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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Adsorption of Diethylstilbestrol Drug into BNNT: DFT/TD-DFT and Spectroscopic (Excited States, UV/Vis and NMR) Studies

Author(s): Maryamossadat Hosseinzadeh, Shiva Masoudi*, Nasrin Masnabadi* and Fatemeh Azarakhshi

Volume 20, Issue 4, 2023

Published on: 28 November, 2022

Page: [347 - 361] Pages: 15

DOI: 10.2174/1570178620666221025162002

Price: $65

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Abstract

Background: Cancer has become a significant universal health problem. Anticancer drugs control the chemicals that sacrifice cancer cells by inhibiting their growth in their cell cycle. Interestingly, as much as boron nitride nanosheets and boron nitride nanotubes are degradable and non-toxic, they can act as suitable drug carriers for antitumor drugs and deliver them into target cells.

Objective: In the present study, the encapsulation of diethylstilbestrol as an anticancer drug into the boron nitride (8,8) nanotube was investigated for the first time using the density functional theory: M06-2X and the natural bond orbital methods in the gas phase.

Methods: Using natural bond orbital analysis, the charge transfer between diethylstilbestrol drug and boron nitride nanotubes (8,8)/ diethylstilbestrol complex was explored.

Results: Based on the results obtained from the calculation of encapsulation energy, it was found that the adsorption process was favorable. The interaction effects of diethylstilbestrol drug and boron nitride (8,8) nanotube on the natural bond orbital charge, the chemical shift parameters, and electronic properties were also evaluated.

Conclusion: This study revealed that boron nitride (8,8) nanotubes can be a suitable carrier for diethylstilbestrol drug delivery. The ultra violet-visible spectra of diethylstilbestrol drug and the boron nitride (8,8) nanotubes/diethylstilbestrol complex were computed using time-dependent density functional theory (: M06-2X calculations.

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[1]
Malkowicz, S.B. Urology, 2001, 58(2), 108-113.
[http://dx.doi.org/10.1016/S0090-4295(01)01252-3]
[2]
Robinson, M.R.G.; Thomas, B.S. BMJ, 1971, 4(5784), 391-394.
[http://dx.doi.org/10.1136/bmj.4.5784.391] [PMID: 5124437]
[3]
Byar, D.P. Cancer, 1973, 32(5), 1126-1130.
[http://dx.doi.org/10.1002/1097-0142(197311)32:5<1126:AIDCNCR2820320518>3.0.CO;2-C] [PMID: 4585929]
[4]
Geier, R.; Adler, S.; Rashid, G.; Klein, A. 2010.
[5]
Wang, H.; Li, J.; Gao, Y.; Xu, Y.; Pan, Y.; Tsuji, I.; Sun, Z.J.; Li, X.M. Asian J. Androl., 2010, 12(4), 535-547.
[http://dx.doi.org/10.1038/aja.2010.14] [PMID: 20436506]
[6]
Raghavan, D.; Klein, E.A. J. Clin. Oncol., 2008, 26(28), 4535-4536.
[http://dx.doi.org/10.1200/JCO.2008.18.3145] [PMID: 18626003]
[7]
Dondoo, T.O.; Fukumori, T.; Daizumoto, K.; Fukawa, T.; Kohzuki, M.; Kowada, M.; Kusuhara, Y.; Mori, H.; Nakatsuji, H.; Takahashi, M.; Kanayama, H.O. Anticancer Res., 2017, 37(1), 125-134.
[http://dx.doi.org/10.21873/anticanres.11297] [PMID: 28011482]
[8]
Orlando, M.; Chacón, M.; Salum, G.; Chacón, D.R. Ann. Oncol., 2000, 11(2), 177-181.
[http://dx.doi.org/10.1023/A:1008360118617] [PMID: 10761752]
[9]
Anderson, J.; Abrahamsson, P.A.; Crawford, D.; Miller, K.; Tombal, B. BJU Int., 2008, 101(12), 1497-1501.
[http://dx.doi.org/10.1111/j.1464-410X.2008.07590.x] [PMID: 18336613]
[10]
Arivazhagan, M.; Rexalin, D.A. Biomol. Spectros, 2013, 104, 451-460.
[http://dx.doi.org/10.1016/j.saa.2012.11.057]
[11]
Nizamia, B.; Mousavinezhad Sarasia, E.; Mominb, M.I.K.; Honarparvara, B. IEEE/ACM Trans. Comput. Biol. Bioinformatics, 2017, 16, 560-568.
[http://dx.doi.org/10.1109/TCBB.2017.2779505]
[12]
Karimi, M.; Ghasemi, A.; Sahandi Zangabad, P.; Rahighi, R.; Moosavi Basri, S.M.; Mirshekari, H.; Amiri, M.; Shafaei Pishabad, Z.; Aslani, A.; Bozorgomid, M.; Ghosh, D.; Beyzavi, A.; Vaseghi, A.; Aref, A.R.; Haghani, L.; Bahrami, S.; Hamblin, M.R. Chem. Soc. Rev., 2016, 45(5), 1457-1501.
[http://dx.doi.org/10.1039/C5CS00798D] [PMID: 26776487]
[13]
Park, J.; Wrzesinski, S.H.; Stern, E.; Look, M.; Criscione, J.; Ragheb, R.; Jay, S.M.; Demento, S.L.; Agawu, A.; Licona Limon, P.; Fer-randino, A.F.; Gonzalez, D.; Habermann, A.; Flavell, R.A.; Fahmy, T.M. Nat. Mater., 2012, 11(10), 895-905.
[http://dx.doi.org/10.1038/nmat3355] [PMID: 22797827]
[14]
Adlakha-Hutcheon, G.; Bally, M.B.; Shew, C.R.; Madden, T.D. Nat. Biotechnol., 1999, 17(8), 775-779.
[http://dx.doi.org/10.1038/11710] [PMID: 10429242]
[15]
Liu, Z.; Cai, W.; He, L.; Nakayama, N.; Chen, K.; Sun, X.; Chen, X.; Dai, H. Nat. Nanotechnol., 2007, 2(1), 47-52.
[http://dx.doi.org/10.1038/nnano.2006.170] [PMID: 18654207]
[16]
Boldrin, L.; Scarpa, F.; Chowdhury, R.; Adhikari, S. Nanotechnology, 2011, 22(50)505702
[http://dx.doi.org/10.1088/0957-4484/22/50/505702] [PMID: 22108443]
[17]
Li, L.H.; Cervenka, J.; Watanabe, K.; Taniguchi, T.; Chen, Y. ACS Nano, 2014, 8(2), 1457-1462.
[http://dx.doi.org/10.1021/nn500059s] [PMID: 24400990]
[18]
Verma, A.; Parashar, A.; Packirisamy, M. J. Appl. Phys., 2018, 124(1)015102
[http://dx.doi.org/10.1063/1.5033542]
[19]
Paszkowicz, W.; Pelka, J.B.; Knapp, M.; Szyszko, T.; Podsiadlo, S. Appl. Phys., A Mater. Sci. Process., 2002, 75(3), 431-435.
[http://dx.doi.org/10.1007/s003390100999]
[20]
Dean, C.R.; Young, A.F.; Meric, I.; Lee, C.; Wang, L.; Sorgenfrei, S.; Watanabe, K.; Taniguchi, T. kim, P.; Shepard, K.L.; Hone. J. Nat. Nanotechnol., 2010, 5, 722-726.
[http://dx.doi.org/10.1038/nnano.2010.172] [PMID: 20729834]
[21]
Naskar, A.K.; Keum, J.K.; Boeman, R.G. Nat. Nanotechnol., 2016, 11(12), 1026-1030.
[http://dx.doi.org/10.1038/nnano.2016.262] [PMID: 27920443]
[22]
Hussain, F.; Hojjati, M.; Okamoto, M.; Gorga, R.E. J. Compos. Mater., 2006, 40(17), 1511-1575.
[http://dx.doi.org/10.1177/0021998306067321]
[23]
Horváth, L.; Magrez, A.; Golberg, D.; Zhi, C.; Bando, Y.; Smajda, R.; Horvath, E.; Forro, L.; Schwaller, B. ACS Nano, 2011, 5, 3800-3810.
[PMID: 21495683]
[24]
Jang, S.K.; Youn, J.; Song, Y.J.; Lee, S. Sci. Rep., 2016, 6(1), 30449.
[http://dx.doi.org/10.1038/srep30449] [PMID: 27458024]
[25]
Zhi, C.Y.; Bando, Y.; Terao, T.; Tang, C.; Golberg, D. Pure Appl. Chem., 2010, 82(11), 2175-2183.
[http://dx.doi.org/10.1351/PAC-CON-09-11-41]
[26]
Golberg, D.; Bando, Y.; Tang, C.C.; Zhi, C.Y. Adv. Mater., 2007, 19(18), 2413-2432.
[http://dx.doi.org/10.1002/adma.200700179]
[27]
Blasé, X.; Rubio, A.; Louie, S.G.; Cohen, M.L. Europhys. Lett., 1994, 28(5), 335-340.
[http://dx.doi.org/10.1209/0295-5075/28/5/007]
[28]
Baierle, R.J.; Schmidt, T.M.; Fazzio, A. Solid State Commun., 2007, 142(1-2), 49-53.
[http://dx.doi.org/10.1016/j.ssc.2007.01.036]
[29]
Yafei, L.; Zhen, Z.; Jijun, Z. Nanotechnology, 2008, 19(1)015202
[http://dx.doi.org/10.1088/0957-4484/19/01/015202] [PMID: 21730524]
[30]
Weng, Q.; Wang, X.; Wang, X.; Bando, Y.; Golberg, D. Chem. Soc. Rev., 2016, 45(14), 3989-4012.
[http://dx.doi.org/10.1039/C5CS00869G] [PMID: 27173728]
[31]
Xu, X.; Zhang, Q.; Hao, M.; Hu, Y.; Peng, L.; Wang, T.; Ren, X.; Wang, C.; Zhao, Z.; Wan, C.; Fei, H.; Wang, L.; Zhu, J.; Sun, K.; Chen, W.; Du, T.; Deng, B.; Cheng, T. Cheng. iScience, 2019, 363, 723-727.
[32]
Benassi, E.; Spagnolo, F. J. Solution Chem., 2010, 39(1), 11-29.
[http://dx.doi.org/10.1007/s10953-009-9483-3]
[33]
Panchal, M.B.; Upadhyay, S.H.; Harsha, S.P. Sens. Actuat. A Phys.,197, 2013, 108, 111-121.
[http://dx.doi.org/10.1016/j.sna.2013.04.011]
[34]
Hosseinzadeh, M.; Masoudi, S.; Masnabadi, N.; Fatemeh Azarakhshi, F. Mater. Res. Express, 2022, 9045002
[http://dx.doi.org/10.1088/2053-1591/ac60e1]
[35]
Glendening, E.D.; Badenhoop, J.K.; Reed, A.E.; Carpenter, J.E.; Bohmann, J.A.C.; Morales, M.; Weinhold, F. NBO Version 5.G; Theoreti-cal Chemistry Institute, University of Wisconsin: Madison, WI, 2004.
[36]
Hehre, W.J.; Radom, L.; Schleyer, P.V.R.; Pople, J.A. Ab initio molecular orbital theory; Wiley: New York, 1986.
[37]
Malkin, V.G.; Malkina, O.I.; Eriksson, L.A.; Salahub, D.R. Modern Density Function Theory; A Tool for Chemistry, J. M. P; Seminario, P., Ed.; Elsevier: Amsterdam, 1995.
[38]
Wolinski, K.; Hinton, J.F.; Pulay, P. J. Am. Chem. Soc., 1990, 112(23), 8251-8260.
[http://dx.doi.org/10.1021/ja00179a005]
[39]
Kondo, N.S.; Danyluk, S.S. Biochemistry, 1976, 15(4), 756-768.
[http://dx.doi.org/10.1021/bi00649a006]
[40]
Stern, N.; Major, D.T.; Gottlieb, H.E.; Weizman, D.; Fischer, B. Org. Biomol. Chem., 2010, 8(20), 4637-4652.
[http://dx.doi.org/10.1039/c005122e] [PMID: 20714505]
[41]
Masnabadi, N. J. Sci. IRI., 2020, 31, 137-146.
[42]
Moffatt, A.C.; Osselton, M.D.; Widdop, B. Clarke’s Analysis of Drugs and Poisons, 3rd ed; Pharmaceutical Press, 2004, pp. 1246-1247.
[43]
Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Montgomery, J.A.; Vreven, T.; Kudin, K.N.; Burant, J.C.; Millam, J.M.; Iyengar, S.S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G.A.; Na-katsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J.E.; Hratchian, H.P.; Cross, J.B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R.E.; Yazyev, O.; Aus-tin, A.J.; Cammi, R.; Pomelli, C.; Ochterski, J.W.; Ayala, P.Y.; Morokuma, K.; Voth, G.A.; Salvador, P.; Dannenberg, J.J.; Zakrzewski, V.G.; Dapprich, S.; Daniels, A.D.; Strain, M.C.; Farkas, O.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Ortiz, J.V.; Cui, Q.; Baboul, A.G.; Clifford, S.; Cioslowski, J.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R.L.; Fox, D.J.; Keith, T.; Laham, A.; Peng, C.Y.; Nanayakkara, A.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Gonzalez, C.; Pople, J.A. Gaussian 03, Revision B.03, 2003.
[44]
Danaie, E.; Masoudi, S.; Masnabadi, N. Lett. Org. Chem., 2020, 17(10), 749-759.
[http://dx.doi.org/10.2174/1570178617666200129144750]

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