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Anti-Cancer Agents in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1871-5206
ISSN (Online): 1875-5992

Research Article

QSAR Study of Novel 1, 8-Naphthimide Derivatives Targeting Nuclear DNA

Author(s): Zheng Lian, Yunheng Tai*, Huanling Xia and Honglin Zhai

Volume 23, Issue 6, 2023

Published on: 19 September, 2022

Page: [726 - 733] Pages: 8

DOI: 10.2174/1871520622666220822010953

Price: $65

Abstract

Background: 1, 8-naphthimide is a novel tumor inhibitor targeting nuclear DNA, which can be used to design and develop anti-osteosarcoma drugs.

Objective: Quantitative structure-activity relationship (QSAR) model was established to predict the physical properties of compounds.

Methods: In this study, gene expression programming (GEP) was used to build a nonlinear quantitative structureactivity relationship (QSAR) model with descriptors and to predict the activity of a serials novel DNA-targeted chemotherapeutic agents. These descriptors were calculated in CODESSA software and selected from the descriptor pool based on heuristics. Three descriptors were selected to establish a multiple linear regression model. The best nonlinear QSAR model with a correlation coefficient of 0.89 and 0.82 and mean error of 0.02 and 0.06 for the training and test sets were obtained.

Results: The results showed that the model established by GEP had better stability and predictive ability. The small molecular docking experiment of 32 compounds was carried out in SYBYL software, and it was found that compound 7A had reliable molecular docking ability.

Conclusion: The established model reveals the factors affecting the activity of DNA inhibitors and provides direction and guidance for the further design of highly effective DNA-targeting drugs for osteosarcoma.

Keywords: DNA targeting drugs, osteosarcoma, quantitative structure-activity relationship, heuristic method, gene expression programming, nuclear DNA.

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[1]
Fletcher, C.; Unni, K.K.; Mertens, F. WHO classification of soft tissue tumours; IARC Press: Lyon, 2002.
[2]
Bernthal, N.M.; Federman, N.; Eilber, F.; Nelson, S.D.; Eckardt, J.J.; Eilber, F.C.; Tap, W.D. Long-term results (>25 years) of a randomized, prospective clinical trial evaluating chem- otherapy in patients with high-grade, operable osteosarcoma. Cancer, 2012, 118(23), 5888-5893.
[http://dx.doi.org/10.1002/cncr.27651] [PMID: 22648705]
[3]
Luo, G.Z.; Xu, H. Anterior cervical plate fixation with iliac bone graft and titanium mesh for the treatment of primary suppurative cervical intervertebral space. Chronic Dis. Prevent. Rev., 2021, 5(17), 1-6.
[4]
Link, M.P.; Goorin, A.M.; Miser, A.W.; Green, A.A.; Pratt, C.B.; Belasco, J.B.; Pritchard, J.; Malpas, J.S.; Baker, A.R.; Kirkpatrick, J.A.; Ayala, A.G.; Shuster, J.J.; Abelson, H.T.; Simone, J.V.; Vietti, T.J. The effect of adjuvant chemotherapy on relapse-free survival in patients with osteosarcoma of the extremity. N. Engl. J. Med., 1986, 314(25), 1600-1606.
[http://dx.doi.org/10.1056/NEJM198606193142502] [PMID: 3520317]
[5]
Collins, M.; Wilhelm, M.; Conyers, R.; Herschtal, A.; Whelan, J.; Bielack, S.; Kager, L.; Kühne, T.; Sydes, M.; Gelderblom, H.; Ferrari, S.; Picci, P.; Smeland, S.; Eriksson, M.; Petrilli, A.S.; Bleyer, A.; Thomas, D.M. Benefits and adverse events in younger versus older patients receiving neoadjuvant chemotherapy for osteosarcoma: Findings from a meta-analysis. J. Clin. Oncol., 2013, 31(18), 2303-2312.
[http://dx.doi.org/10.1200/JCO.2012.43.8598] [PMID: 23669227]
[6]
Meyers, P.A.; Healey, J.H.; Chou, A.J.; Wexler, L.H.; Merola, P.R.; Morris, C.D.; Laquaglia, M.P.; Kellick, M.G.; Abramson, S.J.; Gorlick, R. Addition of pamidronate to chemotherapy for the treatment of osteosarcoma. Cancer, 2011, 117(8), 1736-1744.
[http://dx.doi.org/10.1002/cncr.25744] [PMID: 21472721]
[7]
Harrison, D.J.; Geller, D.S.; Gill, J.D.; Lewis, V.O.; Gorlick, R. Current and future therapeutic approaches for osteosarcoma. Expert Rev. Anticancer Ther., 2018, 18(1), 39-50.
[http://dx.doi.org/10.1080/14737140.2018.1413939] [PMID: 29210294]
[8]
Baker, P.D.; Morzorati, S.L.; Ellett, M.L. The pathophysiology of chemotherapy-induced nausea and vomiting. Gastroenterol. Nurs., 2005, 28(6), 469-480.
[http://dx.doi.org/10.1097/00001610-200511000-00003] [PMID: 16418583]
[9]
Hurley, L.H. DNA and its associated processes as targets for cancer therapy. Nat. Rev. Cancer, 2002, 2(3), 188-200.
[http://dx.doi.org/10.1038/nrc749] [PMID: 11990855]
[10]
Skladanowski, A.; Bozko, P.; Sabisz, M. DNA structure and integrity checkpoints during the cell cycle and their role in drug targeting and sensitivity of tumor cells to anticancer treatment. Chem. Rev., 2009, 109(7), 2951-2973.
[http://dx.doi.org/10.1021/cr900026u] [PMID: 19522503]
[11]
Hengartner, M.O. The biochemistry of apoptosis. Nature, 2000, 407(6805), 770-776.
[http://dx.doi.org/10.1038/35037710] [PMID: 11048727]
[12]
Bloodgood, B.L.; Sharma, N.; Browne, H.A.; Trepman, A.Z.; Greenberg, M.E. The activity-dependent transcription factor NPAS4 regulates domain-specific inhibition. Nature, 2013, 503(7474), 121-125.
[http://dx.doi.org/10.1038/nature12743] [PMID: 24201284]
[13]
Banerjee, S.; Veale, E.B.; Phelan, C.M.; Murphy, S.A.; Tocci, G.M.; Gillespie, L.J.; Frimannsson, D.O.; Kelly, J.M.; Gunnlaugsson, T. Recent advances in the development of 1,8-naphthalimide based DNA targeting binders, anticancer and fluorescent cellular imaging agents. Chem. Soc. Rev., 2013, 42(4), 1601-1618.
[http://dx.doi.org/10.1039/c2cs35467e] [PMID: 23325367]
[14]
Lv, M.; Xu, H. Overview of naphthalimide analogs as anticancer agents. Curr. Med. Chem., 2009, 16(36), 4797-4813.
[http://dx.doi.org/10.2174/092986709789909576] [PMID: 19929786]
[15]
Hansch, C.; Hoekman, D.; Gao, H. Comparative QSAR: Toward a deeper understanding of chemicobiological interactions. Chem. Rev., 1996, 96(3), 1045-1076.
[http://dx.doi.org/10.1021/cr9400976] [PMID: 11848780]
[16]
Chen, H.S. QSAR models of Celecoxib analogues and derivatives as COX-2 inhibitor to predict their anti-inflammatory effect. Cancer Cell Res., 2022, 9(33), 827-835.
[17]
Roy, K.; Kar, S.; Ambure, P. On a simple approach for determining applicability domain of QSAR models. Chemom. Intell. Lab. Syst., 2015, 145, 22-29.
[http://dx.doi.org/10.1016/j.chemolab.2015.04.013]
[18]
Liang, G.B.; Wei, J.H.; Jiang, H.; Huang, R.Z.; Qin, J.T.; Wang, H.L.; Wang, H.S.; Zhang, Y. Design, synthesis and antitumor evaluation of new 1,8-naphthalimide derivatives targeting nuclear DNA. Eur. J. Med. Chem., 2021, 210, 112951.
[http://dx.doi.org/10.1016/j.ejmech.2020.112951] [PMID: 33109400]
[19]
Belka, R.; Piwowarczyk, K. Some aspects of using the Hyperchem software in study of Ni-C nanostructures. Proceedings of SPIE, 2010.
[http://dx.doi.org/10.1117/12.871985]
[20]
Karelson, M.; Lobanov, V.S.; Katritzky, A.R. Quantum-chemical descriptors in QSAR/QSPR studies. Chem. Rev., 1996, 96(3), 1027-1044.
[http://dx.doi.org/10.1021/cr950202r] [PMID: 11848779]
[21]
Cao, C.; Lin, Y. Correlation between the glass transition temperatures and repeating unit structure for high molecular weight polymers. J. Chem. Inf. Comput. Sci., 2003, 43(2), 643-650.
[http://dx.doi.org/10.1021/ci0202990] [PMID: 12653533]
[22]
Wei, L.X.; Hua, C.Z. Application of a novel GEP algorithm in evolutionary modeling and forecasting. Comput. Appl. (Nottm.), 2005, 25, 2783-2786.
[23]
Holland, J.H. Genetic algorithms. Sci. Am., 1992, 267(1), 66-72.
[http://dx.doi.org/10.1038/scientificamerican0792-66]
[24]
Teodorescu, L.; Sherwood, D. High energy physics event selection with gene expression programming. Comput. Phys. Commun., 2008, 178(6), 409-419.
[http://dx.doi.org/10.1016/j.cpc.2007.10.003]
[25]
Kaydani, H.; Mohebbi, A.; Eftekhari, M. Permeability estimation in heterogeneous oil reservoirs by multi-gene genetic programming algorithm. J. Petrol. Sci. Eng., 2014, 123, 201-206.
[http://dx.doi.org/10.1016/j.petrol.2014.07.035]
[26]
Zhang, L.; Chen, J.; Gao, C.; Liu, C.; Xu, K. An efficient model for auxiliary diagnosis of hepatocellular carcinoma based on gene expression programming. Med. Biol. Eng. Comput., 2018, 56(10), 1771-1779.
[http://dx.doi.org/10.1007/s11517-018-1811-6] [PMID: 29546505]
[27]
Zhong, J.; Feng, L.; Ong, Y.S. Gene expression programming: A survey. IEEE Comput. Intell. Mag., 2017, 12(3), 54-72.
[http://dx.doi.org/10.1109/MCI.2017.2708618]
[28]
Stanton, D.T.; Jurs, P.C. Development and use of charged partial surface area structural descriptors in computer-assisted quantitative structure-property relationship studies. Anal. Chem., 1990, 62(21), 2323-2329.
[http://dx.doi.org/10.1021/ac00220a013]
[29]
Katritzky, A.R.; Dobchev, D.A.; Tulp, I.; Karelson, M.; Carlson, D.A. QSAR study of mosquito repellents using Codessa Pro. Bioorg. Med. Chem. Lett., 2006, 16(8), 2306-2311.
[http://dx.doi.org/10.1016/j.bmcl.2005.11.113] [PMID: 16488605]
[30]
Roberts, D.C.; Gasenzer, T.; Burnett, K. Letter to the editor: Exciting relative number-squeezed particles from condensates using stimulated light scattering. J. Phys. B-AT Mol. Opt. 2002, 35(5), L113-L118.

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