脱氢枞基苯甲酰腙衍生物与DNA作用及抗癌活性研究

doi:10.3969/j.issn.0253-2417.2015.02.001

Abstract

Abstract: Dehydroabietyl-2-hydroxy benzoylhydrazone (4) and dehydroabietyl-2-hydroxy-5-bromo benzoylhydrazone (6) were synthesized from dehydroabietic acid and characterized by IR, ¹H NMR, MS spectra and elemental analysis . Their interactions with Salmon sperm DNA were investigated by viscosity analysis, UV, and fluorescence spectrometry, etc. The experimental results showed that they were bound to DNA by intercalation and the binding ability of 4 is stronger than that of 6. The anticancer experiments by MTT method indicated that the compounds has high growth inhibitory activities on the selected cancer cells (HeLa, MCF-7, HL-60, and HepG-2) with the inhibitory rates of 73.9%-92.3% at the concentrations of 25 and 50 μmol/L. Their anticancer activities were all close to or greater than that of Cisplatin (66.3%-92.7%)

Key words: dehydroabietic acid, dehydroabietyl benzoylhydrazone, DNA, anticancer

CLC Number:

TQ351
O629

XU Wu-shuang, HUANG Zhi-xiang, GAO Wei-lin, ZHANG Jie, LONG Jian-ying, LIU Qing-bo, FEI Bao-li. DNA Binding and Anticancer Properties of Dehydroabietyl Benzoylhydrazone Derivatives[J]. Chemistry and Industry of Forest Products, 2015, 35(2): 1-7.

References

[1] LIPPERT B.Multiplicity of metal ion binding patterns to nucleobases[J].Coordination Chemistry Reviews, 2000, 200-202:487-516.
[2] LIU Chang-lin, WANG Ming, ZHANG Tian-le, et al.DNA hydrolysis promoted by di- and multi-nuclear metal complexes[J].Coordination Chemistry Reviews, 2004, 248(1/2):147-168.
[3] QIN Dong-dong, YANG Zheng-yin, ZHANG Fu-hong, et al.Evaluation of the antioxidation, DNA interaction and tumor cell cytotoxicity activities of copper(II) complexes with Paeonol Schiff-base[J].Inorganic Chemistry Communication, 2010, 13(6):727-729.
[4] QIAO Xin, MA Zhong-ying, XIE Cheng-zhi, et al.Study on potential antitumor mechanism of a novel Schiff base copper(II) complex:Synthesis, crystal structure, DNA binding, cytotoxicity and apoptosis induction activity[J].Journal of inorganic biochemistry, 2011, 105(5):728-737.
[5] 饶小平, 宋湛谦, 贾卫红, 等.松香树脂酸及其衍生物的生物活性研究进展[J].化学通报, 2008(10):724-730. RAO Xiao-ping, SONG Zhan-qian, JIA Wei-hong, et al.Research progress on bioactivities of pine resin acids and their derivatives[J].Chemistry, 2008(10):724-730.
[6] 熊轶, 王奎武, 潘远江, 等.一系列新型三环二萜的合成与抗肿瘤活性研究[J].高等学校化学学报, 2006, 27(11):2101-2105. XIONG Yi, WANG Kui-wu, PAN Yuan-jiang, et al.Synthesis and anti-tumor activities of a series of novel tricycle diterpenes[J].Chemical Journal of Chinese Universities, 2006, 27(11):2101-2105.
[7] 崔艳杰, 饶小平, 商士斌, 等.去氢枞酸衍生物生物活性研究新进展[J].林产化学与工业, 2012, 32(6):99-106. CUI Yan-jie, RAO Xiao-ping, SHANG Shi-bin, et al.Recent advances on biologic activity of dehydroabietic acid derivatives[J].Chemistry and Industry of Forest Products, 2012, 32(6):99-106.
[8] 韩春蕊, 宋湛谦, 商士斌, 等.苯乙酮类去氢枞酰腙的合成[J].合成化学, 2008, 16(1):64-66. HAN Chun-rui, SONG Zhan-qian, SHANG Shi-bin, et al.Synthesis of novel acetophenone dehydroabietyl hydrazones[J].Chinese Journal of Synthetic Chemistry, 2008, 16(1):64-66.
[9] SATHYADEVI P, KRISHNAMOORTHY P, BHUVANESH N S P, et al.Organometallic ruthenium(II) complexes:Synthesis, structure and influence of substitution at azomethine carbon towards DNA/BSA binding, radical scavenging and cytotoxicity[J].European Journal of Medicinal Chemistry, 2012, 55:420-431.
[10] 费宝丽, 李雯, 燕庆玲, 等.脱氢枞基-稀土配合物的合成、表征及其与DNA的相互作用[J].林产化学与工业, 2012, 32(1):1-7. FEI Bao-li, LI Wen, YAN Qing-lin, et al.Synthesis, characterization of dehydroabietyl-rare earth complexes and its interaction with DNA[J].Chemistry and Industry of Forest Products, 2012, 32(1):1-7.
[11] 关一富.脱氢松香基-1, 3, 4-噁二唑衍生物的合成及其与DNA相互作用研究[D].桂林:广西师范大学硕士学位论文, 2008. GUAN Yi-fu.Synthesis of dehydroabietyl-1, 3, 4-oxadiazole derivatives and their interactions with DNA[D].Guiling:Master Degree Thesis of Guangxi Normal University, 2008.
[12] WANG Li, JING Huan-wang, BU Xiu-li, et al.Bromination of aromatic aldehydes catalyzed by ceric ammonium nitrate and silica gel[J].Catalysis Communications, 2007, 8(1):80-82.
[13] 费宝丽, 徐武双, 李雯, 等.2, 2'-联吡啶钐(Ⅲ)配合物的合成及生物活性研究[J].广东化工, 2013, 40(3):3-5. FEI Bao-li, XU Wu-shuang, LI Wen, et al.Synthesis of 2, 2'-bipyridine-samaium (Ⅲ) complex and its biological activity[J].Guangdong Chemical Industry, 2013, 40(3):3-5.
[14] PARVEEN S, ARJMAND F.Design, synthesis and spectroscopic characterization of chiral benzimidazole-derived amino acid Zn(II) complexes:Development of tryptophan-derived specific hydrolytic DNA artificial nuclease agent[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy, 2012, 85(1):53-60.
[15] BUDAGUMPI S, KULKARNI N V, KURDEKAR G S, et al.Synthesis and spectroscopy of CoII, NiII, CuII and ZnII complexes derived from 3, 5-disubstituted-1H-pyrazole derivative:A special emphasis on DNA binding and cleavage studies[J].European Journal of Medicinal Chemistry, 2010, 45(2):455-462.
[16] NAFISI S, SABOURY A A, KERAMAT N, et al.Stability and structural features of DNA intercalation with ethidium bromide, acridine orange and methylene blue[J].Journal of Molecular Structure, 2007, 827(1):35-43.
[17] ARJMAND F, AZIZ M.Synthesis and characterization of dinuclear macrocyclic cobalt(II), copper(II) and zinc(II) complexes derived from 2, 2, 2'2'-S, S[bis(bis-N, N-2-thiobenzimidazolyloxalato-1, 2-ethane)] :DNA binding and cleavage studies[J].European Journal of Medicinal Chemistry, 2009, 44(2):834-844.
[18] BECKFORD F, DOURTH D, SHALOSKI M, et al.Half-sandwich ruthenium-arene complexes with thiosemicarbazones:Synthesis and biological evaluation of[(η⁶-p-cymene)Ru (piperonal thiosemicarbazones) Cl] Cl complexes[J].Journal of Inorganic Biochemistry, 2011, 105(8):1019-1029.
[19] JOSE R, CONSUELO V.Novel Bis-C, N-cyclometalated iridium(III) thiosemicarbazide antitumor complexes:Interactions with human serum albumin and DNA, and inhibition of cathepsin B[J].Inorganic Chemistry, 2013, 52(2):974-982.
[20] FEI Bao-li, LI Wen, XU Wu-shuang, et al.Synthesis, crystal structure, DNA binding, antibacterial, and cytotoxic activities of two chiral Copper(II) complexes[J].European Journal of Inorganic Chemistry, 2013, 2013(34):5919-5927.
[21] WU Hui-lu, YUAN Jing-kun, BAI Ying, et al.A seven-coordinated manganese(II) complex with V-shaped ligand bis(N-benzylbenzimidazol-2-ylmethyl)benzylamine:Synthesis, structure, DNA-binding properties and antioxidant activities[J].Journal of Photochemistry and Photobiology B:Biology, 2012, 116:13-21.
[22] ARJMAND F, PARVEEN S, AFZAL M, et al.Synthesis, characterization, biological studies(DNA binding, cleavage, antibacterial and topoisomerase I)and molecular docking of copper(II) benzimidazole complexes[J].Journal of Photochemistry and Photobiology B:Biology, 2012, 114:15-26.
[23] FEI Bao-li, XU Wu-shuang, TAO Hui-wen, et al.Effects of copper ions on DNA binding and cytotoxic activity of a chiral salicylidene Schiff base[J].Journal of Photochemistry and Photobiology B:Biology, 2014, 132:36-44.

DNA Binding and Anticancer Properties of Dehydroabietyl Benzoylhydrazone Derivatives

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	LUO Yunlong, SHEN Minggui, CAI Zhaosheng, SHANG Shibin, SONG Zhanqian. Synthesis and Antiviral Activity Evaluation of Dehydroabietic Acid Amide Derived 3,4-Dihydropyrimidinthiones [J]. Chemistry and Industry of Forest Products, 2019, 39(2): 46-52.
[2]	TAN Guanni, GAO Yanan, GAO Hong, SHANG Shibin, SONG Zhanqian. Synthesis and Spectra Performance of Dehydroabietic Acid-based Triarylamine with Double Naphthalenes [J]. Chemistry and Industry of Forest Products, 2019, 39(1): 61-66.
[3]	QI Zhiwen, WANG Chengzhang, JIANG Jianxin. Synthesis and Anticancer Activity of Dehydroabietyl Primary Amine Derivatives [J]. Chemistry and Industry of Forest Products, 2018, 38(6): 117-123.
[4]	LIU Shaofeng, LU Chuanwei, WANG Chunpeng, CHU Fuxiang, WANG Jifu. Synthesis and Characterization of 2-Methacryloyloxyisopro-panol Ester of Dehydroabietic Acid [J]. Chemistry and Industry of Forest Products, 2017, 37(4): 89-94.
[5]	YIN Bin, XU Wu-shuang, XIE Jing-cong, ZHANG Yu, LIU Qing-bo, LONG Jian-ying, FEI Bao-li. Comparation Study of DNA Binding Property with Dehydrobietic Benzimidazole Schiff Base and Hydrazone Derivatives [J]. Chemistry and Industry of Forest Products, 2016, 36(3): 81-87.
[6]	YU Juan, WANG Li-jun, LIU Shao-feng, WANG Chun-peng, WANG Ji-fu, CHU Fu-xiang. Synthesis and Characterization of Dehydroabietic Acid Derived ATRP Initiator [J]. Chemistry and Industry of Forest Products, 2016, 36(2): 87-93.
[7]	SONG Bing-lei, YU Xiao-na, CHEN Yan, PEI Xiao-mei, ZHOU Ping-ping, ZHAI Zhao-lan. Synthesis and Properties of Rosin-based Gemini Surfactants with Amide Group [J]. Chemistry and Industry of Forest Products, 2015, 35(6): 39-46.
[8]	GAO Hong, SHEN Ming-gui, WANG Xian-kai, SONG Zhan-qian, SHANG Shi-bin. Frontier Orbital Energy Levels of Dehydroabietic Acid-based Diarylamines [J]. Chemistry and Industry of Forest Products, 2015, 35(5): 1-4.
[9]	MO Qi-jin MO Qi-jin, LIU Lu-zhi, DUAN Wen-gui, CEN Bo, LIN Gui-shan, CHEN Nai-yuan, HUANG Yan, LIU Bu-ming. Synthesis and Insecticidal Activities of N-(5- Dehydroabietyl-1,3,4-thiadiazol-2-yl)- N'-substituted Thioureas [J]. Chemistry and Industry of Forest Products, 2015, 35(2): 8-16.
[10]	YU Min, ZHANG Hao, LIU Sheng-quan, JIN Qing, LI Da-zhou. DNA Extraction and Ribosomal DNA-ITS Sequence Molecule Barcode Identification from Wood Tissue of Dalbergia odorifera T. Chen [J]. Chemistry and Industry of Forest Products, 2014, 34(5): 103-108.
[11]	GAO Hong, CHEN Shan-shan, SONG Zhan-qian, SHANG Shi-bin. Structure Optimization by DFT and Solvatochromism of Series of Dehydroabietic Acid-based Arylamines [J]. Chemistry and Industry of Forest Products, 2014, 34(3): 1-6.
[12]	YU Juan, WANG Chun-peng, DING Li-na, CHEN Meng-yao, LIU Yu-peng, FU Li, CAI Zhi-hui, WANG Ji-fu, CHU Fu-xiang. Synthesis, Characterization and Polymerization Activity of Flexible Monomer Derived from Dehydroabietic Acid [J]. Chemistry and Industry of Forest Products, 2014, 34(2): 40-44.
[13]	NIE Yuan-mei;WANG Ying;SHEN Li-qun;YAO Xing-dong;. Structural Characterization of Reaction Product of Dehydroabietic Acid and DMSO and Its Reaction Mechanism [J]. , 2013, 33(6): 25-28.
[14]	QIN Shan;DUAN Wen-gui;LAI Gang;WU Guang-sui;MA Chang-hua. Synthesis and Characterization of Dehydroabietic Acid-alcohol Spice Esters [J]. , 2013, 33(1): 81-84.
[15]	CUI Yan-jie;RAO Xiao-ping;SHANG Shi-bin;SONG Jie. Recent Advances on Biologic Activity of Dehydroabietic Acid Derivatives [J]. , 2012, 32(6): 99-106.