Squaramides with cytotoxic activity against human gastric carcinoma cells HGC-27: synthesis and mechanism of action

Quintana, Mireia; Alegre‐Requena, Juan V.; Marqués‐López, Eugenia; Herrera, Raquel P.; Triola, Gemma

doi:10.1039/c5md00515a

Cited by 17 publications

(9 citation statements)

References 45 publications

(59 reference statements)

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“…The cells in early apoptosis bind only to Annexin V, whereas dead and late stage apoptotic cells bind to both Annexin V-FITC and propidium iodide. 41 In this study, HeLa cells were treated with the compound 6d for 48 h at IC 50 concentrations to examine the apoptotic effect. It was observed that the compound 6d showed significant apoptosis against HeLa cells.…”

Section: Structure-activity Relationship (Sar)mentioning

confidence: 99%

Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells

et al. 2019

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Section: Structure-activity Relationship (Sar)mentioning

confidence: 99%

Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells

et al. 2019

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“…In the biological realm, squaramides have been used for specific cell labeling, to prepare active bioconjugates, or to replace the phosphate- and amide-type groups in bioisosteric replacements . In medicinal chemistry, cell-penetrating squaramides are known to exhibit significant anticancer and antiparasitic activity …”

Section: Introductionmentioning

confidence: 99%

Kinetic Analysis and Mechanism of the Hydrolytic Degradation of Squaramides and Squaramic Acids

et al. 2017

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The hydrolytic degradation of squaramides and squaramic acids, the product of partial hydrolysis of squaramides, has been evaluated by UV spectroscopy at 37 °C in the pH range 3-10. Under these conditions, the compounds are kinetically stable over long time periods (>100 days). At pH >10, the hydrolysis of the squaramate anions shows first-order dependence on both squaramate and OH. At the same temperature and [OH], the hydrolysis of squaramides usually displays biphasic spectral changes (A → B → C kinetic model) with formation of squaramates as detectable reaction intermediates. The measured rates for the first step (k ≈ 10 M s) are 2-3 orders of magnitude faster than those for the second step (k ≈ 10 M s). Experiments at different temperatures provide activation parameters with values of ΔH ≈ 9-18 kcal mol and ΔS ≈ -5 to -30 cal K mol. DFT calculations show that the mechanism for the alkaline hydrolysis of squaramic acids is quite similar to that of amides.

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“…Therefore it suggests that squaramides may serve as a good starting point for identifying the molecules which can specifically target cancer cells. Quintana et al 68 studied a series of squaramides and squaramates for antitumor activity against different cancer cells that confirms the antitumor properties of this class of promising drug candidates. Two cancer cell lines were used -HeLa (cervical carcinoma) and HGC-27 (human gastric cell line).…”

Section: Application Of Squaric Acid and Its Derivatives In Medicinementioning

confidence: 80%

A concise review on application of squaric acid derivatives and their metal complexes in medicine

Bakalova¹,

Ruseva²,

Cherneva³

2022

Arkivoc

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In this review, we summarize the data about applications of squaric acid, its derivatives and their metal complexes in medicine. In recent years, researchers have been concentrated on the study of squaric acid and its derivatives because of their unique properties and the different possible ways to coordinate with metals and form complex compounds. Encouraging results have also been obtained for the cytotoxic activity of some squaric acid analogues and their metal complexes on various human tumor cell lines.

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Squaramides with cytotoxic activity against human gastric carcinoma cells HGC-27: synthesis and mechanism of action

Abstract: A series of squaramates and squaramides have been synthesized and their cytotoxic activity has been investigated in different cancer cell lines.

Cited by 17 publications

References 45 publications

Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells

Synthesis and X-ray study of dispiro 8-nitroquinolone analogues and their cytotoxic properties against human cervical cancer HeLa cells

Kinetic Analysis and Mechanism of the Hydrolytic Degradation of Squaramides and Squaramic Acids

A concise review on application of squaric acid derivatives and their metal complexes in medicine

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