Sulfonate-containing thiiranes as selective gelatinase inhibitors

ACS Medicinal Chemistry Letters

Volumn 2, Issue 2, 2011, Pages 177-181

  Testero, Sebastian A ^a   Lee, Mijoon ^a   Staran, Rachel T ^a   Espahbodi, Mana ^a   Llarrull, Leticia I ^a   Toth, Marta ^a   Mobashery, Shahriar ^a   Chang, Mayland ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

matrix metalloproteinases; Slow binding gelatinase inhibitors; thiiranes

Indexed keywords

GELATINASE; GELATINASE A; GELATINASE B; GELATINASE INHIBITOR; MATRIX METALLOPROTEINASE INHIBITOR; SULFONIC ACID DERIVATIVE; THIIRANE INHIBITOR; UNCLASSIFIED DRUG; WATER;

ARTICLE; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALIA;

EID: 79951531008     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml100254e     Document Type: Article

References (22)

1. Massova, I.; Kotra, L. P.; Fridman, R.; Mobashery, S. Matrix metalloproteinases: structures, evolution, and diversification FASEB J. 1998, 12, 1075-1095 (Pubitemid 28418938)
2. Stamenkovic, I. Extracellular matrix remodelling: the role of matrix metalloproteinases J. Pathol. 2003, 200, 448-464 (Pubitemid 36818245)
3. Sternlicht, M. D.; Coussens, L. M.; Vu, T. H.; Werb, Z. Biology and regulation of the matrix metalloproteinases Matrix Metalloproteinase Inhib. Cancer Ther. 2001, 1-37
4. Fanjul-Fernandez, M.; Folgueras, A. R.; Cabrera, S.; Lopez-Otin, C. Matrix metalloproteinases: evolution, gene regulation and functional analysis in mouse models Biochim. Biophys. Acta 2010, 1803, 3-19
5. Fisher, J. F.; Mobashery, S. Recent advances in MMP inhibitor design Cancer Metastasis Rev. 2006, 25, 115-136 (Pubitemid 43723987)
6. Dorman, G.; Cseh, S.; Hajdu, I.; Barna, L.; Konya, D.; Kupai, K.; Kovacs, L.; Ferdinandy, P. Matrix metalloproteinase inhibitors: a critical appraisal of design principles and proposed therapeutic utility Drugs 2010, 70, 949-964
7. Jacobsen, J. A.; Major Jourden, J. L.; Miller, M. T.; Cohen, S. M. To bind zinc or not to bind zinc: an examination of innovative approaches to improved metalloproteinase inhibition Biochim. Biophys. Acta 2010, 1803, 72-94
8. Egeblad, M.; Werb, Z. New functions for the matrix metalloproteinases in cancer progression Nat. Rev. Cancer 2002, 2, 161-174 (Pubitemid 37328786)
9. Coussens, L. M.; Fingleton, B.; Matrisian, L. M. Cancer therapy: matrix metalloproteinase inhibitors and cancer: trials and tribulations Science 2002, 295, 2387-2392 (Pubitemid 34270240)
10. Tu, G. G.; Xu, W. F.; Huang, H. M.; Li, S. H. Progress in the development of matrix metalloproteinase inhibitors Curr. Med. Chem. 2008, 15, 1388-1395 (Pubitemid 351997789)
11. Brown, S.; Bernardo, M. M.; Li, Z. H.; Kotra, L. P.; Tanaka, Y.; Fridman, R.; Mobashery, S. Potent and selective mechanism-based inhibition of gelatinases J. Am. Chem. Soc. 2000, 122, 6799-6800 (Pubitemid 30490016)
12. Forbes, C.; Shi, Q.; Fisher, J. F.; Lee, M.; Hesek, D.; Llarrull, L. I.; Toth, M.; Gossing, M.; Fridman, R.; Mobashery, S. Active site ring-opening of a thiirane moiety and picomolar inhibition of gelatinases Chem. Biol. Drug Des. 2009, 74, 527-534
13. Tao, P.; Fisher, J. F.; Mobashery, S.; Schlegel, H. B. DFT studies of the ring-opening mechanism of SB-3CT, a potent inhibitor of matrix metalloproteinase 2 Org. Lett. 2009, 11, 2559-2562
14. Tao, P.; Fisher, J.; Shi, Q.; Vreven, T.; Mobashery, S.; Schlgel, H. B. Matrix metalloproteinase 2 (MMP2) inhibition: QM/MM studies of the inhibition mechanism of SB-3CT and its analog Biochemistry 2009, 48, 9839-9847
15. Tao, P.; Fisher, J. F.; Shi, Q.; Mobashery, S.; Schlegel, H. B. Matrix metalloproteinase 2 (MMP2) inhibition: DFT and QM/MM studies of the deprotonation initiated ring opening reaction of sulfoxide analog of SB-3CT J. Phys. Chem. 2010, 114, 1030-1037
16. Lee, M.; Villegas-Estrada, A.; Celenza, G.; Boggess, B.; Toth, M.; Kreitinger, G.; Forbes, C.; Fridman, R.; Mobashery, S.; Chang, M. Metabolism of a highly selective gelatinase inhibitor generates active metabolite Chem. Biol. Drug Des. 2007, 70, 371-382 (Pubitemid 47609962)
17. Lee, M.; Celenza, G.; Boggess, B.; Blase, J.; Shi, Q.; Toth, M.; Bernardo, M. M.; Wolter, W. R.; Suckow, M. A.; Hesek, D.; Noll, B. C.; Fridman, R.; Mobashery, S.; Chang, M. A potent gelatinase inhibitor with anti-tumor-invasive activity and its metabolic disposition Chem. Biol. Drug Des. 2009, 73, 189-202
18. Ikejiri, M.; Bernardo, M. M.; Bonfil, R. D.; Toth, M.; Chang, M.; Fridman, R.; Mobashery, S. Potent mechanism-based inhibitors for matrix metalloproteinases J. Biol. Chem. 2005, 280, 33992-34002 (Pubitemid 41443120)
19. Bernardo, M. M.; Brown, S.; Li, Z. H.; Fridman, R.; Mobashery, S. Design, synthesis and characterization of potent, slow-binding inhibitors that are selective for gelatinases J. Biol. Chem. 2002, 277, 11201-11207 (Pubitemid 34952882)
20. Lee, M.; Bernardo, M. M.; Meroueh, S. O.; Brown, S.; Fridman, R.; Mobashery, S. Synthesis of chiral 2-(4-Phenoxyphenylsulfonylmethyl)-thiiranes as selective gelatinase inhibitors Org. Lett. 2005, 7, 4463-4465 (Pubitemid 41436672)
21. Lu, C.; Li, P.; Gallegos, R.; Uttamsingh, V.; Xia, C. Q.; Miwa, G. T.; Balani, S. K.; Gan, L.-S. Comparison of intrinsic clearance in liver microsomes and hepatocytes from rats and humans: evaluation of free fraction and uptake in hepatocytes Drug Metab. Dispos. 2006, 34, 1600-1605 (Pubitemid 44285402)
22. Toth, M.; Bernardo, M. M.; Gervasi, D. C.; Soloway, P. D.; Wang, Z.; Bigg, H. F.; Overall, C. M.; DeClerk, Y. A.; Tschesche, H.; Cher, M. L.; Brown, S.; Mobashery, S.; Fridman, R. Tissue inhibitor of metalloproteinase (TIMP)-2 acts synergistically with synthetic matrix metalloproteinase (MMP) inhibitors but not with TIMP-4 to enhance the (membrane type 1)-MMP-dependent activation of pro-MMP-2 J. Biol. Chem. 2000, 275, 41415-41423 (Pubitemid 32054977)