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Review

Thalidomide analogues: derivatives of an orphan drug with diverse biological activity

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Pages 215-229 | Published online: 02 Mar 2005

Bibliography

  • SERVICE RF: Can thalidomide be rehabilitated? Science (1995) 269:1340.
  • RICHARDSON P, HIDESHIMA T, ANDERSON K: Thalidomide: emerging role in cancer medicine. Ann. Rev Med. (2002) 53:629–657.
  • MARRIOTT JB, MULLER G, STIRLING D et al.: Immunotherapeutic and antitumour potential of thalidomide analogues. Expert Opin. Biol. Ther. (2001) 1:675–682.
  • MARRIOTT JB, MULLER G, DALGLEISH AG: Thalidomide as an emerging immunotherapeutic agent. Immunol. Today(1999) 20:538–540.
  • RAJE N, ANDERSON K: Thalidomide - a revival story. N Engl. J. Med. (1999) 341:1606–1609.
  • HALES BF: Thalidomide on a comeback trail. Nat. Med. (1999) 5:489–490.
  • FICKENTSCHER K, KIRFEL A, WILL G et al.: Stereochemical properties and teratogenic activity of some tetrahydrophthalimides. Mol. Pharmacol (1977) 13:133–141.
  • HELM F, FRANKUS E, FRIDERICHS E et al.: Comparative teratological investigation of compounds structurally and pharmacologically related to thalidomide Arzneim. Forsch. (1981) 31:941–949.
  • SHESKIN J: Thalidomide in the treatment of the lepra reaction. Clin. Pharmacol Ther. (1965) 6:303.
  • SHESKIN J: The treatment of the lepra reaction in lepromatous leprosy. Fifteen years experience with thalidomide. Int. J. Dermatol (1980) 6:318–322.
  • SAMPAIO EP, SARNO EN, GALILY R et al.: Thalidomide selectively inhibits tumor necrosis factor-a production by stimulated human monocytes J. Exp. Med. (1991) 173:699–703.
  • MULLER GW, CORRAL LG, SHIRE MG et al.: Structural modifications of thalidomide produce analogs with enhanced tumor necrosis factor inhibitory activity J. Med. Chem. (1996) 39:3238–3240.
  • CORRAL LG, MULLER GW, MOREIRA AL et a/.: Selection of novel analogs of thalidomide with enhanced tumor necrosis factor-a inhibitory activity. Molecular. Med. (1996) 2:506–515.
  • D'AMATO RJ, LOUGHNAN MS, FLYNN E et al.: Thalidomide is an inhibitor of angiogenesis. Proc . Nati Acad. ScL USA (1994) 91:4082–4085.
  • REIST M, CARRUPT P-A, FRANCOTTE E et al.: Chiral inversion and hydrolysis of thalidomide: mechanisms and catalysis by bases and serum albumin, and chiral stability of teratogenic metabolites. Chem . Res. Toxicol (1998) 11:1521–1528.
  • MULLER GW, KONNECKE WE, SMITH AM et al: A concise two-step synthesis of thalidomide. Org . Proc. Res. Dev. (1999) 3:139–140.
  • SUZUKI E, SHIBATA N: Three-step synthesis of (A and (5)-thalidomides from ornithine. Enantiomer (2001) 6:275–279.
  • ROBINS, ZHU J, GALONS H et al: A convenient asymmetric synthesis of thalidomide. Tetrahedron Asymmetry (1995) 6:1249–1252.
  • ISHIMURA K, HASHIMOTO Y, IWASAKI S: The (3)-form of a-methyl-N-(a)-phthalimidoglutarimide, but not its (M-form, enhanced phorbol ester-induced tumor necrosis factor-a production by human leukemia cell HL-60: implication of optical resolution of thalidomidal effects. Chem. Pharm. Bull. (1994) 42:1157–1159.
  • LUZZIO FA, MAYOROV AV, FIGG WD:Thalidomide metabolites. Part 1: derivatives of (+) 2 (Nphthalimido)-y-hydroxyglutamic acid. Tetrahedron Lett. (2000) 41:2275–2278.
  • LUZZIO FA, THOMAS EM, FIGG WD: Thalidomide metabolites and analogues. Part 2: cyclic derivatives of 2-N-phthalimido-2S, 3S(3-hydroxy) ornithine. Tetrahedron Lett. (2000) 41:7151–7155.
  • LUZZIO FA, ZACHERL DP, FIGG WD A facile scheme for phthalimide-phthalimidine conversion. Tetrahedron Lett. (1999) 40:2087–2090.
  • LUZZIO FA, MAYOROV AV, NG SSW et al.: Thalidomide metabolites and analogues. Part 3. Synthesis and antiangiogenic activity of the teratogenic and TNF-a-modulatory thalidomide analogue 2- (2,6-dioxopiperidine-3-yflphthalimidine. I Med. Chem. (2003) 46:3793–3799.
  • KNOCHE B, BLASCHKE G: Stereoselectivity of the M vitro metabolism of thalidomide. Chirality (1994) 6:221–224.
  • ERICSSON T, BJORKMAN S, ROTH B et al.: Hydroxylated metabolites of thalidomide: formation M vitro and in vivo in man. Pharm. Pharmacol (1998) 50:1409–1416.
  • CZEJKA MJ, KOCH HP: Determination of thalidomide and its major metabolites by high performance liquid chromatography. .1. Chromatog. (1987) 413:181–187.
  • KIM KJ, LI B, WINER J et al: Inhibition of vascular endothelial growth factor-induced angiogenesis suppresses tumor growth M vivo. Nature (1993) 362:841–844.
  • FOLKMAN J: Tumor angiogenesis: a possible control point in tumor growth Ann. Intern. Med. (1975) 82:96–100.
  • TEUBERT U, ZWINGENBERGER K, WNENDT S et al: 5€-Substituted thalidomide analogs as modulators of TNF-a. Arkiv. Pharmazie (1998) 331:7–12.
  • NG SS, GUTSCHOW M, WEISS M et al: Antiangiogenic activity of N-substituted and tetrafluorinated thalidomide analogues. Cancer Res. (2003) 63:3189–3194.
  • NICOSIA RF, OTTINETTI A: A growth of microvessels in serum-free matrix culture of rat aorta. Lab. Invest. (1990) 63:115–122.
  • BAUER KS, DIXON SC, FIGG WD: Inhibition of angiogenesis by thalidomide requires metabolic activation which is species-dependent. Biochem. Pharmacol (1998) 55:1827–1834.
  • MULLER GW, CHEN R, HUANG S-Y et al.: Amino-substitutedthalidomide analogs: potent inhibitors of TNF-a production. Bioorg. Med. Chem. Lett. (1999) 9:1625–1630.
  • DREDGE K, MARRIOTT JB, MACDONALD CD et al.: Novel thalidomide analogues display antiangiogenic activity independently of immunomodulatory effects. Br. Cancer (2002) 87:1155–1172.
  • DREDGE K, DALGLEISH AG, MARRIOTT JB: Thalidomide analogs as emerging anticancer drugs. Anti-Cancer Drugs (2003) 14:331–335.
  • MAKONKAWKEYOON S, LIMSON -PROBRE RNR, MOREIRA AL et al.: Thalidomide inhibits the replication of human immunodeficiency virus Type 1. Proc. Nati Acad. ScL USA (1993) 90:5974–5978.
  • AGLE LMA, ROSENKRANZ M, LEHMAN TJA: Novel therapies for the treatment of juvenile rheumatoid arthritis (juvenile idiopathic arthritis). Expert Opin. Investig. Drugs (2003) 12:19–28.
  • VOGELSANG GB, FARMER ER, HESS AD et al: Thalidomide for the treatment of chronic graft-versus-host disease. N. Engl.' Med. (1992) 326:1055–1058.
  • TEO SK, CHEN Y, MULLER GW et al:Chiral inversion of the second generation IMiD CC-4047 (ACTIMID) in human plasma and phosphate-buffered saline. Chirality (2003) 15:348–351.
  • LA MAESTRA L, ZANINONI A, MARRIOTT JB et al.: The thalidomide analogue CC-3052 inhibits HIV and tumor necrosis factor-alpha (TNF-a) expression in acutely and chronically infected cells M vitro. Gin. Exp. Immunol (2000) 119:123–129.
  • MARRIOTT JB, WESTBY M, COOKSONS et al: CC-3052: a water-soluble analogue of thalidomide and potent inhibitor of activation-induced TNF-a production. Immunol (1998) 161:4236–4243.
  • ZHU X, GIORDANO T, YU Q-S et al.:Thiothalidomides: novel isosteric analogues of thalidomide with enhanced TNF-a activity. Med. Chem. (2003) 46:5222–5229.
  • HASLETT PAJ, CORRALL LG, ALBERT M et al.: Thalidomide co-stimulates primary human T lymphocytes, preferentially inducing proliferation, cytokine production, and cytotoxic responses in the CD8+ subset. Exp. Med. (1998) 187:1885–1892.
  • SHANNON EJ, SANDOVAL FG: Thalidomide can co-stimulate or suppress CD4+ cells' ability to incorporate [3H] thymidine-dependence on the primary stimulant. Int. Immunopharm. (2002) 2:1143–1153.
  • MARRIOTT JB, CLARK IA, DREDGE K. et al.: Thalidomide and its analogues have distinct and opposing effects on TNF-a and TNER2 during co-stimulation of both CD4+ and CD8+ T cells. Clin. Exp. Immunol (2002) 130:75–84.
  • BEKKER L-G, HASLETT P, MAARTENS G et al.: Thalidomide-induced antigen-specific immune stimulation in patients with human immunodeficiency virus Type I and tuberculosis. Infect. Dis. (2000) 181:954–965.
  • GORI A, ROSSI MC, TRABATTONI Det al.: Tumor necrosis factor-a increased production during thalidomide treatment in patients with tuberculosis and human immunodeficiency virus co-infection. Infect . Dis. (2000) 182:639–640.
  • WOLKENSTEIN P, LATARJET J, ROUJEAU J-C et al: Randomised comparison of thalidomide versus placebo in toxic epidermal necrolysis. Lancet (1998) 352:1–4.
  • JACOBSON JM, GREENSPAN JS, SPRITZLER J et al.: Thalidomide for the treatment of oral aphthous ulcers in patients with human immunodeficiency virus infection. N Engl. I Med. (1997) 336:1487–1493.
  • SCHAFER PH, GANDI AK, LOVELAND MA et al.: Enhancement of cytokine production and AP-1 transcriptional activity in T cells by thalidomide-related immunomodulatory drugs. I Pharm. Exp. The]: (2003) 305:1222–1232.
  • DREDGE K, MARRIOTT JB, TODRYK SM et al.: Protective antitumor activity induced by a co-stimulatory thalidomide analogue in conjunction with whole tumor cell vaccination is mediated by increased T1-type immunity. Immunol (2002) 168:4914–4918.
  • NOGUCHI T, SHIMAZAWA R, NAGASAWA K et al.: Thalidomide and its analogues as cyclooxygenase inhibitors Bioorg. Med. Chem. Lett. (2002) 12:1043–1046.
  • FUJITA J, MESTRE JR, ZELDIS JB et al.: Thalidomide and its analogues inhibit lipopolysaccharide-mediated induction of cyclooxygenase-2. Clin. Cancer Res. (2001) 7:3349–3355.
  • ERIKSSON T, BJORKMAN S, HOGLUND P: Clinical pharmacology of thalidomide. Ear' Clin. Pharmacol (2001) 57:365–376.
  • RICHARDSON P, HIDESHIMA T, ANDERSON K: Thalidomide in multiple myeloma. Biomed. Phamacother. (2002) 56:115–128.
  • SCHEY S, JONES R, RAJ K et al: A Phase I study of an immunomodulatory drug (CC-4047), a structural analogue of thalidomide in relapsed/refractory multiple myeloma. Exp. Hematol (2002) 30(Suppl.):248.
  • MARRIOTT JB, CLARKE IA, DREDGE K et al: Thalidomide analogue CC-5013 is safe and well tolerated by patients with end-stage cancer and shows evidence of clinical responses and extensive immune activation. Br. Cancer (2002) 86(Suppl.):S26.
  • HIDESHIMA T, CHAUAN D, SHIMA Y et al.: Thalidomide and its analogues overcome drug resistance of multiple myeloma cells to conventional therapy. Blood (2000) 96:2943–2950.
  • LENTZSH S, ROGERS M, LEBLANC R et al.: 3-Amino-phthal-imido-glutarimide (S-3APG) inhibits angiogenesis and growth in drug resistant multiple myeloma in vivo. Blood (2001) 98\(Part 1):1976.
  • MESS ORI A, TRIPPOLI S, SANTARLASCI B: Pharmacotherapy of multiple myeloma: an economic perspective. Expert Opin. Pharmacother. (2003) 4:515–524.
  • SINGHAL S, MEHTA J, DESIKAN R et al.: Antitumor activity of thalidomide in refractory multiple melanoma. N Engl.' Med. (1999) 341:1565–1571.
  • RICHARDSON PG, SCHLOSSMAN R, WELLER E et al.: Immunomodulatory drug CC-5013 overcomes drug resistance and is well tolerated in patients with relapsed multiple myeloma. Blood (2002) 100:3063–3067.
  • LU J, PALMER BD, KESTELL P et al.: Thalidomide metabolites in mice and patients with multiple myeloma. Clin. Cancer Res. (2003) 9:1680–1688.
  • SORBERA LA, CASTANER J, BAYES M: CC-5013. Treatment of multiple myeloma, treatment of melanoma, treatment of myelodysplastic syndrome, angiogensis inhibitor, TNF-a production inhibitor. Drugs Fut. (2003) 28:425–431.
  • LIST AF, KURTIN SF, GLINSMANN -GIBSON BJ: High erythropoietic remitting activity of the immunomodulatory thalidomide analogue, CC-5013, in patients with myelodysplastic syndrome (MDS). Blood(2002) 100: (Part 1)353.
  • LIST AF, KURTIN S, GLINSMANN -GIGSON B: Efficacy and safety of CC-5013 for treatment of anemia in patients with myelodysplastic syndrome (MDS). Blood (2003) 102\(Part1):641.

Websites

  • http://www.clinicaltrials.gov National Institutes of Health. Clinical Trials Website. 8 December 2003.
  • http://www.celgene.com Celgene Corporation Website. 8 December 2003.

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