Natural and synthetic acridines/acridones as antitumor agents: their biological activities and methods of synthesis

Grzegorz Cholewiński1, Krystyna Dzierzbicka1, Aleksandra S. Kołodziejczyk1
1Department of Organic Chemistry, Gdansk University of Technology, Narutowicza 11/12, PL 80-233 Gdańsk, Poland

Tóm tắt

Từ khóa


Tài liệu tham khảo

Adams, 2002, Crystal structure of 9-amino-N-[2-(4-morpholinyl)ethyl]-4-acridinecarboxamide bound to d(CGTACG)2: implications for structure-activity relationships of acridinecarboxamide topoisomerase poisons, Nucleic Acids Res, 30, 719, 10.1093/nar/30.3.719

Afloroaei, 2004, New 9-substituted acridine derivatives with potential antitumor activity, Rev Chim, 55, 536

Akanitapichat, 2002, The antiviral agent 5-chloro-1,3-dihydroxyacridone interferes with assembly and maturation of herpes simplex virus, Antiviral Res, 53, 113, 10.1016/S0166-3542(01)00203-0

Albert, 1966

Amato, 2004, Synthesis of 3’–3’-linked pyrimidine oligonucleotides containing an acridine moiety for alternate strand triple helix formation, Eur J Org Chem, 2331, 10.1002/ejoc.200300803

Anderson, 2006, Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum, Bioorg Med Chem, 14, 334, 10.1016/j.bmc.2005.08.017

Antonini, 2002, DNA-binding antitumor agents: from pyrimido[5,6,1-de]acridines to other intriguing classes of acridine derivatives, Curr Med Chem, 9, 1701, 10.2174/0929867023369268

Antonini, 1999, 2,3-Dihydro-1H,7H-pyrimido[5,6,1-de]acridine-1,3,7-trione derivatives, a class of cytotoxic agents active on multidrug-resistant cell lines: Synthesis, biological evaluation, and structure-activity relationships, J Med Chem, 42, 2535, 10.1021/jm9805586

Antonini, 2003, Design, Synthesis, and Biological Properties of New Bis(acridine-4-carboxamides) as Anticancer Agents, J Med Chem, 46, 3109, 10.1021/jm030820x

Antonini, 2004, Rational Design, Synthesis, and biological evaluation of bis(pyrimido[5,6,1-de]acridines) and bis(pyrazolo[3,4,5-kl]acridine-5-carboxamides) as new anticancer agents, J Med Chem, 47, 5244, 10.1021/jm049706k

Antonini, 2006, Synthesis and biological evaluation of new asymmetrical bisintercalators as potential antitumor drugs, J Med Chem, 49, 7198, 10.1021/jm0606793

Asche, 2006, Nitrobenzylcarbamate prodrugs of cytotoxic acridines forpotential use with nitroreductase gene-directed enzyme prodrug therapy, Biorg Med Chem Lett, 16, 1990, 10.1016/j.bmcl.2005.12.089

Ashok, 2006, Pre-clinical toxicology and pathology of 9-(2‘-hydroxyethylamino)-4-methyl-1-nitroacridine (C-1748), a novel anti-cancer agent in male beagle dogs, Life Sci, 79, 1334, 10.1016/j.lfs.2006.03.043

Ashok, 2007, Preclinical toxicological examination of a putative prostate cancer-specific 4-methyl-1-nitroacridine derivative in rodents, Anticancer Drugs, 18, 87, 10.1097/01.cad.0000236316.04199.20

Atwell, 1972, Potential antitumor agents. 12. 9-Anilinoacridines, J Med Chem, 15, 611, 10.1021/jm00276a011

Atwell, 1987, Potential antitumor agents. 48. 3’-dimethylamino derivatives of amsacrine: Redox chemistry and in vivo solid tumor activity, J Med Chem, 30, 652, 10.1021/jm00387a012

Bacherikov, 2005, Synthesis and antitumor activity of 5-(9-acridinylamino)anisidine derivatives, Bioorg Med Chem, 13, 6513, 10.1016/j.bmc.2005.07.018

Bahr, 1997, Highly pPhotoresistant chemosensors using acridone as fluorescent label, Tetrahedron Lett, 38, 1489, 10.1016/S0040-4039(97)00137-8

Belmont, 2004, New methodology for acridine synthesis using a rhodium-catalyzed benzannulation, Tetrahedron Lett, 45, 2783, 10.1016/j.tetlet.2004.02.022

Belmont, 2007, Acridine and acridone derivatives, anticancer properties and synthetic methods: Where are we now?, Anti-Cancer Agents Med Chem, 7, 139, 10.2174/187152007780058669

Belmont, 2008, Acridine/acridone: a simple scaffold with a wide range of application in oncology, Expert Opin Ther Patents, 18, 1211, 10.1517/13543776.18.11.1211

Bongui, 2005, Synthesis and cytotoxic activity of acronycine analogues in the benzo[c]pyrano[3,2-h]-acridin-7-one and naphtho[1,2-b][1,7] and [1,10]- phenanthrolin-7(14H)-one series, Chem Pharm Bull, 53, 1540, 10.1248/cpb.53.1540

Borowski, 2005, Strategies for overcoming ABC-transporters-mediated multidrug resistance (MDR) of tumor cells. Review, Acta Biochim Polon, 52, 609, 10.18388/abp.2005_3421

Bouffier, 2006, Amino- and glycoconjugates of pyrido[4,3,2-kl]acridine. Synthesis, antitumor activity, and DNA binding, Bioorg Med Chem, 14, 7520, 10.1016/j.bmc.2006.07.010

Bouffier, 2004, Reactivity of pyrido[4,3,2-kl]acridines: Regioselective formation of 6 substituted derivatives, J Org Chem, 69, 8144, 10.1021/jo0487855

Boumendjel, 2007, Acridone derivatives: Design, synthesis, and inhibition of breast cancer resistance protein ABCG2, Bioorg Med Chem, 15, 2892, 10.1016/j.bmc.2007.02.017

Bousquet, 1995, Preclinical Evaluation of LU 79553: A novel bis-naphthalimide with potent antitumor activity, Cancer Res, 55, 1176

Campbell, 2008, Structural basis of DNA quadruplex recognition by an acridine drug, J Am Chem Soc, 130

Capps, 1985, Eur Patent, 138302, 1984, Chem Abstr, 103

Chang, 2003, New analogues of AHMA as potential antitumor agents: Synthesis and biological activity, Bioorg Med Chem, 1, 4959, 10.1016/j.bmc.2003.09.001

Charmantray, 2003, 4-Hydroxymethyl-3-aminoacridine derivatives as a new family of anticancer agents, J Med Chem, 46, 967, 10.1021/jm020389w

Chiron, 2004, Reactivity of the acridine ring: A review, Synthesis, 313, 10.1055/s-2003-44379

Cholody, 1995, Bisimidazoacridones and related compounds: New antineoplastic agents with high selectivity against colon tumors, J Med Chem, 38, 3043, 10.1021/jm00016a007

Cholody, 1990, 5-[(Aminoalkyl)amino]imidazo[4,5,1-de]acridin-6-ones as a novel class of antineoplastic agents. Synthesis and biological activity, J Med Chem, 33, 49, 10.1021/jm00163a009

Cortés, 2007, Synthesis and spectral properties of 7-(p-bromophenyl)-10,10-dimethyl-8- alkylthio-7,9,10,11-tetrahydro-benz[c]acridines and deprotection-aromatization of 7-[(o-; and p-substituted)phenyl]-10,10-dimethyl-7,8,9,10,11,12-hexahydrobenz[c]acridin-8-thione, J Heterocycl Chem, 44, 39, 10.1002/jhet.5570440107

Costes, 2000, Synthesis and cytotoxic and antitumor activity of benzo[b]pyrano[3,2-h]acridin-7-one analogues of acronycine, J Med Chem, 43, 2395, 10.1021/jm990972l

Dai, 2007, Convenient synthesis of an N-(1-alkoxyl-9-fluorenyl)serine acridine conjugate, Synth Commun, 37, 129, 10.1080/00397910600978531

Delfourne, 2003, Synthesis and in vitro antitumor activity of an isomer of the marine pyridoacridine alkaloid ascididemin and related compounds, Bioorg Med Chem, 11, 4351, 10.1016/S0968-0896(03)00483-8

Demeunynck, 2004, Antitumor acridines, Expert Opin Ther Pat, 14, 55, 10.1517/13543776.14.1.55

Demeunynck, 2001, Interest of acridine derivatives in the anticancer chemotherapy, Curr Pharm Des, 7, 1703, 10.2174/1381612013397131

Denny, 2002, Acridine derivatives as chemotherapeutic agents, Curr Med Chem, 9, 1655, 10.2174/0929867023369277

Denny, 2003, Dual topoisomerase I/II inhibitors in cancer therapy, Curr Top Med Chem, 3, 339, 10.2174/1568026033452555

Dheyongera, 2005, Synthesis, biological evaluation, and molecular modeling of novel thioacridone derivatives related to the anticancer alkaloid acronycine, Bioorg Med Chem, 13, 689, 10.1016/j.bmc.2004.10.051

Dzierzbicka, 2003, Synthesis and antitumor activity of conjugates of muramyldipeptide or normuramyldipeptide with hydroxyacridine/acridone derivatives, J Med Chem, 46, 183, 10.1021/jm020991m

Dzierzbicka, 2001, Synthesis and antitumor activity of conjugates of muramyldipeptide, normuramyldipeptide, and desmuramylpeptides with acridine/acridone derivatives, J Med Chem, 44, 3606, 10.1021/jm001115g

Faller, 1997, A novel acridone derivative for the fluorescence tagging and mass spectrometric sequencing of peptides, Chem Commun, 16, 1529, 10.1039/a701787a

Ferguson, 2007, Genotoxicity of non-covalent interactions: DNA intercalators, Mutat Res, 623, 14, 10.1016/j.mrfmmm.2007.03.014

Fujiwara, 1999, Acridone derivatives are selective inhibitors of HIV-1 replication in chronically infected cells, Antiviral Res, 43, 189, 10.1016/S0166-3542(99)00045-5

Gaslonde, 2007, Synthesis and cytotoxic cctivity of dimeric analogs of acronycine in the benzo[b]pyrano[3,2-h]acridin-7-one series, Chem Pharm Bull, 55, 734, 10.1248/cpb.55.734

Géci, 2006, Synthesis of twisted intercalating nucleic acids possessing acridine derivatives. Thermal stability studies, Bioconjug Chem, 17, 950, 10.1021/bc060058o

Gniazdowski, 1995, Nitracrine and its congeners – An overview, Gen Pharmacol, 26, 473, 10.1016/0306-3623(94)00143-B

Gunaratnam, 2007, Mechanism of acridine-based telomerase inhibition and telomere shortening, Biochem Pharmacol, 74, 679, 10.1016/j.bcp.2007.06.011

Hamy, 1998, A new class of HIV-1 Tat antagonist acting through Tat-TAR inhibition, Biochemistry, 37, 5086, 10.1021/bi972947s

Harrison, 2003, Trisubstituted acridine derivatives as potent and selective telomerase inhibitors, J Med Chem, 46, 4463, 10.1021/jm0308693

Ishihara, 2005, Reaction of acridine with pyrazolone derivatives. J, Heterocycl Chem, 42, 963, 10.1002/jhet.5570420533

Kelland, 2005, Overcoming the immortality of tumour cells by telomere and telomerase based cancer therapeutics – current status and future prospects, Eur J Cancer, 41, 971, 10.1016/j.ejca.2004.11.024

Konopa, 2003, 9-alkylamino-1-nitroacridine derivatives, Patent US6589961 (B2

Kukowska-Kaszuba, 2007, Synthesis and structure-activity studies of peptide-acridine/acridone conjugates, Curr Med Chem, 14, 3079, 10.2174/092986707782793961

Lemke, 2005, Induction of unique structural changes in guanine-rich DNA regions by the triazoloacridone C-1305, a topoisomerase II inhibitor with antitumor activities, Nucleic Acids Res, 33, 6034, 10.1093/nar/gki904

Ma, 2007, Unexpected reactivity of the 9-aminoacridine chromophore in guanidylation reactions, J Org Chem, 72, 5387, 10.1021/jo0705972

Magnano, 2004, Synthesis and biological evaluation of indazolo[4,3-bc]-[1,5]naphthyridines(10-aza-pyrazolo[3,4,5-kl]acridines): a new class of antitumor agents, Bioorg Med Chem, 12, 5941, 10.1016/j.bmc.2004.08.020

Martinez, 2005, The search of DNA-intercalators as antitumoral drugs: What it worked and what did not work, Curr Med Chem, 12, 127, 10.2174/0929867053363414

Martins, 2007, Structure-based design of benzylamino-acridine compounds as G-quadruplex DNA telomere targeting agents, Bioorg Med Chem Lett, 17, 2293, 10.1016/j.bmcl.2007.01.056

Mazerska, 1990, QSAR of acridines. II, Features of nitracrine analogs for high anti-tumor activity and selectivity on mice, searched by PCA and MRA methods, Anticancer Drug Des, 5, 169

Mazerska, 2003, Molecular mechanism of the enzymatic oxidation investigated for imidazoacridinone antitumor drug, C-1311, Biochem Pharmacol, 66, 1727, 10.1016/S0006-2952(03)00477-5

Michael, 2008, Quinoline, quinazoline and acridone alkaloids, Nat Prod Rep, 25, 166, 10.1039/B612168N

Michael, 2007, Quinoline, quinazoline and acridone alkaloids, Nat Prod Rep, 24, 223, 10.1039/b509528j

Michel, 2004, Benzo[b]acronycine derivatives: a novel class of antitumor agents, Eur J Med Chem, 39, 649, 10.1016/j.ejmech.2004.05.001

Moore, 2006, Trisubstituted acridines as G-quadruplex telomere targeting agents. Effects of extensions of the 3,6- and 9-side chains on quadruplex binding, telomerase activity, and cell proliferation, J Med Chem, 49, 582, 10.1021/jm050555a

Murugan, 2005, Facile and simple route to the synthesis of condensed acridine systems, Synth Commun, 35, 1781, 10.1081/SCC-200063947

Nadaraj, 2007, One-pot multicomponent synthesis of some novel acridines, Indian J Chem Sect B, 46, 1703

Narayanan, 2005, Comparative analysis of mutagenic potency of 1-nitro-acridine derivatives, Life Sci, 77, 2312, 10.1016/j.lfs.2005.03.020

Němcová, 2006, Physicochemical properties of 9-(alkylsulfanyl)- and 9-(arylsulfanyl)acridine derivatives and their interaction with (2-hydroxypropyl)cyclodextrins, Collect Czechoslov Chem Commun, 71, 179, 10.1135/cccc20060179

Nguyen, 2006, Synthesis, antitumor activity, and mechanism of action of benzo[a]pyrano[3,2-h]acridin-7-one analogues of acronycine, J Med Chem, 49, 3383, 10.1021/jm0602007

Nishio, 2006, Synthesis of acridone derivatives using polymer-supported palladium and scandium catalysts, J Comb Chem, 8, 459, 10.1021/cc060011+

Ouberai, 2006, 3,4-Dihydro-1H-[1,3]oxazino[4,5-c]acridines as a new family of cytotoxic drugs, Bioorg Med Chem Lett, 16, 4641, 10.1016/j.bmcl.2006.05.101

Pawlak, 1984, Cytotoxic and antitumor activity of 1-nitroacridines as an aftereffect of their interstrand DNA cross-linking, J Cancer Res, 44, 4289

Patin, 2005, A new route to acridines: Pauson-Khand reaction on quinoline-bearing 1-en-7-ynes leading to novel tetrahydrocyclopenta[c]acridine-2,5-diones, Synthesis (Stuttg, 14, 2400

Perry, 1998, Human telomerase inhibition by regioisomeric disubstituted amidoanthracene-9,10-diones, J Med Chem, 41, 4873, 10.1021/jm981067o

Pleban, 2005, Inhibitors of P-glycoprotein – lead identification and optimisation, Mini Rev Med Chem, 5, 153, 10.2174/1389557053402729

Santelli-Rouvier, 2004, Synthesis of 9-acridinyl sulfur derivatives: sulfides, sulfoxides and sulfones. Comparison of their activity on tumor cells, Eur J Med Chem, 39, 1029, 10.1016/j.ejmech.2004.06.015

Sebestik, 2007, A role of the 9-aminoacridines and their conjugates in a life science, Curr Protein Pept Sci, 8, 471, 10.2174/138920307782411400

Stefańska, 2003, Synthesis and biological evaluation of 2,7-dihydro-3H-dibenzo[de,h]cinnoline-3,7-dione derivatives, a novel group of anticancer agents active on a multidrug resistant cell line, Bioorg Med Chem, 11, 561, 10.1016/S0968-0896(02)00425-X

Stefańska, 2005, 2,7-Dihydro-3H-pyridazino[5,4,3-kl]acridin-3-one derivatives, novel type of cytotoxic agents active on multidrug-resistant cell lines. Synthesis and biological evaluation, Bioorg Med Chem, 13, 1969, 10.1016/j.bmc.2005.01.023

Stefańska, 1999, 8,11-Dihydroxy-6-[(aminoalkyl)amino]-7H-benzo[e]perimidin-7-ones with activity in multidrug-resistant cell lines: Synthesis and antitumor evaluation, J Med Chem, 42, 3494, 10.1021/jm980682p

Su, 1995, 9-Substituted acridine derivatives with long half-life and potent antitumor activity: Synthesis and structure-activity relationships, J Med Chem, 38, 3226, 10.1021/jm00017a006

Su, 2006, Potent antitumor 9-anilinoacridines and acridines bearing an alkylating N-mustard residue on the acridine chromophore: Synthesis and biological activity, J Med Chem, 49, 3710, 10.1021/jm060197r

Tadi, 2007, Pre-clinical evaluation of 1-nitroacridine derived chemotherapeutic agent that has preferential cytotoxic activity towards prostate cancer, Cancer Biol Ther, 6, 1632, 10.4161/cbt.6.10.4790

Thi Mai, 2005, Design, synthesis, and cytotoxic activity of michael acceptors and enol esters in the benzo[b]acronycine series, Chem Pharm Bull, 53, 919, 10.1248/cpb.53.919

Thi Mai, 2003, Structure-activity relationships and mechanism of action of antitumor benzo[b]pyrano[3,2-h]acridin-7-one acronycine analogues, J Med Chem, 46, 3072, 10.1021/jm030790y

Todd, 1999, Major groove binding and “DNA-induced” fit in the intercalation of a derivative of the mixed topoisomerase I/II poison N-(2-(dimethylamino)ethyl)acridine-4-carboxamide (DACA) into DNA: X-ray structure complexed to d(CG(5-BrU)ACG)2 at 1.3-ANG resolution, J Med Chem, 42, 536, 10.1021/jm980479u

Tu, 2007, New reaction of Schiff base with dimedone: New method for the acridine derivatives under microwave irradiation, J Heterocycl Chem, 44, 83, 10.1002/jhet.5570440114

Vispè, 2007, Novel tetra-acridine derivatives as dual inhibitors of topoisomerase II and the human proteasome, Biochem Pharmacol, 73, 1863, 10.1016/j.bcp.2007.02.016

Wang, 2004, New acridone derivatives for the electrochemical DNA-hybridisation labelling, Bioelectrochemistry, 63, 233, 10.1016/j.bioelechem.2003.10.020

Wang, 2008, Restoration of p53 to limit tumor growth, Curr Opin Oncol, 20, 90, 10.1097/CCO.0b013e3282f31d6f

Wang, 2005, Acridine derivatives activate p53 and induce tumor cell death through Bax, Cancer Biol Ther, 4, 893, 10.4161/cbt.4.8.2134

Wang, 2006, A clean procedure for synthesis of benzo[c]acridine derivatives: reaction of N-arylidenenaphthalen-1-amine with 5,5-dimethyl-1,3-cyclohexadione in aqueous medium, Arkivoc, ii, 117, 10.3998/ark.5550190.0007.213

Wesierska-Gadek, 2004, Increased susceptibility of poly(ADP-ribose) polymerase-1 knockout cells to antitumor triazoloacridone C-1305 is associated with permanent G2 cell cycle arrest, Cancer Res, 64, 4487, 10.1158/0008-5472.CAN-03-3410

WHO. Chronicle, World Health Organization, Geneva, 1976, 30, 11

Wysocka-Skrzela, 1982, 1-Nitro-9-hydroxyalkylaminoacridines or their salts, Eur Patent Appl, 0038572, 1981, Chem Abstr, 96

Wysocka-Skrzela, 1984, Process for preparing aminoacid derivatives of 1-nitroacridine or their salts, Polish Patent Appl, 119667, 1983, Chem Abstr, 100

Yang, 2005, Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines: design, synthesis and evaluation of cytotoxic activity, Tetrahedron, 61, 11895, 10.1016/j.tet.2005.09.065

Yang, 2006, Isoquino[4,5-bc]acridines: Design, synthesis and evaluation of DNA binding, anti-tumor and DNA photo-damaging ability, J Photochem Photobiol B, 84, 221, 10.1016/j.jphotobiol.2006.03.005

Zeghida, 2007, Application of 2,2,2-trichloroethoxycarbonyl protection to aminoacridines, Synthesis (Stuttg), 17, 231