Cyclosporin A analogues: recent advances

Bibliography

• DREYFUSS M, HARRI E, HOFMANN H et al.: Cyclosporin A and C. New metabolites from TkhOderIlla pOlySpOr11171. ELIE .1. Appl. Microbial. (1976) 3:125–133.
   Google Scholar
• WENGER RIVI: Synthesis of cyclosporin. Total synthesis of cyclosporin A and cyclosporin H, two fungal metabolites isolated from the species Tohpodadium inflaturn. Hely. China. Ada (1984) 67:502–525.
   Google Scholar
• SPITZFADEN C, BRAUN W, WIDER G et al.: Determination of the NMR solution structure of the cyclophilin A-cyclosporin A complex. J. Biomol. NMR (1994) 4:463–482.
   PubMed Web of Science ®Google Scholar
• MIKOL V, KALLEN J, AFLUENGE G et al.: X-ray structure of a monomeric cyclophilin A-cyclosporin A complex at 2.1.ANG resolution. J. MoL Biol. (1993) 234:1119–1130.
   Google Scholar
• MATOUSCHEK A, ROSPERT S, SCHMID K et al.: Cyclophilin catalyzes protein folding in yeast mitochondria. Proc. Natl. Acad. Sci. USA (1996) 92:6319–6323.
   Web of Science ®Google Scholar
• RAO A, LUO C, HOGAN PG: Transcription factors of the NFAT family: regulation and function. Ann. Rev. Immunol (1997) 15:707–747.
   PubMed Web of Science ®Google Scholar
• HUAI Q, KIM HY, LIU Y et al: Crystal structure of calcineurin-cyclophilin-cyclosporin shows common but distinct recognition of immunophilin drug complexes. Proc. Natl. Acad. Sci. USA (2002) 99:12037–12042.
   PubMed Web of Science ®Google Scholar
• JIN L, HARRISON SC: Crystal structure of human calcineurin complexed with cyclosporin A and human cyclophilin. Proc. Natl. Acad. Sci. USA (2002) 99(21):13522–13526.
   PubMed Web of Science ®Google Scholar
• LOH C, KAREN TY, SHAW JC et al: Calcineurin binds the transcription factor NFAT1 and reversibly regulates its activity. Biol. Chem. (1996) 271:10884–10891.
   Web of Science ®Google Scholar
• SHAW KT, HO AM, RAGHAVAN A et al.: Immunosuppressive drugs prevent a rapid dephosphorylation of transcription factor NFAT1 in stimulated immune cells. Proc. Nati Acad. Sci. USA (1995) 92:11205–11209.
   PubMed Web of Science ®Google Scholar
• KIANI A, RAO A, ARAMBURU J: Manipulating immune responses with immunosuppressive agents that target NFAT. Immunity (2000) 12(4):359–372.
   PubMed Web of Science ®Google Scholar
• ••A recent review on imrnunosuppressive agentsthat modulate NFAT transcription factor.
   Google Scholar
• HO S, CLIPSTONE N, TIMMERMANN L et al.: The mechanism of action of cyclosporin A and FK-506. Cl/n. Immunol Immunopathol (1996) 80:S40–S45.
   Google Scholar
• FAULDS D, GOA KL, BENFILED P: Cyclosporin, a review of its pharmacadynamic and pharmacokinetic properties, and therapeutic use in immunoregulatory disorders. Drug (1993) 45:953–995.
   PubMed Web of Science ®Google Scholar
• RUSH DN: Cyclosporine toxicity to organs other than the kidney. Clin. Biochem. (1991) 24:101–105.
   PubMed Web of Science ®Google Scholar
• KEOWN PA, STILLER CR, WALLACE AC: Effect of cyclosporine on the kidney. J. Pedian: (1987) 111:1029–1033.
   PubMed Web of Science ®Google Scholar
• REMUZZI G, BERTANI T: Renal vascularand thrombotic effects of cyclosporine. Am. J. Kidney Dis. (1989) 13:261–272.
   PubMed Web of Science ®Google Scholar
• KUMAR KV, NAIDU MU, SHIFOW AA et al.: Melatonin: an antioxidant protects against cyclosporine-induced nephrotoxicity. Transplantation (1999) 67:1065–1068.
   PubMed Web of Science ®Google Scholar
• ZHONG Z, CONNOR HD, YIN M et al.: Viral delivery of superoxide dismutase gene reduces cyclosporine A-induced nephrotoxicity. Kidney Int. (2001) 59:1397–1404.
   PubMed Web of Science ®Google Scholar
• ZHONG Z, CONNOR HD, YIN M et al.: Dietary glycine and renal denervation prevents cyclosporin A-induced hydroxyl radical production in rat kidney. MM. Pharmacol (1999) 56:455–463.
   PubMed Web of Science ®Google Scholar
• PALLER MS, WEBER K, PATTEN M: Nitric oxide-mediated renal epithelial cell injury during hypoxia and reoxygenation. Ren. Fail. (1998) 20:459–469.
   PubMed Web of Science ®Google Scholar
• YU L, GENGARO PE, NIEDERBERGER M et al.: Nitric oxide: a mediator in rat tubular hypoxia/ reoxygenation injury. Proc. Nati Acad. Sci. USA (1994) 91:691–1695.
   Web of Science ®Google Scholar
• HORTELANO S, CASTILLA M, TORRES AM et al.: Potentiation by nitric oxide of cyclosporin A and FK-506-induced apoptosis in renal proximal tubule cells. J. Am. Soc. Nephrol (2000) 11:2315–2323.
   PubMed Web of Science ®Google Scholar
• SHEIK-HAMAD D, NADKARNI V, CHOI YJ et al.: Cyclosporine A inhibits the adaptive responses to hypertonicity: a potential mechanism of nephrotoxicity. J Am. Soc. Nephrol (2001) 12:2732–2741.
   PubMed Web of Science ®Google Scholar
• AMERICAN HOSPITAL FORMULARY SERVICE: AHFS Drug Information 91 (33rd Edn). American Society of Hospital Pharmacists, Bethesda, MD, USA (1991).
   Google Scholar
• LYSON T, ERMEL LD, BELSHAW PJ: Cyclosporine- and FK-506-induced sympathetic activation correlates with calcineurin-mediated inhibition of T cell signaling. Circ. Res (1993) 73:596–602.
   PubMed Web of Science ®Google Scholar
• WENGER RIVI: Pharmacology of cyclosporin (sandimmune). II. Chemistry. Pharm. Rev (1989) 41:243–247.
   Google Scholar
• ANGELL YM, THOMAS TL, FLENKLE GR et al.: Solid phase synthesisof cyclosporin peptides.' Am. Chem. Soc. (1995) 117:7279–7280.
   Web of Science ®Google Scholar
• RAMAN P, STOKES S, ANGELL YM, FLENTKE GR, RICH DH: Methods to circumvent a difficult coupling in the solid-phase synthesis of cyclosporin analogs. Org. Chem. (1998) 63(17):5734–5735.
   PubMed Web of Science ®Google Scholar
• RICH DH, SUN CQ, GUILLIAUME D et al.: Synthesis, biological activity and conformational analysis of (2S, 3R, 4.9-MeBmt-cyclosporin, a novel 1-position epimer of cyclosporin A. I Med. Chem. (1989) 32:1982–1987.
   Google Scholar
• TRABER R, HOFMANN H, KOBEL H: Cyclosporins - new analogs by precursor-directed biosynthesis. Antibiotics (1989) 42:591–597.
   PubMed Web of Science ®Google Scholar
• LAWEN A, TRABER R, GEYL D et al: Cell-free biosynthesis of new cyclosporins. .1. Antibiotics (1989) 42:1204–1206.
   Google Scholar
• LOOR F, TIBERGHIEN F, WENANDY T et al.: Cyclosporins: structure-activity relationships for the inhibition of the human MDR1 P-glycoprotein ABC transporter. I Med. Chem. (2002) 45:4598–4612.
   PubMed Web of Science ®Google Scholar
• AEBI AD, DEYO DT, SUN SQ et al: Cyclosporin A modified in the 1-position. Med. Chem. (1990) 33:999–1009.
   Google Scholar
• PAPRICA PA, MARGARITAS A, PETERSEN NO: Preparation of novel cyclosporin A derivatives. Bioconjugate Chem. (1992) 3:32–36.
   PubMed Web of Science ®Google Scholar
• EBERLE MK, JUTZI-EME AM, NUNINGER F: Modifications of the MeBmt side chain of cyclosporin A. Bioorg. Med. Chem. Lett (1995) 5:1725–1728.
   Google Scholar
• EBERLE MK, NUNINGER F: Preparation of functionalized ethers of cyclosporin A. Tetrahedron Lett. (1994) 35:6477–6480.
   Web of Science ®Google Scholar
• EBERLE MK, NUNINGER F, WEBER HP: Preparation of sulfhydryl cyclosporin A. Org. Chem. (1995) 60:2610–2612.
   Google Scholar
• EBERLE MK, NUNINGER F: Synthesis of the main metabolite (0L-17) of cyclosporin A. J. Org. Chem. (1992) 57:2689–2691.
   Web of Science ®Google Scholar
• PARK SB, MEIER GP: A semisynthetic approach to olefinic analogs of amino acid one (MeBMT) in cyclosporin A. Tetrahedron Lett (1989) 30:4215–4218.
   Web of Science ®Google Scholar
• SMULIK JA, DIVER ST, PAN F et al.: Synthesis of cyclosporin A-derived affinity reagents by olefin metathesis. Org. Lett. (2002) 4(12):2051–2054.
   PubMed Web of Science ®Google Scholar
• ••First reported olefin metathesis of CsA.
   Google Scholar
• LAZAROVA T, CHEN JS, HAMMAN B et al.: Synthesis and biological evaluation of novel cyclosporin A analogues: potential soft drugs for the treatment of autoimmune diseases. I Med. Chem. (2003) 46:674–676.
   PubMed Web of Science ®Google Scholar
• •A single step synthesis of CsA analogues using ruthenium-catalysed olefin metathesis with maleates.
   Google Scholar
• CHEN JS, LAZAROVA T, HAMMAN B et al.: Synthesis and biological evaluation of novel cyclosporin A derivatives with potentially improved therapeutic index. 225th National Meeting of the Am. Chem. Soc. New Orleans, LA, USA (March 2003) (Poster presentation).
   Google Scholar
• •A single step synthesis of CsA analogues using ruthenium catalysed olefin metathesis with styrenes.
   Google Scholar
• SEEBACH D, BECK AK, BOSSLER HG et al.: Modification of cyclosporin A (CS): generation of an enolate at the sarcosine residue and reactions with electrophiles. Hely. Chim. Acta (1993) 76:1564–1590.
   Web of Science ®Google Scholar
• ••Pioneering work on generating CsAenolates and subsequent regioselective alkylations.
   Google Scholar
• PAPAGEORGIOU C, KALLEN J, FRANCA J et al.: Conformational control of cyclosporin through substitution of the N-5 position. A new class of cyclosporin antagonists. Bioorg. Med. Chem (1997) 5:187–192.
   PubMed Web of Science ®Google Scholar
• EBERLE MK, JUTZI-EME AM, NUNINGER F: Cyclosporin A; regioselective ring opening and fragmentation reactions via thioamides. A route to semi-synthetic cyclosporins. .1. Org. Chem. (1994) 59:7249–7258.
   Google Scholar
• DUNN CJ, WAGSTAFF AJ, PERRY CM et al.: Cyclosporin: an updated review of the pharmacokinetic properties, clinical efficacy and tolerability of a microemulsion-based formulation (Neoral) in organ transplantation. Drugs (2001) 61:1957–2016.
   PubMed Web of Science ®Google Scholar
• ROTHBARD JB, GARLINGTON S, LIN Q et al.: Conjugation of arginine oligomers to cyclosporin A facilitates topical delivery and inhibition of inflammation. Nat. Med. (2000) 6:1253–1257.
   PubMed Web of Science ®Google Scholar
• ••A novel strategy for enhancing delivery ofCsA across skin.
   Google Scholar
• ROTHBARD JB, KREIDER E, VANDEUSEN CL et al.: Arginine-rich molecular transporters for drug delivery: role of backbone spacing on cellular uptake. Med. Chem. (2002) 45(17):3612–3618.
   Web of Science ®Google Scholar
• LU ZR, GAO SQ, KOPECKOVA P et al.:Modification of cyclosporin A and conjugation of its derivative to HPMA copolymers. Bioconjugate Chem. (2001) 12:129–133.
   PubMed Web of Science ®Google Scholar
• LU ZR, GAO SQ, KOPECKOVA P et al.:Synthesis of bioadhesive lectin-HMPA copolymer-cyclosporin conjugates. Bioconjugate Chem. (2000) 11:3–7.
   PubMed Web of Science ®Google Scholar
• •CsA conjugate for specific delivery to the colon.
   Google Scholar
• QUESNIAUX VFJ, SCHREIER MH, WENGER RIVI, HIESTAND PC, HARDING MW, VAN REGENMORTEL MHV: Cyclophilin binds to the region of cyclosporine involved in its immunosuppressant activity. Ear: Immunol (1987) 17(9):1359–1365.
   PubMed Web of Science ®Google Scholar
• RIZZARDI GP, HARARI A, CAPILUPPI B et al: Treatment of primary HIV-1 infection with cyclosporin A coupled with highly active antiretroviral therapy. Chit. Invest. (2002) 109:681–688.
   PubMed Web of Science ®Google Scholar
• •The first pilot clinical study to demonstrate the effectiveness of CsA in the treatment of primary HIV-1 infection when combined with highly active antiretroviral therapy.
   Google Scholar
• CRON RQ: HIV-1, NFAT, and cyclosporin: immunosuppression for the immunosuppressed? DNA Cell Biol. (2001) 20:761-767.
   Google Scholar
• STREBLOW DN, KITABWALLA M, MALKOVSKY M et al.: Cyclophilin A modulates processing of human immunodeficiency virus Type 1 p55Gag: mechanism for antiviral effects of cyclosporin A. Virology (1998) 245:197–202.
   PubMed Web of Science ®Google Scholar
• BRAATEN D, LUBAN J: Cyclophilin A regulates HIV-1 infectivity, as demonstrated by gene targeting in human T cells. EMBO (2001) 20:1300–1309.
   PubMed Web of Science ®Google Scholar
• •Interesting paper to demonstrate that CyP regulates the infectivity of HIV-1.
   Google Scholar
• FURLANUT M, BARALDO M, GALLA F: Cyclosporin nephrotoxicity in relation to its metabolism in psoriasis. Amin. Res. (1996) 33:349–352.
   Google Scholar
• CHRISTIANS U, SEWING KF: Alternative cyclosporine metabolic pathways and toxicity. Clin. Biochem. (1995) 28:547–559.
   PubMed Web of Science ®Google Scholar
• MAKSYMOWYCH WP, JHANGRI GS, ASPESLET L et al.: Amelioration of accelerated collagen induced arthritis by a novel calcineurin inhibitor, ISA247. J. Rheum. (2002) 29(8):1646–1652.
   PubMed Web of Science ®Google Scholar