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Thermodynamic study of pH and sodium chloride impact on gemcitabine binding to cucurbit[7]uril in aqueous solutions.

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Title: Thermodynamic study of pH and sodium chloride impact on gemcitabine binding to cucurbit[7]uril in aqueous solutions.
Authors: Buczkowski, Adam1 (AUTHOR) adam.buczkowski@chemia.uni.lodz.pl
Source: Journal of Molecular Liquids. Jan2022, Vol. 345, pN.PAG-N.PAG. 1p.
Subjects: Cucurbituril, Salt, Excipients, Aqueous solutions, Gemcitabine, Binding constant
Abstract: [Display omitted] • ITC and ESI MS show the impact of counter-ions on Q[7]-Gem complexation. • Acidification of the solution facilitates binding of Gem to Q[7]. • Increasing NaCl concentration, decreased the binding constant of Gem-Q[7] complex. • Binding enthalpy Gem-Q[7] is less favorable at high NaCl concentration. • Entropic factor confirms hindering effect of the association of Na+ with Q[7]. In solutions of pH < 5, cucurbit[7]uril (Q[7]) spontaneously includes a molecule of the anticancer drug gemcitabine within its cavity, forming a supramolecular complex. The results of ITC calorimetric studies of the gemcitabine cation (Gem) complexation with the Q[7] macrocycle in 20 mM aqueous HCOOH–HCOONa buffer mixtures with pH ranging from 5 to 2, indicate that the acidification of the solution facilitates binding of the drug by cucurbit[7]uril. In mixtures with a fixed pH = 4 and an increasing concentration of sodium chloride (10–4000 mM), the binding constant of Gem by Q[7] decreases rapidly, as is the absolute value of the binding enthalpy. This phenomenon illustrates the hindering effect of the association of sodium cations with Q[7] portals on gemcitabine binding, which is confirmed by ESI MS measurements. However, gemcitabine is still efficiently bound by cucurbit[7]uril (l o g K ≥ 3) in aqueous 10 – 250 mM sodium chloride solutions. The Q[7] macrocycle may therefore be used as a stabilizing agent for this drug in pharmaceutical formulations. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Molecular Liquids is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 154503547
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  Label: Title
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  Data: Thermodynamic study of pH and sodium chloride impact on gemcitabine binding to cucurbit[7]uril in aqueous solutions.
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  Data: &lt;searchLink fieldCode=&quot;AR&quot; term=&quot;%22Buczkowski%2C+Adam%22&quot;&gt;Buczkowski, Adam&lt;/searchLink&gt;&lt;relatesTo&gt;1&lt;/relatesTo&gt; (AUTHOR)&lt;i&gt; adam.buczkowski@chemia.uni.lodz.pl&lt;/i&gt;
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  Data: &lt;searchLink fieldCode=&quot;JN&quot; term=&quot;%22Journal+of+Molecular+Liquids%22&quot;&gt;Journal of Molecular Liquids&lt;/searchLink&gt;. Jan2022, Vol. 345, pN.PAG-N.PAG. 1p.
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  Data: &lt;searchLink fieldCode=&quot;DE&quot; term=&quot;%22Cucurbituril%22&quot;&gt;Cucurbituril&lt;/searchLink&gt;&lt;br /&gt;&lt;searchLink fieldCode=&quot;DE&quot; term=&quot;%22Salt%22&quot;&gt;Salt&lt;/searchLink&gt;&lt;br /&gt;&lt;searchLink fieldCode=&quot;DE&quot; term=&quot;%22Excipients%22&quot;&gt;Excipients&lt;/searchLink&gt;&lt;br /&gt;&lt;searchLink fieldCode=&quot;DE&quot; term=&quot;%22Aqueous+solutions%22&quot;&gt;Aqueous solutions&lt;/searchLink&gt;&lt;br /&gt;&lt;searchLink fieldCode=&quot;DE&quot; term=&quot;%22Gemcitabine%22&quot;&gt;Gemcitabine&lt;/searchLink&gt;&lt;br /&gt;&lt;searchLink fieldCode=&quot;DE&quot; term=&quot;%22Binding+constant%22&quot;&gt;Binding constant&lt;/searchLink&gt;
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  Data: [Display omitted] • ITC and ESI MS show the impact of counter-ions on Q[7]-Gem complexation. • Acidification of the solution facilitates binding of Gem to Q[7]. • Increasing NaCl concentration, decreased the binding constant of Gem-Q[7] complex. • Binding enthalpy Gem-Q[7] is less favorable at high NaCl concentration. • Entropic factor confirms hindering effect of the association of Na+ with Q[7]. In solutions of pH &lt; 5, cucurbit[7]uril (Q[7]) spontaneously includes a molecule of the anticancer drug gemcitabine within its cavity, forming a supramolecular complex. The results of ITC calorimetric studies of the gemcitabine cation (Gem) complexation with the Q[7] macrocycle in 20 mM aqueous HCOOH–HCOONa buffer mixtures with pH ranging from 5 to 2, indicate that the acidification of the solution facilitates binding of the drug by cucurbit[7]uril. In mixtures with a fixed pH = 4 and an increasing concentration of sodium chloride (10–4000 mM), the binding constant of Gem by Q[7] decreases rapidly, as is the absolute value of the binding enthalpy. This phenomenon illustrates the hindering effect of the association of sodium cations with Q[7] portals on gemcitabine binding, which is confirmed by ESI MS measurements. However, gemcitabine is still efficiently bound by cucurbit[7]uril (l o g K ≥ 3) in aqueous 10 – 250 mM sodium chloride solutions. The Q[7] macrocycle may therefore be used as a stabilizing agent for this drug in pharmaceutical formulations. [ABSTRACT FROM AUTHOR]
– Name: AbstractSuppliedCopyright
  Label:
  Group: Ab
  Data: &lt;i&gt;Copyright of Journal of Molecular Liquids is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder&#39;s express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.&lt;/i&gt; (Copyright applies to all Abstracts.)
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RecordInfo BibRecord:
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    Identifiers:
      – Type: doi
        Value: 10.1016/j.molliq.2021.117857
    Languages:
      – Code: eng
        Text: English
    PhysicalDescription:
      Pagination:
        PageCount: 1
        StartPage: N.PAG
    Subjects:
      – SubjectFull: Cucurbituril
        Type: general
      – SubjectFull: Salt
        Type: general
      – SubjectFull: Excipients
        Type: general
      – SubjectFull: Aqueous solutions
        Type: general
      – SubjectFull: Gemcitabine
        Type: general
      – SubjectFull: Binding constant
        Type: general
    Titles:
      – TitleFull: Thermodynamic study of pH and sodium chloride impact on gemcitabine binding to cucurbit[7]uril in aqueous solutions.
        Type: main
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            NameFull: Buczkowski, Adam
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          Dates:
            – D: 01
              M: 01
              Text: Jan2022
              Type: published
              Y: 2022
          Identifiers:
            – Type: issn-print
              Value: 01677322
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            – Type: volume
              Value: 345
          Titles:
            – TitleFull: Journal of Molecular Liquids
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