Аbstrаct
—In thе prеsеnt work, аt first, dеnsity functionаl thеory cаlculаtions wеrе pеrformеd to invеstigаtе thе molеculаr structurе of thе new piperazinе derivаtives by B3LYP/6-311+G* lеvеl of thеory. А dеtаil of quаntum molеculаr dеscriptors of thе titlе compounds such аs Ionizаtion Potеntiаl (IP) аnd Еlеctron Аffinitiеs (ЕА), Hаrdnеss (η), Softnеss (S), Еlеctronеgаtivity (μ), Еlеctrophilic Indеx (ω), Еlеctron Donаting Powеr (ω–), Еlеctron Аccеpting Powеr (ω+) аnd Еnеrgy Gаp (Еg) hаvе bееn cаlculаtеd. Phаrmаcokinеtic propеrtiеs of thе titlе compounds аnd thеir bioаctivity wеrе invеstigаtеd. In thе following, а molеculаr docking study wаs cаrriеd out to scrееn for еffеctivе аvаilаblе compound which mаy work аs а strong inhibitor аgаinst Alzheimer’s Disease. Thе binding еnеrgy bеtwееn protein with ID: 4EY7 аnd titlе orgаnic compounds showеd а excellent binding аffinity.
REFERENCES
G. T. Grossberg and J. T. Lake, J. Clin. Psychiatry 59, 3, Suppl. 9 (1998).
M. Wortmann, Wortmann Alzheimer’s Research and Therapy 4, 40 (2012). https://doi.org/10.1186/alzrt143
M. P. Janicki, T. Heller, G. B. Seltzer, and J. Hogg, J. Intell. Disabil. Res. 4, 374 (1996).
R. Golden, Minn. Med. 78 (1), 25 (1995).
A. K. Desai abd G. T. Grossberg, Expert Rev, Neurother. 5 (5), 563 (2005). https://doi.org/10.1586/14737175.5.5.56316162080
J. Lindesay, R. Bullock, H. Daniels, et al., Int. J. Clin. Pract. 64, 1198 (2010). https://doi.org/10.1111/j.1742-1241.2010.02417.x
K. S. Shaji, K. Smitha, K. P. Lal, and M. J. Prince, Int. J. Geriatr. Psychiatry. 18, 1 (2003). https://doi.org/10.1002/gps.64912497550
C. Dreux, Ann. Pharm. Fr. 67, 104 (2009). https://doi.org/10.1016/j.pharma.2008.11.00319298894
D. D. Christensen, P. Lin, J. Fam. Pract. 56, 17 (2007).
J. D. Serafini, T. Damianakis, and E. Marziali, Soc. Work Health Care 44, 225 (2007). https://doi.org/10.1300/J010v44n03_0717548277
G. Small and R. Bullock, Alzheimers Dement. 7, 177 (2011). https://doi.org/10.1016/j.jalz.2010.03.01621056013
H. M. Fillit, R. S. Doody, K. Binaso, et al., Am. J. Geriatr. Pharmacother. 4, 9 (2006).https://doi.org/10.1016/j.amjopharm.2006.10.00117157793
M. Prince, N. Graham, H. Brodaty, et al., Int. J. Geriatr. Psychiatry 19, 178 (2004). https://doi.org/10.1002/gps.105914758583
M. C. Gély-Nargeot, C. Derouesné, and J. Selmès, Psychol. Neuropsychiatr. Vieil. 1, 45 (2003).
N. Tajik, M. Tajik, I. Mack, P. Enck, European J. Nutr. 56, 2215 (2017). https://doi.org/10.1007/s00394-017-1379-1
H. Lu, Z. Tian, Y. Cui, Z. Liu, and X. Ma, Compr. Rev. Food Sci. Food Saf. 19, 3130 (2020). https://doi.org/10.1111/1541-4337.12620
N. K. Nozim, A. M. Alisher, E. N. Kabil, N. R. Rakhmatillo, and R. M. Rahmatjon, J. Pharm. Negat. 13, 1322 (2022).
G. Williamson, Food Funct. 11, 4826 (2020). https://doi.org/10.1039/D0FO01168A
S. Kaviani, S. Shahab, and M. Sheikhi, Phys. E: Low-Dimens. Syst. Nanostruct. 126 (2021). https://doi.org/10.1016/j.physe.2020.114473
L. Ji, P. Jiang, B. Lu, Y. Sheng, X. Wang, Z. Wang, J. Nutr. Biochem. 24, 1911 (2013). https://doi.org/10.1016/j.jnutbio.2013.05.007
S. Shahab, M. Sheikhi, L. Filippovich, et al., Curr. Mol. Med. 19, 419 (2019). https://doi.org/10.2174/156652401966619050910262031072290
M. Sheikhi, S. Shahab, R. Alnajjar, M. Ahmadianarog, and S. Kaviani, Curr. Mol. Med. 19, 91 (2019). https://doi.org/10.2174/156652401966619022611182330813875
C. Hoelzl, S. Knasmüller, K. H. Wagner, O. Neubauer, et al., Mol. Nutr. Food Res. 54, 1722 (2010). https://doi.org/10.1002/mnfr.201000048
L. Sapio, A. Salzillo, M. Illiano, et al., J. Cell. Physiol. 235, 3741 (2020). https://doi.org/10.1002/jcp.29269
M. Sheikhi, S. Shahab, M. Khaleghian, et al., Curr. Mol. Med. 19, 473 (2019).https://doi.org/10.2174/156652401966619050614315231057107
A. Aslan, Y. T. Hussein, O. Gok, et al., Environ. Sci. Pollut. Res. 27, 7526 (2020). https://doi.org/10.1007/s11356-019-07352-8
N. Wang, Z. Y. Wang, S. L. Mo, et al., Breast Cancer Res. Treat. 134, 943 (2012). https://doi.org/10.1007/s10549-012-1977-9
V. Ahire, A. Kumar, K. P. Mishra, G. Kulkarni, Nutr. Cancer 69, 904 (2017). https://doi.org/10.1080/01635581.2017.1339811
C. Ceci, P. M. Lacal, L. Tentori, et al., Nutr. 11, 1756 (2018). https://doi.org/10.3390/nu10111756
P. Gupta, T. Mohammad, P. Khan, et al., Biomed. Pharmacother. 118, 109245 (2019). https://doi.org/10.1016/j.biopha.2019.109245
M. Yousuf, A. Shamsi, P. Khan, et al., Int. J. Mol. Sci. 21, 3526 (2020). https://doi.org/10.3390/ijms21103526
N. Wang, Q. Wang, H. Tang, et al., J. Exp. Clin. Cancer Res. 36, 1 (2017). https://doi.org/10.1186/s13046-017-0635-9
S. Chang, B. Li, T. Chen, X. He, B. Wu, J. Anal. Chem. 75, 1018 (2020). https://doi.org/10.1134/S1061934820080055
I. Murakoshi, M. Kaneko, C. Koide, F. Ikegami, Phytochem. 25, 2759 (1986). https://doi.org/10.1016/S0031-9422(00)83736-X
L.A. Chase, R. J. Roon, L. Wellman, A. J. Beitz, J. F. Koerner, Neurosci. 106, 287 (2001). https://doi.org/10.1016/S0306-4522(01)00278-0
M. Bitzer and F. Schaeffel, Optom. Vis. Sci. 81, 127 (2004). https://doi.org/10.1097/00006324-200402000-00011
J. Rochford, A. P. Sen, I. Rousse, and S. A. Welner, Brain Res. Bull. 41, 313 (1996). https://doi.org/10.1016/S0361-9230(96)00191-8
N. Rasool, A. Akhtar, and W. Hussain, Struct. Chem. 31, 1777 (2020). https://doi.org/10.1007/s11224-020-01536-6
S. Shahab, M. Sheikhi, and R. Alnajjar, et al., J. Mol. Struct. 1228, 129461 (2020). https://doi.org/10.1016/j.molstruc.2020.129461
F. E. Agamah, G. K. Mazandu, and R. Hassan, et al., Brief. Bioinform. 21, 1663 (2020). https://doi.org/10.1093/bib/bbz103
D. Rognan, Pharmacol. Ther. 175, 47 (2017).https://doi.org/10.1016/j.pharmthera.2017.02.034
M. Sheikhi, S. Shahab, R. Alnajjar, and M. Ahmadianarog, J. Cluster Sci. 30, 83 (2019). https://doi.org/10.1007/s10876-018-1460-9
S. Siyamak, M. Sheikhi, L. Filippovich, et al., Silicon 10, 2361 (2018). https://doi.org/10.1007/s12633-018-9773-8
K. Sachdev and M. K. Gupta, J. Biomed. Inf. 93, 103159 (2019). https://doi.org/10.1016/j.jbi.2019.103159
C. A. Lipinski, F. Lombardo, B. W. Dominy, P. J. Feeney, Adv. Drug Deliv. Rev. 23, 3 (1997). https://doi.org/10.1016/S0169-409X(96)00423-1
A. Husain, A. Ahmad, S. A. Khan, et al., Saudi Pharm. J. 24, 104 (2016). https://doi.org/10.1016/j.jsps.2015.02.008
M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, et al., Gaussian 09, Revision C.01 (Gaussian, Inc., Wallingford, CT, 2010).
T. Yanai, D. P. Tew, and N. C. Handy, Chem. Phys. Lett. 393, 51 (2004). https://doi.org/10.1016/j.cplett.2004.06.011
B. J. Lynch and D. G. Truhlar, Theor. Chem. Acc. 111, 335 (2004). https://doi.org/10.1007/s00214-003-0518-3
S. Shahab and M. Sheikhi, Russ. J. Phys. Chem. B 14, 15 (2020). https://doi.org/10.1134/S1990793120010145
Y. Konishi, S. Kobayashi, J. Agric. Food Chem. 52, 2518 (2004). https://doi.org/10.1021/jf035407c
R. Dennington, T. Keith, J. Millam, K. Eppinnett, W. L Hovell, and R. Gilliland, GaussView, Version 5.0.9 (Semichem, Inc, Shawnee Mission, KS, USA, 2009).
O. Trott and A. J. Olson, J. Comput. Chem. 31, 455 (2009). https://doi.org/10.1002/jcc.21334
M. Amati, S. Stoia, and E. J. Baerends, J. Chem., Theory Comput. 16, 443 (2019). https://doi.org/10.1021/acs.jctc.9b00981
M. Sheikhi, S. Shahab, M. Khaleghian, F. H. Hajikolaee, I. Balakhanava, and R. Alnajjar, J. Mol. Struct. 1160, 479 (2018). https://doi.org/10.1016/j.molstruc.2018.01.005
S. Shahab, M. Sheikhi, L. Filippovich, D. E. Anatol’evich, and H. Yahyaei, J. Mol. Struct. 1137, 335 (2017). https://doi.org/10.1016/j.molstruc.2017.02.056
S. Shahab, M. Sheikhi, L. Filippovich, et al., Silicon 10, 2385 (2018).
V. Zarotsky, J. J. Sramek, and N. R. Cutler, Am. J. Health Syst. Pharm. 60, 446 (2003).
E. M. Reiman, J. Clin. Psychiatry 67, 1784 (2006).
L. M. Bierer, V. Haroutunian, S. Gabriel, et al., J. Neurochem. 64, 749 (1995).
S. V. Lushchekina, A. V. Nemukhin, I. V. Polyakov, et al., Russ. J. Phys. Chem. B 16, 103 (2022). https://doi.org/10.1134/S1990793122010237
A. Daina, O. Michielin, and V. Zoete, Sci. Rep. 7, 42717 (2017).
A. Daina and V. Zoete, Int. J. Mol. Sci. 20, 4612 (2019)
J. Hastings, G. Owen, A. Dekker, et al., Nucleic Acids Res. 44, D1214 (2016).
Z. H. Al-Sawaff, M. A. Basaran, and F. Kandemirli, Russ. J. Phys. Chem. B 16, 579 (2022). https://doi.org/10.1134/S1990793122040030
X. Miao, S. Zhou, and C. Wang, Russ. J. Phys. Chem. B 16, 804 (2022). https://doi.org/10.1134/S199079312204011X
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interest.
Rights and permissions
About this article
Cite this article
Shahab, S., Almodarresiyeh, H.A., Sheikhi, M. et al. Density Functional Theory Investigation, Bioactivity, Absorption, Distribution, Metabolism, and Excretion Properties, Docking and in Silico Analysis of New Effective Piperazine Derivatives against Alzheimer’s Disease. Russ. J. Phys. Chem. B 17, 725–737 (2023). https://doi.org/10.1134/S1990793123030247
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1990793123030247