用户名: 密码: 验证码:
Cytotoxicity and DNA-binding property of water-soluble naphthalene diimide derivatives bearing 2-oligoethoxy ethanamine side chain end-labeled with tertiary amino groups
详细信息    查看全文
  • 作者:Haiying Wei (1)
    Mengjiao Lv (1)
    Xiaoxu Duan (1)
    Shuai Li (1)
    Yuchao Yao (1)
    Kerang Wang (1)
    Pingzhu Zhang (1)
    Xiaoliu Li (1)
    Hua Chen (1)
  • 关键词:Naphthalene diimides ; Polyethylene glycol ; Water solubility ; Anti ; tumor activity ; DNA ; binding property
  • 刊名:Medicinal Chemistry Research
  • 出版年:2014
  • 出版时间:May 2014
  • 年:2014
  • 卷:23
  • 期:5
  • 页码:2277-2286
  • 全文大小:890 KB
  • 参考文献:1. Allenmark S (2003) Induced circular dichroism by chiral molecular interaction. Chirality 15:409鈥?22 CrossRef
    2. Berman HM, Young PR (1981) The interaction of intercalating drugs with nucleic acids. Annu Rev Biophys Bioeng 10:87鈥?14 CrossRef
    3. Campbell NH, Parkinson GN, Reszka AP, Neidle S (2008) Structural basis of DNA quadruplex recognition by an acridine drug. J Am Chem Soc 130:6722鈥?724 CrossRef
    4. Collie GW, Promontorio R, Hampel SM, Micco M, Neidle S, Parkinson GN (2012) Structural basis for telomeric G-quadruplex targeting by naphthalene diimide ligands. J Am Chem Soc 134:2723鈥?731 CrossRef
    5. Corpet DE, Parnaud G, Delverdier M, Peiffer G, Tache S (2000) Consistent and fast inhibition of colon carcinogenesis by polyethylene glycol in mice and rats given various carcinogens. Cancer Res 60:3160鈥?164
    6. Cragg GM, Grothaus PG, Newman DJ (2009) Impact of natural products on developing new anti-cancer agents. Chem Rev 109:3012鈥?043 CrossRef
    7. Cuenca F, Greciano O, Gunaratnam M, Haider S, Munnur D, Nanjunda R, Wilson WD, Neidle S (2008) Tri- and tetra-substituted naphthalene diimides as potent G-quadruplex ligands. Bioorg Med Chem Lett 18:1668鈥?673 CrossRef
    8. Di Antonio M, Doria F, Richter SN, Bertipaglia C, Mella M, Sissi C, Palumbo M, Freccero M (2009) Quinone methides tethered to naphthalene diimides as selective G-quadruplex alkylating agents. J Am Chem Soc 131:13132鈥?3141 CrossRef
    9. Doria F, Nadai M, Sattin G, Pasotti L, Richter SN, Freccero M (2012) Water soluble extended naphthalene diimides as pH fluorescent sensors and G-quadruplex ligands. Org Biomol Chem 10:3830鈥?840 CrossRef
    10. Faulhaber K, Granzhan A, Ihmels H, Otto D, Thomas L, Wells S (2011) Studies of the fluorescence light-up effect of amino-substituted benzo[b]quinolizinium derivatives in the presence of biomacromolecules. Photochem Photobiol Sci 10:1535鈥?545 CrossRef
    11. Gunaratnam M, Swank S, Haider SM, Galesa K, Reszka AP, Beltran M, Cuenca F, Fletcher JA, Neidle S (2009) Targeting human gastrointestinal stromal tumor cells with a quadruplex-binding small molecule. J Med Chem 52:3774鈥?783 CrossRef
    12. Gunaratnam M, de la Fuente M, Hampel SM, Todd AK, Reszka AP, Schatzlein A, Neidle S (2011) Targeting pancreatic cancer with a G-quadruplex ligand. Bioorg Med Chem 19:7151鈥?157 CrossRef
    13. Hampel SM, Sidibe A, Gunaratnam M, Riou JF, Neidle S (2010) Tetrasubstituted naphthalene diimide ligands with selectivity for telomeric G-quadruplexes and cancer cells. Bioorg Med Chem Lett 20:6459鈥?463 CrossRef
    14. Jain AK, Paul A, Maji B, Muniyappa K, Bhattacharya S (2012) Dimeric 1,3-phenylene-bis(piperazinyl benzimidazole)s: synthesis and structure-activity investigations on their binding with human telomeric G-quadruplex DNA and telomerase inhibition properties. J Med Chem 55:2981鈥?993 CrossRef
    15. Janovec L, Ko啪urkov谩 M, Sabolov谩 D, Ungvarsk媒 J, Paul铆kov谩 H, Pl拧铆kov谩 J, Vantov谩 Z, Imrich J (2011) Cytotoxic 3,6-bis((imidazolidinone) imino) acridines: synthesis, DNA binding and molecular modeling. Bioorg Med Chem 19:1790鈥?801 CrossRef
    16. Jiang X, Shang L, Wang ZX, Dong S (2005) Spectrometric and voltammetric investigation of interaction of neutral red with calf thymus DNA: pH effect. Biophys Chem 118:42鈥?0 CrossRef
    17. Long EC, Barton JK (1990) On demonstrating DNA intercalation. Acc Chem Res 23:271鈥?73 CrossRef
    18. Lv M, Xu H (2009) Overview of naphthalimide analogs as anticancer agents. Curr Med Chem 16:4797鈥?813 CrossRef
    19. McKnight RE, Reisenauer E, Pintado MV, Polasani SR, Dixon DW (2011) Substituent effect on the preferred DNA binding mode and affinity of a homologous series of naphthalene diimides. Bioorg Med Chem Lett 21:4288鈥?291 CrossRef
    20. Micco M, Collie GW, Dale AG, Ohnmacht SA, Pazitna I, Gunaratnam M, Reszka AP, Neidle S (2013) Structure-based design and evaluation of naphthalene diimide G-quadruplex ligands as telomere targeting agents in pancreatic cancer cells. J Med Chem 56:2959鈥?974 CrossRef
    21. Mosmann TJ (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Immunol Meth 65:55鈥?3 CrossRef
    22. Pandey S, Baker GA, Kane MA, Bonzagni NJ, Bright FV (2000) O2 quenching of ruthenium(II) tris(2,2鈥?bypyridyl)2+ within the water pool of perfluoropolyether-based reverse micelles formed in supercritical carbon dioxide. Langmuir 16:5593鈥?599 CrossRef
    23. Peduto A, Pagano B, Petronzi C, Massa A, Esposito V, Virgilio A, Paduano F, Trapasso F, Fiorito F, Florio S, Giancola C, Galeone A, Filosa R (2011) Design, synthesis, biophysical and biological studies of trisubstituted naphthalimides as G-quadruplex ligands. Bioorg Med Chem 19:6419鈥?429 CrossRef
    24. Purcell M, Neault JF, Tajmir-Riahi HA (2000) Interaction of taxol with human serum albumin. Biochem Biophys Acta 1478:61鈥?8
    25. Read MA, Neidle S (2000) Structural characterization of a guanine-quadruplex ligand complex. Biochemistry 39:13422鈥?3432 CrossRef
    26. Sahoo D, Bhattacharya P, Chakravorti S (2010) Reverse micelle induced flipping of binding site and efficiency of albumin protein with an ionic styryl dye. J Phys Chem B 114:10442鈥?0450 CrossRef
    27. Tumiatti V, Milelli A, Minarini A, Micco M, Campani AG, Roncuzzi L, Baiocchi D, Marinello J, Capranico G, Zini M, Stefanelli C, Melchiorre C (2009) Design, synthesis, and biological evaluation of substituted naphthalene imides and diimides as anticancer agent. J Med Chem 52:7873鈥?877 CrossRef
    28. Uma Maheswari P, Palaniandavar M (2004) DNA binding and cleavage activity of (Ru(NH3)4(diimine))Cl2 complexes. Inorg Chim Acta 357:901鈥?12 CrossRef
    29. Uma V, Kanthimathi M, Weyhermuller T, Nair BU (2005) Oxidative DNA cleavage mediated by a new copper (II) terpyridine complex: crystal structure and DNA binding studies. J Inorg Biochem 99:2299鈥?307 CrossRef
    30. Wang J, Wang D, Miller EK, Moses D, Bazan GC, Heeger AJ (2000a) Photoluminescence of water-soluble conjugated polymers: origin of enhanced quenching by charge transfer. Macromolecules 33:5153鈥?158 CrossRef
    31. Wang Z, Liu D, Dong S (2000b) Voltammetric and spectroscopic studies on methyl green and cationic lipid bound to calf thymus DNA. Biophys Chem 87:179鈥?84 CrossRef
    32. Wang YX, Zhang XB, Zhao J, Xie SQ, Wang CJ (2012a) Nonhematotoxic naphthalene diimide modified by polyamine: synthesis and biological evaluation. J Med Chem 55:3502鈥?512 CrossRef
    33. Wang SX, Li HD, Chen C, Zhang JC, Li SH, Qin XY, Li XL, Wang KR (2012b) Cytotoxicity and DNA binding property of phenanthrene imidazole with polyglycol side chains. Bioorg Med Chem Lett 22:6347鈥?351 CrossRef
    34. Williamson JR (1993) Guanine quarters. Curr Opin Struct Biol 3:357鈥?62 CrossRef
    35. Xie LJ, Cui JN, Qian XH (2011) 5-Non-amino aromatic substituted naphthalimides as potential antitumor agents: synthesis via Suzuki reaction, antiproliferative activity, and DNA-binding behavior. Bioorg Med Chem 19:961鈥?67 CrossRef
    36. Zhang ZC, Yang YY, Zhang DN, Wang YY, Qian XH, Liu FY (2006) Acenaphtho[1,2-b]pyrrole derivatives as new family of intercalators: various DNA binding geometry and interesting antitumor capacity. Bioorg Med Chem 14:6962鈥?970 CrossRef
    37. Zhang PZ, Wei C, Duan XX, Zhang XY, Wang KR, Chen H, Li XL (2012) Selective synthesis of bromo-substituted naphthalene dianhydride derivatives. Chem J Chin Univ 33:1466鈥?470
  • 作者单位:Haiying Wei (1)
    Mengjiao Lv (1)
    Xiaoxu Duan (1)
    Shuai Li (1)
    Yuchao Yao (1)
    Kerang Wang (1)
    Pingzhu Zhang (1)
    Xiaoliu Li (1)
    Hua Chen (1)

    1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding, 071002, China
  • ISSN:1554-8120
文摘

© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号

地址:北京市海淀区学院路29号 邮编:100083

电话:办公室:(+86 10)66554848;文献借阅、咨询服务、科技查新:66554700