FK506-binding protein 12 ligands: a patent review

Bibliography

• Zhang J, Nakatsu Y, Sinjo T, et al. Par14 associates with IRS-1, thereby enhancing insulin-induced IRS-1 phosphorylation and metabolic actions. J Biol Chem 2013; published online 29 May 2013; doi: 10.1074/jbc.M113.485730
   Google Scholar
• Somarelli J, Lee S, Skolnick J, et al. Structure-based classification of 45 FK506-binding proteins. Proteins 2008;72:197-208
   Google Scholar
• Nakamura K, Kosugi I, Lee DY, et al. Prolyl isomerase Pin1 regulates neuronal differentiation via beta-catenin. Mol Cell Biol 2012;32:2966-78
   PubMedGoogle Scholar
• Teng BL, Hacker KE, Chen S, et al. Tumor suppressive activity of prolyl isomerase Pin1 in renal cell carcinoma. Mol Oncol 2011;5:465-74
   Google Scholar
• Kang CB, Hong Y, Dhe-Paganon S, et al. FKBP family proteins: immunophilins with versatile biological functions. Neurosignals 2008;16:318-25
   PubMed Web of Science ®Google Scholar
• Aghdasi B, Ye K, Resnick A, et al. FKBP12, the 12-kDa FK506-binding protein, is a physiologic regulator of the cell cycle. Proc Natl Acade Sci 2001;98:2425-30
   PubMedGoogle Scholar
• Markowitz SD, Roberts AB. Tumor suppressor activity of the TGF-beta pathway in human cancers. Cytokine Growth Factor Rev 1996;7:93-102
   PubMedGoogle Scholar
• Stockwell BR, Schreiber SL. TGF-beta-signaling with small molecule FKBP12 antagonists that bind myristoylated FKBP12-TGF-beta type I receptor fusion proteins. Chem Biol 1998;5:385-95
   PubMedGoogle Scholar
• Shi Y, Massagué J. Mechanisms of TGF-beta signaling from cell membrane to the nucleus. Cell 2003;113:685-700
   PubMed Web of Science ®Google Scholar
• Cameron AM, Steiner JP, Sabatini DM, et al. Immunophilin FK506 binding protein associated with inositol 1, 4, 5-trisphosphate receptor modulates calcium flux. Proc Natl Acad Sci 1995;92:1784-8
   PubMed Web of Science ®Google Scholar
• Mathea S, Li S, Schierhorn A, et al. Suppression of EGFR autophosphorylation by FKBP12. Biochemistry 2011;50:10844-50
   Google Scholar
• Lopez-Ilasaca M, Schiene C, Küllertz G, et al. Effects of FK506-binding protein 12 and FK506 on autophosphorylation of epidermal growth factor receptor. J Biol Chem 1998;273:9430-4
   PubMedGoogle Scholar
• Hemenway CS, Heitman J. Immunosuppressant target protein FKBP12 is required for P-glycoprotein function in yeast. J Biol Chem 1996;271:18527-34
   PubMed Web of Science ®Google Scholar
• Marks AR. Cellular functions of immunophilins. Physiol Rev 1996;76:631-49
   PubMed Web of Science ®Google Scholar
• Wu X, Wang L, Han Y, et al. Creating diverse target-binding surfaces on FKBP12: synthesis and evaluation of a rapamycin analogue library. ACS Comb Sci 2011;13:486-95
   Google Scholar
• Carroll CL, Fleischer J, Alan B. Tacrolimus ointment: the treatment of atopic dermatitis and other inflammatory cutaneous disease. Expert Opin Pharmacother 2004;5:2127-37
   PubMed Web of Science ®Google Scholar
• Fasolo A, Sessa C. mTOR inhibitors in the treatment of cancer. Expert Opin Investig Drugs 2008;17:1717-34
   PubMed Web of Science ®Google Scholar
• Stuetz A, Grassberger M, Meingassner JG. Pimecrolimus (Elidel, SDZ ASM 981)–preclinical pharmacologic profile and skin selectivity. Semin Cutan Med Surg 2001;20:233-41
   PubMed Web of Science ®Google Scholar
• Wei TQ, Hudson DR. Tacrolimus standard and methods of using same. US008153594B2; 2012
   Google Scholar
• Sikkink R, Haddy A, MacKelvie S, et al. Calcineurin subunit interactions: mapping the calcineurin B binding domain on calcineurin A. Biochemistry 1995;34:8348-56
   Google Scholar
• Weiwad M, Edlich F, Kilka S, et al. Comparative analysis of calcineurin inhibition by complexes of immunosuppressive drugs with human FK506 binding proteins. Biochemistry 2006;45:15776-84
   PubMedGoogle Scholar
• Dumont FJ. FK506, an immunosuppressant targeting calcineurin function. Curr Med Chem 2000;7:731-48
   PubMed Web of Science ®Google Scholar
• Hamawy MM, Knechtle SJ. An overview of the actions of cyclosporine and FK506. Transplant Rev 2003;17:165-71
   Google Scholar
• Choi J, Chen J, Schreiber SL, et al. Structure of the FKBP12-rapamycin complex interacting with binding domain of human FRAP. Science 1996;273:239-42
   PubMed Web of Science ®Google Scholar
• Fung J, Abu-Elmagd K, Jain A, et al. A randomized trial of primary liver transplantation under immunosuppression with FK 506 vs cyclosporine. Transplant Proc 1991;23:2977-83
   PubMed Web of Science ®Google Scholar
• Calderón-Sánchez E, Rodriguez-Moyano M, Smani T. Immunophilins and cardiovascular complications. Curr Med Chem 2011;18:5408-13
   Google Scholar
• Szabó L, Szentandrássy N, Kistamás K, et al. Effects of tacrolimus on action potential configuration and transmembrane ion currents in canine ventricular cells. Naunyn Schmiedebergs Arch Pharmacol 2013;386:239-46
   Google Scholar
• Zadrazil J, Horak P, Zahalkova J, et al. Improvement of cardiovascular risk factors and cosmetic side effects in kidney transplant recipients after conversion to tacrolimus. Biomed Pap 2009;153:67-73
   Google Scholar
• Hohage H, Welling U, Heck M, et al. Conversion from cyclosporine to tacrolimus after renal transplantation improves cardiovascular risk factors. Int Immunopharmacol 2005;5:117-23
   PubMed Web of Science ®Google Scholar
• Desai S, Hong JC, Saab S. Cardiovascular risk factors following orthotopic liver transplantation: predisposing factors, incidence and management. Liver Int 2010;30:948-57
   PubMed Web of Science ®Google Scholar
• Gordon RD, Holm P, Lademann AM, et al. Tacrolimus for improved treatment of transplant patients. US20120029009Al; 2012
   Google Scholar
• Wakata N, Saito T, Tanaka S, et al. Tacrolimus hydrate (FK506): therapeutic effects and selection of responders in the treatment of myasthenia gravis. Clin Neurol Neurosurg 2003;106:5-8
   PubMed Web of Science ®Google Scholar
• Guo X, Dillman JF, Dawson VL, et al. Neuroimmunophilins: novel neuroprotective and neuroregenerative targets. Neurol Prog 2001;50:6-16
   Google Scholar
• Yao Z, Wu H. A method of FK506 release membrane preparation for nerve injury repairment. CN2008102285753; 2008
   Google Scholar
• Takashi U. The vision cell dysfunction therapeutic agent. CN998162760; 1999
   Google Scholar
• Pople PV, Singh KK. Targeting tacrolimus to deeper layers of skin with improved safety for treatment of atopic dermatitis. Int J Pharm 2010;398:165-78
   PubMed Web of Science ®Google Scholar
• Bierer BE, Somers PK, Wandless TJ, et al. Probing immunosuppressant action with a nonnatural immunophilin ligand. Science 1990;250:556-9
   PubMed Web of Science ®Google Scholar
• Reeves C, Chu D, Khosla C, et al. Polynucleotides encoding the fkbA gene of the FK-520 polyketide synthase gene cluster. US006759536B2; 2004
   Google Scholar
• Dumont FJ, Staruch M, Koprak S, et al. The immunosuppressive and toxic effects of FK-506 are mechanistically related: pharmacology of a novel antagonist of FK-506 and rapamycin. J Exp Med 1992;176:751-60
   PubMed Web of Science ®Google Scholar
• März AM, Fabian A-K, Kozany C, et al. Large FK506-binding proteins shape the pharmacology of rapamycin. Mol Cell Biol 2013;33:1357-67
   PubMed Web of Science ®Google Scholar
• Powell JD, Pollizzi KN, Heikamp EB, et al. Regulation of immune responses by mTOR. Annu Rev Immunol 2012;30:39-68
   PubMed Web of Science ®Google Scholar
• Araki K, Youngblood B, Ahmed R. The role of mTOR in memory CD8+ T-cell differentiation. Immunol Rev 2010;235:234-43
   PubMed Web of Science ®Google Scholar
• Waickman AT, Powell JD. mTOR, metabolism, and the regulation of T-cell differentiation and function. Immunol Rev 2012;249:43-58
   PubMed Web of Science ®Google Scholar
• Danielpour D. Functions and regulation of transforming growth factor-beta (TGF-beta) in the prostate. Eur J Cancer 2005;41:846-57
   PubMed Web of Science ®Google Scholar
• Falcon BL, Barr S, Gokhale PC, et al. Reduced VEGF production, angiogenesis, and vascular regrowth contribute to the antitumor properties of dual mTORC1/mTORC2 inhibitors. Cancer Res 2011;71:1573-83
   PubMed Web of Science ®Google Scholar
• Carew JS, Kelly KR, Nawrocki ST. Mechanisms of mTOR inhibitor resistance in cancer therapy. Targeted Oncol 2011;6:17-27
   PubMed Web of Science ®Google Scholar
• Alessi DR, Pearce LR, Garcia-Martinez JM. New insights into mTOR signaling: mTORC2 and beyond. Sci Signal 2009;2:pe27
   Google Scholar
• Garcia-Martinez J, Alessi D. mTOR complex 2 (mTORC2) controls hydrophobic motif phosphorylation and activation of serum-and glucocorticoid-induced protein kinase 1 (SGK1). Biochem J 2008;416:375-85
   PubMed Web of Science ®Google Scholar
• Hong F, Larrea MD, Doughty C, et al. mTOR-raptor binds and activates SGK1 to regulate p27 phosphorylation. Mol Cell 2008;30:701-11
   PubMed Web of Science ®Google Scholar
• Janes MR, Fruman DA. Targeting TOR dependence in cancer. Oncotarget 2010;1:69-76
   Google Scholar
• Chaturvedi D, Gao X, Cohen MS, et al. Rapamycin induces transactivation of the EGFR and increases cell survival. Oncogene 2009;28:1187-96
   PubMed Web of Science ®Google Scholar
• Naing A. Overcoming resistance to mTOR inhibition for enhanced strategies in clinical trials. Expert Opin Investig Drugs 2013;22:679-85
   PubMed Web of Science ®Google Scholar
• Wander SA, Hennessy BT, Slingerland JM. Next-generation mTOR inhibitors in clinical oncology: how pathway complexity informs therapeutic strategy. J Clin Invest 2011;121:1231-41
   PubMed Web of Science ®Google Scholar
• McMullen JR, Sherwood MC, Tarnavski O, et al. Inhibition of mTOR signaling with rapamycin regresses established cardiac hypertrophy induced by pressure overload. Circulation 2004;109:3050-5
   PubMed Web of Science ®Google Scholar
• Azroland NI, Segal SN. Methods for the treatment of cardiovascular disease. CN018112129; 2001
   Google Scholar
• Tsang CK, Qi H, Liu LF, et al. Targeting mammalian target of rapamycin (mTOR) for health and diseases. Drug Discov Today 2007;12:112-24
   PubMed Web of Science ®Google Scholar
• Serruys PW, Kutryk MJB, Ong ATL. Coronary-artery stents. N Engl J Med 2006;354:483-95
   PubMed Web of Science ®Google Scholar
• Moses JW, Leon MB, Popma JJ, et al. Sirolimus-eluting stents versus standard stents in patients with stenosis in a native coronary artery. N Engl J Med 2003;349:1315-23
   PubMed Web of Science ®Google Scholar
• Vezina C, Kudelski A, Sehgal S. Rapamycin (AY-22,989), a new antifungal antibiotic. I. Taxonomy of the producing streptomycete and isolation of the active principle. J Antibiot (Tokyo) 1975;28:721-6
   PubMed Web of Science ®Google Scholar
• Sehgal S, Baker H, Vézina C. Rapamycin (AY-22,989), a new antifungal antibiotic. II. Fermentation, isolation and characterization. J Antibiot (Tokyo) 1975;28:727-32
   PubMed Web of Science ®Google Scholar
• Chen G, Zheng H, Deng J. An acne endermic agent. CN201210013571X; 2012
   Google Scholar
• Steiner JP, Snyder S, Hamilton GS, et al. Inhibitors of rotamase enzyme activity. US20030114365Al; 2003
   Google Scholar
• Roberts M, Arabshahi L, Boyd J, et al. Immunoassays for everolimus. US007223553B2; 2007
   Google Scholar
• Houghton PJ. Everolimus. Clin Cancer Res 2010;16:1368-72
   PubMed Web of Science ®Google Scholar
• Bukowski RM. Temsirolimus: a safety and efficacy review. Expert Opin Drug Saf 2012;11:861-79
   PubMed Web of Science ®Google Scholar
• Rubino JT, Siskavich V, Harrison MM, et al. Parenteral formulations. US20110294845Al; 2011
   Google Scholar
• Rivera VM, Squillace RM, Miller D, et al. Ridaforolimus (AP23573; MK-8669), a potent mTOR inhibitor, has broad antitumor activity and can be optimally administered using intermittent dosing regimens. Mol Cancer Ther 2011;10:1059-71
   PubMed Web of Science ®Google Scholar
• Vladyka RS, Dalgarno DC, Iuliucci JD. Oral formulations. US20100247643Al; 2010
   Google Scholar
• Colombo N, McMeekin D, Schwartz P, et al. Ridaforolimus as a single agent in advanced endometrial cancer: results of a single-arm, phase 2 trial. Br J Cancer 2013;108(5):1021-6
   PubMed Web of Science ®Google Scholar
• Demetri GD, Chawla SP, Ray-Coquard I, et al. Results of an international randomized phase III trial of the mammalian target of rapamycin inhibitor ridaforolimus versus placebo to control metastatic sarcomas in patients after benefit from prior chemotherapy. J Clin Oncol 2013;31(19):2485-92
   PubMed Web of Science ®Google Scholar
• Ebbinghaus S. Combination therapy. WO2010044893; 2010
   Google Scholar
• Reeves CD, Chung LM, Liu Y, et al. A new substrate specificity for acyl transferase domains of the ascomycin polyketide synthase in Streptomyces hygroscopicus. J Biol Chem 2002;277:9155-9
   PubMedGoogle Scholar
• Chakraborty T, Weber H, Nicolaou K. Design and Synthesis of a rapamycin-based high affinity binding FKBP12 ligand. Chem Biol 1995;2:157-61
   PubMedGoogle Scholar
• Gyollai V, Szabo C. Methods for preparing pimecrolimus. WO2006060614A1; 2006
   Google Scholar
• Hoetzenecker W, Ecker R, Kopp T, et al. Pimecrolimus leads to an apoptosis-induced depletion of T cells but not Langerhans cells in patients with atopic dermatitis. J Allergy Clin Immunol 2005;115:1276-83
   PubMed Web of Science ®Google Scholar
• Assmann T, Homey B, Ruzicka T. Applications of tacrolimus for the treatment of skin disorders. Immunopharmacology 2000;47:203-13
   Google Scholar
• Gupta A, Chow M. Pimecrolimus: a review. J Eur Acad Dermatol Venereol 2003;17:493-503
   PubMed Web of Science ®Google Scholar
• Salituro GM, Zink DL, Dahl A, et al. Meridamycin: a novel nonimmunosuppressive FKBP12 ligand from streptomyces hygroscopicus. Tetrahedron Lett 1995;36:997-1000
   Google Scholar
• Graziani EI, Pong K. Non-immunosuppressive immunophilin ligands as neuroprotective and/or neuroregenerative agents. US20050197356Al; 2005
   Google Scholar
• Gregory MA, Gaisser S, Petkovic H, et al. Production of polyketides and other natural products. US20080287482A; 2008
   Google Scholar
• Fehr T, Sanglier JJ, Schuler W, et al. Antascomicins A, B, C, D and E novel FKBP12 binding compounds from a Micromonospora strain. J Antibiot (Tokyo) 1996;49:230-3
   Google Scholar
• Blackburn EA, Walkinshaw MD. Targeting FKBP isoforms with small-molecule ligands. Curr Opin Pharmacol 2011;11:365-71
   Google Scholar
• Gold BG, Armistead DM, Wang MS. Non-FK506-binding protein-12 neuroimmunophilin ligands increase neurite elongation and accelerate nerve regeneration. J Neurosci Res 2005;80:56-65
   PubMed Web of Science ®Google Scholar
• Gold BG, Densmore V, Shou W, et al. Immunophilin FK506-binding protein 52 (not FK506-binding protein 12) mediates the neurotrophic action of FK506. J Pharmacol Exp Ther 1999;289:1202-10
   PubMed Web of Science ®Google Scholar
• Quintá H, Galigniana M. The neuroregenerative mechanism mediated by the Hsp90-binding immunophilin FKBP52 resembles the early steps of neuronal differentiation. Br J Pharmacol 2012;166:637-49
   PubMed Web of Science ®Google Scholar
• Armistead DM. Methods and compositions for stimulating neurite growth. US006037370A; 2000
   Google Scholar
• Mutz MW, Gestwicki JE. Combinatorial improvement of bifunctional drug properties. US20090054334Al; 2009
   Google Scholar
• Babine RE, Villafranca JE, Gold BG. FKBP immunophilin patents for neurological disorders. Expert Opin Ther Patents 2005;15:555-73
   Web of Science ®Google Scholar
• Gaali S, Gopalakrishnan R, Wang Y, et al. The chemical biology of immunophilin ligands. Curr Med Chem 2011;18:5355-79
   PubMedGoogle Scholar
• Klettner A, Herdegen T. The immunophilin-ligands FK506 and V-10,367 mediate neuroprotection by the heat shock response. Br J Pharmacol 2003;138:1004-12
   PubMed Web of Science ®Google Scholar
• Klettner A, Baumgrass R, Zhang Y, et al. The neuroprotective actions of FK506 binding protein ligands: neuronal survival is triggered by de novo RNA synthesis, but is independent of inhibition of JNK and calcineurin. Mol Brain Res 2001;97:21-31
   PubMedGoogle Scholar
• Sauer H, Francis JM, Jiang H, et al. Systemic treatment with GPI 1046 improves spatial memory and reverses cholinergic neuron atrophy in the medial septal nucleus of aged mice. Brain Res 1999;842:109-18
   PubMed Web of Science ®Google Scholar
• Steiner JP, Hamilton GS, Ross DT, et al. Neurotrophic immunophilin ligands stimulate structural and functional recovery in neurodegenerative animal models. Proc Natl Acad Sci 1997;94:2019-24
   PubMed Web of Science ®Google Scholar
• Marshall V, Grosset D. GPI-1485 (Guilford). Curr Opin Investig Drugs (London, England: 2000) 2004;5:107-12
   Google Scholar
• Ninds N-P. A randomized clinical trial of coenzyme Q10 and GPI-1485 in early Parkinson disease. Neurology 2007;68:20-8
   Google Scholar
• Ross DT, Hamilton GS, Steiner JP. Heterocyclic esters or amides for vision and memory disorders. US007338976Bl; 2008
   Google Scholar
• Choi C, Li JH, Vaal M, et al. Use of parallel-synthesis combinatorial libraries for rapid identification of potent FKBP12 inhibitors. Bioorg Med Chem Lett 2002;12:1421-8
   PubMedGoogle Scholar
• Kosley RW Jr, Baron B, Jimonet P, et al. FKBP binding composition and pharmaceutical use thereof. WO2006012256; 2006
   Google Scholar
• Vrudhula VM, Dubowchik GM, Dasgupta B, et al. Neurotrophic difluoroamide agents. US006239146Bl; 2001
   Google Scholar
• Kemp MI, Palmer MJ, Sanner MA, et al. Heterocyclic compounds as inhibitors of rotamase enzymes. US006562964B1; 2003
   Google Scholar
• Harper S, Bilsland J, Young L, et al. Analysis of the neurotrophic effects of GPI-1046 on neuron survival and regeneration in culture and in vivo. Neuroscience 1999;88:257-67
   PubMed Web of Science ®Google Scholar
• Bocquet A, Lorent G, Fuks B, et al. Failure of GPI compounds to display neurotrophic activity in vitro and in vivo. Eur J Pharmacol 2001;415:173-80
   PubMed Web of Science ®Google Scholar
• Martina MR, Tenori E, Bizzarri M, et al. The precise chemical-physical nature of the pharmacore in FK506 binding protein inhibition: elteX, a new class of nanomolar FKBP12 ligands. J Med Chem 2013;56:1041-51
   PubMed Web of Science ®Google Scholar
• Christner C, Wyrwa R, Marsch S, et al. Synthesis and cytotoxic evaluation of cycloheximide derivatives as potential inhibitors of FKBP12 with neuroregenerative properties. J Med Chem 1999;42:3615-22
   PubMed Web of Science ®Google Scholar
• Edlich F, Weiwad M, Wildemann D, et al. The specific FKBP38 inhibitor N-(N′, N′-dimethylcarboxamidomethyl) cycloheximide has potent neuroprotective and neurotrophic properties in brain ischemia. J Biol Chem 2006;281:14961-70
   PubMedGoogle Scholar
• Gopalakrishnan R, Kozany C, Gaali S, et al. Evaluation of Synthetic FK506 Analogues as Ligands for the FK506-Binding Proteins 51 and 52. J Med Chem 2012;55:4114-22
   PubMedGoogle Scholar
• Limburg DC, Thomas BE IV, Li JH, et al. Synthesis and evaluation of chiral bicyclic proline FKBP12 ligands. Bioorg Med Chem Lett 2003;13:3867-70
   Google Scholar
• Dubowchik GM, Provencal DP. Neurotrophic bicyclic diamides. US006818643Bl; 2004
   Google Scholar
• Wang Y, Kirschner A, Fabian A-K, et al. Increasing the efficiency of ligands for FK506-binding protein 51 by conformational control. J Med Chem 2013;56:3922-35
   PubMedGoogle Scholar
• Burkhard P, Hommel U, Sanner M, et al. The discovery of steroids and other novel FKBP inhibitors using a molecular docking program. J Mol Biol 1999;287:853-8
   PubMed Web of Science ®Google Scholar
• Steiner JP, Snyder S, Hamilton GS, et al. Inhibitors of rotamase enzyme activity. US006500843B2; 2002
   Google Scholar
• Jin YJ, Albers MW, Lane WS, et al. Molecular cloning of a membrane-associated human FK506-and rapamycin-binding protein, FKBP-13. Proc Natl Acad Sci 1991;88:6677-81
   PubMedGoogle Scholar