The Tumor Inhibitor and Antiangiogenic Agent Withaferin A Targets the Intermediate Filament Protein Vimentin

Chemistry & Biology - Tập 14 - Trang 623-634 - 2007
Paola Bargagna-Mohan1, Adel Hamza2, Yang-eon Kim1, Yik Khuan (Abby) Ho2, Nirit Mor-Vaknin3, Nicole Wendschlag1, Junjun Liu2, Robert M. Evans4, David M. Markovitz3,5, Chang-Guo Zhan2, Kyung Bo Kim2, Royce Mohan1,2
1Department of Ophthalmology and Visual Sciences, University of Kentucky, Lexington, KY 40536, USA
2Department of Pharmaceutical Sciences, University of Kentucky, Lexington, KY 40536, USA
3Department of Internal Medicine, Division of Infectious Diseases, University of Michigan, Medical Center, Ann Arbor, MI 48109, USA
4Department of Pathology, University of Colorado Health Sciences Center, Denver, CO 80045, USA
5Cellular and Molecular Biology Program, University of Michigan Medical Center, Ann Arbor, MI 48109, USA

Tài liệu tham khảo

Zhang, 2006, A chemical and genetic approach to the mode of action of fumagillin, Chem. Biol., 13, 1001, 10.1016/j.chembiol.2006.07.010 Shen, 2003, Virtual screening on natural products for discovering active compounds and target information, Curr. Med. Chem., 10, 2327, 10.2174/0929867033456729 Folkman, 1995, Angiogenesis in cancer, vascular, rheumatoid and other disease, Nat. Med., 1, 27, 10.1038/nm0195-27 Phung, 2006, In-vitro and in-vivo assays for angiogenesis-modulating drug discovery and development, J. Pharm. Pharmacol., 58, 153, 10.1211/jpp.58.2.0001 Mohan, 2004, Withaferin A is a potent inhibitor of angiogenesis, Angiogenesis, 7, 115, 10.1007/s10456-004-1026-3 Upton, 2000 Mishra, 2000, Scientific basis for the therapeutic use of Withania somnifera (ashwagandha): a review, Altern. Med. Rev., 5, 334 Shohat, 1967, Antitumor activity of withaferin A (NSC-101088), Cancer Chemother. Rep., 51, 271 Bargagna-Mohan, 2006, Small molecule anti-angiogenic probes of the ubiquitin proteasome pathway: potential application to choroidal neovascularization, Invest. Ophthalmol. Vis. Sci., 47, 4138, 10.1167/iovs.05-1452 Crews, 1999, Chemical genetics: exploring and controlling cellular processes with chemical probes, Trends Biochem. Sci., 24, 317, 10.1016/S0968-0004(99)01425-5 Schreiber, 1998, Chemical genetics resulting from a passion for synthetic organic chemistry, Bioorg. Med. Chem., 6, 1127, 10.1016/S0968-0896(98)00126-6 Yokota, 2006, Development of withaferin A analogs as probes of angiogenesis, Bioorg. Med. Chem. Lett., 16, 2603, 10.1016/j.bmcl.2006.02.039 Meng, 1999, Epoxomicin, a potent and selective proteasome inhibitor, exhibits in vivo antiinflammatory activity, Proc. Natl. Acad. Sci. USA, 96, 10403, 10.1073/pnas.96.18.10403 Kim, 1999, Proteasome inhibition by the natural products epoxomicin and dihydroeponemycin: insights into specificity and potency, Bioorg. Med. Chem. Lett., 9, 3335, 10.1016/S0960-894X(99)00612-5 Sin, 1997, The anti-angiogenic agent fumagillin covalently binds and inhibits the methionine aminopeptidase, MetAP-2, Proc. Natl. Acad. Sci. USA, 94, 6099, 10.1073/pnas.94.12.6099 Griffith, 1997, Methionine aminopeptidase (type 2) is the common target for angiogenesis inhibitors AGM-1470 and ovalicin, Chem. Biol., 4, 461, 10.1016/S1074-5521(97)90198-8 Eckes, 2000, Impaired wound healing in embryonic and adult mice lacking vimentin, J. Cell Sci., 113, 2455, 10.1242/jcs.113.13.2455 van Beijnum, 2006, Gene expression of tumor angiogenesis dissected: specific targeting of colon cancer angiogenic vasculature, Blood, 108, 2339, 10.1182/blood-2006-02-004291 Lundkvist, 2004, Under stress, the absence of intermediate filaments from Muller cells in the retina has structural and functional consequences, J. Cell Sci., 117, 3481, 10.1242/jcs.01221 Soellner, 1985, Identification of a distinct soluble subunit of an intermediate filament protein: tetrameric vimentin from living cells, Proc. Natl. Acad. Sci. USA, 82, 7929, 10.1073/pnas.82.23.7929 Leung, 2002, Plakins: a family of versatile cytolinker proteins, Trends Cell Biol., 12, 37, 10.1016/S0962-8924(01)02180-8 Clarke, 2002, Intermediate filaments: vimentin moves in, Curr. Biol., 12, R596, 10.1016/S0960-9822(02)01102-8 Esue, 2006, A direct interaction between actin and vimentin filaments mediated by the tail domain of vimentin, J. Biol. Chem., 281, 30393, 10.1074/jbc.M605452200 Fuska, 1984, Novel cytotoxic and antitumor agents. IV. Withaferin A: relation of its structure to the in vitro cytotoxic effects on P388 cells, Neoplasma, 31, 31 Strelkov, 2002, Conserved segments 1A and 2B of the intermediate filament dimer: their atomic structures and role in filament assembly, EMBO J., 21, 1255, 10.1093/emboj/21.6.1255 Bandhoria, 2006, Crystal structure of 5beta, 6beta-epoxy-4beta, 27-dihydroxy-1-oxo-22R-witha-2,24-dienolide isolated from Withania somnifera leaves, Anal. Sci., 22, x91 Schaffeld, 2001, Vimentin and desmin of a cartilaginous fish, the shark Scyliorhinus stellaris: sequence, expression patterns and in vitro assembly, Eur. J. Cell Biol., 80, 692, 10.1078/0171-9335-00206 Rogers, 1989, Cytoskeletal rearrangement by oxidative stress, Int. J. Tissue React., 11, 309 Rogers, 1996, Characterization of disulfide crosslink formation of human vimentin at the dimer, tetramer, and intermediate filament levels, J. Struct. Biol., 117, 55, 10.1006/jsbi.1996.0069 Liu, 2006, Impairment of the ubiquitin-proteasome system in desminopathy mouse hearts, FASEB J., 20, 362, 10.1096/fj.05-4869fje Bar, 2006, Forced expression of desmin and desmin mutants in cultured cells: impact of myopathic missense mutations in the central coiled-coil domain on network formation, Exp. Cell Res., 312, 1554, 10.1016/j.yexcr.2006.01.021 Yang, 2007, The tumor proteasome is a primary target for the natural anticancer compound withaferin A isolated from “Indian Winter Cherry”, Mol. Pharmacol., 71, 426, 10.1124/mol.106.030015 Holwell, 1997, Tetracycline regulated expression of vimentin in fibroblasts derived from vimentin null mice, J. Cell Sci., 110, 1947, 10.1242/jcs.110.16.1947 Ishizaki, 1994, Dynamics of the expression of cytoskeleton components and adherens molecules by fibroblastic cells in alkali-burned and lacerated corneas, Exp. Eye Res., 59, 537, 10.1006/exer.1994.1139 Terzi, 1997, Reduction of renal mass is lethal in mice lacking vimentin: role of endothelin-nitric oxide imbalance, J. Clin. Invest., 100, 1520, 10.1172/JCI119675 Falsey, 2006, Actin microfilament aggregation induced by withaferin A is mediated by annexin II, Nat. Chem. Biol., 2, 33, 10.1038/nchembio755 Berger, 2004, Activity-based protein profiling: applications to biomarker discovery, in vivo imaging and drug discovery, Am. J. Pharmacogenomics, 4, 371, 10.2165/00129785-200404060-00004 Ermakova, 2005, The intermediate filament protein vimentin is a new target for epigallocatechin gallate, J. Biol. Chem., 280, 16882, 10.1074/jbc.M414185200 Hordijk, 2006, Endothelial signalling events during leukocyte transmigration, FEBS J., 273, 4408, 10.1111/j.1742-4658.2006.05440.x Bar, 2004, The biology of desmin filaments: how do mutations affect their structure, assembly, and organisation?, J. Struct. Biol., 148, 137, 10.1016/j.jsb.2004.04.003 Mor-Vaknin, 2003, Vimentin is secreted by activated macrophages, Nat. Cell Biol., 5, 59, 10.1038/ncb898 Singh, 2003, Overexpression of vimentin: role in the invasive phenotype in an androgen-independent model of prostate cancer, Cancer Res., 63, 2306 Hamza, 2006, How Can (−)-epigallocatechin gallate from green tea prevent HIV-1 infection? mechanistic insights from computational modeling and the implication for rational design of anti-HIV-1 entry inhibitors, J. Phys. Chem. B, 110, 2910, 10.1021/jp0550762 Colucci-Guyon, 1994, Mice lacking vimentin develop and reproduce without an obvious phenotype, Cell, 79, 679, 10.1016/0092-8674(94)90553-3 Ambati, 2003, Sustained inhibition of corneal neovascularization by genetic ablation of CCR5, Invest. Ophthalmol. Vis. Sci., 44, 590, 10.1167/iovs.02-0685