Synthesis, crystal structure, cholinesterase inhibitory activity, evaluation of insecticidal activities, and computational studies of new phosphonic acids
In an attempt to obtain the modified and novel insecticides with low human toxicity, a series of novel mono-, bis-, and tetraphosphonic acid derivatives were designed and characterized by infrared, 1 H, 13 C, and 31 P NMR spectroscopy and X-ray crystallography. The inhibitory effects of the synthesi...
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| Published in | Molecular diversity Vol. 26; no. 3; pp. 1519 - 1530 |
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| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Cham
Springer International Publishing
01.06.2022
Springer Nature B.V |
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| Online Access | Get full text |
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| Abstract | In an attempt to obtain the modified and novel insecticides with low human toxicity, a series of novel mono-, bis-, and tetraphosphonic acid derivatives were designed and characterized by infrared,
1
H,
13
C, and
31
P NMR spectroscopy and X-ray crystallography. The inhibitory effects of the synthesized compounds were evaluated using the in vitro Ellman method on human and insect acetylcholinesterase (AChE). Some of these compounds, which had low human and high insect toxicity, were chosen to assess the killing effects (in vivo) on third larval instar of elm leaf beetle (X. luteola). In vivo and in vitro evidence has revealed that bisphosphonic acids, containing hydrophobic systems, have a good selectivity of insect AChE inhibition. In the present study, docking results showed that bisphosphonic acids had lower binding energy and higher inhibition compared with tetraphosphonic acids due to the type of their topology and the ability of their hydrogen to interact with the catalytic triad (the main active site of the enzyme). Additionally, the QSAR results demonstrated that the major effecting factors on the insecticidal activity of the subject compounds are the hydrophobicity, size, shape, and ability to form a hydrogen bond. The present study can be helpful in the development of new insecticides.
Graphic abstract |
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| AbstractList | In an attempt to obtain the modified and novel insecticides with low human toxicity, a series of novel mono-, bis-, and tetraphosphonic acid derivatives were designed and characterized by infrared, 1H, 13C, and 31P NMR spectroscopy and X-ray crystallography. The inhibitory effects of the synthesized compounds were evaluated using the in vitro Ellman method on human and insect acetylcholinesterase (AChE). Some of these compounds, which had low human and high insect toxicity, were chosen to assess the killing effects (in vivo) on third larval instar of elm leaf beetle (X. luteola). In vivo and in vitro evidence has revealed that bisphosphonic acids, containing hydrophobic systems, have a good selectivity of insect AChE inhibition. In the present study, docking results showed that bisphosphonic acids had lower binding energy and higher inhibition compared with tetraphosphonic acids due to the type of their topology and the ability of their hydrogen to interact with the catalytic triad (the main active site of the enzyme). Additionally, the QSAR results demonstrated that the major effecting factors on the insecticidal activity of the subject compounds are the hydrophobicity, size, shape, and ability to form a hydrogen bond. The present study can be helpful in the development of new insecticides. Graphic abstract In an attempt to obtain the modified and novel insecticides with low human toxicity, a series of novel mono-, bis-, and tetraphosphonic acid derivatives were designed and characterized by infrared, 1 H, 13 C, and 31 P NMR spectroscopy and X-ray crystallography. The inhibitory effects of the synthesized compounds were evaluated using the in vitro Ellman method on human and insect acetylcholinesterase (AChE). Some of these compounds, which had low human and high insect toxicity, were chosen to assess the killing effects (in vivo) on third larval instar of elm leaf beetle (X. luteola). In vivo and in vitro evidence has revealed that bisphosphonic acids, containing hydrophobic systems, have a good selectivity of insect AChE inhibition. In the present study, docking results showed that bisphosphonic acids had lower binding energy and higher inhibition compared with tetraphosphonic acids due to the type of their topology and the ability of their hydrogen to interact with the catalytic triad (the main active site of the enzyme). Additionally, the QSAR results demonstrated that the major effecting factors on the insecticidal activity of the subject compounds are the hydrophobicity, size, shape, and ability to form a hydrogen bond. The present study can be helpful in the development of new insecticides. Graphic abstract In an attempt to obtain the modified and novel insecticides with low human toxicity, a series of novel mono-, bis-, and tetraphosphonic acid derivatives were designed and characterized by infrared, 1H, 13C, and 31P NMR spectroscopy and X-ray crystallography. The inhibitory effects of the synthesized compounds were evaluated using the in vitro Ellman method on human and insect acetylcholinesterase (AChE). Some of these compounds, which had low human and high insect toxicity, were chosen to assess the killing effects (in vivo) on third larval instar of elm leaf beetle (X. luteola). In vivo and in vitro evidence has revealed that bisphosphonic acids, containing hydrophobic systems, have a good selectivity of insect AChE inhibition. In the present study, docking results showed that bisphosphonic acids had lower binding energy and higher inhibition compared with tetraphosphonic acids due to the type of their topology and the ability of their hydrogen to interact with the catalytic triad (the main active site of the enzyme). Additionally, the QSAR results demonstrated that the major effecting factors on the insecticidal activity of the subject compounds are the hydrophobicity, size, shape, and ability to form a hydrogen bond. The present study can be helpful in the development of new insecticides.In an attempt to obtain the modified and novel insecticides with low human toxicity, a series of novel mono-, bis-, and tetraphosphonic acid derivatives were designed and characterized by infrared, 1H, 13C, and 31P NMR spectroscopy and X-ray crystallography. The inhibitory effects of the synthesized compounds were evaluated using the in vitro Ellman method on human and insect acetylcholinesterase (AChE). Some of these compounds, which had low human and high insect toxicity, were chosen to assess the killing effects (in vivo) on third larval instar of elm leaf beetle (X. luteola). In vivo and in vitro evidence has revealed that bisphosphonic acids, containing hydrophobic systems, have a good selectivity of insect AChE inhibition. In the present study, docking results showed that bisphosphonic acids had lower binding energy and higher inhibition compared with tetraphosphonic acids due to the type of their topology and the ability of their hydrogen to interact with the catalytic triad (the main active site of the enzyme). Additionally, the QSAR results demonstrated that the major effecting factors on the insecticidal activity of the subject compounds are the hydrophobicity, size, shape, and ability to form a hydrogen bond. The present study can be helpful in the development of new insecticides. |
| Author | EbrahimiValmoozi, Ali Asghar Yaghoubi, Rouhollah Rahimzadeh Dashtaki, Maryam Sharifi, Mahboobeh Roohzadeh, Roohollah Pooyan, Mahsa Mohammadpanah, Fahimeh Rahmani, Hamidreza Gholivand, Khodayar Roshanian, Zahra |
| Author_xml | – sequence: 1 givenname: Khodayar surname: Gholivand fullname: Gholivand, Khodayar email: gholi_kh@modares.ac.ir organization: Department of Chemistry, Tarbiat Modares University – sequence: 2 givenname: Fahimeh surname: Mohammadpanah fullname: Mohammadpanah, Fahimeh organization: Department of Chemistry, Tarbiat Modares University – sequence: 3 givenname: Rouhollah surname: Yaghoubi fullname: Yaghoubi, Rouhollah organization: Department of Chemistry, Tarbiat Modares University – sequence: 4 givenname: Maryam surname: Rahimzadeh Dashtaki fullname: Rahimzadeh Dashtaki, Maryam organization: Department of Chemistry, Tarbiat Modares University – sequence: 5 givenname: Mahsa surname: Pooyan fullname: Pooyan, Mahsa organization: Department of Chemistry, Tarbiat Modares University – sequence: 6 givenname: Hamidreza surname: Rahmani fullname: Rahmani, Hamidreza organization: Department of Chemistry, Tarbiat Modares University – sequence: 7 givenname: Zahra surname: Roshanian fullname: Roshanian, Zahra organization: Department of Chemistry, Tarbiat Modares University – sequence: 8 givenname: Mahboobeh surname: Sharifi fullname: Sharifi, Mahboobeh organization: Department of Plant Protection, Agricultural and Natural Resources Research Center, ARREO – sequence: 9 givenname: Ali Asghar surname: EbrahimiValmoozi fullname: EbrahimiValmoozi, Ali Asghar organization: Department of Advanced Materials, Imam Hossein University – sequence: 10 givenname: Roohollah surname: Roohzadeh fullname: Roohzadeh, Roohollah organization: Department of Chemistry, Tarbiat Modares University |
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| Cites_doi | 10.1016/j.pestbp.2013.05.012 10.1007/s00726-009-0254-7 10.1016/j.cbi.2012.08.002 10.1016/j.medidd.2020.100063 10.1016/j.molbiopara.2012.10.006 10.1016/j.emc.2014.09.010 10.1016/S0169-409X(96)00423-1 10.3109/14756361003691860 10.1016/j.bioorg.2019.01.064 10.1021/jf990691m 10.1201/9781439822685 10.1021/ja01609a037 10.1016/j.pestbp.2019.03.010 10.3390/molecules17032408 10.1016/S0021-9673(00)01274-7 10.1080/10426509708043566 10.1002/1522-2683(200207)23:14<2333::AID-ELPS2333>3.0.CO;2-5 10.1016/S0965-1748(01)00057-1 10.1134/S1070363215090091 10.1016/0003-2697(68)90092-4 10.1021/tx0499259 10.1080/14756360500456699 10.1016/j.bmcl.2014.04.082 |
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| Keywords | Acetylcholinesterase inhibitors Docking Insecticide Phosphonic acid derivatives QSAR Xanthogaleruca luteola |
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| References | LipinskiCALombardoFDominyBWFeeneyPJAdv Drug Deliv Rev1997233251:CAS:528:DyaK2sXktlKlsQ%3D%3D10.1016/S0169-409X(96)00423-1 BandyopadhyayPSatheMTikarSNYadavRSharmaPKumarAKaushikMBioorg Med Chem Lett201424293429391:CAS:528:DC%2BC2cXosV2hs7Y%3D10.1016/j.bmcl.2014.04.082 ZhangZHeDChenRPhosphorus Sulfur Silicon Relat Elem19971262732811:CAS:528:DyaK1cXks12qu7c%3D10.1080/10426509708043566 Wagner-JaureggTHackleyBEJrLiesTOwensOProperRJ Am Chem Soc1955779229291:CAS:528:DyaG2MXltlymsw%3D%3D10.1021/ja01609a037 GholivandKMohammadpanahFPooyanMValmooziAAESharifiMMani-VarnosfaderaniAHosseiniZPestic Biochem Physiol20191571221371:CAS:528:DC%2BC1MXls1els7s%3D10.1016/j.pestbp.2019.03.010 KingAMAaronCKEmerg Med Clin20153313315110.1016/j.emc.2014.09.010 SparksTCPestic Biochem Physiol20131078171:CAS:528:DC%2BC3sXps1ykt7g%3D10.1016/j.pestbp.2013.05.012 NaydenovaEDTodorovPTTroevKDAmino Acids20103823301:CAS:528:DC%2BC3cXhtVeht7k%3D10.1007/s00726-009-0254-7 R. Eisenthal and M. J. Danson, (2002) Enzyme assays: a practical approach, Practical Approach (Paperback) L. Software, (1987) A user's guide to probit and logit analysis. LeOra Software Company, Berkeley, CA CasidaJEDurkinKAChem Biol Interact20132032212251:CAS:528:DC%2BC38Xhtl2ksbbP10.1016/j.cbi.2012.08.002 GholivandKGhazianiFYaghoubiRHosseiniZShariatiniaZJ Enzyme Inhib Med Chem2010258278351:CAS:528:DC%2BC3cXhtl2rtr7O10.3109/14756361003691860 CasidaJEQuistadGBChem Res Toxicol2004179839981:CAS:528:DC%2BD2cXltl2lurw%3D10.1021/tx0499259 SedlakJLindsayRHAnal Biochem1968251922051:CAS:528:DyaF1MXhslCktA%3D%3D10.1016/0003-2697(68)90092-4 TsebrikovaGBaulinVKalashnikovaIRagulinVZavel’skiiVMarukAYLunevAKlement’evaOKodinaGTsivadzeAYRuss J Gen Chem201585207120791:CAS:528:DC%2BC2MXhslSmsbvI10.1134/S1070363215090091 YuHYangHShiETangWMed Drug Discov202081000631:CAS:528:DC%2BB3MXitFamurfI10.1016/j.medidd.2020.100063 ChauhanMSShuklaJPandeyUBhadauriaSInt J Res Bot201333743 GholivandKShariatiniaZKhajehKNaderimaneshHJ Enzyme Inhib Med Chem20062131351:CAS:528:DC%2BD28XjtFCitrk%3D10.1080/14756360500456699 N. Zerangue, Q. Gao and W. J. Dower (2010) Creatine phosphate analog prodrugs, compositions and uses thereof, Google Patents BashariEGhadamyariMSendiJJJ Entomol Soc Iran2014343546 MolinaMSilvaMElectrophoresis200223233323401:CAS:528:DC%2BD38XmtFaqtr0%3D10.1002/1522-2683(200207)23:14<2333::AID-ELPS2333>3.0.CO;2-5 GholivandKPooyanMMohammadpanahFPirastefarFJunkPCWangJValmooziAAEMani-VarnosfaderaniABioorg Chem2019864824931:CAS:528:DC%2BC1MXjtFOgsLw%3D10.1016/j.bioorg.2019.01.064 RechciglJERechciglNAInsect pest management: techniques for environmental protection2016LondonCRC Press10.1201/9781439822685 LountosGTTropeaJEWaughDSMol Biochem Parasitol2013187181:CAS:528:DC%2BC3sXhslCgsr0%3D10.1016/j.molbiopara.2012.10.006 TodeschiniRConsonniVHandbook of molecular descriptors2008LondonWiley GwaramNSAliHMAbdullaMABuckleMJSukumaranSDChungLYOthmanRAlhadiAAYehyeWAHadiAHAMolecules201217240824271:CAS:528:DC%2BC38Xjs12ru78%3D10.3390/molecules17032408 GaoJ-RZhuKYInsect Biochem Mol Biol200131109511041:CAS:528:DC%2BD3MXmtV2hsrw%3D10.1016/S0965-1748(01)00057-1 Jalali-HeraviMFatemiMJ Chromatogr A20019151771831:CAS:528:DC%2BD3MXisF2mt78%3D10.1016/S0021-9673(00)01274-7 AlcocerMDillonPManningBDoyenCLeeHDalySO’kennedyRMorganMJ Agric Food Chem200048222822331:CAS:528:DC%2BD3cXjs1KmsLs%3D10.1021/jf990691m K Gholivand (10283_CR28) 2019; 86 10283_CR5 K Gholivand (10283_CR8) 2019; 157 G Tsebrikova (10283_CR12) 2015; 85 JE Casida (10283_CR2) 2004; 17 M Jalali-Heravi (10283_CR27) 2001; 915 TC Sparks (10283_CR3) 2013; 107 JE Rechcigl (10283_CR1) 2016 K Gholivand (10283_CR17) 2010; 25 Z Zhang (10283_CR16) 1997; 126 R Todeschini (10283_CR26) 2008 M Molina (10283_CR11) 2002; 23 10283_CR19 NS Gwaram (10283_CR24) 2012; 17 AM King (10283_CR4) 2015; 33 J-R Gao (10283_CR7) 2001; 31 J Sedlak (10283_CR18) 1968; 25 K Gholivand (10283_CR23) 2006; 21 M Alcocer (10283_CR10) 2000; 48 CA Lipinski (10283_CR29) 1997; 23 H Yu (10283_CR14) 2020; 8 E Bashari (10283_CR20) 2014; 34 MS Chauhan (10283_CR21) 2013; 3 ED Naydenova (10283_CR9) 2010; 38 GT Lountos (10283_CR15) 2013; 187 10283_CR22 T Wagner-Jauregg (10283_CR13) 1955; 77 P Bandyopadhyay (10283_CR6) 2014; 24 JE Casida (10283_CR25) 2013; 203 |
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Danson, (2002) Enzyme assays: a practical approach, Practical Approach (Paperback) – reference: TodeschiniRConsonniVHandbook of molecular descriptors2008LondonWiley – reference: ChauhanMSShuklaJPandeyUBhadauriaSInt J Res Bot201333743 – reference: RechciglJERechciglNAInsect pest management: techniques for environmental protection2016LondonCRC Press10.1201/9781439822685 – reference: ZhangZHeDChenRPhosphorus Sulfur Silicon Relat Elem19971262732811:CAS:528:DyaK1cXks12qu7c%3D10.1080/10426509708043566 – reference: LountosGTTropeaJEWaughDSMol Biochem Parasitol2013187181:CAS:528:DC%2BC3sXhslCgsr0%3D10.1016/j.molbiopara.2012.10.006 – reference: AlcocerMDillonPManningBDoyenCLeeHDalySO’kennedyRMorganMJ Agric Food Chem200048222822331:CAS:528:DC%2BD3cXjs1KmsLs%3D10.1021/jf990691m – reference: GwaramNSAliHMAbdullaMABuckleMJSukumaranSDChungLYOthmanRAlhadiAAYehyeWAHadiAHAMolecules201217240824271:CAS:528:DC%2BC38Xjs12ru78%3D10.3390/molecules17032408 – reference: NaydenovaEDTodorovPTTroevKDAmino Acids20103823301:CAS:528:DC%2BC3cXhtVeht7k%3D10.1007/s00726-009-0254-7 – reference: Jalali-HeraviMFatemiMJ Chromatogr A20019151771831:CAS:528:DC%2BD3MXisF2mt78%3D10.1016/S0021-9673(00)01274-7 – reference: GaoJ-RZhuKYInsect Biochem Mol Biol200131109511041:CAS:528:DC%2BD3MXmtV2hsrw%3D10.1016/S0965-1748(01)00057-1 – reference: CasidaJEDurkinKAChem Biol Interact20132032212251:CAS:528:DC%2BC38Xhtl2ksbbP10.1016/j.cbi.2012.08.002 – reference: BandyopadhyayPSatheMTikarSNYadavRSharmaPKumarAKaushikMBioorg Med Chem Lett201424293429391:CAS:528:DC%2BC2cXosV2hs7Y%3D10.1016/j.bmcl.2014.04.082 – reference: LipinskiCALombardoFDominyBWFeeneyPJAdv Drug Deliv Rev1997233251:CAS:528:DyaK2sXktlKlsQ%3D%3D10.1016/S0169-409X(96)00423-1 – reference: MolinaMSilvaMElectrophoresis200223233323401:CAS:528:DC%2BD38XmtFaqtr0%3D10.1002/1522-2683(200207)23:14<2333::AID-ELPS2333>3.0.CO;2-5 – reference: SparksTCPestic Biochem Physiol20131078171:CAS:528:DC%2BC3sXps1ykt7g%3D10.1016/j.pestbp.2013.05.012 – reference: GholivandKGhazianiFYaghoubiRHosseiniZShariatiniaZJ Enzyme Inhib Med Chem2010258278351:CAS:528:DC%2BC3cXhtl2rtr7O10.3109/14756361003691860 – reference: KingAMAaronCKEmerg Med Clin20153313315110.1016/j.emc.2014.09.010 – reference: BashariEGhadamyariMSendiJJJ Entomol Soc Iran2014343546 – reference: L. Software, (1987) A user's guide to probit and logit analysis. LeOra Software Company, Berkeley, CA – reference: SedlakJLindsayRHAnal Biochem1968251922051:CAS:528:DyaF1MXhslCktA%3D%3D10.1016/0003-2697(68)90092-4 – reference: N. Zerangue, Q. Gao and W. J. 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| SubjectTerms | Acids Antibiotics Biochemistry Biomedical and Life Sciences Insecticides Life Sciences Organic Chemistry Original Article Pharmacy Polymer Sciences |
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| Title | Synthesis, crystal structure, cholinesterase inhibitory activity, evaluation of insecticidal activities, and computational studies of new phosphonic acids |
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