Literature DB >> 29788780

Isoform selectivity of harmine-conjugated 1,2,3-triazoles against human monoamine oxidase.

Saqlain Haider1, Manal Alhusban2, Narayan D Chaurasiya1, Babu L Tekwani1, Amar G Chittiboyina1, Ikhlas A Khan1.   

Abstract

AIM: There is little information available on the monoamine oxidase isoform selectivity of N-alkyl harmine analogs, which exhibit a myriad of activities including MAO-A, DYRK1A and cytotoxicity to several select cancer cell lines.
RESULTS: Compounds 3e and 4c exhibited an IC50 of 0.83 ± 0.03 and 0.43 ± 0.002 μM against MAO-A and an IC50 of 0.26 ± 0.04 and 0.36 ± 0.001 μM against MAO-B, respectively. Molecular docking studies revealed π-π interactions between the synthesized molecules and aromatic amino acid residues. Conclusion & future perspective: The current study delineates the structural requirements for MAO-A selectivity and such information may be helpful in designing selective analogs for kinase, DYRK1A and harmine-based cytotoxics without apparent MAO enzyme inhibition.

Entities:  

Keywords:  1,2,3-triazoles; click chemistry; harmine; monoamine oxidase

Mesh:

Substances:

Year:  2018        PMID: 29788780      PMCID: PMC6021913          DOI: 10.4155/fmc-2018-0006

Source DB:  PubMed          Journal:  Future Med Chem        ISSN: 1756-8919            Impact factor:   3.808


  24 in total

Review 1.  Interactions of nitrogen-containing xenobiotics with monoamine oxidase (MAO) isozymes A and B: SAR studies on MAO substrates and inhibitors.

Authors:  A S Kalgutkar; D K Dalvie; N Castagnoli; T J Taylor
Journal:  Chem Res Toxicol       Date:  2001-09       Impact factor: 3.739

Review 2.  Click chemistry: 1,2,3-triazoles as pharmacophores.

Authors:  Sandip G Agalave; Suleman R Maujan; Vandana S Pore
Journal:  Chem Asian J       Date:  2011-08-29

3.  Computational & experimental evaluation of the structure/activity relationship of β-carbolines as DYRK1A inhibitors.

Authors:  Binia Drung; Christoph Scholz; Valéria A Barbosa; Azadeh Nazari; Maria H Sarragiotto; Boris Schmidt
Journal:  Bioorg Med Chem Lett       Date:  2014-09-02       Impact factor: 2.823

4.  cDNA cloning of human liver monoamine oxidase A and B: molecular basis of differences in enzymatic properties.

Authors:  A W Bach; N C Lan; D L Johnson; C W Abell; M E Bembenek; S W Kwan; P H Seeburg; J C Shih
Journal:  Proc Natl Acad Sci U S A       Date:  1988-07       Impact factor: 11.205

5.  Synthesis and structure-activity relationships of harmine derivatives as potential antitumor agents.

Authors:  Rihui Cao; Wenxi Fan; Liang Guo; Qin Ma; Guoxian Zhang; Jianru Li; Xuemei Chen; Zhenghua Ren; Liqin Qiu
Journal:  Eur J Med Chem       Date:  2012-12-08       Impact factor: 6.514

6.  Synthesis, acute toxicities, and antitumor effects of novel 9-substituted beta-carboline derivatives.

Authors:  Rihui Cao; Qi Chen; Xuerui Hou; Hongsheng Chen; Huaji Guan; Yan Ma; Wenlie Peng; Anlong Xu
Journal:  Bioorg Med Chem       Date:  2004-09-01       Impact factor: 3.641

7.  Distinct monoamine oxidase A and B populations in primate brain.

Authors:  K N Westlund; R M Denney; L M Kochersperger; R M Rose; C W Abell
Journal:  Science       Date:  1985-10-11       Impact factor: 47.728

8.  Structure of human monoamine oxidase A at 2.2-A resolution: the control of opening the entry for substrates/inhibitors.

Authors:  Se-Young Son; Jichun Ma; Youhei Kondou; Masato Yoshimura; Eiki Yamashita; Tomitake Tsukihara
Journal:  Proc Natl Acad Sci U S A       Date:  2008-04-07       Impact factor: 11.205

9.  Monoamine oxidase inhibitory constituents of propolis: kinetics and mechanism of inhibition of recombinant human MAO-A and MAO-B.

Authors:  Narayan D Chaurasiya; Mohamed A Ibrahim; Ilias Muhammad; Larry A Walker; Babu L Tekwani
Journal:  Molecules       Date:  2014-11-18       Impact factor: 4.411

10.  An appraisal of the use of monoamine oxidase as an enzyme marker for the outer membrane of rat liver mitochondria.

Authors:  J W Greenawalt; C Schnaitman
Journal:  J Cell Biol       Date:  1970-07       Impact factor: 10.539

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  2 in total

1.  Identification of harmine and β-carboline analogs from a high-throughput screen of an approved drug collection; profiling as differential inhibitors of DYRK1A and monoamine oxidase A and for in vitro and in vivo anti-cancer studies.

Authors:  Michael Tarpley; Helen O Oladapo; Dillon Strepay; Thomas B Caligan; Lhoucine Chdid; Hassan Shehata; Jose R Roques; Rhashad Thomas; Christopher P Laudeman; Rob U Onyenwoke; David B Darr; Kevin P Williams
Journal:  Eur J Pharm Sci       Date:  2021-03-27       Impact factor: 5.112

2.  Selective Interactions of O-Methylated Flavonoid Natural Products with Human Monoamine Oxidase-A and -B.

Authors:  Narayan D Chaurasiya; Jacob Midiwo; Pankaj Pandey; Regina N Bwire; Robert J Doerksen; Ilias Muhammad; Babu L Tekwani
Journal:  Molecules       Date:  2020-11-17       Impact factor: 4.411

  2 in total

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