Research advance of anticancer drugs with coumarin structures

Chinese Journal of New Drugs

Volumn 22, Issue 20, 2013, Pages 2392-2404

  Xia, Ling Xian ^a   Wang, Yu Bin ^b   Huang, Wen Long ^a   Qian, Hai ^b  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

^b NANJING TECH UNIVERSITY   (China)

Author keywords

Anti tumor; Coumarins; Research advance

Indexed keywords

ANTINEOPLASTIC AGENT; COUMARIN DERIVATIVE;

ARTICLE; DRUG RESEARCH; DRUG STRUCTURE;

EID: 84887774599     PISSN: 10033734     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (96)

1. LIN H C, TSAI S H, CHEN C S, et al. Structure-activity relationship of coumarin derivatives on xanthine oxidase-inhibiting and free radical-scavenging activities[J]. Biochem Pharmacol, 2008, 75(6): 1416-1425.
2. YANG J Y, DELLA-FERA M, BAILE C. Esculetin induces mitochondria-mediated apoptosis in 3T3-L1 adipocytes[J]. Apoptosis, 2006, 11(8): 1371-1378.
3. KOK S H, YEH C C, CHEN M L, et al. Esculetin enhances TRAIL-induced apoptosis through DR5 upregulation in human oral cancer SAS cells[J]. Oral Oncol, 2009, 45(12): 1067-1072.
4. PARK S S, PARK S K, LIM J H, et al. Esculetin inhibits cell proliferation through the Ras/ERK1/2 pathway in human colon cancer cells[J]. Oncol Rep, 2011, 25(1): 223-230.
5. VÁZQUEZ R, RIVEIRO M E, VERMEULEN M, et al. Structure-anti-leukemic activity relationship study of ortho-dihydroxycoumarins in U-937 cells: Key role of the δ-lactone ring in determining differentiation-inducing potency and selective pro-apoptotic action[J]. Bioorg Med Chem, 2012, 20(18): 5537-5549.
6. YOU L, FENG S, AN R, et al. Osthole: a promising lead compound for drug discovery from a traditional Chinese medicine(TCM)[J]. Nat Prod Commun, 2009, 4(2): 297-302.
7. HUNG C M, KUO D H, CHOU C H, et al. Osthole suppresses hepatocyte growth factor (HGF)-induced epithelial-mesenchymal transition via repression of the c-Met/Akt/mTOR pathway in human breast cancer cells[J]. J Agr Food Chem, 2011, 59(17): 9683-9690.
8. XU X, ZHANG Y, QU D, et al. Osthole suppresses migration and invasion of A549 human lung cancer cells through inhibition of matrix metalloproteinase-2 and matrix metallopeptidase-9 in vitro[J]. Mol Med Rep, 2012, 6(5): 1018-1012.
9. YOU L, AN R, WANG X, et al. Discovery of novel osthole derivatives as potential anti-breast cancer treatment[J]. Bioorg Med Chem Lett, 2010, 20(24): 7426-7428.
10. 2011, 42(2): 107-111.
11. JERRIS P J, SMITH A B. Synthesis and configurational assignment of geiparvarin: a novel antitumor agent[J]. J Org Chem, 1981, 46(3): 577-585.
12. CHIMICHI S, BOCCALINI M, COSIMELLI B, et al. New geiparvarin analogues from 7-(2-oxoethoxy)coumarins as efficient in vitro antitumoral agents[J]. Tetrahedron Lett, 2002, 43(42): 7473-7476.
13. CHIMICHI S, BOCCALINI M, SALVADOR A, et al. Synthesis and biological evaluation of new geiparvarin derivatives[J]. Chem Med Chem, 2009, 4(5): 769-779.
14. ISMAIL M M, RATEB H S, HUSSEIN M M. Synthesis and docking studies of novel benzopyran-2-ones with anticancer activity[J]. Eur J Med Chem, 2010, 45(9): 3950-3959.
15. ZHANG Y, LV Z, ZHONG H, et al. Convenient synthesis of novel geiparvarin analogs with potential anti-cancer activity via click chemistry[J]. Eur J Med Chem, 2012, 53: 356-363.
16. CHEN Y L, LU C M, LEE S J, et al. Synthesis, antiproliferative, and vasorelaxing evaluations of coumarin α-methylene-γ-butyrolactones[J]. Bioorg Med Chem, 2005, 13(20): 5710-5716.
17. PATIL P O, BARI S B, FIRKE S D, et al. A comprehensive review on synthesis and designing aspects of coumarin derivatives as monoamine oxidase inhibitors for depression and Alzheimer's disease[J]. Bioorg Med Chem, 2013, doi: http://dx.doi.org/10.1016/j.bmc.2013.02.017.
18. DAVIS R A, VULLO D, MARESCA A, et al. Natural product coumarins that inhibit human carbonic anhydrases[J]. Bioorg Med Chem, 2013, 21(6): 1539-1543.
19. VAZQUEZ R, RIVEIRO M E, VERMEULEN M, et al. Toddaculin, a natural coumarin from Toddalia asiatica, induces differentiation and apoptosis in U-937 leukemic cells[J]. Phytomedicine, 2012, 19(8): 737-746.
20. LUO X, HE W, YIN H, et al. Two new coumarins from micromelum falcatum with cytotoxicity and brine shrimp larvae toxicity[J]. Molecules, 2012, 17(6): 6944-6952.
21. TER Haar E, KOWALSKI R J, HAMEL E, et al. Discodermolide, a cytotoxic marine agent that stabilizes microtubules more potently than taxol[J]. Biochemistry, 1996, 35(1): 243-250.
22. SMITH III A B, SHAW S J, MYLES D C. Discodermolide analogues and method of their use: WO, 2009006184[P]. 2009-08-01.
23. MARESCA A, TEMPERINI C, VU H, et al. Non-zinc mediated inhibition of carbonic anhydrases: coumarins are a new class of suicide inhibitors[J]. J Am Chem Soc, 2009, 131(8): 3057-3062.
24. TOUISNI N, MARESCA A, MCDONALD P C, et al. Glycosyl coumarin carbonic anhydrase IX and XII inhibitors strongly attenuate the growth of primary breast tumors[J]. J Med Chem, 2011, 54(24): 8271-8277.
25. LEE K, MIN K H, LEE K, et al. Preparation of coumarin-based compounds and their pharmaceutical compositions as multidrug resistance inhibitors: WO, 2010064817A2[P]. 2010-06-10.
26. AMIN K M, EISSA A A, ABOU-SERI S M, et al. Synthesis and biological evaluation of novel coumarin-pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents[J]. Eur J Med Chem, 2013, 60: 187-198.
27. MADUREIRA A M, MOLNAR A, ABREU P M, et al. A new sesquiterpene-coumarin ether and a new abietane diterpene and their effects as inhibitors of P-glycoprotein[J]. Planta Med, 2004, 70(9): 828-833.
28. GAMBARI R, LAMPRONTI I, BIANCHI N, et al. Structure and Biological Activity of Furocoumarins [M]//KHAN M. Bioactive Heterocycles III. J Heterocyclic Chem, 2007(9): 265-276.
29. KOENIGS L L, TRAGER W F. Mechanism-based inactivation of P450 2A6 by furanocoumarins[J]. Biochemistry, 1998, 37(28): 10047-10061.
30. 2007, 26(3): 255-260.
31. 2004, 31(3): 30-32.
32. LEE Y M, WU T H, CHEN S F, et al. Effect of 5-methoxypsoralen (5-MOP) on cell apoptosis and cell cycle in human hepatocellular carcinoma cell line[J]. Toxicol In Vitro, 2003, 17(3): 279-287.
33. SALVADOR A, DALL'ACQUA S, SARDO M S, et al. Erythroid induction of chronic myelogenous leukemia K562 cells following treatment with a photoproduct derived from the UV-A irradiation of 5-methoxypsoralen[J]. Chem Med Chem, 2010, 5(9): 1506-1512.
34. 2/M cell cycle arrest in Karpas 299 T-lymphoma cells[J]. J Photochem Photobiol B, 2006, 85(1): 39-48.
35. PENG Y, LIU W, XIONG J, et al. Down regulation of differentiated embryonic chondrocytes 1 (DEC1) is involved in 8-methoxypsoralen-induced apoptosis in HepG2 cells[J]. Toxicology, 2012, 301(1-3): 58-65.
36. ABDEL Hafez O M, AMIN K M, ABDEL-LATIF N A, et al. Synthesis and antitumor activity of some new xanthotoxin derivatives[J]. Eur J Med Chem, 2009, 44(7): 2967-2974.
37. KANG T J, LEE S Y, SINGH R P, et al. Anti-tumor activity of oxypeucedanin from Ostericum koreanum against human prostate carcinoma DU145 cells[J]. Acta Oncol, 2009, 48(6): 895-900.
38. LUO K W, SUN J G, CHAN J W, et al. Anticancer effects of imperatorin isolated from Angelica dahurica: induction of apoptosis in HepG2 cells through both death-receptor-and mitochondria-mediated pathways[J]. Chemotherapy, 2011, 57(6): 449-459.
39. 2012, 18(6): 203-205.
40. WU S B, PANG F, WEN Y, et al. Antiproliferative and apoptotic activities of linear furocoumarins from notopterygium incisum on cancer cell lines[J]. Planta Med, 2010, 76(1): 82-85.
41. ZHENG B, QING C, WANG J L, et al. A new furanocoumarin from the roots of Angelica oncosepala[J]. Chem Nat Compd, 2012, 48(5): 748-750.
42. MORITA H, DOTA T, KOBAYASHI J. Antimitotic activity of glaupalol-related coumarins from Glaucidium palmatum[J]. Bioorg Med Chem Lett, 2004, 14(14): 3665-3668.
43. DONG Y, SHI Q, PAI HC, et al. Antitumor agents. 272. structure-activity relationships and in vivo selective anti-breast cancer activity of novel neo-tanshinlactone analogues[J]. J Med Chem, 2010, 53(5): 2299-2308.
44. DALLA V L, MAMMI S, URIARTE E, et al. New furan side tetracyclic allopsoralen derivatives: synthesis and photobiological evaluation[J]. J Med Chem, 2006, 49(14): 4317-4326.
45. FRANCISCO C S, RODRIGUES L R, CERQUEIRA N M, et al. Synthesis of novel benzofurocoumarin analogues and their anti-proliferative effect on human cancer cell lines[J]. Eur J Med Chem, 2012, 47(1): 370-376.
46. BORGATTI M, CHILIN A, PICCAGLI L, et al. Development of a novel furocoumarin derivative inhibiting NF-κB dependent biological functions: Design, synthesis and biological effects[J]. Eur J Med Chem, 2011, 46(10): 4870-4877.
47. SAKASAI M, SHIBUYA Y, NAGASAWA A. Nfat signal inhibitor and hair-growing agent[P]. EP, 2348025 A1.2011-07-27.
48. WANG S Q, LI X, WANG X N, et al. Reversal of P-glycoprotein-mediated multidrug resistance in human leukemia cell line K562/A02 by archangelicin[J]. Chin J Nat Med, 2011, 9(2): 146-150.
49. HSIEH H P, CHANG J Y, KUO C C, et al. Coumarin compounds and their use for treating cancer[P]. US, 20090312317 A1. 2011-11-15.
50. BARTHOMEUF C, GRASSI J, DEMEULE M, et al. Inhibition of P-glycoprotein transport function and reversion of MDR1 multidrug resistance by cnidiadin[J]. Cancer Chemoth Pharm, 2005, 56(2): 173-181.
51. AHN K S, SIM W S, KIM I H. Decursin: a cytotoxic agent and protein kinase C activator from the root of angelica gigas[J]. Planta Med, 1996, 62(1): 7-9.
52. GUO J, JIANG C, WANG Z, et al. A novel class of pyranocoumarin anti-androgen receptor signaling compounds[J]. Mol Cancer Ther, 2007, 6(3): 907-917.
53. ZHANG Y, SHAIK A, XING C, et al. A synthetic decursin analog with increased in vivo stability suppresses androgen receptor signaling in vitro and in vivo[J]. Invest New Drugs, 2012, 30(5): 1820-1829.
54. JUNG S Y, CHOI J H, KWON S M, et al. Decursin inhibits vasculogenesis in early tumor progression by suppression of endothelial progenitor cell differentiation and function[J]. J Cell Biochem, 2012, 113(5): 1478-1487.
55. Kim H H, Sik Bang S, Seok Choi J, et al. Involvement of PKC and ROS in the cytotoxic mechanism of anti-leukemic decursin and its derivatives and their structure-activity relationship in human K562 erythroleukemia and U937 myeloleukemia cells[J]. Cancer Lett, 2005, 223(2): 191-201.
56. SU C R, YEH S F, LIU C M, et al. Anti-HBV and cytotoxic activities of pyranocoumarin derivatives[J]. Bioorg Med Chem, 2009, 17(16): 6137-6143.
57. KATHURIA A, JALAL S, TIWARI R, et al. Substituted coumarin derivatives: Synthesis and evaluation of antiproliferative and src kinase inhibitory activities[J]. Chem Biol Interface, 2011, 1(2): 279-296.
58. FONG W F, ZHANG J X, WU J Y, et al. Pyranocoumarin (+/-)-4'-o-acetyl-3'-o-angeloyl-cis-khellactone induces mitochondrial-dependent apoptosis in HL-60 cells[J]. Planta Med, 2004, 70(6): 489-495.
59. ZHANG J X, FONG W F, WU J Y, et al. Pyranocoumarins isolated from peucedanum praeruptorum as differentiation inducers in human leukemic HL-60 cells[J]. Planta Med, 2003, 69(3): 223-229.
60. WU J Y, FONG W F, ZHANG J X, et al. Reversal of multidrug resistance in cancer cells by pyranocoumarins isolated from Radix Peucedani[J]. Eur J Pharmacol, 2003, 473(1): 9-17.
61. FONG W F, SHEN X L, GLOBISCH C, et al. Methoxylation of 3', 4'-aromatic side chains improves P-glycoprotein inhibitory and multidrug resistance reversal activities of 7, 8-pyranocoumarin against cancer cells[J]. Bioorg Med Chem, 2008, 16(7): 3694-3703.
62. SHEN X, CHEN G, ZHU G, et al. (+/-)-3'-O, 4'-O-dicynnamoyl-cis-khellactone, a derivative of (+/-)-praeruptorin A, reverses P-glycoprotein mediated multidrug resistance in cancer cells[J]. Bioorg Med Chem, 2006, 14(21): 7138-7145.
63. SHEN X, CHEN G, ZHU G, et al. 3'-O, 4'-O-aromatic acyl substituted 7, 8-pyranocoumarins: a new class of P-glycoprotein modulators[J]. J Pharm Pharmacol, 2012, 64(1): 90-100.
64. ZHOU T, SHI Q, BASTOW K F, et al. Antitumor agents 286. design, synthesis, and structure-activity relationships of 3'r, 4'r-disubstituted -2', 2'-dimethyldihydropyrano [2, 3-f] chromone (DSP) analogues as potent chemosensitizers to overcome multidrug resistance[J]. J Med Chem, 2010, 53(24): 8700-8708.
65. JU Y, STILL C C, SACALIS J N, et al. Cytotoxic coumarins and lignans from extracts of the northern prickly ash (Zanthoxylum americanum)[J]. Phytother Res, 2001, 15(5): 441-443.
66. MAO W W, WANG T T, ZENG H P, et al. Synthesis and evaluation of novel substituted 5-hydroxycoumarin and pyranocoumarin derivatives exhibiting significant antiproliferative activity against breast cancer cell lines[J]. Bioorg Med Chem Lett, 2009, 19(16): 4570-4573.
67. OLDENBURG J, WATZKA M, ROST S, et al. VKORC1: molecular target of coumarins[J]. J Thromb Haemost, 2007, 5(Suppl 1): S1-S6.
68. MCCULLOCH P, GEORGE W. Warfarin inhibits metastasis of Mtln3 rat mammary carcinoma without affecting primary tumour growth[J]. Brit J Cancer, 1989, 59(2): 179.
69. PELTIER-PAIN P, TIMMONS S C, GRANDEMANGE A, et al. Warfarin glycosylation invokes a switch from anticoagulant to anticancer activity[J]. Chem Med Chem, 2011, 6(8): 1347-1350.
70. MAXWELL A. The interaction between coumarin drugs and DNA gyrase[J]. Mol Microbiol, 1993, 9(4): 681-686.
71. MARCU M G, CHADLI A, BOUHOUCHE I, et al. The heat shock protein 90 antagonist novobiocin interacts with a previously unrecognized ATP-binding domain in the carboxyl terminus of the chaperone[J]. J Biol Chem, 2000, 275(47): 37181-37186.
72. YU X M, SHEN G, NECKERS L, et al. Hsp90 inhibitors identified from a library of novobiocin analogues[J]. J Am Chem Soc, 2005, 127(37): 12778-12779.
73. BURLISON J A, NECKERS L, SMITH A B, et al. Novobiocin: redesigning a DNA gyrase inhibitor for selective inhibition of hsp90[J]. J Am Chem Soc, 2006, 128(48): 15529-15536.
74. DONNELLY A C, MAYS J R, BURLISON J A, et al. The design, synthesis, and evaluation of coumarin ring derivatives of the novobiocin scaffold that exhibit antiproliferative activity[J]. J Org Chem, 2008, 73(22): 8901-8920.
75. BURLISON J A, AVILA C, VIELHAUER G, et al. Development of novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines[J]. J Org Chem, 2008, 73(6): 2130-2137.
76. Le Bras G, RADANYI C, PEYRAT J F, et al. New novobiocin analogues as antiproliferative agents in breast cancer cells and potential inhibitors of heat shock protein 90[J]. J Med Chem, 2007, 50(24): 6189-6200.
77. ZHAO H, BLAGG B S. Novobiocin analogues with second-generation noviose surrogates[J]. Bioorg Med Chem Lett, 2013, 23(2): 552-557.
78. ZHAO H, DONNELLY A C, KUSUMA B R, et al. Engineering an antibiotic to fight cancer: optimization of the novobiocin scaffold to produce anti-proliferative agents[J]. J Med Chem, 2011, 54(11): 3839-3853.
79. ZHAO H, KUSUMA B R, BLAGG B S. Synthesis and evaluation of noviose replacements on novobiocin that manifest antiproliferative activity[J]. ACS Med Chem Lett, 2010, 1(7): 311-315.
80. STANWAY S J, PUROHIT A, WOO L W, et al. Phase I study of STX 64 (667 Coumate) in breast cancer patients: The first study of a steroid sulfatase inhibitor[J]. Clin Cancer Res, 2006, 12(5): 1585-1592.
81. WOO L W, PUROHIT A, MALINI B, et al. Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates[J]. Chem Biol, 2000, 7(10): 773-791.
82. WOO L W, GANESHAPILLAI D, THOMAS M P, et al. Structure-activity relationship for the first-in-class clinical steroid sulfatase inhibitor irosustat (STX64, BN83495)[J]. Chem Med Chem, 2011, 6(11): 2019-2034.
83. Saulnier Sholler G L, BRARD L, STRAUB J A, et al. Nifurtimox induces apoptosis of neuroblastoma cells in vitro and in vivo[J]. J Pediat Hematol Oncol, 2009, 31(3): 187-193.
84. SINGH R, LANGE T, KIM K, et al. A coumarin derivative (RKS262) inhibits cell-cycle progression, causes pro-apoptotic signaling and cytotoxicity in ovarian cancer cells[J]. Invest New Drugs, 2011, 29(1): 63-72.
85. HAN S, ZHOU V, PAN S, et al. Identification of coumarin derivatives as a novel class of allosteric MEK1 inhibitors[J]. Bioorg Med Chem Lett, 2005, 15(24): 5467-5473.
86. CHENG J F, CHEN M, WALLACE D, et al. Discovery and structure-activity relationship of coumarin derivatives as TNF-α inhibitors[J]. Bioorg Med Chem Lett, 2004, 14(10): 2411-2415.
87. HEMMER M, KEMPEN I, De Tullio P, et al. New biological investigations on 3-bromophenyl 6-acetoxymethyl-2-oxo-2H-1-benzopyran-3-carboxylate as anti-angiogenic agent[J]. Drug Develop Res, 2010, 71(3): 209-218.
88. SERRA S, CHICCA A, GERTSCH J, et al. Synthesis of a series of different hydroxycoumarins and their cytotoxic activity [C]. Proceedings of the MDPI AG, 2012: b008/001-b008/004.
89. CHEN S, CHO M, KARLSBERG K, et al. Biochemical and biological characterization of a novel anti-aromatase coumarin derivative[J]. J Biol Chem, 2004, 279(46): 48071-48078.
90. LIU X H, LI J, SHI J B, et al. Design and synthesis of novel 5-phenyl-N-piperidine ethanone containing 4, 5-dihydropyrazole derivatives as potential antitumor agents[J]. Eur J Med Chem, 2012, 51: 294-299.
91. LIU X H, LIU H F, CHEN J, et al. Synthesis and molecular docking study of novel coumarin derivatives containing 4, 5-dihydropyrazole moiety as potential antitumor agents[J]. Bioorg Med Chem Lett, 2010, 20(19): 5705-5708.
92. BENCI K, MANDIC L, SUHINA T, et al. Novel coumarin derivatives containing 1, 2, 4-triazole, 4, 5-dicyanoimidazole and purine moieties: synthesis and evaluation of their cytostatic activity[J]. Molecules, 2012, 17(9): 11010-11025.
93. MUSA M A, BADISA V L, LATINWO L M, et al. Cytotoxic activity of new acetoxycoumarin derivatives in cancer cell lines[J]. Anticancer Res, 2011, 31(6): 2017-2022.
94. SASHIDHARA K V, KUMAR A, KUMAR M, et al. Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents[J]. Bioorg Med Chem Lett, 2010, 20(24): 7205-7211.
95. REDDY N S, MALLIREDDIGARI M R, COSENZA S, et al. Synthesis of new coumarin 3-(N-aryl) sulfonamides and their anticancer activity[J]. Bioorg Med Chem Lett, 2004, 14(15): 4093-4097.
96. PAUL K, BINDAL S, LUXAMI V. Synthesis of new conjugated coumarin-benzimidazole hybrids and their anticancer activity[J]. Bioorg Med Chem Lett, 2013, 23(12): 3667-3672.