Preclinical investigation of tolerance and antitumour activity of new fluorodeoxyglucose-coupled chlorambucil alkylating agents

Investigational New Drugs

Volumn 29, Issue 3, 2011, Pages 424-433

  Miot Noirault, Elisabeth ^a,b,c   Reux, Bastien ^a,b,c   Debiton, Eric ^a,b,c   Madelmont, Jean Claude ^a,b,c   Chezal, Jean Michel ^a,b,c   Coudert, Pascal ^a,b,c   Weber, Valérie ^a,b,c  

^a UNIVERSITÉ CLERMONT AUVERGNE   (France)

^b INSERM   (France)

^c CENTRE JEAN PERRIN   (France)

Author keywords

Antitumour activity; FDG conjugates; Glycolysis; Solid tumours; Toxicity; Vectorization

Indexed keywords

ANTINEOPLASTIC AGENT; CHLORAMBUCIL; DRUG CARRIER; FLUORODEOXYGLUCOSE; N [2 (3,4,6 TRI O ACETYL 2 DEOXY 2 FLUORO BETA DEXTRO GLUCOPYRANOSYLAMINO) 2 OXOETHYL] 4 [4 [BIS(2 CHLOROETHYL)AMINO]PHENYL]BUTANAMIDE; N [2 [4 (3,4,6 TRI O ACETYL 2 DEOXY 2 FLUORO BETA DEXTRO GLUCOPYRANOSYLOXY)PHENYL]AMINO 2 OXOETHYL] 4 [4 [BIS(2 CHLOROETHYL)AMINO]PHENYL]BUTANAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CELL CYCLE G1 PHASE; CELL CYCLE S PHASE; CELL PROLIFERATION; COLON CARCINOMA; CONTROLLED STUDY; DISSEMINATED CANCER; DRUG ACCUMULATION; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG TOLERANCE; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MALE; MELANOMA; MITOSIS INHIBITION; MOUSE; NONHUMAN; PRIMARY TUMOR; PRIORITY JOURNAL; TOXICITY TESTING;

ANIMALS; ANTINEOPLASTIC AGENTS, ALKYLATING; CELL CYCLE; CELL LINE, TUMOR; CELL PROLIFERATION; CHLORAMBUCIL; FLUORODEOXYGLUCOSE F18; HUMANS; MAXIMUM TOLERATED DOSE; MICE; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 79955634152     PISSN: 01676997     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10637-009-9371-0     Document Type: Article

References (35)

1. Juillerat-Jeanneret L, Schmitt F (2007) Chemical modification of therapeutic drugs or drug vector systems to achieve targeted therapy: looking for the grail. Med Res Rev 27:574-590 (Pubitemid 46984660)
2. Jang SH, Wientjes MG, Lu D, Au JL (2003) Drug delivery and transport to solid tumours. Pharm Res 20:1337-1350 (Pubitemid 37164040)
3. Bielawski K, Bielowska A (2008) Small-molecule based delivery systems for alkylating antineoplastic compounds. Chem Med Chem 3:536-542
4. Chezal JM, Papon J, Labarre P, Lartigue C, Galmier MJ, Decombat C, Chavignon O, Maublant J, Teulade JC, Madelmont JC, Moins N (2008) Evaluation of radiolabeled (hetero)aromatic analogues of N-(2-diethylaminoethyl)-4- iodobenzamide for imaging and targeted radionuclide therapy of melanoma. J Med Chem 51:3133-3144 (Pubitemid 351821874)
5. Rapp M, Giraud I, Maurizis JC, Madelmont JC (2003) Synthesis and pharmacokinetic profile of a quaternary ammonium derivative of chlorambucil, a potential anticancer drug for the chemotherapy of chondrosarcoma. Bioorg Med Chem 11:5007-5012 (Pubitemid 37352988)
6. Rapp M, Giraud I, Maurizis JC, Galmier MJ, Madelmont JC (2003) Synthesis and in vivo biodisposition of [14C]-quaternary ammonium-melphalan conjugate, a potential cartilage-targeted alkylating drug. Bioconjug Chem 14:500-506
7. Gatenby RA, Gillies RJ (2004) Why do cancers have high aerobic glycolysis? Nat Rev Cancer 4:891-899
8. Gambhir SS (2002) Molecular imaging of cancer with positron emission tomography. Nat Rev Cancer 2:683-693
9. Kelloff GJ, Hoffman JM, Johnson B, Scher HI, Siegel BA, Cheng EY, Cheson BD, O'shaughnessy J, Guyton KZ, Mankoff DA, Shankar L, Larson SM, Sigman CC, Schilsky RL, Sullivan DC (2005) Progress and promise of FDG-PET imaging for cancer patient management and oncologic drug development. Clin Cancer Res 11:2785-2808 (Pubitemid 40525178)
10. Rohren EM, Turkington TG, Coleman RE (2004) Clinical applications of PET in oncology (2004). Radiology 231:305-332
11. Reux B, Weber V, Galmier MJ, Borel M, Madesclaire M, Madelmont JC, Debiton E, Coudert P (2008) Synthesis and cytotoxic properties of new fluorodeoxyglucose-coupled chlorambucil derivatives. Bioorg Med Chem 16:5004-5020 (Pubitemid 351635770)
12. Boyd MR (1995) The NCI in vitro anticancer drug discovery screen. Concept, implementation, and operation; Part 1, in vitro methods. In: Teicher B (ed) Anticancer drug development guide: preclinical screening, clinical trials and approval. Humana Press, Totowa, pp 23-42
13. O'Brien J, Wilson I, Orton T, Pognan F (2000) Investigation of the Alamar blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur J Biochem 267:5421-5426
14. Workman P, Twentyman P, Balkwill F, Balmain A, Chaplin D, Double J, Embleton J, Newell D, Raymond R, Stables J, Stephens T, Wallace J (1998) United Kingdom Coordinating Committee on Cancer Research (UKCCCR) guidelines for the welfare of animals in experimental neoplasia (2nd edition). Br J Cancer 77:1-10 (Pubitemid 28029765)
15. Miot-Noirault E, Legault J, Cachin F, Mounetou E, Degoul F, Gaudreault RC, Moins N, Madelmont JC (2004) Antineoplastic potency of arylchloroethylurea derivatives in murine colon carcinoma. Invest New Drugs 22:369-378 (Pubitemid 39619814)
16. Bissery MC, Guenard D, Gueritte-Voegelein F, Lavelle F (1991) Experimental antitumour activity of Taxotere (RP 56976, NSC 628503), a taxol analogue. Cancer Res 51:4845-4852
17. Polin L, White K, Kushner J, Paluch J, Simpson C, Pugh S, Edelstein MK, Hazeldine S, Fontana J, LoRusso P, Horwitz JP, Corbett TH (2002) Preclinical efficacy evaluations of XK-469: Dose schedule, route and cross-resistance behaviour in tumour-bearing mice. Invest New Drugs 20:13-22 (Pubitemid 34251647)
18. Rose WC, Wild R (2004) Therapeutic synergy of oral taxane BMS-275183 and cetuximab versus human tumour xenografts. Clin Cancer Res 10:7413-7417 (Pubitemid 39487730)
19. Beverly AT (1997) Anticancer drug development guide. Humana Press, Totowa
20. Hait WN (2009) Targeted cancer therapeutics. Cancer Res 69:1263-1267
21. Torchilin VP (2000) Drug targeting. Eur J Pharm Sci 11(suppl 2): S81-S91
22. Warburg O (1931) The metabolism of tumours. Richard Smith, New York, pp 29-169
23. Maryanoff BE, Costanzo MJ, Nortey SO, Greco MN, Shank RP, Schupsky JJ, Ortegon MP, Vaught JL (1998) Structure-activity studies on anticonvulsivant sugar sulfamates related to topiramate. Enhanced potency with cyclic sulphate derivatives. J Med Chem 41:1315-1343 (Pubitemid 28208186)
24. Iglesias-Guerra F, Candela JI, Banco E, Alcudia F, Vega-Perez JM (2002) Alkylating agents from sugars: synthesis of chlorambucil derivatives carriers by chiral glycosyl glycerols derived from D-glucosamine. Chirality 14:199-203 (Pubitemid 34113153)
25. Cantuaria G, Magalhaes A, Angioli R, Mendez L, Mirhashemi R, Wang J, Wang P, Penalver M, Averette H, Braunschweiger P (2000) Antitumour activity of a novel glycol-nitric oxide conjugate in ovarian carcinoma. Cancer 88:381-388 (Pubitemid 30051824)
26. Pohl J, Bertram B, Hilgard P, Nowroussian MR, Stuben J, Wiessler M (1995) D-19575-a sugar-linked isophosphoramide mustard derivative exploiting transmembrane glucose transport. Cancer Chemother Pharmacol 35:364-370
27. Seker H, Bertram B, Burkle A, Kaina B, Pohl J, Koepsell H, Wiessler M (2000) Mechanistic aspects of the cytotoxic activity of glufosfamide, a new tumour therapeutic agent. Br J Cancer 82:629-634 (Pubitemid 30085201)
28. Sorg BL, Hull WE, Kliem HC, Mier W, Wiessler M (2005) Synthesis and NMR characterization of hydroxyurea and mesylglycol glycoconjugates as drug candidates for targeted cancer chemotherapy. Carbohydr Res 340:181-189 (Pubitemid 40091812)
29. Briasoulis E, Pavlidis N, Terret C, Bauer J, Fiedler W, Schöffski P, Raoul JL, Hess D, Selvais R, Lacombe D, Bachmann P, Fumoleau P (2003) Glufosfamide administered using a 1-hour infusion given as first-line treatment for advanced pancreatic cancer. A phase II trial of the EORTC-new drug development group. Eur J Cancer 39:2334-2340 (Pubitemid 37214857)
30. Rohren EM, Turkington TG, Coleman RE (2004) Clinical applications of PET in oncology. Radiology 231:305-332 (Pubitemid 38552885)
31. Kelloff GJ, Hoffman JM, Johnson B et al (2005) Progress and promise of FDG-PET imaging for cancer patient management and oncologic drug development. Clin Cancer Res 11:2785-2808 (Pubitemid 40525178)
32. Matsumoto T, Fujimoto-Ouchi K, Tamura S, Tanaka Y, Ishitsuka H (1999) Tumour inoculation site-dependent induction of cachexia in mice bearing colon 26 carcinoma. Br J Cancer 79:764-769 (Pubitemid 29082103)
33. Garbe C, Eigentler TK (2007) Diagnosis and treatment of cutaneous melanoma: state of the art 2006 (2007). Melanoma Res 17:117-127
34. Miller AJ, Mihm MC (2006) Melanoma. N Engl J Med 355:51-65
35. Tarhini AA, Agarwala SS (2006) Cutaneous melanoma: available therapy for metastatic disease. Dermatol Ther 19:19-25