix metalloproteinases regulate cell behavior. Annu Rev Cell Dev Biol 17 : 463 516.
8. Bergers G., Benjamin L.E. (2003) Angiogenesis: tumorigenesis and the angiogenic switch. Nat Rev Cancer 3 : 401 410.
9. Kerbel R., Folkman J. (2002) Clinical translation of angiogenesis inhibitors. Nat Rev Cancer 2 : 727 739.
10. Steeg P.S. (2003) Angiogenesis inhibitors: motivators of metastasis? Nat Med 9 : 822 823.
11. Van't Veer Laura J., Weigelt B. (2003) Road map to metastasis. Nat Med 9 : 999 1000.
12. Egeblad M., Werb Z. (2002) New functions for the matrix metalloproteinases in cancer progression. Nat Rev Cancer 2 : 161 174.
13. Brown S., Bernardo M.M., Li Z.H., Kotra L.P., Tanaka Y., Fridman R., Mobashery S. (2000) Potent and selective mechanism-based inhibition of gelatinases. J Am Chem Soc 122 : 6799 6800.
14. Lee M., Villegas-Estrada A., Celenza G., Boggess B., Toth M., Kreitinger G., Forbes C., Fridman R., Mobashery S., Chang M. (2007) Metabolism of a highly selective gelatinase inhibitor generates active metabolite. Chem Biol Drug Des 70 : 371 382.
15. Celenza G., Villegas-Estrada A., Lee M., Boggess B., Forbes C., Wolter W.R., Suckow M.A., Mobashery S., Chang M. (2008) Metabolism of (4-phenoxyphenylsulfonyl)methylthiirane, a selective gelatinase inhibitor. Chem Biol Drug Des 71 : 187 196.
16. Ikejiri M., Bernardo M.M., Bonfil R.D., Toth M., Chang M.L., Fridman R., Mobashery S. (2005) Potent mechanism-based inhibitors for matrix metalloproteinases. J Biol Chem 280 : 33992 34002.
17. Elkins P.A., Ho Y.S., Smith W.W., Janson C.A., D'Alessio K.J., McQueney M.S., Cummings M.D., Romanic A.M. (2002) Structure of the C-terminally truncated human ProMMP9, a gelatin-binding matrix metalloproteinase. Acta Crystallogr D Biol Crystallogr 58 : 1182 1192.
18. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shelley M., Perry J.K., Shaw D.E., Francis P., Shenkin P.S. (2004) Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 47 : 1739 1749.
19. Ewing T.J.A., Kuntz I.D. (1997) Critical evaluation of search algorithms for automated molecular docking and database screening. J Comput Chem 18 : 1175 1189.
20. Kleifeld O., Kotra L.P., Gervasi D.C., Brown S., Bernardo M.M., Fridman R., Mobashery S., Sagi I. (2001) X-ray absorption studies of human matrix metalloproteinase-2 (MMP-2) bound to a highly selective mechanism-based inhibitor - comparison with the latent and active forms of the enzyme. J Biol Chem 276 : 17125 17131.
21. Ma D.W., Cai Q. (2003) N,N-Dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides. Org Lett 5 : 3799 3802.
22. Lee M., Bernardo M.M., Meroueh S.O., Brown S., Fridman R., Mobashery S. (2005) Synthesis of chiral 2-(4-phenoxyphenylsulfonylmethyl)thiiranes as selective gelatinase inhibitors. Org Lett 7 : 4463 4465.
23. Lim I.T., Brown S., Mobashery S. (2004) A convenient synthesis of a selective gelatinase inhibitor as an antimetastatic agent. J Org Chem 69 : 3572 3573.
24. Chen Q., Doss G.A., Tung E.C., Liu W.S., Tang Y.S., Braun M.P., Didolkar V., Strauss J.R., Wang R.W., Stearns R.A., Evans D.C., Baillie T.A., Tang W. (2006) Evidence for the bioactivation of zomepirac and tolmetin by an oxidative pathway: identification of glutathione adducts in vitro in human liver microsomes and in vivo in rats. Drug Metab Dispos 34 : 145 151.
25. Pakenham G., Lango J., Buonarati M., Morin D., Buckpitt A. (2002) Urinary naphthalene mercapturates as biomarkers of exposure and stereoselectivity of naphthalene epoxidation. Drug Metab Dispos 30 : 247 253.
26. Bonfil R.D., Sabbota A., Nabha S., Bernardo M.M., Dong Z., Meng H., Yamamoto H., Chinni S.R., Lim I.T., Chang M., Filetti L.C., Mobashery S., Cher M.L., Fridman R. (2006) Inhibition of human prostate cancer growth, osteolysis and angiogenesis in a bone metastasis model by a novel mechanism-based selective gelatinase inhibitor. Int J Cancer 118 : 2721 2726.
27. Kruger A., Arlt M.J.E., Gerg M., Kopitz C., Bernardo M.M., Chang M., Mobashery S., Fridman R. (2005) Antimetastatic activity of a novel mechanism-based gelatinase inhibitor. Cancer Res 65 : 3523 3526.