Design, synthesis and biological evaluation of selected 3-[3-(amino) propoxy] benzenamines as acetylcholinesterase inhibitors.

Abstract:

:The present paper describes design, synthesis, and biological evaluation of a series of some 3-[3-(amino)propoxy]benzenamines as acetylcholinesterase inhibitors using mice as a model and piracetam as a reference drug. The structures of these compounds were confirmed by spectral analysis and compounds were tested for memory enhancing activity using elevated plus maze test and acetylcholinesterase inhibitory assay. The inhibitory range of synthesized compounds was from 8.99 to 28.31 μM. The synthesized compounds possessed higher or equivalent percent retention as compared to piracetam at 1 mg/kg with no other CNS-related activities (locomotor and muscle relaxant, analgesic and anticonvulsant activities). Compound 3-[3-(imidazolo)propoxy]benzenamine has shown significant dose-dependent (1 and 3 mg/kg) memory enhancing activity, while 3-[3-(pyrrolidino)propoxy]benzenamine also showed activity equivalent to reference drug piracetam at 1 mg/kg. Both compounds 3-[3-(pyrrolidino)propoxy]benzenamine and 3-[3-(imidazolo)propoxy]benzenamine were also found to show AChE inhibition with IC50 value of 8.99 and 17.87 μM. The molecular docking, MM-GBSA and molecular dynamics simulation studies were performed in order to establish a relationship between the biological results. RMSD, root-mean-square fluctuations, and interaction patterns of 10a-AChE and Sck-AChE complexes proved that the binding affinity of 10a toward AChE was highly stable with the proposed binding orientations.

journal_name

J Biomol Struct Dyn

authors

Malik R,Gupta R,Srivastava S,Choudhary BS,Sharma M

doi

10.1080/07391102.2016.1220330

subject

Has Abstract

pub_date

2017-08-01 00:00:00

pages

2382-2394

issue

11

eissn

0739-1102

issn

1538-0254

journal_volume

35

pub_type

杂志文章
  • An NMR study of d(CTACTGCTTTAG).d(CTAAAGCAGTAG) showing hydration water molecules in the minor groove of a TpA step.

    abstract::The hydration properties of the non-palindromic duplex d(CTACTGCTTTAG). d(CTAAAGCAGTAG) were investigated by NMR spectroscopy. The oligonucleotide possesses a heterogeneous B-DNA structure. The H2(n)-H1'(m+1) distances reflect a minor groove narrowing within the TTT/AAA segment (approximately 3.9A) and a sudden wideni...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1998.10508276

    authors: Leporc S,Mauffret O,El Antri S,Convert O,Lescot E,Tevanian G,Fermandjian S

    更新日期:1998-12-01 00:00:00

  • The terminal phosphate in d(pGpG) reduces self-association.

    abstract::An investigation of the self-association behavior of 2'-deoxy[5'-phosphate-guanylyl-(3'-5')-guanosine] (d(pGpG)) in the presence of Na+ and K+ ions has been carried out by 1H and 31P NMR and FTIR spectroscopy. A comparison has been made of the self- association behavior of d(pGpG) with that of the related dinucleotide...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1999.10508386

    authors: Kawasaki MM,Walmsley JA

    更新日期:1999-12-01 00:00:00

  • MOWGLI: prediction of protein-MannOse interacting residues With ensemble classifiers usinG evoLutionary Information.

    abstract::Proteins interact with carbohydrates to perform various cellular interactions. Of the many carbohydrate ligands that proteins bind with, mannose constitute an important class, playing important roles in host defense mechanisms. Accurate identification of mannose-interacting residues (MIR) may provide important clues t...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2015.1106978

    authors: Pai PP,Mondal S

    更新日期:2016-10-01 00:00:00

  • Intermolecular contacts between the lambda-Cro repressor and the operator DNA characterized by nuclear magnetic resonance spectroscopy.

    abstract::The specific interaction between lambda phage Cro repressor and the DNA fragment bearing the consensus sequence of operators has been studied using nuclear magnetic resonance (NMR). Using both 15N- and 13C/15N- labeled lambda-Cro in complex with unlabeled DNA, chemical shift assignments of the lambda-Cro-DNA complex w...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1999.10508309

    authors: Tochio H,Kojima C,Matsuo H,Yamazaki T,Kyogoku Y

    更新日期:1999-04-01 00:00:00

  • Investigation of arc repressor DNA-binding specificity by comparative molecular dynamics simulations.

    abstract::Transcription factors regulate gene expression through binding to specific DNA sequences. How transcription factors achieve high binding specificity is still not well understood. In this paper, we investigated the role of protein flexibility in protein-DNA-binding specificity by comparative molecular dynamics (MD) sim...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2014.997797

    authors: Song W,Guo JT

    更新日期:2015-01-01 00:00:00

  • Synthesis of carbazole based α-aminophosphonate derivatives: design, molecular docking and in vitro cholinesterase activity.

    abstract::A series of novel carbazole based α-aminophosphonate derivatives were synthesized under solvent-free condition, characterized and evaluated for their cholinesterase inhibition, enzyme kinetic inhibition, in-vitro cell viability using N2a cells, neuroprotective studies against H2O2-induced stress using N2a cells and an...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2020.1861981

    authors: Shaikh S,Dhavan P,Singh P,Uparkar J,Vaidya SP,Jadhav BL,Ramana MV

    更新日期:2020-12-21 00:00:00

  • In silico site-directed mutagenesis of neutralizing mAb 4C4 and analysis of its interaction with G-H loop of VP1 to explore its therapeutic applications against FMD.

    abstract::Investigating the behaviour of bio-molecules through computational mutagenesis is gaining interest to facilitate the development of new therapeutic solutions for infectious diseases. The antigenetically variant genotypes of foot and mouth disease virus (FMDV) and their subsequent infections are challenging to tackle w...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2018.1494631

    authors: Sahu TK,Pradhan D,Rao AR,Jena L

    更新日期:2019-07-01 00:00:00

  • Aggregation of mucin by chromium(III) complexes as revealed by electrokinetic and rheological studies: influence on the tryptic and O-glycanase digestion of mucin.

    abstract::In the present study, the impact of chromium(III) complexes ([Cr(salen)(H2O)2](+) (1), [Cr(en)3]3+ (2) and [Cr(EDTA)(H2O)]- (3)) on the biophysical properties of mucin like specific viscosity, zeta potential and particle size has been investigated. It is evident from the present investigation that the nature of the co...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2004.10506958

    authors: Shrivastava HY,Sreeram KJ,Nair BU

    更新日期:2004-04-01 00:00:00

  • Fi-score: a novel approach to characterise protein topology and aid in drug discovery studies.

    abstract::Target evaluation is at the centre of rational drug design and biologics development. In order to successfully engineer antibodies, T-cell receptors or small molecules it is necessary to identify and characterise potential binding or contact sites on therapeutically relevant target proteins. Currently, there are numer...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2020.1854859

    authors: Kanapeckaitė A,Beaurivage C,Hancock M,Verschueren E

    更新日期:2020-12-10 00:00:00

  • Unusual stability exhibited by (AT)XN12(AT)Y motif associated with high fetal hemoglobin levels.

    abstract::Quasi-palindromic sequences (AT) X N12(AT) Y present in HS2 (hypersensitive site 2) of the human β-globin locus are known to be significantly associated with increased fetal hemoglobin (HbF) levels. High HbF levels in some adults ...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2018.1532320

    authors: Roy K,Mahendru S,Kukreti R,Kukreti S

    更新日期:2019-09-01 00:00:00

  • An NMR study of the polymorphous behavior of the mismatched DNA octamer d(m5C-G-m5C-G-T-G-m5C-G) in solution. The B, Z, and hairpin forms.

    abstract::The polymorphism exhibited by the mismatched octamer d(m5C-G-m5C-G-T-G-m5C-G), as a function of the temperature, DNA concentration and ionic strength, was investigated by means of NMR spectroscopy. It is shown that this partly self-complementary DNA fragment, under conditions of low DNA concentration (0.4 mM) and low ...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1987.10507691

    authors: Orbons LP,van der Marel GA,van Boom JH,Altona C

    更新日期:1987-06-01 00:00:00

  • Monoclonal antibody against DNA adducts with osmium structural probes.

    abstract::Osmium tetroxide complexes with nitrogen ligands (Os,L) have been widely used as probes of the DNA structure. A monoclonal antibody OsBP7H8 against DNA adducts with Os,L was produced in mice. OsBP7H8 does not bind to proteins or total yeast RNA modified with Os,2,2'-bipyridine (bipy) nor to the unmodified nucleic acid...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1999.10508339

    authors: Bůzek J,Kuderová A,Pexa T,Stanková V,Lauerová L,Palecek E

    更新日期:1999-08-01 00:00:00

  • Conformations of complexes derived from the interactions of two stereoisomeric bay-region 5-methylchrysene diol epoxides with DNA.

    abstract::The reaction mechanisms of two isomeric bay-region diol epoxides of 5-methylchrysene (trans-1,2-dihydroxy-anti-3,4-epoxy-1,2,3,4-tetrahydro-5-methylchrysene (DE-I) and trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydro-5-methylchrysene (DE-II) with double-stranded DNA in aqueous solutions were studied utilizing k...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1986.10508476

    authors: Kim MH,Roche CJ,Geacintov NE,Pope M,Pataki J,Harvey RG

    更新日期:1986-04-01 00:00:00

  • Improved annotation of a plant pathogen genome Xanthomonas oryzae pv. oryzae PXO99A.

    abstract::Many bacterial genomes have been sequenced and stored in public databases now, of which Reference Sequence (RefSeq) is the most widely used one. However, the annotation in RefSeq is still unsatisfactory. The present analysis is focused on the re-annotation of an important plant pathogen genome Xanthomonas oryzae pv. o...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2012.698218

    authors: Lei Y,Kang SK,Gao J,Jia XS,Chen LL

    更新日期:2013-03-01 00:00:00

  • New tailored substituted benzothiazole Schiff base Cu(II)/Zn(II) antitumor drug entities: effect of substituents on DNA binding profile, antimicrobial and cytotoxic activity.

    abstract::New tailored Cu(II) & Zn(II) metal-based antitumor drug entities were synthesized from substituted benzothiazole o‒vanillin Schiff base ligands. The complexes were thoroughly characterized by elemental analysis, spectroscopic studies {IR, 1H & 13C NMR, ESI-MS, EPR} and magnetic susceptibility measurements. The structu...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2018.1467794

    authors: Zehra S,Shavez Khan M,Ahmad I,Arjmand F

    更新日期:2019-04-01 00:00:00

  • 3D QSAR pharmacophore-based virtual screening for the identification of potential inhibitors of tyrosinase.

    abstract::Tyrosinase plays an important role in melanin biosynthesis and protects skin against ultraviolet radiations. Functional deficiency of tyrosinase results in serious dermatological diseases. Tyrosinase also participates in neuromelanin formation in the human brain, which leads to neurodegeneration resulting in Parkinson...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2019.1647287

    authors: Ghayas S,Ali Masood M,Parveen R,Aquib M,Farooq MA,Banerjee P,Sambhare S,Bavi R

    更新日期:2020-07-01 00:00:00

  • New heat shock protein (Hsp90) inhibitors, designed by pharmacophore modeling and virtual screening: synthesis, biological evaluation and molecular dynamics studies.

    abstract::Inhibition of heat shock protein 90 (Hsp90) is known to be a significantly effective strategy in cancer therapy. Here, pyrazolopyranopyrimidine derivatives were characterized as new Hsp90 inhibitors. The molecules' key structure (ZINC02819805) was determined by utilizing a pharmacophore model virtual screening workflo...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2019.1660216

    authors: Abbasi M,Amanlou M,Aghaei M,Bakherad M,Doosti R,Sadeghi-Aliabadi H

    更新日期:2020-08-01 00:00:00

  • Unprecedented hydrophobic stabilizations from a reverse wobble T·T mispair in DNA minidumbbell.

    abstract::Minidumbbell (MDB) is a newly found non-B DNA structure formed by short single-strand sequences. Up to now, three MDBs have been reported to form at neutral pH by sequences containing two repeats of TTTA, CCTG and CTTG. Among them, the thermodynamically less stable TTTA and CCTG MDBs have been proposed to be the struc...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2019.1621211

    authors: Guo P,Lam SL

    更新日期:2020-04-01 00:00:00

  • Zinc metal carboxylates as potential anti-Alzheimer's candidate: in vitro anticholinesterase, antioxidant and molecular docking studies.

    abstract::In search of suitable therapy for the management of Alzheimer's disease, this study was designed to evaluate metal complexes against its biochemical targets. Zinc metal carboxylates (AAZ1-AAZ6) were evaluated against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The antioxidant in combination with anti...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2020.1724569

    authors: Zafar R,Zubair M,Ali S,Shahid K,Waseem W,Naureen H,Haider A,Jan MS,Ullah F,Sirajuddin M,Sadiq A

    更新日期:2020-02-13 00:00:00

  • Poly(dA-dT).poly(dA-dT) in low salt appears to be a left-handed B-helix combined use of chemical theory, fiber diffraction and NMR spectroscopy.

    abstract::Poly(dA-dT).poly(dA-dT) can adopt the B- and D- forms in the fibrous state. Theoretical energy calculations and fiber diffraction analyses suggest that there can be three structural models of poly(dA-dT).poly(dA-dT) in each of these two forms viz right and left-handed Watson Crick models and left-handed Hoogsteen--a t...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1983.10507450

    authors: Gupta G,Sarma MH,Dhingra MM,Sarma RH,Rajagopalan M,Sasisekharan V

    更新日期:1983-10-01 00:00:00

  • A comparative spectroscopic and calorimetric investigation of the interaction of amsacrine with heme proteins, hemoglobin and myoglobin.

    abstract::The binding of the anilido aminoacridine derivative amsacrine with the heme proteins, hemoglobin, and myoglobin, was characterized by various spectroscopic and calorimetric methods. The binding affinity to hemoglobin was (1.21 ± .05) × 105 M-1, while that to myoglobin was three times higher (3.59 ± .15) × 105 M-1. The...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2016.1176958

    authors: Bhowmik D,Suresh Kumar G

    更新日期:2017-05-01 00:00:00

  • Identification of novel antiplasmodial compound by hierarquical virtual screening and in vitro assays.

    abstract::Malaria is an infectious disease caused by protozoa of the genus Plasmodium spp. with approximately 219 million cases in 2017. P. falciparum is main responsible for the most severe form of the disease, cerebral malaria. Despite of public health impacts, chemotherapy against malaria is still limited due to the emergenc...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2020.1763837

    authors: Costa Júnior DB,Araújo JSC,de Mattos Oliveira L,Neri FSM,Moreira POL,Taranto AG,Fonseca AL,de Pilla Varotti F,Leite FHA

    更新日期:2020-05-13 00:00:00

  • The DMRT gene family in amphioxus.

    abstract::Doublesex and Mab-3-related transcription factor (DMRT) gene family is widely known for its involvement in sex determination and/or differentiation among different phyla. In this study, we identify eight DMRT genes in the cephalochordate amphioxus, a protochordate holding a key phylogenetic position. The eight DMRTs c...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2012.677770

    authors: Wang F,Yu Y,Ji D,Li H

    更新日期:2012-01-01 00:00:00

  • Conformational studies on calcium binding by tBoc-Leu-Pro-Tyr-Ala-NHCH3, a tyrosine kinase substrate, in a nonpolar solvent.

    abstract::With a view to understanding the structural requirement for tyrosine phosphorylation, we have examined the free and Ca(2+)-bound conformations of the synthetic peptide tBoc-Leu-Pro-Tyr-Ala-NHCH3, a substrate for a protein tyrosine kinase, using circular dichroism (CD), 1H and 13C nuclear magnetic resonance (NMR) and m...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1993.10508012

    authors: Ananthanarayanan VS,Saint-Jean A,Cheesman BV,Hughes DW,Bain AD

    更新日期:1993-12-01 00:00:00

  • Theory of helix-coil transition on DNA-ligand complexes: the effect to two types of interaction of ligand on the parameters of transition.

    abstract::The effect of ligand interacting with native DNA by two types on the parameters of helix-coil transition in homopolymers is considered using the most probable distribution method (Yu.S. Lazurkin et al., Biopolymers 1970). It is shown that at a small relative concentration of ligand the melting enthalpy (delta H) of DN...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1990.10507793

    authors: Karapetian AT,Vardevanian PO,Tarzikian GA,Frank-Kamenetskii MD

    更新日期:1990-08-01 00:00:00

  • New wrinkles on polynucleotide duplexes.

    abstract::Most fibrous polynucleotides of general sequence exhibit secondary structures that are described adequately by regular helices with a repeated motif of only one nucleotide. Such helices exploit the fact that A:T, T:A, G:C, and C:G pairs are essentially isomorphous and have dyadically-related glycosylic bonds. Polynucl...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1983.10507453

    authors: Arnott S,Chandrasekaran R,Banerjee AK,He R,Walker JK

    更新日期:1983-10-01 00:00:00

  • Genome-wide codon usage profiling of ocular infective Chlamydia trachomatis serovars and drug target identification.

    abstract::Chlamydia trachomatis (C.t) is a Gram-negative obligate intracellular bacteria and is a major causative of infectious blindness and sexually transmitted diseases. Among the varied serovars of this organism, A, B and C are reported as prominent ocular pathogens. Genomic studies of these strains shall aid in deciphering...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2017.1343685

    authors: Sadhasivam A,Vetrivel U

    更新日期:2018-06-01 00:00:00

  • Study on the interaction of taiwaniaquinoids with FTO by spectroscopy and molecular modeling.

    abstract::In this work, an attempt has been made to study the interaction of four taiwaniaquinoids with fat mass and obesity-associated protein (FTO) by UV-vis absorption, fluorescence spectroscopy, and molecular docking techniques. The results indicated that taiwaniaquinoids effectively quenched the intrinsic fluorescence of F...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2016.1249957

    authors: Ren T,Zhang L,Wang J,Song C,Wang R,Chang J

    更新日期:2017-11-01 00:00:00

  • Tetraplex structure formation in the thrombin-binding DNA aptamer by metal cations measured by vibrational spectroscopy.

    abstract::Formation of intramolecular tetraplex structures by the thrombin-binding DNA aptamer (TBA) in the presence of K(+), Pb(2+), Ba(2+), Sr(2+) and Mn(2+) has been studied by vibrational spectroscopy. All tetraplex structures contain G-G Hoogsteen type base pairing, both C2'endo/anti and C2'endo/syn deoxyguanosine glycosid...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.2004.10507008

    authors: Mondragon-Sanchez JA,Liquier J,Shafer RH,Taillandier E

    更新日期:2004-12-01 00:00:00

  • NMR and molecular dynamics studies of tachykinins: conformation of substance P fragment 4-11.

    abstract::The conformation of the C-terminal octapeptide fragment of Substance P (SP4-11, Pro-Gln-Gln-Phe-Phe-Gly-Leu-Met-NH2) has been investigated by 2D-NMR and MD methods. The octapeptide exists in a blend of conformations. The molecule seems to shuttle between conformations with gamma-bends either at Phe5 or Gly6 or Gln3 or...

    journal_title:Journal of biomolecular structure & dynamics

    pub_type: 杂志文章

    doi:10.1080/07391102.1998.10508286

    authors: Coutinho E,Kamath S,Saran A,Srivastava S

    更新日期:1998-12-01 00:00:00