Alessio Zavaroni, Elena Riva, Valentina Borghesani, Greta Donati, Federica Santoro, Vincenzo Maria D'Amore, Matteo Tegoni, Giorgio Pelosi, Annamaria Buschini, Dominga Rogolino, Mauro Carcelli
{"title":"两种新型水溶性双(硫)羧肼及其铜(II)和锌(II)配合物的合成及其体外生物活性的初步研究。","authors":"Alessio Zavaroni, Elena Riva, Valentina Borghesani, Greta Donati, Federica Santoro, Vincenzo Maria D'Amore, Matteo Tegoni, Giorgio Pelosi, Annamaria Buschini, Dominga Rogolino, Mauro Carcelli","doi":"10.3390/ijms251910831","DOIUrl":null,"url":null,"abstract":"<p><p>Research in the field of metallodrugs is continually increasing. However, it is often limited by the poor solubility in water of the metal complexes. To try to overcome this problem, the two new ligands bis-(sodium 3-methoxy-5-sulfonate-salicylaldehyde)thiocarbohydrazone (<b>bis-TCH</b>, Na<sub>2</sub>H<sub>4</sub>L<sup>1</sup>) and bis-(sodium 3-methoxy-5-sulfonate-salicylaldehyde)carbohydrazone (<b>bis-CH</b>, Na<sub>2</sub>H<sub>4</sub>L<sup>2</sup>) were synthesized and characterized, both achieving high solubility in water. The speciation of the ligands and their coordinating behaviour towards the biologically relevant Cu(II) and Zn(II) ions were studied spectroscopically and potentiometrically, determining the p<i>K</i><sub>a</sub>s of the ligands and the formation constants of the complex species. The monometallic and bimetallic Cu(II) and Zn(II) complexes were isolated, and the single-crystal X-ray structure of [Cu<sub>2</sub>(NaHL<sup>1</sup>)(H<sub>2</sub>O)<sub>7</sub>]<sup>.</sup>3.5H<sub>2</sub>O was discussed. Finally, preliminary studies of the in vitro cytotoxic properties of the new compounds were started on normal (Hs27) and cancer (U937) cell lines. <b>bis-TCH</b> was able to induce a growth inhibition effect between 40% and 45% in both cell lines; <b>bis-CH</b> did not produce a reduction in cell viability in Hs27 cells but revealed mild antiproliferative activity after 72 h of treatment in U937 cancer cells (GI<sub>50</sub> = 46.5 ± 4.94 μg/mL). Coordination of the Cu(II) ions increased the toxicity of the compounds, while, in contrast, Zn(II) complexes were not cytotoxic.</p>","PeriodicalId":14156,"journal":{"name":"International Journal of Molecular Sciences","volume":null,"pages":null},"PeriodicalIF":5.6000,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11476552/pdf/","citationCount":"0","resultStr":"{\"title\":\"Synthesis and Preliminary Studies for In Vitro Biological Activity of Two New Water-Soluble Bis(thio)carbohydrazones and Their Copper(II) and Zinc(II) Complexes.\",\"authors\":\"Alessio Zavaroni, Elena Riva, Valentina Borghesani, Greta Donati, Federica Santoro, Vincenzo Maria D'Amore, Matteo Tegoni, Giorgio Pelosi, Annamaria Buschini, Dominga Rogolino, Mauro Carcelli\",\"doi\":\"10.3390/ijms251910831\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Research in the field of metallodrugs is continually increasing. However, it is often limited by the poor solubility in water of the metal complexes. To try to overcome this problem, the two new ligands bis-(sodium 3-methoxy-5-sulfonate-salicylaldehyde)thiocarbohydrazone (<b>bis-TCH</b>, Na<sub>2</sub>H<sub>4</sub>L<sup>1</sup>) and bis-(sodium 3-methoxy-5-sulfonate-salicylaldehyde)carbohydrazone (<b>bis-CH</b>, Na<sub>2</sub>H<sub>4</sub>L<sup>2</sup>) were synthesized and characterized, both achieving high solubility in water. The speciation of the ligands and their coordinating behaviour towards the biologically relevant Cu(II) and Zn(II) ions were studied spectroscopically and potentiometrically, determining the p<i>K</i><sub>a</sub>s of the ligands and the formation constants of the complex species. The monometallic and bimetallic Cu(II) and Zn(II) complexes were isolated, and the single-crystal X-ray structure of [Cu<sub>2</sub>(NaHL<sup>1</sup>)(H<sub>2</sub>O)<sub>7</sub>]<sup>.</sup>3.5H<sub>2</sub>O was discussed. 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Synthesis and Preliminary Studies for In Vitro Biological Activity of Two New Water-Soluble Bis(thio)carbohydrazones and Their Copper(II) and Zinc(II) Complexes.
Research in the field of metallodrugs is continually increasing. However, it is often limited by the poor solubility in water of the metal complexes. To try to overcome this problem, the two new ligands bis-(sodium 3-methoxy-5-sulfonate-salicylaldehyde)thiocarbohydrazone (bis-TCH, Na2H4L1) and bis-(sodium 3-methoxy-5-sulfonate-salicylaldehyde)carbohydrazone (bis-CH, Na2H4L2) were synthesized and characterized, both achieving high solubility in water. The speciation of the ligands and their coordinating behaviour towards the biologically relevant Cu(II) and Zn(II) ions were studied spectroscopically and potentiometrically, determining the pKas of the ligands and the formation constants of the complex species. The monometallic and bimetallic Cu(II) and Zn(II) complexes were isolated, and the single-crystal X-ray structure of [Cu2(NaHL1)(H2O)7].3.5H2O was discussed. Finally, preliminary studies of the in vitro cytotoxic properties of the new compounds were started on normal (Hs27) and cancer (U937) cell lines. bis-TCH was able to induce a growth inhibition effect between 40% and 45% in both cell lines; bis-CH did not produce a reduction in cell viability in Hs27 cells but revealed mild antiproliferative activity after 72 h of treatment in U937 cancer cells (GI50 = 46.5 ± 4.94 μg/mL). Coordination of the Cu(II) ions increased the toxicity of the compounds, while, in contrast, Zn(II) complexes were not cytotoxic.
期刊介绍:
The International Journal of Molecular Sciences (ISSN 1422-0067) provides an advanced forum for chemistry, molecular physics (chemical physics and physical chemistry) and molecular biology. It publishes research articles, reviews, communications and short notes. Our aim is to encourage scientists to publish their theoretical and experimental results in as much detail as possible. Therefore, there is no restriction on the length of the papers or the number of electronics supplementary files. For articles with computational results, the full experimental details must be provided so that the results can be reproduced. Electronic files regarding the full details of the calculation and experimental procedure, if unable to be published in a normal way, can be deposited as supplementary material (including animated pictures, videos, interactive Excel sheets, software executables and others).