Antitumour acridines

Bibliography

• DEMEUNYNCK M, CHARMANTRAY F, MARTELLI A: Interest of acridine derivatives in the anticancer chemotherapy. Curl: Amin. Des. (2001) 7(17):1703–1724.
   Google Scholar
• DENNY WA: Acridine-based antitumour agents. In: Chemistry of antitumour agents, Mackie and Son Ltd, Glasgow and London, UK (1990):1–29.
   Google Scholar
• DENNY WA: Acridine derivatives as chemotherapeutic agents. Curl: Med. Chem. (2002) 9(18):1655–1665.
   PubMedGoogle Scholar
• ADAMS A: Crystal structures of acridines complexed with nucleic acids. Curl: Med. Chem. (2002) 9:1667–1675.
   PubMedGoogle Scholar
• 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 M nucleic add—drug interactions. Kluwer Academic Publishers, Dordrecht, Germany (1990191–206.
   Google Scholar
• BORITZKI TJ, PALMER BD, CODDINGTON JM, DENNY WA: Identification of the major lesion from the reaction of an acridine-targeted aniline mustard with DNA as an adenine Ni adduct. Chem. Res. Toxicol (1994) 7:41–46.
   PubMedGoogle Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• AT WELL 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. I Med. Chem. (1998) 41:4744–4754.
   Google Scholar
• FAN J-Y, TERCEL M, DENNY WA: Synthesis, DNA binding and cytotoxicity of 1- N-(9-acridinyl)amino]alkyl]carbony1-3-(chloro-methyl)-6-hydroxyindolines, a new class of DNA-targeted alkylating agents. Anticancer Drug Des. (1997) 12:277–293.
   PubMedGoogle Scholar
• BOWLER BE, HOLLIS LS, LIPPARD SJ: Synthesis and DNA binding and photonicking properties of acridine orange linked by a polymethylene tether to (1, 2-diamino ethane) dichloroplatinum (II). J. Am. Chem. Soc. (1984) 106:6102–6104.
   Web of Science ®Google Scholar
• SUNDQUIST WJ, BANCROFT DP, LIPPARD SJ: Synthesis, characterization, and biological activity of cis-diammineplatinium (II) complexes of the DNA intercalators 9-aminoacridine and chloroquine.i. Am. Chem. Soc. (1990) 112:1590–1596.
   Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• GUILBAUD N, LEONCE S, TILLEQUIN F et al.: Acronycine derivatives as promising antitumor agents. Anticancer Drugs (2002) 13:445–449.
   PubMed Web of Science ®Google Scholar
• •A recent review on the use of acronycine analogues as antiturnour agents.
   Google Scholar
• MICHEL S, SEGUIN E, TILLEQUIN F: Structure-activity relationships in the acronycine series. Curc Med. Chem. (2002) 9:1689–1700.
   PubMedGoogle Scholar
• THI MAT HD, GASLONDE T, MICHEL S et al.: Structure-activity relationships and mechanism of action of antitumor benzo [b] pyrano, 2-h] acridin- 7-one acronycine analogues. Med. Chem. (2003) 46:3072–3082.
   Google Scholar
• COSTES N, LE DEIT H, MICHEL S et al.: Synthesis and cytotoxic and antitumor activity of benzorblpyrano [3,2-h]acridin-7-one analogue of acronycine. J. Med. Chem. (2000) 43:2395–2402.
   PubMed Web of Science ®Google Scholar
• CHARMANTRAY F, DEMEUNYNCK M, CARREZ D et al: 4-Hydroxymethy1-3-aminoacridine derivatives as a new family of anticancer agents. J. Med. Chem. (2003) 46:967–977.
   PubMedGoogle Scholar
• CHARMANTRAY F, DUFLOS A, LHOMME J, DEMEUNYNCK M: Synthesis and study of 4-hydroxymethy1-3-alkylaminoacridines as models of a new class of DNA intercalating-alkylating agents. Chem. Soc., Perkin Trans. I (2001):2962–2968.
   Google Scholar
• FOYE WO: Cancer chemotherapeutic agents,American Chemical Society, Washington, USA (1995):483–500.
   Google Scholar
• SHANNON AM, BOUCHIER-HAYES DJ, CONDRON CM, TOOMEY D: Tumor hypwda, chemotherapeutic resistance and hypwda-related therapies. Cancer Treatment Rev (2003) 29:297–307.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• BARTOSZEK 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) 103:141–151.
   PubMedGoogle Scholar
• GNIAZDOWSKI M, SZMIGIERO L: Nitracrine and its congeners: an overview. Gen. Pharmacol (1995) 26:473–481.
   PubMedGoogle Scholar
• SKLADANOWSKI A: Modulation of G2 arrest enhances cell death induced by the antitumor 1-nitroacridine derivative, Nitracrine. Apoptosis (2002) 7:347–359.
   PubMedGoogle Scholar
• ADJEI AA: Current status of pyrazoloacridine as an anticancer agent. Invest. New Drugs (1999) 17:43–48.
   PubMed Web of Science ®Google Scholar
• ••A recent review on pyrazoloacridinederivatives.
   Google Scholar
• DEES EC, ROWINSKY EK, NOE DA et al.: A Phase I and pharmacologic study of pyrazoloacridine and cisplatin in patients with advanced cancer. Invest. New Drugs (2003) 21:75–84.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• WILSON 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 Sapp]. (1996) 27:S43–47.
   Google Scholar
• 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 bis-bioreductive agent nitracrine N-oxide..1. Med. Chem. (1996) 39:2508–2517.
   Google Scholar
• 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.
   Google Scholar
• CORBETT AH, OSHEROFF N: When good enzymes go bad: conversion of topoisomerase II to a cellular toxin by antineoplastic drugs. Chem. Res. Toxicol (1993) 6:585–597.
   PubMed Web of Science ®Google Scholar
• BAGULEY BC, FERGUSON LR: Mutagenic properties of topoisomerase-targeted drugs. Biochim. Biophys. Acta (1998) 1400:213–222.
   PubMedGoogle Scholar
• DENNY WA, CAIN BF, AT WELL 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. I Merl Chem. (1982) 25:276–315.
   Google Scholar
• FINLAY GJ, AT WELL 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMedGoogle Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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 non-proliferating cells. Ear: I Cancer (1997) 33: 1668-1676.
   Google Scholar
• TURNBULL RIVI, MECZES EL, ROGERS MP et al.: Carbamate analogues of amsacrine active against non-cycling cells: relative activity against topoisomerases II a and 13. Cancer Chemother. Pharmacol. (1999) 44:275–282.
   PubMedGoogle Scholar
• FOSSE P, RENE 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.
   PubMedGoogle Scholar
• 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. Med. Chem. (1995) 38:3226–3235.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• DENNY WA, AT WELL GJ, REWCASTLE GW, BAGULEY BC: Potential antitumor agents. 49. 5-Substituted derivatives of N-(dimethylamino)ethyl]-9-aminoacridine-4-carboxamide with in vivo solid-tumor activity. J. Med. Chem. (1987) 30:658–663.
   Google Scholar
• DENNY WA: Dual topoisomerase I/II poisons as anticancer drugs. Expert Opin. Investig. Drugs (1997) 6:1845–1851.
   PubMedGoogle Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• SCHOFIELD PC, ROBERTSON IG, PAXTON JW et al.: Metabolism of N-(dimethylamino)ethyl]acridine-4-carboxamide in cancer patients undergoing a Phase I clinical trial. Cancer Chemother: Pharmacol. (1999) 44:51–58.
   PubMed Web of Science ®Google Scholar
• 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. Cancer (1999) 80:1786–1791.
   Google Scholar
• ANTONINI I, POLUCCI P, JENKINS TC et al.: 1- [(w-Aminoalkyl)amino]-4- [(co-aminoalkyl) carbamoyl] -9 -oxo-9, 10 - dihydroacridines as intercalating cytotoxic agents: synthesis, DNA binding and biological evaluation. J. Med. Chem. (1997) 40:3749–3755.
   PubMed Web of Science ®Google Scholar
• ANTONINI I, POLUCCI P, KELLAND LLOYD R et al.: N4-(w-aminoalkyl)-1-[(w-aminoalkyl)amino]-4-acridinecarboxamides: novel, potent, cytotoxic, and DNA-binding agents.' Med. Chem. (2000) 43:4801–4805.
   Google Scholar
• ANTONINI I, POLUCC1P, 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.
   Google Scholar
• 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.
   PubMedGoogle Scholar
• 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.
   PubMedGoogle Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• HEALD RA, MODI C, COOKSON JC et al.: Antitumor polycyclic acridines. 8. Synthesis and telomerase-inhibitory activity of methylated pentacyclic acridinium salts. Med. Chem. (2002) 45:590–597.
   Google Scholar
• GOWAN SM, HEALD R, STEVENS MF, KELLAND LR: Potent inhibition of telomerase by small-molecule pentacyclic acridines capable of interacting with G-quadruplexes. Mol. Pharmacol. (2001) 60:981–988.
   PubMed Web of Science ®Google Scholar
• MISSAILIDIS S, STANSLAS J, MODI C et al.: Antitumor polycyclic acridines. Part 12. Physical and biological properties of 8,13-diethy1-6-methylquino [4,3,2-kl]acridinium iodide: a lead compound in anticancer drug design. Oncology Res. (2002) 13:175–189.
   Google Scholar
• DELFOURNE E, BASTIDE J: Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents. Med. Res. Rev (2003) 23:234–252.
   PubMed Web of Science ®Google Scholar
• MOLINSKI TF: Marine pyridoacridine alkaloids: structure, synthesis and biological chemistry. Chem. Rev (1993) 93:1825–1838.
   Web of Science ®Google Scholar
• DING Q, CHICHAK K, LOWN JW: Pyrroloquinoline and pyridoacridine alkaloids from marine sources. Curr: Med. Chem. (1999) 6:1–27.
   PubMed Web of Science ®Google Scholar
• McDONALD LA, ELDREDGE GS, BARROWS LR, IRELAND CM: Inhibition of Topoisomerase II catalytic activity by pyridoacridine alkaloids from a Cystodytts sp. ascidian: a mechanism for the apparent intercalator-induced inhibition of topoisomerase II. J. Med. Chem. (1994) 37:3819–3827.
   Google Scholar
• 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.
   PubMedGoogle Scholar
• MATSUMOTO SS, BIGGS J, COPP BR,HOLDEN JA, BARROWS LR: Mechanism of ascididemin-induced cytotoxicity. Chem. Res. Toxicol. (2003) 16:113–122.
   PubMed Web of Science ®Google Scholar
• CHOLODY WM, HOROWSKA B, PARADZIEJ-LUKOWICZ J, MARTELLI S, KONOPA J: Structure-activity relationship for antineoplastic imidazoacridinones: synthesis and antileukemic activity in vivo. I Med. Chem. (1996) 39:1028–1032.
   PubMed Web of Science ®Google Scholar
• 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.
   Google Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• KIRSHENBAUM MR, CHEN SF, BEHRENS CH et al: (R,/i)-2,2'- [1,2-ethane diylbis[imino (1 -methyl-2, 1 - ethanediy1)]1- bis[5-nitro-1H-benz [de] isoquinoline- 1,3- (2H) -dionel dimethanesulfonate (DMP-840), a novel bis-naphthalimide with potent non-selective tumoricidal activity in vitro. Cancer Res. (1994) 54:2199–2206.
   PubMed Web of Science ®Google Scholar
• ANTONINI I: DNA-binding antitumor agents: from pyrimido[5,6,1-de]acridines to other intriguing classes of acridine derivatives. Carr. Med. Chem. (2002) 9:1701–1716.
   PubMedGoogle Scholar
• SENDEROWICZ AM: Novel direct and indirect cyclin-dependent kinase modulators for the prevention and treatment of human neoplasms. Cancer Chemother. Pliannacol. (2003) 52:S61–S73.
   Google Scholar
• LEHNE G: P-Glycoprotein as a drug target in the treatment of multidrug resistant cancer. Carr. Drug Targets (2000) 1:85–99.
   PubMedGoogle Scholar
• 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.
   PubMed Web of Science ®Google Scholar
• ••A review presenting the importance ofP-gp in chemotherapy.
   Google Scholar
• 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.
   PubMedGoogle Scholar