DNA binding and anticancer activity of naphthalimides with 4-hydroxyl-alkylamine side chains at different lengths

被引：37
|
作者：
Wang, Kerang [1 ,2 ]
Wang, Yueqing [1 ]
Yan, Xinhao [1 ]
Chen, Hua [1 ]
Ma, Gang [1 ]
Zhang, Pingzhu [1 ]
Li, Jinmei [2 ,3 ]
Li, Xiaoliu [1 ,2 ]
Zhang, Jinchao [1 ]
机构：
[1] Hebei Univ, Key Lab Chem Biol Hebei Prov, Coll Chem & Environm Sci, Baoding 071002, Peoples R China
[2] Hebei Univ, Key Lab Med Chem & Mol Diag, Minist Educ, Baoding 071002, Peoples R China
[3] First Cent Hosp Baoding, Dept Pathol, Baoding 071000, Peoples R China
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 02期
基金：
中国国家自然科学基金;
关键词：
Naphthalimide; DNA binding; Fluorescence; Anticancer; Hydroxyl-alkylamine; DESIGN; INTERCALATORS; DERIVATIVES; UNBS5162; ANALOGS; AGENTS;
D O I：
10.1016/j.bmcl.2011.12.018
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
A series of novel naphthalimide derivatives modified with various hydroxyl-alkylamines at 4-position have been synthesized. Their DNA binding properties were investigated by UV-Vis, fluoescence, and circular dichroism (CD) spectroscopies and thermal denaturation. The results showed that compounds 3a-e as the DNA intercalator exhibited middle binding affinities with Ct-DNA. The anticancer activities of 3a-e were preliminarily evaluated, compounds 3c and 3e exhibited potent anticancer activities against Bel-7402 cell line with IC50 values of 5.57 and 9.17 mu M, respectively. More interestingly, enhancement of the fluorescence emission was found in the complexes of 3a-e with Ct-DNA, especially for 3c. This would make these compounds as potential DNA staining agents. (C) 2011 Elsevier Ltd. All rights reserved.
引用
下载
收藏
页码：937 / 941
页数：5
相关论文
共 31 条
  • [21] Conformational flexibility of mammalian cytochrome P4502B4 in binding imidazole inhibitors with different ring chemistry and side chains - Solution thermodynamics and molecular modeling
    Muralidhara, BK
    Negi, S
    Chin, CC
    Braun, W
    Halpert, JR
    JOURNAL OF BIOLOGICAL CHEMISTRY, 2006, 281 (12) : 8051 - 8061
  • [22] Synthesis, DNA-binding ability and anticancer activity of benzothiazole/benzoxazole-pyrrolo[2,1-c][1,4]benzodiazepine conjugates
    Kamal, Ahmed
    Reddy, K. Srinivasa
    Khan, M. Naseer A.
    Shetti, Rajesh V. C. R. N. C.
    Ramaiah, M. Janaki
    Pushpavalli, S. N. C. V. L.
    Srinivas, Chatla
    Pal-Bhadra, Manika
    Chourasia, Mukesh
    Sastry, G. Narahari
    Juvekar, Aarti
    Zingde, Surekha
    Barkume, Madan
    BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (13) : 4747 - 4761
  • [23] Facile synthesis of 1,2,3-triazole-fused indolo- and pyrrolo[1,4]diazepines, DNA-binding and evaluation of their anticancer activity
    Gour, Jitendra
    Gatadi, Srikanth
    Pooladanda, Venkatesh
    Ghouse, Shaik Mahammad
    Malasala, Satyaveni
    Madhavi, Y. V.
    Godugu, Chandraiah
    Nanduri, Srinivas
    BIOORGANIC CHEMISTRY, 2019, 93
  • [24] INVIVO ACTIVITY AND BIOCHEMICAL-CHARACTERIZATION OF SUBSTITUTED [1]BENZOTHIOPYRANO[4,3,2-CD]INDAZOLES, A NOVEL CLASS OF DNA-BINDING ANTICANCER AGENTS
    LEOPOLD, WR
    FRY, DW
    NELSON, JM
    PLOWMAN, J
    PROCEEDINGS OF THE AMERICAN ASSOCIATION FOR CANCER RESEARCH, 1985, 26 (MAR): : 253 - 253
  • [25] Synthesis, DNA binding affinity and anticancer activity of novel 4H-benzo[g][1,2,3]triazolo[5,1-c] [1,4] oxazocines
    Sastry, K. N. Visweswara
    Routhu, Sunitha Rani
    Datta, Soma Gupta
    Nagesh, Narayana
    Babu, Bathini Nagendra
    Nanubolu, Jagadeesh Babu
    Kumar, C. Ganesh
    Maurya, Ram Awatar
    Kamal, Ahmed
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (39) : 9294 - 9305
  • [26] Synthesis, DNA Binding Ability and Anticancer Activity of 2-heteroaryl Substituted Benzimidazoles Linked Pyrrolo[2,1-c][1,4] benzodiazepine Conjugates
    Kamal, Ahmed
    Pogula, Praveen Kumar
    Khan, Mohammed Naseer Ahmed
    Seshadri, Bobburi Naga
    Sreekanth, Kokkonda
    MEDICINAL CHEMISTRY, 2013, 9 (05) : 651 - 659
  • [27] DINUCLEAR COMPLEXES OF PLATINUM HAVING ANTICANCER PROPERTIES - DNA-BINDING STUDIES AND BIOLOGICAL-ACTIVITY OF BIS(4,4'-DIPYRAZOLYLMETHANE-N,N')-BIS[DICHLOROPLATINUM(II)] AND RELATED COMPLEXES
    BROOMHEAD, JA
    RENDINA, LM
    WEBSTER, LK
    JOURNAL OF INORGANIC BIOCHEMISTRY, 1993, 49 (03) : 221 - 234
  • [28] Studies on the DNA binding and anticancer activity of Ru(II) polypyridyl complexes by using a (2-(4-(diethoxymethyl)-1H-imidazo[4,5-f][1,10] phenanthroline)) intercalative ligand
    Vuradi, Ravi Kumar
    Dandu, Kamakshi
    Yata, Praveen Kumar
    Rani, Vinoda M.
    Mallepally, Rajender Reddy
    Chintakuntla, Nagamani
    Ch, Ravi
    Thakur, Suman S.
    Rao, Ch Mohan
    Satyanarayana, S.
    NEW JOURNAL OF CHEMISTRY, 2018, 42 (02) : 846 - 859
  • [29] Studies on the DNA binding and anticancer activity of Ru(II) polypyridyl complexes by using a (2-(4-(diethoxymethyl)-1H-imidazo[4,5-f][1,10] phenanthroline)) intercalative ligand (vol 42, pg 846, 2018)
    Vuradi, Ravi Kumar
    Dandu, Kamakshi
    Yata, Praveen Kumar
    Rani, Vinoda M.
    Mallepally, Rajender Reddy
    Chintakuntla, Nagamani
    Ravi, Ch.
    Thakur, Suman S.
    Rao, Ch. Mohan
    Satyanarayana, S.
    NEW JOURNAL OF CHEMISTRY, 2019, 43 (32) : 12874 - 12874
  • [30] New [Ru(5,6-dmp/3,4,7,8-tmp)2(diimine)]2+ complexes: Non-covalent DNA and protein binding, anticancer activity and fluorescent probes for nuclear and protein components
    Rajendiran, Venugopal
    Palaniandavar, Mallayan
    Periasamy, Vaiyapuri Subbarayan
    Akbarsha, Mohammad Abdulkader
    JOURNAL OF INORGANIC BIOCHEMISTRY, 2012, 116 : 151 - 162
1234