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Volumn 13, Issue 6, 2003, Pages 751-760

The silatecans, a novel class of lipophilic camptothecins

Author keywords

Camptothecin (CPT); Chemotherapy; Cytotoxic agents; Silatecan; Topoisomerase I (topo I)

Indexed keywords

7 ETHYL 10 HYDROXYCAMPTOTHECIN; ANTINEOPLASTIC AGENT; CAMPTOTHECIN; CAMPTOTHECIN DERIVATIVE; CYTOTOXIC AGENT; DNA TOPOISOMERASE; GIMATECAN; IRINOTECAN; KARENITECIN; LACTONE DERIVATIVE; SILANE DERIVATIVE; SILATECAN DERIVATIVE; TOPOTECAN; UNCLASSIFIED DRUG;

EID: 0038647786     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.13.6.751     Document Type: Review
Times cited : (13)

References (45)
  • 1
    • 7144248725 scopus 로고
    • Plant antitumor agents I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata
    • WALL M, WANI M, COOK CE, PALMER KH, MCPHAIL HT, SIM GA: Plant antitumor agents I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J. Am. Chem. Soc. (1966) 88:3888-3890.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 3888-3890
    • Wall, M.1    Wani, M.2    Cook, C.E.3    Palmer, K.H.4    Mcphail, H.T.5    Sim, G.A.6
  • 2
    • 0031682217 scopus 로고    scopus 로고
    • Camptothecin and taxol: Discovery to clinic
    • WALL M: Camptothecin and taxol: discovery to clinic. Med. Res. Rev. (1998) 18:299-314.
    • (1998) Med. Res. Rev. , vol.18 , pp. 299-314
    • Wall, M.1
  • 3
    • 0022340594 scopus 로고
    • Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I
    • HSIANG YH, HERTZBERG R, HECHT S, LIU L: Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J. Biol. Chem. (1985) 260:14873-14878.
    • (1985) J. Biol. Chem. , vol.260 , pp. 14873-14878
    • Hsiang, Y.H.1    Hertzberg, R.2    Hecht, S.3    Liu, L.4
  • 4
    • 0032189683 scopus 로고    scopus 로고
    • Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme
    • 1400
    • POMMIER Y, POURQUIER P, FAN Y, STRUMBERG D: Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme. Biochim. Biophys. Acta (1998) 1400:83-105.
    • (1998) Biochim. Biophys. Acta , pp. 83-105
    • Pommier, Y.1    Pourquier, P.2    Fan, Y.3    Strumberg, D.4
  • 5
    • 0036304427 scopus 로고    scopus 로고
    • Current perspectives on the clinical experience, pharmacology, and continued development of the camptothecins
    • GARCIA-CARBONERO R, SUPKO JG: Current perspectives on the clinical experience, pharmacology, and continued development of the camptothecins. Clin. Cancer Res. (2002) 8:641-661.
    • (2002) Clin. Cancer Res. , vol.8 , pp. 641-661
    • Garcia-Carbonero, R.1    Supko, J.G.2
  • 7
    • 0024420685 scopus 로고
    • Arrest of replication forks by drug-stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin
    • HSIANG YH, LIHOU MG, LIU LF: Arrest of replication forks by drug-stabilized topoisomerase I-DNA cleavable complexes as a mechanism of cell killing by camptothecin. Cancer Res. (1989) 49:5077-5082.
    • (1989) Cancer Res. , vol.49 , pp. 5077-5082
    • Hsiang, Y.H.1    Lihou, M.G.2    Liu, L.F.3
  • 9
    • 0028267240 scopus 로고
    • Camptothecins: From bench research to hospital wards
    • POTMESIL M: Camptothecins: from bench research to hospital wards. Cancer Res. (1994) 54:1431-1439.
    • (1994) Cancer Res. , vol.54 , pp. 1431-1439
    • Potmesil, M.1
  • 10
    • 0024560495 scopus 로고
    • Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: Evidence for a specific receptor site and a relation to antitumor activity
    • JAXEL C, KOHN KW, WANI MC, WALL ME, POMMIER Y: Structure-activity study of the actions of camptothecin derivatives on mammalian topoisomerase I: evidence for a specific receptor site and a relation to antitumor activity. Cancer Res. (1989) 49:1465-1469.
    • (1989) Cancer Res. , vol.49 , pp. 1465-1469
    • Jaxel, C.1    Kohn, K.W.2    Wani, M.C.3    Wall, M.E.4    Pommier, Y.5
  • 11
    • 0027096415 scopus 로고
    • A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogs
    • FASSBERG J, STELLA VJ: A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogs. J. Pharm. Sci. (1992) 81:676-684.
    • (1992) J. Pharm. Sci. , vol.81 , pp. 676-684
    • Fassberg, J.1    Stella, V.J.2
  • 12
    • 0027276081 scopus 로고
    • Lipid bilayer partitioning and stability of camptothecin drugs
    • BURKE TG, MISHRA AK, WANI MC, WALL ME: Lipid bilayer partitioning and stability of camptothecin drugs. Biochemistry (1993) 32:5352-5364.
    • (1993) Biochemistry , vol.32 , pp. 5352-5364
    • Burke, T.G.1    Mishra, A.K.2    Wani, M.C.3    Wall, M.E.4
  • 13
    • 0027184132 scopus 로고
    • Ethyl substitution at the 7-position extends the half-life of 10-hydroxycamptothecin in the presence of human serum albumin
    • BURKE TG, MI Z: Ethyl substitution at the 7-position extends the half-life of 10-hydroxycamptothecin in the presence of human serum albumin. J. Med. Chem. (1993) 36:2580-2582.
    • (1993) J. Med. Chem. , vol.36 , pp. 2580-2582
    • Burke, T.G.1    Mi, Z.2
  • 14
    • 0028012774 scopus 로고
    • The structural basis of camptothecin interactions with human serum albumin: Impact on drug stability
    • BURKE TG, MI Z: The structural basis of camptothecin interactions with human serum albumin: impact on drug stability. J. Med. Chem. (1994) 37:40-46.
    • (1994) J. Med. Chem. , vol.37 , pp. 40-46
    • Burke, T.G.1    Mi, Z.2
  • 15
    • 0027930186 scopus 로고
    • Differential interactions of camptothecin lactone and carboxylate forms with human blood components
    • MI Z, BURKE TG: Differential interactions of camptothecin lactone and carboxylate forms with human blood components. Biochemistry (1994) 33:10325-10336.
    • (1994) Biochemistry , vol.33 , pp. 10325-10336
    • Mi, Z.1    Burke, T.G.2
  • 16
    • 0028844445 scopus 로고
    • Reduced albumin binding promotes the stability and activity of topotecan in human blood
    • MI Z, MALAK H, BURKE TG: Reduced albumin binding promotes the stability and activity of topotecan in human blood. Biochemistry (1995) 34:13722-13728.
    • (1995) Biochemistry , vol.34 , pp. 13722-13728
    • Mi, Z.1    Malak, H.2    Burke, T.G.3
  • 17
    • 0015291595 scopus 로고
    • Phase II study of camptothecin (NSC-100880) in the treatment of advanced gastrointestinal cancer
    • MOERTEL CG, SCHUTT AJ, REITEMEIER RJ, HAHN RG: Phase II study of camptothecin (NSC-100880) in the treatment of advanced gastrointestinal cancer. Cancer Chemo. Rep. Part 1 (1972) 56:95-101.
    • (1972) Cancer Chemo. Rep. Part 1 , vol.56 , pp. 95-101
    • Moertel, C.G.1    Schutt, A.J.2    Reitemeier, R.J.3    Hahn, R.G.4
  • 18
    • 0028343055 scopus 로고
    • Urinary and biliary disposition of the lactone and carboxylate forms of 20(2)-camptothecin in rats
    • SCOTT DO, BINDRA D, SUTTON SC, STELLA VJ: Urinary and biliary disposition of the lactone and carboxylate forms of 20(2)-camptothecin in rats. Drug Metab. Disp. (1994) 22:438-442.
    • (1994) Drug. Metab. Disp. , vol.22 , pp. 438-442
    • Scott, D.O.1    Bindra, D.2    Sutton, S.C.3    Stella, V.J.4
  • 19
    • 0030752757 scopus 로고    scopus 로고
    • Topoisomerase I inhibitors: The relevance of prolonged exposure for present clinical development
    • GERRITS CJ, de JONGE MJ, SCHELLENS JH, STOTER G, VERWEIJ J: Topoisomerase I inhibitors: the relevance of prolonged exposure for present clinical development. Br. J. Cancer (1997) 76:952-962.
    • (1997) Br. J. Cancer , vol.76 , pp. 952-962
    • Gerrits, C.J.1    de Jonge, M.J.2    Schellens, J.H.3    Stoter, G.4    Verweij, J.5
  • 20
    • 0028150946 scopus 로고
    • Marked interspecies variations concerning the interactions of camptothecin with serum albumins: A frequency-domain fluorescence spectroscopic study
    • MI Z, BURKE TG: Marked interspecies variations concerning the interactions of camptothecin with serum albumins: a frequency-domain fluorescence spectroscopic study. Biochemistry (1994) 33:12540-12545.
    • (1994) Biochemistry , vol.33 , pp. 12540-12545
    • Mi, Z.1    Burke, T.G.2
  • 21
    • 0031443765 scopus 로고    scopus 로고
    • Clinical use of irinotecan: Current status and future considerations
    • SALTZ LB: Clinical use of irinotecan: current status and future considerations. Oncologist (1997) 2:402-409.
    • (1997) Oncologist , vol.2 , pp. 402-409
    • Saltz, L.B.1
  • 22
    • 0028357995 scopus 로고
    • Phase I trial of low-dose continuous topotecan infusion in patients with cancer: An active and well-tolerated regimen
    • HOCHSTER H, LIEBES L, SPEYER J et al.: Phase I trial of low-dose continuous topotecan infusion in patients with cancer: an active and well-tolerated regimen. J. Clin. Onc. (1994) 12:553-559.
    • (1994) J. Clin. Onc. , vol.12 , pp. 553-559
    • Hochster, H.1    Liebes, L.2    Speyer, J.3
  • 23
    • 0032925377 scopus 로고    scopus 로고
    • A comparison of clinical pharmacodynamics of different administration schedules of oral topotecan (hycamtin)
    • GERRITS CJH: SCHELLENS JHM, BURRIS H et al.: A comparison of clinical pharmacodynamics of different administration schedules of oral topotecan (hycamtin). Clin. Cancer Res. (1999) 5:69-75.
    • (1999) Clin. Cancer Res. , vol.5 , pp. 69-75
    • Gerrits, C.J.H.1    Schellens, J.H.M.2    Burris, H.3
  • 24
    • 0032589190 scopus 로고    scopus 로고
    • Oral topotecan: Bioavailability and effect of food co-administration
    • HERBEN VM, ROSING H, TEN BOKKEL HUININK WW et al.: Oral topotecan: bioavailability and effect of food co-administration. Br. J. Cancer (1999) 80:1380-1386.
    • (1999) Br. J. Cancer , vol.80 , pp. 1380-1386
    • Herben, V.M.1    Rosing, H.2    Ten Bokkel Huinink, W.W.3
  • 25
    • 0025689565 scopus 로고
    • 10,11-Methylenedioxycamptothecin, a topoisomerase I inhibitor of increased potency: DNA damage and correlation to cytotoxicity in human colon carcinoma (HT-29) cells
    • O'CONNOR PM, KERRIGAN D, BERTRAND R, KOHN KW, POMMIER Y: 10,11-Methylenedioxycamptothecin, a topoisomerase I inhibitor of increased potency: DNA damage and correlation to cytotoxicity in human colon carcinoma (HT-29) cells. Cancer Comm. (1990) 2:395-400.
    • (1990) Cancer Comm. , vol.2 , pp. 395-400
    • O'Connor, P.M.1    Kerrigan, D.2    Bertrand, R.3    Kohn, K.W.4    Pommier, Y.5
  • 26
    • 0035960061 scopus 로고    scopus 로고
    • Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity
    • DALLAVALLE S, FERRARI A, BIASOTTI B, MERLINI L, PENCO S, GALLO G et al.: Novel 7-oxyiminomethyl derivatives of camptothecin with potent in vitro and in vivo antitumor activity. J. Med. Chem. (2001) 44:3264-3274.
    • (2001) J. Med. Chem. , vol.44 , pp. 3264-3274
    • Dallavalle, S.1    Ferrari, A.2    Biasotti, B.3    Merlini, L.4    Penco, S.5    Gallo, G.6
  • 27
    • 0344074659 scopus 로고    scopus 로고
    • 7-Silylcamptothecins (silatecans): A new family of camptothecin antitumor agents
    • JOSIEN H, BOM D, CURRAN DP, ZHENG YH, CHOU TC: 7-Silylcamptothecins (silatecans): a new family of camptothecin antitumor agents. Bioorg. Med. Chem. Lett. (1997) 7:3189-3194.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 3189-3194
    • Josien, H.1    Bom, D.2    Curran, D.P.3    Zheng, Y.H.4    Chou, T.C.5
  • 28
    • 0030931517 scopus 로고    scopus 로고
    • BN 80245: An E-ring-modified camptothecin with potent antiproliferative and topoisomerase I inhibitory activities
    • LAVERGNE O, LESUEUR-GINOT L, RODAS FP, BIGG DCH: BN 80245: an E-ring-modified camptothecin with potent antiproliferative and topoisomerase I inhibitory activities. Bioorg. Med. Chem. Lett. (1997) 7:2235-2238.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 2235-2238
    • Lavergne, O.1    Lesueur-Ginot, L.2    Rodas, F.P.3    Bigg, D.C.H.4
  • 29
    • 0032585548 scopus 로고    scopus 로고
    • Homo camptothecins: Synthesis and antitumor activity of novel E-ring-modified camptothecin analogs
    • LAVERGNE O, LESUEUR-GINOT L, RODAS FP et al.: Homo camptothecins: synthesis and antitumor activity of novel E-ring-modified camptothecin analogs. J. Med. Chem. (1998) 41:5410-5419.
    • (1998) J. Med. Chem. , vol.41 , pp. 5410-5419
    • Lavergne, O.1    Lesueur-Ginot, L.2    Rodas, F.P.3
  • 30
    • 0037212083 scopus 로고    scopus 로고
    • Homocamptothecins: Potent topoisomerase I inhibitors and promising anticancer drugs
    • BAILLY C: Homocamptothecins: potent topoisomerase I inhibitors and promising anticancer drugs. Crit. Rev. Onc. Hem. (2003) 45:91-108.
    • (2003) Crit. Rev. Onc. Hem. , vol.45 , pp. 91-108
    • Bailly, C.1
  • 32
    • 0038043815 scopus 로고    scopus 로고
    • Concerted escalation of dose and dosing-duration in a Phase I study of the oral camptothecin gimatecan (ST1481) in patients with advanced solid tumors
    • Abst.386
    • SESSA C, HESS D, BASELGA J et al.: Concerted escalation of dose and dosing-duration in a Phase I study of the oral camptothecin gimatecan (ST1481) in patients with advanced solid tumors. ASCO Annual Meeting (2002):Abst.386.
    • (2002) ASCO Annual Meeting
    • Sessa, C.1    Hess, D.2    Baselga, J.3
  • 33
    • 0034917320 scopus 로고    scopus 로고
    • Therapeutic activity of 7-[(2-trimethylsilyl)ethyl)]-20(S)-camptothecin [karenitecin] against central nervous system tumor-derived xenografts in athymic mice
    • KEIR ST, HAUSHEER F, LAWLESS AA, BIGNER DD, FRIEDMAN HS: Therapeutic activity of 7-[(2-trimethylsilyl)ethyl)]-20(S)-camptothecin [karenitecin] against central nervous system tumor-derived xenografts in athymic mice. Cancer Chemo. Pharm. (2001) 48:83-87.
    • (2001) Cancer Chemo. Pharm. , vol.48 , pp. 83-87
    • Keir, S.T.1    Hausheer, F.2    Lawless, A.A.3    Bigner, D.D.4    Friedman, H.S.5
  • 34
    • 0038043747 scopus 로고    scopus 로고
    • Phase I trial of karenitecin (KT) administered intravenously daily for five consecutive days in patients with advanced solid tumors using accelerated dose titration
    • Abst.758
    • SCHILSKY R, HAUSHEER F, BERTUCCI D, BERGHORN E, KINDLER H, RATAIN M: Phase I trial of karenitecin (KT) administered intravenously daily for five consecutive days in patients with advanced solid tumors using accelerated dose titration. ASCO Annual Meeting (2000):Abst.758.
    • (2000) ASCO Annual Meeting
    • Schilsky, R.1    Hausheer, F.2    Bertucci, D.3    Berghorn, E.4    Kindler, H.5    Ratain, M.6
  • 35
    • 0033549870 scopus 로고    scopus 로고
    • Novel A,B,E-ring-modified camptothecins displaying high lipophilicity and markedly improved human blood stabilities
    • BOM D, CURRAN DP, CHAVAN AJ et al.: Novel A,B,E-ring-modified camptothecins displaying high lipophilicity and markedly improved human blood stabilities. J. Med. Chem. (1999) 42:3018-3022.
    • (1999) J. Med. Chem. , vol.42 , pp. 3018-3022
    • Bom, D.1    Curran, D.P.2    Chavan, A.J.3
  • 36
    • 0034502460 scopus 로고    scopus 로고
    • The combinatorial synthesis of racemic homosilatecan libraries via a cascade radical annulation
    • Liehr JG, Giovanella BC, Verschraegen CF (Eds), New York Academy of Sciences, USA Unfolding their Anti-cancer Potential
    • DU W, GABARDA AE, BOM D, CURRAN DP: The combinatorial synthesis of racemic homosilatecan libraries via a cascade radical annulation. In: The Camptothecins. Unfolding their Anti-cancer potential. Liehr JG, Giovanella BC, Verschraegen CF (Eds), New York Academy of Sciences, USA (2000) 922:317-319.
    • (2000) The Camptothecins , vol.922 , pp. 317-319
    • Du, W.1    Gabarda, A.E.2    Bom, D.3    Curran, D.P.4
  • 37
    • 0037293483 scopus 로고    scopus 로고
    • Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals
    • DU W, KASKAR B, BLUMBERGS P, SUBRAMANIAN PK, CURRAN D: Semisynthesis of DB-67 and other silatecans from camptothecin by thiol-promoted addition of silyl radicals. Bioorg. Med. Chem. (2003) 11:451-458.
    • (2003) Bioorg. Med. Chem. , vol.11 , pp. 451-458
    • Du, W.1    Kaskar, B.2    Blumbergs, P.3    Subramanian, P.K.4    Curran, D.5
  • 38
    • 0034687233 scopus 로고    scopus 로고
    • The novel silatecan 7-tertbutyldimethylsilyl-10-hydroxycamptothecin displays high lipophilicity, improved human blood stability, and potent anticancer activity
    • BOM D, CURRAN DP, KRUSZEWSKI S, ZIMMER SG, STRODE JT, KOHLHAGEN G: The novel silatecan 7-tertbutyldimethylsilyl-10-hydroxycamptothecin displays high lipophilicity, improved human blood stability, and potent anticancer activity. J. Med. Chem. (2000) 43:3970-3980.
    • (2000) J. Med. Chem. , vol.43 , pp. 3970-3980
    • Bom, D.1    Curran, D.P.2    Kruszewski, S.3    Zimmer, S.G.4    Strode, J.T.5    Kohlhagen, G.6
  • 39
    • 0033213921 scopus 로고    scopus 로고
    • Potent topoisomerase I inhibition by novel silatecans eliminates glioma proliferation in vitro and in vivo
    • POLLACK IF, ERFF M, BOM D, BURKE TG, STRODE JT, CURRAN DP: Potent topoisomerase I inhibition by novel silatecans eliminates glioma proliferation in vitro and in vivo. Cancer Res. (1999) 59:4898-4905.
    • (1999) Cancer Res. , vol.59 , pp. 4898-4905
    • Pollack, I.F.1    Erff, M.2    Bom, D.3    Burke, T.G.4    Strode, J.T.5    Curran, D.P.6
  • 40
    • 4243840865 scopus 로고    scopus 로고
    • The development of a liposomal formulation of highly lipophilic 7-t-butyldimethylsilyl-10-hydroxycamptothecin (db67)
    • (P.I.) National Cancer Institute RAID Project
    • BURKE TG (P.I.): The development of a liposomal formulation of highly lipophilic 7-t-butyldimethylsilyl-10-hydroxycamptothecin (db67). National Cancer Institute RAID Project.
    • Burke, T.G.1
  • 41
    • 0033809224 scopus 로고    scopus 로고
    • New highly lipophilic camptothecin BNP1350 is an effective drug in experimental human cancer
    • VAN HATTUM AH, PINEDO HM, SCHLUPER HMM, HAUSHEER FH, BOVEN E: New highly lipophilic camptothecin BNP1350 is an effective drug in experimental human cancer. Int. J. Cancer (2000) 88:260-266.
    • (2000) Int. J. Cancer , vol.88 , pp. 260-266
    • Van Hattum, A.H.1    Pinedo, H.M.2    Schluper, H.M.M.3    Hausheer, F.H.4    Boven, E.5
  • 42
    • 0036643756 scopus 로고    scopus 로고
    • Novel camptothecin derivative BNP1350 in experimental human ovarian cancer: Determination of efficacy and possible mechanisms of resistance
    • VAN HATTUM AH, SCHLUPER HMM, HAUSHEER FH, PINEDO HM BOVEN E: Novel camptothecin derivative BNP1350 in experimental human ovarian cancer: determination of efficacy and possible mechanisms of resistance. Int. J. Cancer (2002) 100:22-29.
    • (2002) Int. J. Cancer , vol.100 , pp. 22-29
    • Van Hattum, A.H.1    Schluper, H.M.M.2    Hausheer, F.H.3    Pinedo, H.M.4    Boven, E.5
  • 43
    • 0034906472 scopus 로고    scopus 로고
    • Circumvention of breast cancer resistance protein (BCRP)-mediated resistance to camptothecins in vitro using nonsubstrate drugs or the BCRP inhibitor GF 120918
    • MALIEPAARD M, VAN GASTELEN MA. TOHGO A et al.: Circumvention of breast cancer resistance protein (BCRP)-mediated resistance to camptothecins in vitro using nonsubstrate drugs or the BCRP inhibitor GF 120918. Clin. Cancer Res. (2001) 7:935-941.
    • (2001) Clin. Cancer Res. , vol.7 , pp. 935-941
    • Maliepaard, M.1    Van Gastelen, M.A.2    Tohgo, A.3
  • 44
    • 0001744641 scopus 로고    scopus 로고
    • Multidrug resistance and pharmacological protection mediated by the breast cancer resistance protein (BCRP/ABCG2)
    • ALLEN JD, SCHINKEL AH: Multidrug resistance and pharmacological protection mediated by the breast cancer resistance protein (BCRP/ABCG2). Mol. Cancer Therap. (2002) 1:427-434.
    • (2002) Mol. Cancer Therap. , vol.1 , pp. 427-434
    • Allen, J.D.1    Schinkel, A.H.2


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