Synthesis of Schiff base derivatives of 4-(2-aminoethyl)-benzenesulfonamide with inhibitory activity against carbonic anhydrase isoforms I, II, IX and XII

Durgun, Mustafa; Türkmen, Hasan; Ceruso, Mariangela; Supuran, Claudiu T.

doi:10.1016/j.bmcl.2015.04.007

Cited by 40 publications

(25 citation statements)

References 75 publications

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“…The aromatic sulfonamides used in this study were reported in our previous study 13 . Briefly, the imine compound derivatives ( A1-A3 ) were synthesised through the reaction of 4–(2-aminoethyl)benzenesulfonamide with substituted aromatic aldehydes with catalytic amounts of formic acid in methanol at the refluxing temperature for 3–5 h. The secondary amine derivatives ( B1-B3 ) were prepared by reduction of the imine compounds ( A1-A3 ) with NaBH 4 in methanol.…”

Section: Methodsmentioning

confidence: 99%

“…In a previous study, we have reported the synthesis and inhibitory activity against carbonic anhydrase isoforms I, II, IX, and XII of new sulfonamide derivatives 13 . Furthermore, their cytotoxic effects were examined on several cancer cell lines as well as normal cells 14 , 15 .…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, their cytotoxic effects were examined on several cancer cell lines as well as normal cells 14 , 15 . In this study, six different synthesised imine and amine sulfonamide derivatives with documented CA IX inhibitor activity 13 have been tested in terms of their cytotoxic effects in cancer cells (HT-29, HeLa and MDA-MB-231), and in normal cells (PNT1A, HEK-293). The underlying molecular mechanisms of the potential anti-tumoral activity of the CA IX inhibitor sulfonamide A1 with strong cytotoxic effects were also assessed, including the cellular proliferation, intracellular radical and mitochondrial membrane potential, intra-/extracellular pH changes, apoptosis, and autophagy.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Assessment of the antiproliferative and apoptotic roles of sulfonamide carbonic anhydrase IX inhibitors in HeLa cancer cell line

Koyuncu

Gönel

Durgun

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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Carbonic anhydrase IX (CA IX) has recently been validated as an antitumor/antimetastatic drug target. In this study, we examined the underlying molecular mechanisms and the anticancer activity of sulfonamide CA IX inhibitors against cervical cancer cell lines. The effects of several sulfonamides on HeLa, MDA-MB-231, HT-29 cancer cell lines, and normal cell lines (HEK-293, PNT-1A) viability were determined. The compounds showed high cytotoxic and apoptotic activities, mainly against HeLa cells overexpressing CA IX. We were also examined for intracellular reactive oxygen species (ROS) production; intra-/extracellular pH changes, for inhibition of cell proliferation, cellular mitochondrial membrane potential change and for the detection of caspase 3, 8, 9, and CA IX protein levels. Of the investigated sulfonamides, one compound was found to possess high cytotoxic and anti-proliferative effects in HeLa cells. The cytotoxic effect occurred via apoptosis, being accompanied by a return of pHe/pHi towards normal values as for other CA IX inhibitors investigated earlier.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Assessment of the antiproliferative and apoptotic roles of sulfonamide carbonic anhydrase IX inhibitors in HeLa cancer cell line

Koyuncu

Gönel

Durgun

et al. 2018

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Chemical characteristics of the Schiff bases, which came into the limelight as biologically active compounds, are quite well known. Another reason for the interest of researchers in Schiff bases is their electron donor properties arising from the double bonds between their oxygen and nitrogen atoms [15]. Their metal complexes are also known to stop tumor growth [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

“…Another reason for the interest of researchers in Schiff bases is their electron donor properties arising from the double bonds between their oxygen and nitrogen atoms [15]. Their metal complexes are also known to stop tumor growth [15][16][17][18]. The effects of Schiff bases on carbonic anhydrase isoenzymes have been investigated for the past 20 years [2,15,[18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Effect of Some Optically Active Imine Compounds on the Enzyme Activities of hCA‐I and hCA‐II under In Vitro Conditions: An Experimental and Theoretical Study

Tektas

Akkemik

Baykara

2016

J Biochem & Molecular Tox

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Inhibitors of carbonic anhydrase (hCA; EC 4.2.1.1) are used as medicines for many diseases. Therefore, they are very important. In this study, a known series of Schiff bases were synthesized and their effects on the activities of hCA-I and hCA-II, which are cytosolic isoenzymes of carbonic anhydrase, were investigated under in vitro conditions. The synthesized compounds (H1, H2, H3, and H4) were found to cause inhibition on enzyme activities of hCA-1 and hCA-II. IC50 values of H1, H2, H3, and H4 compounds were 140, 88, 201, and 271 μM for hCA-I enzyme activity and 134, 251, 79, and 604 μM for hCA-II enzyme activity, respectively. The synthesized Schiff bases were characterized by several methods, including (1) H NMR, FT-IR, elemental analysis, and polarimetric measurements. Correlation coefficient square values (R(2) ) of comparison of the theoretical and experimental (1) H NMR shifts for H1, H2, H3, and H4 compounds were found as 0.9781, 0.9814, 0.9758, and 0.8635, respectively.

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Effective Anticancer Potential of a New Sulfonamide as a Carbonic Anhydrase IX Inhibitor Against Aggressive Tumors

Koyuncu,

Temiz,

Güler

et al. 2024

ChemMedChem

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This study examines efficiency of a newly synthesized sulfonamide derivative 2‐bromo‐N‐(4‐sulfamoylphenyl)propanamide (MMH‐1) on the inhibition of Carbonic Anhydrase IX, which is overexpressed in many solid tumors including breast cancer. The inhibitory potential of MMH‐1 compound against hCA I, II, IX, and XII, was evaluated. To this context, the cytotoxic effect of MMH‐1 on cancer and normal cells was tested and found to selectively affect MDA‐MB‐231 cells. MMH‐1 reduced cell proliferation by holding cells in the G0/G1 phase (72%) and slowed the cells' wound healing capacity. MMH‐1 inhibited CA IX under both hypoxic and normoxic conditions and altered the morphology of triple negative breast cancer cells. In MDA‐MB‐231 cells, inhibition of CA IX was accompanied by a decrease in extracellular pH acidity (7.2), disruption of mitochondrial membrane integrity (80%), an increase in reactive oxygen levels (25%), and the triggering of apoptosis (40%). In addition, the caspase cascade was activated in MDA‐MB‐231 cells, triggering both the extrinsic and intrinsic apoptotic pathways. TThese results propose that the MMH‐1 compound could triggers apoptosis in MDA‐MB‐231 cells via the pH/MMP/ROS pathway through the inhibition of CA IX. This compound is thought to have high potential and promising anticancer properties in the treatment of aggressive tumors.

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Synthesis of Schiff base derivatives of 4-(2-aminoethyl)-benzenesulfonamide with inhibitory activity against carbonic anhydrase isoforms I, II, IX and XII

Cited by 40 publications

References 75 publications

Assessment of the antiproliferative and apoptotic roles of sulfonamide carbonic anhydrase IX inhibitors in HeLa cancer cell line

Assessment of the antiproliferative and apoptotic roles of sulfonamide carbonic anhydrase IX inhibitors in HeLa cancer cell line

Investigation of the Effect of Some Optically Active Imine Compounds on the Enzyme Activities of hCA‐I and hCA‐II under In Vitro Conditions: An Experimental and Theoretical Study

Effective Anticancer Potential of a New Sulfonamide as a Carbonic Anhydrase IX Inhibitor Against Aggressive Tumors

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