CarbORev-5901: The First Carborane-Based Inhibitor of the 5-Lipoxygenase Pathway.
作者： Robert Kuhnert , Menyhárt-Botond Sárosi , Sven George , Peter Lönnecke , Bettina Hofmann
关键词:
摘要: The progression of cancer is accelerated by increased proliferation, angiogenesis, and inflammation. These processes are mediated leukotrienes. Several cell lines overexpress 5-lipoxygenase, an enzyme that converts arachidonic acid into An early inhibitor the 5-lipoxygenase pathway Rev-5901, which, however, lacks in in vivo efficacy, as it rapidly metabolized. We investigated introduction carboranes highly hydrophobic metabolically stable pharmacophores lipoxygenase inhibitors. Carboranes icosahedral boron clusters remarkably used to increase metabolic stability unstable pharmaceutics without changing their biological activity. By meta-carborane first carborane-based was obtained. report synthesis inhibitory cytotoxic behavior these compounds toward several melanoma colon related anticancer mechanisms.
sci-hub.se 参考文章(38)
Elizabeth A. Grimm, Julie Ellerhorst, Chi-Hui Tang, Suhendan Ekmekcioglu, Constitutive intracellular production of iNOS and NO in human melanoma: possible role in regulation of growth and resistance to apoptosis. Nitric Oxide. ,vol. 19, pp. 133- 137 ,(2008) , 10.1016/J.NIOX.2008.04.009
J EVANS, A FERGUSON, R MOSLEY, J HUTCHINSON, What's all the FLAP about?: 5-lipoxygenase-activating protein inhibitors for inflammatory diseases Trends in Pharmacological Sciences. ,vol. 29, pp. 72- 78 ,(2008) , 10.1016/J.TIPS.2007.11.006
Paul von Ragué Schleyer, Katayoun Najafian, Stability and Three-Dimensional Aromaticity of closo-Monocarbaborane Anions, CBn-1Hn-, and closo-Dicarboranes, C2Bn-2Hn Inorganic Chemistry. ,vol. 37, pp. 3454- 3470 ,(1998) , 10.1021/IC980110V
John H. Musser, Utpal R. Chakraborty, Stanley Sciortino, Robert J. Gordon, Atul Khandwala, Edward S. Neiss, Thaddeus P. Pruss, Richard Van Inwegen, Ira Weinryb, Stephen M. Coutts, Substituted arylmethyl phenyl ethers. 1. A novel series of 5-lipoxygenase inhibitors and leukotriene antagonists. Journal of Medicinal Chemistry. ,vol. 30, pp. 96- 104 ,(1987) , 10.1021/JM00384A017
Shinya Fujii, Tokuhito Goto, Kiminori Ohta, Yuichi Hashimoto, Tomoharu Suzuki, Shigeru Ohta, Yasuyuki Endo, Potent Androgen Antagonists Based on Carborane as a Hydrophobic Core Structure Journal of Medicinal Chemistry. ,vol. 48, pp. 4654- 4662 ,(2005) , 10.1021/JM050115J
Kiminori Ohta, Tokuhito Goto, Hiroto Yamazaki, Fabio Pichierri, Yasuyuki Endo, Facile and efficient synthesis of C-hydroxycarboranes and C,C'-dihydroxycarboranes. Inorganic Chemistry. ,vol. 46, pp. 3966- 3970 ,(2007) , 10.1021/IC062025Q
Ling Ma, Julie Hamdi, Francis Wong, M. Frederick Hawthorne, Closomers of high boron content: synthesis, characterization, and potential application as unimolecular nanoparticle delivery vehicles for boron neutron capture therapy. Inorganic Chemistry. ,vol. 45, pp. 278- 285 ,(2006) , 10.1021/IC051214Q
René Hennig, Xian-Zhong Ding, Wei-Gang Tong, Matthias B Schneider, Jens Standop, Helmut Friess, Markus W Büchler, Parviz M Pour, Thomas E Adrian, None, 5-Lipoxygenase and Leukotriene B4 Receptor Are Expressed in Human Pancreatic Cancers But Not in Pancreatic Ducts in Normal Tissue American Journal of Pathology. ,vol. 161, pp. 421- 428 ,(2002) , 10.1016/S0002-9440(10)64198-3
Katarzyna Bednarska, Agnieszka B. Olejniczak, Magdalena Klink, Zofia Sułowska, Zbigniew J. Leśnikowski, Modulation of human neutrophil activity by adenosine modified with a carborane pharmacophore. Bioorganic & Medicinal Chemistry Letters. ,vol. 24, pp. 3073- 3078 ,(2014) , 10.1016/J.BMCL.2014.05.010
Shinya Fujii, Ayumi Yamada, Eiichi Nakano, Yuki Takeuchi, Shuichi Mori, Hiroyuki Masuno, Hiroyuki Kagechika, Design and synthesis of nonsteroidal progesterone receptor antagonists based on C,C′-diphenylcarborane scaffold as a hydrophobic pharmacophore European Journal of Medicinal Chemistry. ,vol. 84, pp. 264- 277 ,(2014) , 10.1016/J.EJMECH.2014.07.034