Alkylating agents and cancer therapy

Expert Opinion on Therapeutic Patents

Volumn 17, Issue 9, 2007, Pages 1061-1075

  Ralhan, Ranju ^a   Kaur, Jatinder ^a  

^a ALL INDIA INSTITUTE OF MEDICAL SCIENCES   (India)

Author keywords

Alkylating agents; Antineoplastic; Cancer therapy; Cyclophosphamide; DNA damaging agents

Indexed keywords

5,6 DIMETHYLXANTHENONE 4 ACETIC ACID; ALKB PROTEIN; ALKYLATING AGENT; AMONAFIDE; ANTINEOPLASTIC AGENT; BACTERIAL PROTEIN; CAMPTOTHECIN; CISPLATIN; CYCLOOXYGENASE 2 INHIBITOR; CYCLOPHOSPHAMIDE; DACARBAZINE; DNA TOPOISOMERASE INHIBITOR; DOCETAXEL; DOXORUBICIN; FLUOROURACIL; FOTEMUSTINE; HYDROXYUREA; IFOSFAMIDE; IMATINIB; IRINOTECAN; MELPHALAN; MESNA; METHYLATED DNA PROTEIN CYSTEINE METHYLTRANSFERASE; MITOMYCIN C; NONSTEROID ANTIINFLAMMATORY AGENT; PROTEIN TYROSINE KINASE INHIBITOR; TEMOZOLOMIDE; TOPOTECAN; UNCLASSIFIED DRUG; UNINDEXED DRUG; VASCULAR TARGETING AGENT;

ACUTE GRANULOCYTIC LEUKEMIA; ALKYLATION; AMENORRHEA; ANTIINFLAMMATORY ACTIVITY; APOPTOSIS; BLOOD TOXICITY; BREAST ADENOCARCINOMA; BREAST CANCER; CANCER THERAPY; CELL CYCLE G1 PHASE; CELL CYCLE S PHASE; CHROMOSOME ABERRATION; CLINICAL TRIAL; COLON CANCER; DIARRHEA; DIGESTIVE SYSTEM ULCER; DNA REPAIR; DNA SYNTHESIS; DOWN REGULATION; DRUG BIOAVAILABILITY; DRUG DOSE COMPARISON; DRUG EFFICACY; DRUG MECHANISM; DRUG MEGADOSE; DRUG METABOLISM; DRUG SAFETY; ENZYME ACTIVATION; ENZYME INHIBITION; EXCISION REPAIR; GASTROINTESTINAL HEMORRHAGE; GENE DIRECTED ENZYME PRODRUG THERAPY; GLIOBLASTOMA; HEMORRHAGIC CYSTITIS; HUMAN; INFERTILITY; LEUKEMIA; LOW DRUG DOSE; MELANOMA; NAUSEA; NONHUMAN; PROTEIN EXPRESSION; REVIEW; SIDE EFFECT; SINGLE DRUG DOSE; SISTER CHROMATID EXCHANGE; SOLID TUMOR; SPERMATOGENESIS; STOMACH CANCER; TESTIS CANCER; UNSPECIFIED SIDE EFFECT; VOMITING;

EID: 35448989427     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.17.9.1061     Document Type: Review

References (84)

1. PODOLSKY ML: Cures Out of Chaos. Harwood Academic Publishers, New York, USA (1997):271.
2. DENNY WA: DNA minor groove alkylating agents. Expert Opin. Ther. Patents (2000) 10(4):459-474.
3. KAINA B, CHRISTMANN M, NAUMANN S, ROOS WP: MGMT: key node in the battle against genotoxicity, carcinogenicity and apoptosis induced by alkylating agents. DNA Repair (Amst.) (2007).
4. BRANDES AA, TOSONI A, FRANCESCHI E: Adjuvant therapy in glioblastomas: false steps and real advances. Expert Rev. Anticancer Ther. (2007) 7(5):607-608.
5. CASSIER PA, DUFRESNE A, FAYETTE J et al.: Emerging drugs for the trearment of soft tissue sarcomas. Expert Opin. Emerging Drugs (2007) 12(1):139-153.
6. 6-methylguanine-DNA-methyltransferase (MGMT) to sensitize cancer cells to anticancer therapy. Expert Opin. Ther. Targets (2007) 11(3):349-361.
7. CHOI JY, NOWELL SA, BLANCO JG, AMBROSONE CB: The role of genetic variability in drug metabolism pathways in breast cancer prognosis. Pharmacogenomics (2006) 7(4):613-624.
8. 6-alkylguanine DNA alkyltransferase as a means to enhance chemotherapy. Cancer Treat. Rev. (2006) 32(4):261-276.
9. KOBER T, HULSEWEDE H, BOHLIUS J, ENGERT A. Fourth biannual report of the Cochrane haematological malignancies group. J. Natl. Cancer Inst. (2006) 98(8):E1.
10. BROGGINI M, HARTLEY JA, MATTES WB et al.: DNA damage and sequence specificity of DNA binding of the new anti-cancer agent 1,4-bis(2′-chloroet.hyl)-1,4-diazabicyclo-[2.2.1] heptane dimaleate (Dabis maleate). Br. J. Cancer (1990) 61(2):285-289.
11. ZHANG K, YANG EB, WONG KP, MACK P: GSH, GSH-related enzymes and GS-X pump in relation to sensitivity of human tumor cell lines to chlorambucil and adriamycin. Int. J. Oncol. (1999) 14(5):861-867.
12. COLVIN OM, FRIEDMAN HS, GAMCSIK MP, FENSELAU C, HILTON J: Role of glutathione in cellular resistance to alkylating agents. Adv. Enzyme Regul. (1993) 33:19-26.
13. ROOSEBOOM M, COMMANDEUR JN, VERMEULEN NP: Enzyme-catalyzed activation of anticancer prodrugs. Pharmacol. Rev. (2004) 56(1):53-102.
14. DACHS GU, TUPPER J, TOZER GM: From bench to bedside for gene-directed enzyme prodrug therapy of cancer. Anticancer Drugs (2005) 16(4):349-359.
15. AGHI M, HOCHBERG F, BREAKEFIELD XO: Prodrug activation enzymes in cancer gene therapy. J. Gene Med. (2000) 2(3):148-164.
16. KIRN D, NICULESCU-DUVAZ I, HALLDEN G, SPRINGER CJ: The emerging fields of suicide gene therapy and virotherapy. Trends Mol. Med. (2002) 8(4 Suppl.):S68-S73.
17. DENNY WA. Prodrugs for gene-directed enzyme-prodrug therapy (Suicide gene therapy). J. Biomed. Biotechnol. (2003) 2003(1):48-70.
18. CLARKE L, WAXMAN DJ: Oxidative metabolism of cyclophosphamide: identification of the hepatic monooxygenase catalysts of drug activation. Cancer Res. (1989) 49(9):2344-2350.
19. SLADEK NE: Metabolism of oxazaphosphorines. Pharmacol. Ther. (1988) 37(3):301-355.
20. MARKMAN M, KENNEDY A, WEBSTER K et al.: Continuous subcutaneous administration of mesna to prevent ifosfainide-induced hemorrhagic cystitis. Semin. Oncol. (1996) 23(3 Suppl. 6):97-98.
21. ROY P, WAXMAN DJ: Activation of oxazaphosphorines by cytochrome P450: application to gene-directed enzyme prodrug therapy for cancer. Toxicol. In Vitro (2006) 20(2):176-186.
22. CHEN L, WAXMAN DJ: Intratumoral activation and enhanced chemotherapeutic effect of oxazaphosphorines following cytochrome P450 gene transfer: development of a combined chemotherapy/cancer gene therapy strategy. Cancer Res. (1995) 55(3):581-589.
23. WEI MX, TAMIYA T, CHASE M et al.: Experimental tumor therapy in mice using the cyclophosphamide-activating cytochrome P450 2B1 gene. Hum. Gene Ther. (1994) 5(8):969-978.
24. WILSKER D, BUNZ F: Loss of ataxia telangiectasia mutated- and Rad3-related function potentiates the effects of chemotherapeutic drugs on cancer cell survival. Mol. Cancer Ther. (2007) 6(4):1406-1413.
25. KOCH D, HUNDSBERGER T, BOOR S, KAINA B: Local intracerebral administration of O(6)-benzylguanine combined with systemic chemotherapy with temozolomide of a patient suffering from a recurrent glioblastoma. J. Neurooncol. (2007) 82(1):85-89.
26. YU B, EDSTROM WC, BENACH J et al.: Crystal structures of catalytic complexes of the oxidative DNA/RNA repair enzyme AlkB. Nature (2006) 439(7078):879-884.
27. ADACHI N, SO S, KOYAMA H: Loss of nonhomologous end joining confers camptothecin resistance in DT40 cells. Implications for the repair of topoisomerase I-mediated DNA damage. J. Biol. Chem. (2004) 279(36):37343-37348.
28. POMMIER Y. Topoisomerase I inhibitors: camptothecins and beyond. Nat. Rev. Cancer (2006) 6(10):789-802.
29. EMERSON DL, BESTERMAN JM, BROWN HR et al.: In vivo antitumor activity of two new seven-substituted water-soluble camptothecin analogues. Cancer Res. (1995) 55(3):603-609.
30. ABIGERGES D, ARMAND JR CHABOT GG et al.: Phase I and pharmacology study of intoplicine (RP 60475; NSC 645008), novel topoisomerase I and II inhibitor, in cancer patients. Anticancer Drugs (1996) 7(2):166-174.
31. GIOVANELLA BC, STEHLIN JS, WALL ME et al.: DNA topoisomerase I-targeted chemotherapy of human colon cancer in xenografts. Science (1989) 246(4933):1046-1048.
32. DRUKER BJ: Inhibition of the Bcr-Abl tyrosine kinase as a therapeutic strategy for CML. Oncogene (2002) 21(56):8541-8546.
33. SALESSE S, VERFAILLIE CM: BCR/ABL: from molecular mechanisms of leukemia induction to treatment of chronic myelogenous leukemia. Oncogene (2002) 21(56):8547-8559.
34. YU C, KRYSTAL G, VARTICOVKSI L et al.: Pharmacologic mitogen-activated protein/extracellular signal-regulated kinase kinase/ mitogen-activated protein kinase inhibitors interact synergistically with ST1571 to induce apoptosis in Bcr/Abl-expressing human leukemia cells. Cancer Res. (2002) 62(1):188-199.
35. SONOYAMA J, MATSUMURA I, EZOE S et al.: Functional cooperation among Ras, STAT5, and phosphatidylinositol 3-kinase is required for full oncogenic activities of BCR/ABL in K562 cells. J. Biol. Chem. (2002) 277(10):8076-8082.
36. NIMMANAPALLI R, BHALLA K: Novel targeted therapies for Bcr-Abl positive acute leukemias: beyond ST1571. Oncogene (2002) 21(56):8584-8590.
37. AMARANTE-MENDES GP,:, MCGAHON AJ, NISHIOKA WK et al.: Bcl-2-independent Bcr-Abl-mediated resistance to apoptosis: protection is correlated with up regulation of Bcl-xL. Oncogene (1998) 16(11):1383-1390.
38. AMARANTE-MENDES GP NAEKYUNG KIM C, LIU L et al.: Bcr-Abl exerts its antiapoptonc effect against diverse apoptotic stimuli through blockage of mitochondrial release of cytochrome C and activation of caspase-3. Blood (1998) 91(5):1700-1705.
39. GAMBACORTI-PASSERINI C, LE COUTRE P MOLOGNI L et al.: Inhibition of the ABL kinase activity blocks the proliferation of BCR/ABL+ leukemic cells and induces apoptosis. Blood Cells Mol. Dis. (1997) 23(3):380-394.
40. DEININGER MW, GOLDMAN JM, LYDON N, MELO JV. The tyrosine kinase inhibitor CGP57148B selectively inhibits the growth of BCR-ABL-positive cells. Blood (1997) 90(9):3691-3698.
41. BERAN M, CAO X, ESTROV Z et al.: Selective inhibition of cell proliferation and BCR-ABL phosphorylation in acute lymphoblastic leukemia cells expressing Mr 190,000 BCR-ABL protein by a tyrosine kinase inhibitor (CGP-57148). Clin. Cancer Res. (1998) 4(7):1661-1672.
42. DAN S, NAITO M, TSURUO T. Selective induction of apoprosis; in Philadelphia chromosome-positive chronic myelogenous leukemia cells by an inhibitor of BCR - ABL ryrosine kimse, CGP 57148. Cell Death Differ. (1998) 5(8):710-715.
43. OKADA M, ADACHI S, IMAI T et al.: A novel mechanism for imatinib mesylate-induced cell death of BCR-ABL-positive human leukemic cells: caspase-independent, necrosis-like programmed cell death mediated by serine protease activity. Blood (2004) 103(6):2299-2307.
44. DRESEMANN G: Imatinib and hydroxyurea in pretreated progressive glioblastoma multiforme: a patient series. Ann. Oncol. (2005) 16(10):1702-1708.
45. REARDON DA, EGORIN MJ, QUINN JA et al.: Phase II study of imatinib mesylate plus hydroxyurea in adults with recurrent glioblastoma multiforme. J. Clin. Oncol. (2005) 23(36):9359-9368.
46. BREEDVELD P, PLUIM D, CIPRIANI G et al.: The c1lect of Bcrp1 (Abcg2) on the in vivo pharmacokinetics and brain penetration of imatinib mesylate (Gleevec): implications for the use of breast cancer resistance protein and P-glycoprotein inhibitors to enable the brain penetration of imatinib in patients. Cancer Res. (2005) 65(7):2577-2582.
47. BERGENHEIM AT, HENRIKSSON K- Pharmacokinetics and pharmacodynamics of estramustine phosphate. Clin. Pharmacokinet. (1998) 34(2):163-172.
48. PIENTA KJ, KAMRADT JM, SMITH DC: Oral chemotherapy in the treatment of hormone-refractory prostate cancer. Drugs (1999) 58(Suppl. 3):127-131.
49. COLVIN OM: An overview of cyclophosphamide development and clinical applications. Curr. Pharm. Des. (1999) 5(8):555-560.
50. HONN KV, BOCKMAN RS, MARNETT LJ: Prostaglandins and cancer: a review of tumor initiation through tumor metastasis. Prostaglandins (1981) 21(5):833-864.
51. FURUTA Y. HALL EF, SANDUJA S, BARKLEY T Jr, MILAS L: Prostaglandin production by murine tumors as a predictor for therapeutic response to indomethacin. Cancer Res. (1988) 48(11):3002-3007.
52. TAKETO MM: Cyclooxygenase-2 inhibitors in tumorigenesis (part II). J. Natl. Cancer Inst. (1998) 90(21):1609-1620.
53. MILAS L, HANSON WR: Eicosanoids and radiation. Eur. J. Cancer (1995) 31A(10):1580-1585.
54. ISAKSON P, SEIBERT K, MASFERRER J et al.: Discovery of a better aspirin. Adv. Prostaglandin Thromboxane Leukot. Res. (1995) 23:49-54.
55. MILAS L, FURUTA Y, HUNTER N, NISHIGUCHI I, RUNKEL S: Dependence of indomethacin-induced potentiation of routine tumor radioresponse on tumor host immunocompetence. Cancer Res. (1990) 50(15):4473-4477.
56. WEPPELMANN B, MONKEMEIER D: The influence of prostaglandin antagonists on radiation therapy of carcinoma of the cervix. Gynecol. Oncol. (1984) 17(2):196-199.
57. GATELY S: The contributions of cyclooxygenase-2 to tumor angiogenesis. Cancer Metastasis Rev. (2000) 19(1-2)-19-27.
58. FOSSLIEN E: Biochemistry of cyclooxygenase (COX)-2 inhibitors and molecular pathology of COX-2 in neoplasia. Crit. Rev. Clin. Lab. Sci. (2000) 37(5):431-502.
59. GUPTA RA, DUBOIS RN: Translational studies on Cox-2 inhibitors in the prevention and treatment of colon cancer. Ann. NY Acad. Sci. (2000) 910:196-204; discussion 204-206.
60. HOWE LR, SUBBARAMAIAH K, BROWN AM, DANNENBERG AJ: Cyclooxygenase-2: a target for the prevention and treatment of breast cancer. Endocr. Relat. Cancer (2001) 8(2):97-114.
61. STRAUSFELD U, LABBE JC, FESQUET D et al.: Dephosphorylation and activation of a p34cdc2/cyclin B complex in vitro by human CDC25 protein. Nature (1991) 351(6323):242-245.
62. BULAVIN DV, HIGASHIMOTO Y, POPOFF IJ et al.: Initiation of a G2/M checkpoint after ultraviolet radiation requires p38 kinase. Nature (2001) 411(6833):102-107.
63. GOULD KL, MORENO S, TONKS NK, NURSE P: Complementation of the mitotic activator, p80cdc25, by a human protein-tyrosine phosphatase. Science (1990) 250(4987):1573-1576.
64. CANGI MG, CUKOR B, SOUNG P et al.: Role of the Cdc25A phosphatase in human breast cancer. J. Clin. Invest. (2000) 106(6):753-761.
65. HERNANDEZ S, HERNANDEZ L, BEA S et al.: cdc25a and the splicing variant cdc25b2, but not cdc25B1, -B3 or -C, are over-expressed in aggressive human non-Hodgkin's lymphomas. Int. J. Cancer (2000) 89(2):148-152.
66. HERNANDEZ S, HERNANDEZ L, BEA S et al.: cdc25 cell cycle-activating phosphatases and c-myc expression in human non-Hodgkin's lymphomas. Cancer Res. (1998) 58(8):1762-1767.
67. GASPAROTTO D, MAESTRO R, PICCININ S et al.: Overexpression of CDC25A and CDC25B in head and neck cancers. Cancer Res. (1997) 57(12):2366-2368.
68. YU L, ORLANDI L, WANG P et al.: UCN-01 abrogates G2 arrest through a Cdc2-dependent pathway that is associated with inactivation of the Wee1Hu kinase and activation of the Cdc25C phosphatase. J. Biol. Chem. (1998) 273(50):33455-33464.
69. GRAVES PR, YU L, SCHWARZ JK et al.: The Chk1 protein kinase and the Cdc25C regulatory pathways are targets of the anticancer agent UCN-01. J. Biol. Chem. (2000) 275(8):5600-5605.
70. BRIEGERT M, KAINA B: Human monocytes, but not dendritic cells derived from them, are defective in base excision repair and hypersensitive to methylating agents. Cancer Res. (2007) 67(1):26-31.
71. CELIKLER S, BILALOGLU R, AYDEMIR N: Genotoxic effects induced by fotemustine and vinorelbine in human lymphocytes. Z. Naturforsch. [C] (2006) 61(11-12):903-910.
72. BHATIA K, RAHMAN S, ALI M, RAISUDDIN S: In vitro andoxidant activity of Juglans regia L. bark extract and its protective effect on cyclophosphamide-induced urotoxicity in mice. Redox Rep. (2006) 11(6):273-279.
73. TASHIRO H, SAGAWA T, OKADA K et al.: The safety of docetaxel with cyclophosphamide (TC) therapy as adjuvant chemotherapy for Japanese women with operable breast cancer. Gan To Kagaku Ryoho (2007) 34(3):393-396.
74. BRACCI L, MOSCHELLA F, SESTILI P et al.: Cyclophosphamide enhances the antitumor efficacy of adoptively transferred immune cells through the induction of cytokine expression, B-ceil and T-cell homeostatic proliferation, and specific rumor infiltration. Clin. Cancer Res. (2007) 13(2 Pt 1):644-653.
75. HOU DY, MULLER AJ, SHARMA MD et al.: Inhibition of indoleamine 2,3-dioxygenase in dendritic cells by stereoisomers of 1-methyl-tryptophan correlates with antitumor responses. Cancer Res. (2007) 67(2):792-801.
76. BIGNER DD, BROWN MT, FRIEDMAN AH et al.: Iodine-131-labeled antitenascin monoclonal antibody 81C6 treatment of patients with recurrent malignant gliomas: Phase I trial results. J. Clin. Oncol. (1998) 16(6):2202-2212.
77. RIZZIERI DA, AKABANI G, ZALUTSKY MR et al.: Phase I trial study of 131I-labeled chimeric 81C6 monoclonal antibody for the treatment of patients with non-Hodgkin lymphoma. Blood (2004) 104(3):642-648.
78. AKABANI G, COKGOR I, COLEMAN RE et al.: Dosimetry and dose-response relationships in newly diagnosed patients with malignant gliomas treated with iodine-131-labeled anti-tenascin monoclonal antibody 81C6 therapy. Int. J. Radiat. Oncol. Biol. Phys. (2000) 46(4):947-958.
79. SMITHERMAN PK, TOWNSEND AJ, KUTE TE, MORROW CS: Role of multidrug resistance protein 2 (MRP2, ABCC2) in alkylating agent detoxification: MRP2 potentiates glutathione S-transferase A1-1-mediated resistance to chlorambucil cyto toxicity. J. Pharmacol. Exp. Ther. (2004) 308(1):260-267.
80. TEW KD, MONKS A, BARONE L et al. Glutathione-associated enzymes in the human cell lines of the national cancer institute drug screening program. Mol Pharmacol. (1996) 50(1):149-159.
81. FURONAKA O, TAKESHIMA Y, AWAYA H et al.: Aberrant methylation and loss of expression of O-methyiguanine-DNA methyltransferase in pulmonary squamous cell carcinoma and adenocarcinoma. Pathol Int. (2005) 55(6):303-309.
82. MAIER S, DAHLSTROEM C, HAEFLIGER C, PLUM A, PIEPENBROCK C: Identifying DNA methylation biomarkers of cancer drug response. Am. J. Pharmacogenomics (2005) 5(4):223-232.
83. 6-methylguanine-DNA methyltransferase determined by promoter hypermethylation and immunohistochemical expression in anaplastic gliomas. Clin. Cancer Res. (2005) 11(14):5167-5174.
84. SCHILDHAUS HU, KROCKEL I, LIPPERT H et al.: Promoter hypermethylation of p16INK4a, E-cadherin, O6-MGMT, DAPK and FHIT in adenocarcinomas of the esophagus, esophagogastric junction and proximal stomach. Int. J. Oncol. (2005) 26(6):1493-1500.