Quinolones in the search for new anticancer agents

Current Pharmaceutical Design

Volumn 22, Issue 39, 2016, Pages 6009-6020

  Batalha, Pedro Netto ^a   de Souza, Maria Cecília Bastos Vieira ^a   Peña Cabrera, Eduardo ^b   Cruz, David Cruz ^b   Boechat, Fernanda da Costa Santos ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b UNIVERSITY OF GUANAJUATO   (Mexico)

Author keywords

Anticancer activity; Cancer; Complexes; Natural products; Photochemistry; Quinolones; Topoisomerase

Indexed keywords

ANTINEOPLASTIC AGENT; HETEROCYCLIC COMPOUND; METAL COMPLEX; PHOTOSENSITIZING AGENT; QUINOLONE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; BIOLOGICAL ACTIVITY; CANCER CHEMOTHERAPY; DERIVATIZATION; DRUG SYNTHESIS; HUMAN; MALIGNANT NEOPLASM; MOLECULAR HYBRIDIZATION; NONHUMAN; PHASE 3 CLINICAL TRIAL (TOPIC); PRIORITY JOURNAL; REVIEW; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; NEOPLASM; PATHOLOGY;

ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; HUMANS; NEOPLASMS; QUINOLONES;

EID: 85009262101     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612822666160715115025     Document Type: Review

References (62)

1. Solomon VR, Lee H. Quinoline as a privileged scaffold in cancer drug discovery. Curr Med Chem 2011; 18: 1488-508.
2. Du W. Towards new anticancer drugs: a decade of advances in synthesis of camptothecins and related alkaloids. Tetrahedron 2003; 59: 8649-87.
3. Thomas CJ, Rahier NJ, Hecht SM. Camptothecin: current perspectives. Bioorg Med Chem 2004; 12: 1585-604.
4. Ahmed A, Daneshtalab M. Nonclassical biological activities of quinolone derivatives. J Pharm Pharm Sci 2012; 15(1): 52-72.
5. Mugnaini C, Pasquini S, Corelli F. The 4-quinolone-3-carboxylic acid motif as a multivalent scaffold in medicinal chemistry. Curr Med Chem 2009; 16: 1747-67.
6. Stein EM, Tallman MS. Advances in Acute Myeloid Leikemia. Emerging therapeutic drugs for AML. Blood 2016; 127(1): 71-8.
7. Kantarjian H. Acute myeloid leukemia-Major progress over four decades and glimpses into the future. Am J Hematol 2016; 91(1): 131-45.
8. Ni ZJ, Barsanti P, Brammeier N, et al. 4-(Aminoalkylamino)-3-benzimidazole-quinolinones as potent CHK-1 inhibitors. Bioorg Med Chem Lett 2006; 16: 3121-24.
9. Jarak I, Krali M, Süman L, et al. Novel cyano-and Nisopropylamidino-substituted derivatives of benzo[b]thiophene-2-carboxanilides and benzo[b]thieno[2, 3-c]quinolones: synthesis, photochemical synthesis, crystal structure determination, and antitumor evaluation. J Med Chem 2005; 48: 2346-60.
10. Renhowe PA, Pecchi S, Shafer CM, et al. Design, Structure-Activity Relationships and in Vivo Characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: A Novel Class of Receptor Tyrosine Kinase Inhibitors. J Med Chem 2009; 52: 278-92.
11. Claassen G, Brn E, Crogan-Grundy C, et al. Selective activation of apoptosis by a novel set of 4-aryl-3-(3-aryl-1-oxo-2-propenyl)-2(1H)-quinolinones through a Myc-dependent pathway. Cancer Lett 2009; 274: 243-49.
12. Chou L, Tsai M, Hsu M, et al. Design, synthesis, and preclinical evaluation of new 5, 6-(or 6, 7-) disubstituted-2-(fluorophenyl)quinolin-4-one derivatives as potent antitumor agents. J Med Chem 2010; 53: 8047-58.
13. Cheng Y, Liu C, Tsai M, et al. Design, synthesis, and mechanism of action of 2-(3-hydroxy-5-methoxyphenyl)-6-pyrrolidinylquinolin-4-one as a potent anticancer lead. Bioorg Med Chem Lett 2013; 23: 5223-7.
14. Gim HJ, Jeon R, Li H, et al. Design and synthesis of azaisoflavone analogs as phytoestrogen mimetics. Eur J Med Chem 2014; 85: 107-18.
15. Kumar N, Raj VP, Jayshree BS, et al. Elucidation of structureactivity relationship of 2-quinolone derivatives and exploration of their antitumor potential through bax-induced apoptotic pathway. Chem Biol Drug Des 2012; 80: 291-9.
16. Chen Y, Lin Y, Huang P, et al. Design and synthesis of 6, 7-methylenedioxy-4-substituted phenylquinolin-2(1H)-one derivatives as novel anticancer agents that induce apoptosis with cell cycle arrest at G2/M phase. Bioorg Med Chem 2013; 21: 5064-75.
17. Komarnicka UK, Starosta R, Guz-Regner K, Bugla-Płoskon ́G, Kyzioł A, Jezowska-Bojczuk M. Phosphine derivatives of sparfloxacin-Synthesis, structures and in vitro activity. J Mol Struct 2015; 1096: 55-63.
18. Shou K, Li J, Jin Y, Lv W. Design, synthesis, biological evaluation, and molecular docking studies of quinolone derivatives as potential antitumor topoisomerase I inhibitors. Chem Pharm Bull 2013; 61(6): 631-6.
19. Forezi LSM, Tolentino NMC, Souza AMT et al. Synthesis, cytotoxicity and mechanistic evaluation of 4-oxoquinoline-3-carboxamide derivatives: finding new potential anticancer drugs. Molecules 2014; 19: 6651-70.
20. Via LD, Marzaro G, Ferrarese A, Gia O, Chilin A.. Pyrroloquinolinone-based dual topoisomerase I/II inhibitor. Eur J Med Chem 2014; 77: 103-9.
21. Aleksić M, Bertosa B, Nhili R, et al. Novel substituted benzothiophene and thienothiophene carboxanilides and quinolones: synthesis, photochemical synthesis, DNA-binding properties, antitumor evaluation and 3D-derived QSAR analysis. J Med Chem 2012; 55: 5044-60.
22. Boteva AA, Krasnykh OP. The methods of synthesis, modification, and biological activity of 4-quinolones (review). Chem Heterocycl Comp 2009; 45: 757-85.
23. Azéma J, Guidetti B, Dewelle J, et al. 7-((4-Substituted)piperazin-1-yl) derivatives of ciprofloxacin: Synthesis and in vitro biological evaluation as potential antitumor agents. Bioorg Med Chem 2009; 17: 5396-407.
24. Dinakaran M, Senthilkumar P, Yogeeswari P, China A, Nagaraja V, Sriram D. Novel ofloxacin derivatives: Synthesis, antimycobacterial and toxicological evaluation. Bioorg Med Chem Lett 2008; 18: 1229-36.
25. Stahlmann R. Clinical toxicological aspects of fluoroquinolones. Toxicol Lett 2002; 127: 269-77.
26. Rosen JE. Proposed mechanism for the photodynamic generation of 8-oxo-7, 8-dihydro-2’-deoxyguanosine produced in cultured cells by exposure to lomefloxacin. Mutat Res Fund Mol Mech Mutagen 1997; 381: 117-29.
27. Rosen JE, Prahalad AK, Schlüter G, Chen D, Williams GM. Quinolone antibiotic photodynamic production of 8-oxo-7, 8-dihydro-2’-deoxyguanosine in cultured liver epithelial cells. Photochem Photobiol 1997; 65: 990-6.
28. Martinez LJ, Sik RH, Chignell CF. Fluoroquinolone antimicrobials: singlet oxygen, superoxide and phototoxicity. Photochem Photobiol 1998; 67: 399-403.
29. Wainwright M. Photodynamic therapy: the development of new photosensitisers. Anti-Cancer Agents Med Chem 2008; 8: 280-91.
30. Barbierikova Z, Bella M, Kucerák J, et al. Photoinduced superoxide radical anion and singlet oxygen generation in the presence of novel selenadiazoloquinolones (an EPR study). Photochem Photobiol 2011; 87: 32-44.
31. Barbierikova Z, Bella M, Sekeráková L, et al. Spectroscopic characterization, photo induced processes and cytotoxic properties of substituted N-ethyl selenadiazoloquinolones. Phys Org Chem 2013; 26: 565-74.
32. Hiramatsu K, Morimoto Y, Baba T, Hayakawa I. Preparation of novel 2-quinolinones (analogs) as antibacterial agents, pharmaceuticals containing them (and conventional quinolones) for prevention and/or treatment of infectious diseases. WO Patent 2014171527, 2014.
33. Isaacs JT, Pili R, Qian DZ, et al. Identification of ABR-215050 as lead second generation quinoline-3-carboxamide anti-angiogenic agent for the treatment of prostate cancer. Prostate 2006; 66: 1768-78.
34. Tedesco R, Shaw AN, Bambal R, et al. Synthesis and antimicrobial screening of some 3-[4-(3-aryl-1-phenyl-1H-pyrazol-4-yl)-6-arylpyridin-2-yl] and 4-methyl-3-phenyl-6-[4-(3-aryl-1-phenyl-1Hpyrazol-4-yl)-6-aryl-pyridin-2-yl] coumarins. J Med Chem 2006; 49: 971-83.
35. Ukrainets IV, Mospanova EV, Bereznyakova NL, Naboka OI.4-Hydroxy-2-quinolones. Part 138. Synthesis and study of structurebiological activity relationships in a series of 1-hydroxy-3-oxo-5, 6-dihydro-3H-pyrrolo[3, 2, 1-ij]quinoline-2-carboxylic acid anilides, Chem Heterocycl Compd 2007; 43: 1532-39.
36. Barraja P, Diana P, Montalbano A, et al. Pyrrolo[3, 4-h]quinolinones a new class of photochemotherapeutic agents. Bioorg Med Chem 2011; 19: 2326-2341.
37. Spanó V, Parrino B, Carbone A, et al. Pyrazolo[3, 4-h]quinolines promising photosensitizing agents in the treatment of cancer. Eur J Med Chem 2015; 102: 334-51.
38. Jantová S, Koňariková K, Letašiová S, Paulovičová E, Milata V, Brezová V. Photochemical and phototoxic properties of ethyl 1, 4-dihydro-8-nitro-4-oxoquinoline-3-carboxylate, a new quinoline derivative. J Photochem Photobiol Biol; 2011; 102: 77-91.
39. Hasinoff BB, Wu X, Nitiss JL, Kanagasabai R, Yalowich JC. The anticancer multi-kinase inhibitor dovitinib also targets topoisomeraseI and topoisomerase II. Biochem Pharmacol 2012; 84: 1617-26.
40. Suthar SK, Tiwari A, Jaiswal V, Alex AT, Lohan S, Joesph A. Novel quinolone substituted thiazolidin-4-ones as antiinflammatory, anticancer agents: Design, synthesis and biological screening. Eur J Med Chem 2013; 63: 589-602.
41. Han S, Lee K, Choi JW, et al. Design and synthesis of 3-(4, 5, 6, 7-tetrahydro-3H-imidazo[4, 5-c]pyridin-2-yl)-1H-quinolin-2-ones as VEGFR-2 kinase inhibitors. Bioorg Med Chem Lett 2012; 22: 2837-42.
42. Cano C, Barbeau OR, Bailey C, et al. DNA-dependent protein kinase (DNA-PK) inhibitors. synthesis and biological activity of quinolin-4-one and pyridopyrimidin-4-one surrogates for the chromen-4-one chemotype. J Med Chem 2010; 53: 8498-507.
43. Raghavan S, Manogaran P, Narasimha KKG, et al. Synthesis and anticancer activity of novel curcumin-quinolone hybrids. Bioorg Med Chem Lett 2015; 25: 3601-5.
44. Kljun J, Bytzek AK, Kandioller W, et al. Physicochemical studies and anticancer potency of ruthenium η6-p-cymene complexes containing antibacterial quinolones. Organometallics 2011; 30: 2506-12.
45. Kljun J, Bratsos I, Alessio E, et al. New uses for old drugs: attempts to convert quinolone antibacterials into potential anticancer agents containing ruthenium. Inorg Chem 2013; 52: 9039-52.
46. Wang C, Wu Q, Zeng Y, et al. Synthesis, characterization and DNA-binding properties of Ru(II) complexes coordinated by ofloxacin as potential antitumor agents. J Coord Chem 2015; 6(9): 1489-99.
47. Ramachandran E, Raja DS, Bhuvanesh NSP, Natarajan K. Synthesis, characterization and in vitro pharmacological evaluation of new water soluble Ni(II) complexes of 4N-substituted thiosemicarbazones of 2-oxo-1, 2-dihydroquinoline-3-carbaldehyde. Eur J Med Chem 2013; 64: 179-89.
48. Creaven BS, Duff B, Egan DA, et al. Anticancer and antifungal activity of copper(II) complexes of quinolin-2(1H)-one-derived Schiff bases. Inorg Chim Acta 2010; 363: 4048-58.
49. Raja DS, Ramachandran E, Bhuvanesh NSP, Natarajan K. Synthesis, structure and in vitro pharmacological evaluation of a novel 2-oxo-1, 2-dihydroquinoline-3-carbaldehyde (2’-methylbenzoyl) hydrazone bridge copper(II) coordination polymer. Eur J Med Chem 2013; 64: 148-59.
50. Furrer J, Süss-Fink G. Thiolato-bridged dinucleararene ruthenium complexes and their potential as anticancer drugs. Coord Chem Rev 2016; 309: 36-50.
51. Turel I, Kljun J, Perdih F, et al. First ruthenium organometallic complex of antibacterial agent ofloxacin. crystal structure and interactions with DNA. Inorg Chem 2010; 49: 10750-2.
52. Pröhl M, Schubert US, Weigand W, Gottschaldt M. Metal complexes of curcumin and curcumin derivatives for molecular imaging and anticancer therapy. Coord Chem Rev 2016; 307: 32-41.
53. Srivastava V, Lee H. Chloroquine-based hybrid molecules as promising novel chemotherapeutic agents. Eur J Pharmacol 2015; 762: 472-86.
54. Medici S, Peana M, Nurchi VM, Lachowicz JI, Crisponi G, Zoroddu MA. Noble metals in medicine: Latest advances. Coord Chem Rev 2015; 284: 329-50.
55. Brissos RF, Caubet A, Gamez P. Possible DNA-interacting pathways for metal-based compounds exemplified with copper coordination compounds. Eur J Inorg Chem 2015; 2633-45.
56. Wang XX, Zan K, Shi SP, et al. Quinolone alkaloids with antibacterial and cytotoxic activities from the fruits of Evodia rutaecarpa. Fitoterapia 2013; 89: 1-7.
57. Zhao N, Li ZL, Li DH, et al. Quinolone and indole alkaloids from the fruits of Euodia rutaecarpa and their cytotoxicity against two human cancer cell lines. Phytochemistry 2015; 109: 133-9.
58. Huang X, Li W, Yang XW. New cytotoxic quinolone alkaloids from fruits of Evocadia rutaecarpa. Fitoterapia 2012; 83: 709-14.
59. Wang CF, Fan L, Tian M, et al. Radiosensitizing effect of schinifoline from Zanthoxylum schinifolium siebt et zucc on human nonsmall cell lung cancer A549 cells: a preliminary in vitro investigation. Molecules 2014; 19: 20128-38.
60. Kawada M, Inoue H, Ohba S, et al. Intervenolin, a new antitumor compound with anti-Helicobacter pylori activity, from Nocardia sp. ML96-86F2. J Antibiot 2013; 66(9): 543-8.
61. Abe H, Kawada M, Inoude H, et al. Synthesis of intervenolin, an antitumor natural quinolone with unusual substituents. Org Lett 2013; 15: 9; 2124-7.
62. Song WW, Zeng GZ, Peng WW, Chen KX, Tan NH. Cytotoxic amides and quinolones from Clausena lansium. Helvet Chim Acta 2014; 97: 298-305.