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OUTLINE

 1.  Highlights
 2.  Abstract
 3.  Graphical abstract
 4.  Keywords
 5.  1. Introduction
 6.  2. Results and Discussion
 7.  3. Conclusion
 8.  4. Experimental
 9.  Conflicts of interest
 10. Declaration of competing interest
 11. Acknowledgement
 12. Appendix A. Supplementary data
 13. References

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CITED BY (5)




FIGURES (13)

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TABLES (2)

 1. Table 1
 2. Table 2




EXTRAS (1)

 1. Multimedia component 1




EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY

Volume 228, 15 January 2022, 114008



NATURAL INSPIRED LIGUSTRAZINE-BASED SLC-0111 ANALOGUES AS NOVEL CARBONIC
ANHYDRASE INHIBITORS

Author links open overlay panelDiaaeldin M. Elimam a b, Wagdy M. Eldehna c,
Rofaida Salem c, Alessandro Bonardi d e, Alessio Nocentini d, Sara T. Al-Rashood
f, Mahmoud M. Elaasser g, Paola Gratteri e, Claudiu T. Supuran d, Heba
Abdelrasheed Allam h
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Cite
https://doi.org/10.1016/j.ejmech.2021.114008Get rights and content





HIGHLIGHTS



•

New series of Ligustrazine-based sulfonamides were designed and synthesized.

•

Inhibitory activities of all derivatives were evaluated toward hCA I, II, IX and
XII isoforms.

•

The primary sulfonamides efficiently inhibited hCA IX and XII in the
sub-micromolar ranges.

•

Compounds 6c and 18 were examined for its potential anticancer and pro-apoptotic
activities.

•

A molecular modelling study was performed to unveil the plausible binding
interactions.




ABSTRACT

Ligustrazine is the principle bioactive alkaloid in the widely-used Chinese herb
Chuan Xiong rhizome. Herein, a series of novel derivatives has been designed as
human carbonic anhydrases inhibitors (hCAIs) starting from the natural product
Ligustrazine inserted as a tail instead of the 4-fluorophenyl tail of SLC-0111,
a front-runner selective hCA IX inhibitor currently in clinical trials as
antitumor/antimetastatic agent. Other derivatives were designed via
incorporation of different linkers, of amide and ester type, or incorporation of
different zinc anchoring groups such as secondary sulfamoyl and carboxylic acid
functionalities. The newly designed molecules were prepared following different
synthetic pathways, and were assessed for their inhibitory actions against four
isoforms: the widespread cytosolic (hCA I and II), and the transmembrane
tumor-related (hCA IX and XII). The primary sulfonamides efficiently inhibited
the target hCA IX and hCA XII in the nanomolar range (KIs: 6.2–951.5 nM and
3.3–869.3 nM, respectively). The most selective hCA IX inhibitors 6c and 18 were
assessed for their potential anticancer effects, and displayed
anti-proliferative activity against MCF-7 cancer cell line with IC50s of 11.9
and 36.7 μM, respectively. Molecular modelling studies unveiled the relationship
between structural features and inhibitory profiles against the off-target hCA
II and the target, tumor-related isoforms hCA IX and XII.


GRAPHICAL ABSTRACT

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KEYWORDS

Anticancer agents
SLC-0111 analogues
Carbonic anhydrase inhibitors
Ligustrazine
Tail approach
Ureido benzenesulfonamides
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CITED BY (5)


 * INSIGHTS INTO THE EFFECT OF ELABORATING COUMARIN-BASED ARYL ENAMINONES WITH
   SULFONAMIDE OR CARBOXYLIC ACID FUNCTIONALITY ON CARBONIC ANHYDRASE INHIBITORY
   POTENCY AND SELECTIVITY
   
   2022, Bioorganic Chemistry
   Show abstract
   
   Recently, different mechanisms for inhibition of carbonic anhydrases (CAs)
   have been reported, such as the classical zinc-binding (exerted by
   sulfonamides and carboxylic acids) as well as occluding the entrance of the
   CA active site (exerted by coumarins). In this manuscript, we studied the
   effect of combining the pharmacopheric parts responsible for these two
   mechanisms on CA inhibitory potency and selectivity through the design and
   synthesis of novel coumarins tethered with the zinc-binding sulfonamide
   (5a-f, 11a-b and 13a-b) or carboxylic acid (7a-f) groups. In addition,
   another set of coumarin derivatives (9a-b) with no zinc-binding group (ZBG)
   was designed to act as non-classical CA inhibitors. The synthesized coumarins
   were examined for their inhibitory activities towards four hCA isoforms I,
   II, IX and XII. Coumarin sulfonamides (5a-f, 11a-b and 13a-b) effectively
   inhibited both tumor-associated hCA IX (KIs: 8.9–133.5 nM) and hCA XII (KIs:
   3.4–42.9 nM) isoforms, whereas coumarin carboxylic acids (7a-f) weakly
   affected hCA IX (KIs: 0.49–11.2 μM) and hCA XII (KIs: 0.51–10.1 μM) isoforms.
   The coumarin based inhibitors featuring zinc-binding sulfonamide or
   carboxylic acid group achieved low to moderate hCA IX/XII selectivity.
   Interestingly, the ZBG-free coumarin derivatives (9a-b) emerged not only as
   effective hCA IX (KIs = 93.3 and 63.8 nM, respectively) and hCA XII
   (KIs = 85.7 and 72.1 nM, respectively) inhibitors, but also as a highly hCA
   IX/XII selective inhibitors over the off-target hCA I/II isoforms
   (SIs > 1000). Coumarin 9a was further evaluated for its anti-proliferative
   effect on MCF-7 and PANC-1 cancer cell lines, as well as its effect on the
   cell cycle and apoptosis towards MCF-7 cell line.


 * SYNTHESIS AND ANTICANCER ACTIVITY OF NEW BENZENSULFONAMIDES INCORPORATING
   S-TRIAZINES AS CYCLIC LINKERS FOR INHIBITION OF CARBONIC ANHYDRASE IX
   
   2022, Scientific Reports
   
   


 * DESIGN AND SYNTHESIS OF BENZOTHIAZOLE-BASED SLC-0111 ANALOGUES AS NEW
   INHIBITORS FOR THE CANCER-ASSOCIATED CARBONIC ANHYDRASE ISOFORMS IX AND XII
   
   2022, Journal of Enzyme Inhibition and Medicinal Chemistry
   
   


 * ENAMINONE-BASED CARBOXYLIC ACIDS AS NOVEL NON-CLASSICAL CARBONIC ANHYDRASES
   INHIBITORS: DESIGN, SYNTHESIS AND IN VITRO BIOLOGICAL ASSESSMENT
   
   2022, Journal of Enzyme Inhibition and Medicinal Chemistry
   
   


 * TARGETING CARBONIC ANHYDRASE IX AND XII ISOFORMS WITH SMALL MOLECULE
   INHIBITORS AND MONOCLONAL ANTIBODIES
   
   2022, Journal of Enzyme Inhibition and Medicinal Chemistry
   
   

View full text
© 2021 Elsevier Masson SAS. All rights reserved.


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