Spectroscopic and Modelling Analysis on the Interaction of 3′-Azidodaunorubicin Semicarbazone with ctDNA
Fengling Cui A B , Jianhua Jin A , Xiaoqing Niu A , Qingfeng Liu A and Guisheng Zhang A BA College of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang 453007, China.
B Corresponding authors. Email: fenglingcui@hotmail.com; zgs@htu.cn
Australian Journal of Chemistry 67(2) 234-240 https://doi.org/10.1071/CH13372
Submitted: 16 July 2013 Accepted: 16 September 2013 Published: 17 October 2013
Abstract
The synthesis and characterisation of a new anthracycline, 3′-azidodaunorubicin semicarbazone (ADNRS) is reported. The interaction between ADNRS and calf thymus DNA (ctDNA) was investigated by absorption and fluorescence spectroscopy in combination with melting temperature (Tm) curves and molecular modelling in physiological buffer (pH 7.4). Evidence indicates that ADNRS binds in the groove of ctDNA and the fluorescence quenching mechanism is a static quenching type. Calculated thermodynamic parameters show that hydrophobic interactions may play a predominant role in the binding. Furthermore, molecular modelling results corroborate the spectroscopic investigations.
References
[1] M. H. Banitaba, S. S. H. Davarani, A. Mehdinia, Anal. Biochem. 2011, 411, 218.| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjsFOrtb4%3D&md5=5c580c269aba63853542d82f5b30c47bCAS | 21238426PubMed |
[2] G. W. Zhang, P. Fu, L. Wang, M. M. Hu, J. Agric. Food Chem. 2011, 59, 8944.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXpt1Cju74%3D&md5=3ccf51fd27bfbd88a333b564253e370dCAS |
[3] T. Zo1ek, D. Maciejewska, Eur. J. Med. Chem. 2010, 45, 1991.
| Crossref | GoogleScholarGoogle Scholar |
[4] Y. Lu, M. H. Xu, G. K. Wang, Y. Zheng, J. Lumin. 2011, 131, 926.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjtVCqtLo%3D&md5=540a5412860a003237676655e8d66677CAS |
[5] H. K. Choi, J. H. Chang, I. I. Hwan Ko, J. H. Lee, B. Y. Jeong, J. H. Kim, J. B. Kim, J. Solid State Chem. 2011, 184, 805.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXktFKmsb8%3D&md5=bbf1e69eba97e4f45368d5d387e041abCAS |
[6] Q. X. Wang, K. Jiao, F. Q. Liu, X. L. Yuan, W. Sun, J. Biochem. Biophys. Methods 2007, 70, 427.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXislKjtrk%3D&md5=1af8c9a30f21cd2d452953b2166c78e6CAS | 17222457PubMed |
[7] M. B. Prouse, M. M. Campbell, Biochim. Biophys. Acta 2012, 1819, 67.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsVelug%3D%3D&md5=019c1b4fbc1964d543a5c15545e8c51cCAS | 22067744PubMed |
[8] J. Wang, M. Ozsoz, X. H. Cai, G. Rivas, H. Shiraishi, D. H. Grant, M. Chicharro, J. Fernandes, E. Palecek, Bioelectrochem. Bioenerg. 1998, 45, 33.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXjvFCls7o%3D&md5=50628b1830dc367ec042b2aec83b1012CAS |
[9] C. Temperini, M. Cirilli, M. Aschi, G. Ughetto, Bioorg. Med. Chem. 2005, 13, 1673.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVKjsrw%3D&md5=ea91bb425ceaf09cd25fa5dc6cef06f9CAS | 15698785PubMed |
[10] L. Fang, G. Zhang, C. Li, X. Zheng, L. Zhu, J. J. Xiao, G. Szakacs, J. Nadas, K. K. Chan, P. G. Wang, D. Sun, J. Med. Chem. 2006, 49, 932.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XitVCrtw%3D%3D&md5=8dde20dcba18ce2700b6a700c7439a4aCAS | 16451059PubMed |
[11] Y. Lu, Q. Q. Feng, F. L. Cui, W. W. Xing, G. S. Zhang, X. J. Yao, Bioorg. Med. Chem. Lett. 2010, 20, 6899.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtl2gtLrK&md5=725b0bc82b60746a0691c82f60b7d56dCAS | 21035338PubMed |
[12] F. L. Cui, G. Q. Hui, X. Y. Jiang, G. S. Zhang, Int. J. Biol. Macromol. 2012, 50, 1121.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XjtF2isrY%3D&md5=785305cc98d6bfb2a09da8f32b15607eCAS |
[13] R. Vijayabharathi, P. Sathyadevi, P. Krishnamoorthy, D. Senthilraja, P. Brunthadevi, S. Sathyabama, V. B. Priyadarisini, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2012, 89, 294.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XitFOntbc%3D&md5=2f295893fd2b1ca1e0238108bd5defbcCAS | 22285949PubMed |
[14] G. W. Song, Z. X. Cai, Y. He, Z. W. Lou, Sens. Actuators B Chem. 2004, 102, 320.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXmvFOms7s%3D&md5=0d4a5cc9e018723e6cf38752fa0c6f39CAS |
[15] F. L. Cui, R. N. Huo, G. Q. Hui, X. X. Lv, J. H. Jin, G. S. Zhang, W. W. Xing, J. Mol. Struct. 2011, 1001, 104.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXps1aksbg%3D&md5=11d2cd52c306ff53040bc7673878a4dfCAS |
[16] Y. Lu, G. K. Wang, W. Tang, X. X. Hao, M. H. Xu, X. Li, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2011, 82, 247.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtF2ku7%2FN&md5=4ecb1a9de279722801d5bff95f4d4dffCAS | 21820952PubMed |
[17] G. W. Zhang, J. B. Guo, N. Zhao, J. R. Wang, Sens. Actuators B Chem. 2010, 144, 239.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptlOlug%3D%3D&md5=b7f0b930c82c1e703d8eb351d278ee63CAS |
[18] Y. T. Sun, S. Y. Bi, D. Q. Song, C. Y. Qiao, D. Mu, H. Q. Zhang, Sens. Actuators B Chem. 2008, 129, 799.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXitVKhur4%3D&md5=aa4b22700854265e82e912185b1c9820CAS |
[19] J. H. Huang, X. M. Wang, J. Mol. Struct. 2012, 1010, 73.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVCls74%3D&md5=d3545ed53547dd83ea1da5a3ed623252CAS |
[20] S. Kashanian, M. M. Khodaei, H. Roshanfekr, N. Shahabadi, G. Mansouri, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2012, 86, 351.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhs1CgurfJ&md5=787d1ac1b8ba0d4f19426c8e6d3a7c3cCAS | 22093523PubMed |
[21] B. K. Sahoo, K. S. Ghosh, R. Bera, S. Dasgupta, Chem. Phys. 2008, 351, 163.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXntlSktLg%3D&md5=0bfe7c14bd885ef1ae77eb660d0b6a09CAS |
[22] Y. J. Sun, F. Y. Ji, R. T. Liu, J. Lin, Q. F. Xu, C. Z. Gao, J. Lumin. 2012, 132, 507.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsVWksrjF&md5=ae7fe2fbad18c06d03a6e74af3756b7bCAS |
[23] G. W. Zhang, J. B. Guo, J. H. Pan, X. X. Chen, J. J. Wang, J. Mol. Struct. 2009, 923, 114.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXkt1Snurg%3D&md5=9dd6a82d0322ae5fd94d6a3f7373aa6dCAS |
[24] D. S. Lu, Y. Nonaka, M. Tsuboi, K. Nakamoto, J. Raman Spectrosc. 1990, 21, 321.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXltVyrsLc%3D&md5=45f5fe25140f12aefd7ffd743165119dCAS |
[25] L. H. Jin, L. F. Tan, X. Q. Zou, J. Liu, F. Luan, Inorg. Chim. Acta 2012, 387, 253.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xmt1Gmsbo%3D&md5=f45a5f181a410420408ac50f3e39e9e0CAS |
[26] M. B. Gholivand, S. Kashanian, H. Peyman, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2012, 87, 232.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XptlKq&md5=b004d547773533515036ae3a7b078839CAS | 22192418PubMed |
[27] G. W. Zhang, X. Hu, P. Fu, J. Photochem. Photobiol. B 2012, 108, 53.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhvVCnt7s%3D&md5=d3cae5d3eed112087d4656fa514b52d1CAS |
[28] M. Xu, Z. R. Ma, L. Huang, F. J. Chen, Z. Z. Zeng, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2011, 78, 503.
| Crossref | GoogleScholarGoogle Scholar | 21156349PubMed |
[29] Y. T. Sun, H. Q. Zhang, S. Y. Bi, X. F. Zhou, L. Wang, Y. S. Yan, J. Lumin. 2011, 131, 2299.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXosF2rsr8%3D&md5=21a026a07f8cb2d4477072cff0c225f5CAS |
[30] J. H. Li, J. F. Dong, H. Cui, T. Xu, L. Z. Li, Transition Met. Chem. 2012, 37, 175.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xit1Sjur4%3D&md5=7d649bbe7bd3c367b69e2cca01f8d0abCAS |
[31] G. W. Zhang, X. Hu, J. H. Pan, Spectrochim. Acta A Mol. Biomol. Spectrosc. 2011, 78, 687.
| Crossref | GoogleScholarGoogle Scholar |
[32] S. Y. Bi, C. Y. Qiao, D. Q. Song, Y. Tian, D. J. Gao, Y. Sun, H. Q. Zhang, Sens. Actuators B Chem. 2006, 119, 199.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XptlGjsLw%3D&md5=92035a33acc8eb2f912e6daf17b9116dCAS |
[33] R. N. Huo, C. Li, F. L. Cui, G. S. Zhang, Q. F. Liu, X. J. Yao, J. Fluoresc. 2012, 22, 111.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtVCltrw%3D&md5=1ea3e434d7b27a28014b97fc064008e3CAS |
[34] B. K. Sahoo, K. S. Ghosh, R. Bera, S. Dasgupta, Chem. Phys. 2008, 351, 163.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXntlSktLg%3D&md5=0bfe7c14bd885ef1ae77eb660d0b6a09CAS |
[35] F. L. Cui, G. Q. Hui, X. Y. Jiang, G. S. Zhang, Int. J. Biol. Macromol. 2012, 50, 1121.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XjtF2isrY%3D&md5=785305cc98d6bfb2a09da8f32b15607eCAS |