Antitumour acridines

Expert Opinion on Therapeutic Patents

Volumn 14, Issue 1, 2004, Pages 55-70

  Demeunynck, Martine ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Acridine; Acridone; Amsacrine; Anticancer; Imidazoacridone; Pyrazoloacridine; Pyrimidoacridine

Indexed keywords

3 CHLOROMETHYL 6 HYDROXYINDOLINE; ACRANIL; ACRIDINE DERIVATIVE; ACRIFLAVINE; ACRONINE; ACRONINE DERIVATIVE; ACRONINE EPOXIDE; ALKYLATING AGENT; AMINOACRIDINE; AMINOACRIDINE DERIVATIVE; AMSACRINE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; CHLORMETHINE DERIVATIVE; CISPLATIN; CYCLIN DEPENDENT KINASE; DNA; DNA TOPOISOMERASE; DRUG METABOLITE; DUOCARMYCIN DERIVATIVE; ETHACRIDINE LACTATE; IMIDAZOLE DERIVATIVE; MEPACRINE; NITRACRINE; PROFLAVINE; PYRROLIZINE DERIVATIVE; S 23906 1; TACRINE; TELOMERASE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

BASE PAIRING; CANCER; CANCER CHEMOTHERAPY; CLINICAL STUDY; CLINICAL TRIAL; DNA METABOLISM; DNA STRUCTURE; DRUG APPROVAL; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVITY; HUMAN; INTERCALATION COMPLEX; MOLECULAR INTERACTION; MULTIDRUG RESISTANCE; NONHUMAN; PARASITOSIS; PHARMACOPHORE; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 0347917053     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543776.14.1.55     Document Type: Review

References (72)

1. DEMEUNYNCK M, CHARMANTRAY F, MARTELLI A: Interest of acridine derivatives in the anticancer chemotherapy. Curr. Pharm. Des. (2001) 7(17):1703-1724.
2. DENNY WA: Acridine-based antitumour agents. In: Chemistry of antitumour agents, Blackie and Son Ltd, Glasgow and London, LTK (1990):1-29.
3. DENNY WA: Acridine derivatives as chemotherapeutic agents. Curr. Med. Chem. (2002) 9(18):1655-1665.
4. ADAMS A: Crystal structures of acridines complexed with nucleic acids. Curr. Med. Chem. (2002) 9:1667-1675.
5. WAKELIN LPG, DENNY WA: Kinetic and equilibrium binding studies of a series of intercalating agents that bind by threading a sidechain through the DNA helix. In: Molecular basis of specificity in nucleic acid-drug interactions. Kluwer Academic Publishers, Dordrecht, Germany (1990):191-206.
6. BORITZKI TJ, PALMER BD, CODDINGTON JM, DENNY WA: Identification of the major lession from the reaction of an acridine-targeted aniline mustard with DNA as an adenine N1 adduct. Chem. Res. Toxicol. (1994) 7:41-46.
7. GOURDIE TA, PRAKASH AS, WAKELIN LPG, WOODGATE PD, DENNY WA: Synthesis and evaluation of DNA-targeted spatially separated bis(aniline mustards) as potential alkylating agents with enhanced DNA cross-linking capability. J. Med. Chem. (1991) 34:240-248.
8. ATWELL GJ, FAN J-Y, TAN K, DENNY WA: DNA-directed alkylating agents. 7. Synthesis, DNA interaction, and antitumor activity of bis(hydroxymethyl)-and bis(carbamate)-substituted pyrrolizines and imidazoles. J. Med. Chem. (1998) 41:4744-4754.
9. FAN J-Y, TERCEL M. DENNY WA: Synthesis, DNA binding and cytotoxicity of 1-[[ω)-(9-acridinyl)amino]alkyl]carbonyl-3-(chloro-methyl)- 6-hydroxyindolines, a new class of DNA-targeted alkylating agents. Anticancer Drug Des. (1997) 12:277-293.
10. BOWLER BE, HOLLIS LS, LIPPARD SJ: Synthesis and DNA binding and photonicking properties of acridine orange linked by a polymethylene tether to (1,2-diaminoethane)dichloroplatinum(II). J. Am. Chem. Soc. (1994) 106:6102-6104.
11. SUNDQUIST WJ, BANCROFT DP, LIPPARD SJ: Synthesis, characterization, and biological activity of cis-diammineplatinium(II) complexes of the DNA interscalators 9-aminoacridine and chloroquine. J. Am. Chem. Soc. (1990) 112:1590-1596.
12. TEMPLE MD, MCFADYEN WD, HOLMES RJ, DENNY WA, MURRAY V: Interaction of cisplatin and DNA-targeted 9-aminoacridine platinum complexes with DNA. Biochemistry (2000) 39:5593-5599.
13. TILLEQUIN F, MICHEL S, SKALTSOUNIS A-L: Acronycine-type alkaloids: chemistry and biology. In: Alkaloids: chemical and biological properties. Pergamon, Oxford, UK (1998):1-102.
14. GUILBAUD N, LEONCE S, TILLEQUIN F et al.: Acronycine derivatives as promising antitumor agents. Anticancer Drugs (2002) 13:445-449.
15. MICHEL S, SEGUIN E, TILLEQUIN F: Structure-activity relationships in the acronycine series. Curr. Med. Chem. (2002) 9:1689-1700.
16. THI MAI HD, GASLONDE T, MICHEL S et al.: Structure-activity relationships and mechanism of action of antitumor benzo[b]pyrano[3,2-h]acridin-7-one acronycine analogues. J. Med. Chem. (2003) 46:3072-3082.
17. COSTES N, LE DEIT H, MICHEL S et al.: Synthesis and cytotoxic and antitumor activity of benzo[b]pyrano[3,2-h]acridin-7-one analogue of acronycine. J. Med. Chem. (2000) 43:2395-2402.
18. CHARMANTRAY F, DEMEUNYNCK M, CARREZ D et al.: 4-Hydroxymethyl-3-aminoacridine derivatives as a new family of anticancer agents. J. Med. Chem. (2003) 46:967-977.
19. CHARMANTRAY F, DUFLOS A, LHOMME J, DEMEUNYNCK M: Synthesis and study of 4-hydroxymethyl-3-alkylaminoacridines as models of a new class of DNA intercalating-alkylating agents. J. Chem. Soc., Perkin Trans. 1 (2001):2962-2968.
20. FOYE WO: Cancer chemotherapeutic Agents, American Chemical Society, Washington, USA (1995):483-500.
21. SHANNON AM, BOUCHIER,HAYES DJ, CONDRON CM, TOOMEY D: Tumor hypoxia, chemotherapeutic resistance and hypoxia-related therapies. Cancer Treatment Rev. (2003) 29:297-307.
22. WOYNAROWSKI JM, McNAMEE H, SZMIGIERO L, BEERMAN TA, KONOPA J: Induction of DNA-protein crosslinks by antitumor 1-nitro-9-aminoacridines in L1210 leukemia cells. Biochem. Pharmacol. (1989) 38:409-4101.
23. BAKTOSZEK A, DACKIEWICZ P, SKLADANOWSKI A, KONOPA J: In vitro DNA crosslinking by Ledakrin, an antitumor derivative of 1-nitro-9-aminoacridine. Chem. Biol. Interact. (1997) 103:141-451.
24. GNIAZDOWSKI M, SZMIGIERO L: Nitracrine and its congeners: an overview. Gen. Pharmacol. (1995) 26:473-481.
25. SKLADANOWSKI A: Modulation of G2 arrest enhances cell death induced by the antitumor 1-nitroacridine derivative, Nitracrine. Apoptosis (2002) 7:347-359.
26. ADJEI AA: Current starts of pyrazoloacridine as an anticancer agent. Invest. New Drugs (1999) 17:43-48.
27. DEES EC, ROWINSKY EK, NOE DA et al.: A Phase I and pharmacologic study o pyrazoloacridine and cisplatin in patients with advanced cancer. Invest. New Drugs (2003) 21:75-84.
28. ANTONINI I, POLUCCI P, MAGNANO A et al.: Rational design, synthesis and biological evaluation of thiadiazinoacridines: a new class of antitumor agents. Bioorg. Med. Chem. (2003) 11:399-405.
29. WELSON WR, DENNY WA, PULLEN SM et al.: Tertiary amine N-oxides as bioreductive drugs: DACA N-oxide, nitracrine N-oxide and AQ4N. Br. J. Cancer Suppl. (1996) 27:S43-47.
30. LEE HH, WILSON WR, FERRY DM et al.: Hypoxia-selective antitumor agents. 13. Effects of acridine substitution on the hypoxia-selective cytotoxicity and metabolic reduction of the his-bioreductive agent nitracrine N-oxide. J. Med. Chem. (1996) 39:2508-2517.
31. SIIM BG, HICKS KO, PULLEN SM et al.: Comparison of aromatic and tertiary amine N-oxides of acridine DNA intercalators as bioreductive drugs. Cytotoxicity, DNA binding, cellular uptake, and metabolism. Biochem. Pharmacol. (2000) 60:969-978.
32. CORBETT AH, OSHEROFF N: When good enzymes go bad: conversion of topoisomerase II to a cellular train by antineoplastic drugs. Chem. Res. Toxicol. (1993) 6:585-597.
33. BAGULEY BC, FERGUSON LR: Mutagenic properties of topoisomerase-targeted drugs. Biochem. Biophys. Acta (1998) 1400:213-222.
34. DENNY WA, CAIN BF, ATWELL GJ et al.: Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents. J. Med. Chem. (1982) 25:276-315.
35. FINLAY GJ, ATWELL GJ, BAGULEY BC: Inhibition of the action of the topoisomerase II poison amsacrine by simple aniline derivatives: evidence for drug-protein interactions. Oncol. Res. (1999) 11:249-254.
36. HARVEY VJ, HARDY JR, SMITH S, GROVE W, BAGULEY BC: Phase II study of the amsacrine analogue CI-921 (NSC 343499) in non-small cell lung cancer. Eur. J. Cancer (1991) 27:1617-1620.
37. SKLARIN NT, WIERNIK PH, GROVE WR et al.: A Phase II trial of CI-921 in advanced malignancies. Invest. New Drugs (1992) 10:309-312.
38. MORELAND N, FINLAY GJ, DRAGUNOW M, HOLDAWAY KM, BAGULEY BC: Cellular responses to methyl-N-[4-(9-acridinylamino)-2-methoxyphenyl] carbamate hydrochloride, an analogue of amsacrine active against nonproliferating cells. Eur. J. Cancer (1997) 33:1668-1676.
39. TURNBULL RM, MECZES EL, ROGERS MP et al.: Carbamate analogues of amsacrine active against non-cycling cells: relative activity against topoisomerases II α and β. Cancer Chemother. Pharmacol. (1999) 44:275-282.
40. FOSSÉ P, RENÉ B, SAUCIER J-M et al.: Stimulation of site-specific topoisomerase II-mediated DNA cleavage by an N-methylpyrrolecarboxamide-anilinoacridine conjugate: relation to DNA binding. Biochemistry (1994) 33:9865-9874.
41. SU TL, CHOU T-C, KIM JY et al.: 9-substituted acridine derivatives with long half-life and potent antitumor activity: synthesis and structure-activity relationships. J. Med. Chem. (1995) 38:3226-3235.
42. SU TL: Development of DNA topoisomerase II-mediated anticancer agents, 3-(9-acridinylamino)-5-hydroxymethylanilines (AHMAs) and related compounds. Curr. Med. Chem. (2002) 9:1677-1688.
43. DENNY WA, ATWELL GJ, REWCASTLE GW, BAGULEY BC: Potential antitumor agents. 49. 5-Substituted derivatives of N-[2-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide with in vivo solid-tumor activity. J. Med. Chem. (1987) 30:658-663.
44. DENNY WA: Dual topoisomerase I/II poisons as anticancer drugs. Expert Opin. Investig. Drugs (1997) 6:1845-1851.
45. DITTRICH C, COUDERT B, PAZ-ARES L et al.: Phase II study of XR-5000 (DACA), an inhibitor of topoisomerase I and II, administered as a 120-h infusion in patients with non-small cell lung cancer. Eur. J. Cancer (2003) 39:330-334.
46. SCHOFIELD PC, ROBERTSON IG, PAXTON JW et al.: Metabolism of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide in cancer patients undergoing a Phase I clinical trial. Cancer Chemother. Pharmacol. (1999) 44:51-58.
47. TWELVES CJ, GARDNER C, FLAVIN A et al.: Phase I and pharmacokinetic study of DACA (XR-5000): a novel inhibitor of topoisomerase I and II. Br. J. Cancer (1999) 80:1786-1791.
48. ANTONINI I, POLUCCI P, JENKINS TC et al.: 1-[(ω-Aminoalkyl)amino]-4-[(ω-aminoalkyl)carbamoyl]-9-oxo-9, 10-dihydroacridines as intercalating cytotoxic agents: synthesis, DNA binding and biological evaluation. J. Med. Chem. (1997) 40:3749-3755.
49. ANTONINI I, POLUCCI P, KELLAND LLOYD R et al.: N4-(ω-aminoalkyl)-1-[(ω-aminoalkyl amino]-4-acridinecarboxamides: novel, potent, cytotoxic, and DNA-binding agents. J. Med. Chem. (2000) 43:4801-4805.
50. ANTONINI I, POLUCCIP, MAGNANO A et al.: Design, synthesis, and biological properties of new bis(acridine-4-carboxamides) as anticancer agents. J. Med. Chem. (2003) 46:3109-3115.
51. MERGNY JL, MAILLIET P, LAVELLE F et al.: The development of telomerase inhibitors: the G-quartet approach. Anti-Cancer Drug Des. (1999) 14:327-339.
52. PERRY PJ, JENKINS TC: Recent advances in the development of telomerase inhibitors for the treatment of cancer. Expert Opin. Investig. Drugs (1999) 8:1981-2008.
53. GOWAN SM, HARRISON JR, PATTERSON L et al.: A G-quadruplex-interactive potent small-molecule inhibitor of telomerase exhibiting in vitro and in vivo antitumor activity. Mol. Pharmacol. (2002) 61:1154-1162.
54. GOMEZ D, MERGNY JL, RIOU JF: Detection of telomerase inhibitors based on G-quadruplex ligands by a modified telomeric repeat amplification protocol assay. Cancer Res. (2002) 62:3365-3368.
55. HEALD RA, MODI C, COOKSON JC et al.: Antitumor polycyclic acridines. 8. Synthesis and telomerase-inhibitory activity of methylated pentacydic acridinium salts. J. Med. Chem. (2002) 45:590-597.
56. GOWAN SM, HEALD R, STEVENS MF, KELLAND LR: Potent inhibition of telomerase by small-molecule pentacydic acridines capable of interacting with G-quadruplexes. Mol. Pharmacol. (2001) 60:981-988.
57. MISSAILIDIS S, STANSLAS J, MODI C et al.: Antitumor polycyclic acridines. Part 12. Physical and biological properties of 8,13-diethyl-6-methylquino[4,3,2-kl]acridinium iodide: a lead compound in anticancer drug design. Oncology Res. (2002) 13:175-189.
58. DELFOURNE E, BASTIDE J: Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents. Med. Res. Rev. (2003) 23:234-252.
59. MOLINSKI TF: Marine pyridoacridine alkaloids: structure, synthesis and biological chemistry. Chem. Rev. (1993) 93:1825-1838.
60. DING Q, CHICHAK K, LOWN JW: Pyrroloquinoline and pyridoacridine alkaloids from marine sources. Curr. Med. Chem. (1999) 6:1-27.
61. McDONALD LA, ELDREDGE GS, BARROWS LR, IRELAND CM: Inhibition of Topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytes sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II. J. Med. Chem. (1994) 37:3819-3827.
62. DASSONNEVILLE L, WATTEZ N, BALDEYROU B et al.: Inhibition of topoisomerase II by the marine alkaloid ascididemin and induction of apoptosis in leukemia cells. Biochem. Pharmacol. (2000) 60:527-537.
63. MATSUMOTO SS, BIGGS J, COPP BR, HOLDEN JA, BARROWS LR: Mechanism of ascididemin-induced cytotoxicity. Chem. Res. Toxicol. (2003) 16:113-122.
64. CHOLODY WM, HOROWSKA B, PARADZIEJ-LUKOWICZ J, MARTELLI S, KONOPA J: Structure-activity relationship for antineoplastic imidazoacridinones: synthesis and antileukemic activity in vivo. J. Med. Chem. (1996) 39:1028-1032.
65. BURGER AM, JENKINS TC, DOUBLE JA, BIBBY MC: Cellular uptake, cytotoxicity and DNA-binding studies of the novel imidazoacridinone antineoplastic agent C1311. Br. J. Cancer (1999) 81:367-375.
66. MAZERSKA Z, DZIEGIELEWSKI J, KONOPA J: Enzymatic activation of a new antitumour drug, 5-diethylaminoethylamino-8-hydroxyimidazoacridinone, C-1311, observed after its intercalation into DNA. Biochem. Pharmacol. (2001) 61:685-694.
67. KIRSHENBAUM MR, CHEN SF, BEHRENS CH et al.: (R,R)-2,2′-[1,2-ethanediylbis[imino(1-methyl-2,1-ethanediyl)]]- bis[5-nitro-1H-benz[de]isoquinoline-1,3-(2H)-dione] dimethanesulfonate (DMP-840), a novel bis-naphthatalimide with potent non-selective tumoricidal activity in vitro. Cancer Res. (1994) 54:2199-2206.
68. ANTONINI I: DNA-binding antitumor agents: from pyrimido[5,6,1-de]acridines to other intriguing classes of acridine derivatives. Curr. Med. Chem. (2002) 9:1701-1716.
69. SENDEROWICZ AM: Novel direct and indirect cyclin-dependent kinase modulators for the prevention and treatment of human neoplasms. Cancer Chemother. Pharmacol. (2003) 52:S61-S73.
70. LEHNE G: P-Glycoprotein as a drug target in the treatment of multidrug resistant cancer. Curr. Drug Targets (2000) 1:85-99.
71. HYAFIL F, VERGELY C, DU VIGNAUD P, GRAND-PERRET T: In vitro and in vivo reversal of multidrug resistance by GF-120918, an acridonecarboxamide derivative. Cancer Res. (1993) 53:4595-4602.
72. KEMPER EM, VAN ZANDBERGEN, CLEYPOOL C et al.: Increased penetration of paclitaxel into the brain by inhibition of P-glycoprotein. Clin. Cancer Res. (2003) 9:2849-2855.