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Research Paper

Selenium-analogs based on natural sources as cancer-associated carbonic anhydrase isoforms IX and XII inhibitors

Nora Astrain-Redina Department of Pharmaceutical Technology and Chemistry, University of Navarra, Pamplona, Spain

https://orcid.org/0000-0001-8593-8994 View further author information

Niccolò Paolettib Department NEUROFARBA – Pharmaceutical and nutraceutical section, Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Firenze, Sesto Fiorentino, Florence, Italy;c Department NEUROFARBA – Pharmaceutical and nutraceutical section, University of Firenze, Sesto Fiorentino, Florence, ItalyView further author information

Daniel Planoa Department of Pharmaceutical Technology and Chemistry, University of Navarra, Pamplona, Spain

https://orcid.org/0000-0002-8266-0445 View further author information

Alessandro Bonardib Department NEUROFARBA – Pharmaceutical and nutraceutical section, Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Firenze, Sesto Fiorentino, Florence, Italy;c Department NEUROFARBA – Pharmaceutical and nutraceutical section, University of Firenze, Sesto Fiorentino, Florence, ItalyView further author information

Paola Gratterib Department NEUROFARBA – Pharmaceutical and nutraceutical section, Laboratory of Molecular Modeling Cheminformatics & QSAR, University of Firenze, Sesto Fiorentino, Florence, ItalyCorrespondence[email protected]

https://orcid.org/0000-0002-9137-2509 View further author information

Andrea Angelic Department NEUROFARBA – Pharmaceutical and nutraceutical section, University of Firenze, Sesto Fiorentino, Florence, Italy

https://orcid.org/0000-0002-1470-7192 View further author information

Carmen Sanmartina Department of Pharmaceutical Technology and Chemistry, University of Navarra, Pamplona, SpainCorrespondence[email protected]

https://orcid.org/0000-0003-3431-7826 View further author information

Claudiu T. Supuranc Department NEUROFARBA – Pharmaceutical and nutraceutical section, University of Firenze, Sesto Fiorentino, Florence, Italy

https://orcid.org/0000-0003-4262-0323 View further author information

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Figures & data

Figure 1. Chemical structures of synthetic compounds 1a–19a and 1b–19b.Citation³⁰

Figure 1. Chemical structures of synthetic compounds 1a–19a and 1b–19b.Citation30

Figure 2. Allylic and propargylic molecules of natural products.Citation³⁰

Figure 2. Allylic and propargylic molecules of natural products.Citation30

Scheme 1. Synthesis procedure to yield 1a–19a and 1b–19b derivatives. Reagents and conditions: (i) H₂O, 20 min, and room temperature; (ii) THF/H₂O, 60 min, and room temperature; (iii) ClCOCOCl, CH₂Cl₂, 12 h, and room temperature; (iv) BrCH₂CH = CH₂ or BrCH₂C≡CH, THF/H₂O, 90 min, and room temperature.Citation³⁰

Scheme 1. Synthesis procedure to yield 1a–19a and 1b–19b derivatives. Reagents and conditions: (i) H2O, 20 min, and room temperature; (ii) THF/H2O, 60 min, and room temperature; (iii) ClCOCOCl, CH2Cl2, 12 h, and room temperature; (iv) BrCH2CH = CH2 or BrCH2C≡CH, THF/H2O, 90 min, and room temperature.Citation30

Table 1. Inhibition of hCA I, II, VA, IX, and XII activity for compounds 1a–19a and 1b–19b.

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Figure 3. Predicted binding mode of propargyl selenol (violet) and allyl selenol (cyan) within the (A) CA I (yellow), (B) CA II (white), (C) CA IX (blue) and (D) CA XII (green) active site.

Figure 4. (A) Superposition of (A) X-ray solved structures of phenyl selenol-CA II (red, PDB:6HX5)Citation²⁵ and benzyl selenol-CA II (green, PDB:7QBH)Citation⁵³ complex. (B) Superposition of ligands benzyl selenol (green), propargyl selenol (cyan), and allyl selenol (violet). (C) Superposition of X-ray solved structures of benzyl selenol-CA II (green)Citation⁵³ and predicted binding mode of allyl (violet)/propargyl (cyan) selenol within CA II active site.

Figure 4. (A) Superposition of (A) X-ray solved structures of phenyl selenol-CA II (red, PDB:6HX5)Citation25 and benzyl selenol-CA II (green, PDB:7QBH)Citation53 complex. (B) Superposition of ligands benzyl selenol (green), propargyl selenol (cyan), and allyl selenol (violet). (C) Superposition of X-ray solved structures of benzyl selenol-CA II (green)Citation53 and predicted binding mode of allyl (violet)/propargyl (cyan) selenol within CA II active site.

Table 2. Geometric parameters of docking and crystallography data.

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Selenium-analogs based on natural sources as cancer-associated carbonic anhydrase isoforms IX and XII inhibitors

Table 1. Inhibition of hCA I, II, VA, IX, and XII activity for compounds 1a–19a and 1b–19b.

Table 2. Geometric parameters of docking and crystallography data.

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Selenium-analogs based on natural sources as cancer-associated carbonic anhydrase isoforms IX and XII inhibitors

Figures & data

Table 1. Inhibition of hCA I, II, VA, IX, and XII activity for compounds 1a–19a and 1b–19b.

Table 2. Geometric parameters of docking and crystallography data.

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