Synthesis and cytotoxic activities of novel copper and silver complexes of 1,3-diaryltriazene-substituted sulfonamides

Abstract

In this study, a series of 10 novel copper (II) and silver complexes of 1,3-diaryltriazene-substituted sulfonamides was synthesised. All the synthesised ligands and their metal complexes were assessed for in vitro cytotoxicity against human colorectal adenocarcinoma (DLD-1), cervix carcinoma (HeLa), breast adenocarcinoma (MDA-MB-231), colon adenocarcinoma (HT-29), endometrial adenocarcinoma (ECC-1), prostate cancer (DU-145 and PC-3), normal embryonic kidney (HEK-293), normal prostate epithelium (PNT-1A), and normal retinal pigment epithelium (ARPE-19) cells. Most of the metal complexes from the series showed to be more active against all cancerous cells than the uncomplexed 1,3-diaryltriazene-substituted sulfonamides, and lower cytotoxic effects observed on normal cells. Most of the Cu (II) and Ag (I) metal complexes from the presented series showed high cytotoxic activity against HeLa cells with IC50 values ranging from 2.08 to >300 µM. Specifically, compound L3-Ag showed one of the highest cytotoxicity against all cancer cell lines with IC50 values between 3.30 to 16.18 µM among other tested compounds.

Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3‐diaryltriazene‐substituted sulfathiazole derivatives

“…[31] In a previous study, a series of aromatic and heterocyclic bis-sulfonamide Schiff bases against hCA I, II, VII, and IX was investigated, and many of the compounds showed a low nanomolar potency against hCA II, with K I values in the range of 0.4-861.1 nM. [32] In the present study, a series of novel, structurally diverse ST1-11 was synthesized as a modified procedure presented in our previous studies [3,25,26] and outlined in Scheme 1. Briefly, the diazonium salt of ST was obtained by using sodium nitrite solution in the The use of inhibitor compounds for various hCA isozymes is well established for the management of elevated intraocular pressure, hypertension, memory impairments, depression, arteriosclerosis, epilepsy, obesity, and hypoxic cancers.…”

“…is based on our most recent studies, in which we indicated that novel synthesized 1,3-diaryltriazene-substituted sulphanilamide and metanilamide derivatives have a potent and selective inhibition against one of the most abundant isoform hCA II. [3,25,26] Therefore, in the current work, our aim was to change the sulfonamide group from primary to secondary amine and apply it to hCA I, hCA II, AChE, and α-GLY enzymes, [27][28][29] to see the effect of the binding group against potency and selectivity. We aimed to improve the biological potency of 1,3-dirayltriazene-substituted sulfonamides by changing the amine part from primary to secondary (sulphanilamide to sulfathiazole) and observing the potency of these type of compounds against different metabolic enzymes rather than hCA I and II, such as AChE and α-GLY.…”

Novel sulphonamides incorporating triazene moieties show powerful carbonic anhydrase I and II inhibitory properties

“…CA inhibition assay was done as described in our previous studies by using an esterase assay with 4-nitrophenyl acetate as standard [21][22][23][24][25][26][27][28][29][30][31] . The enzymes were purified from human blood as described earlier 27,28 .…”

Antimicrobial and Anticancer Application of Silver(I) Dipeptide Complexes

“…They can be divided into five classes: Ag(I)-NHC complexes, Ag(I) -carboxylate complexes, Ag(I) -N-ligand complexes, Ag(I)-P-ligand complexes and mixed Ag(I) ligand complexes. These were tested against several tumour lines (e.g., kidney cancer [18][19][20][21][22], breast cancer MCF-7 [23][24][25], colorectal cancer (HCT 116) [20], lung cell lines A549 [26] tongue cancer (Cale27), HepG2, and renal adenocarcinoma (Ae498)) and in three murine cell lines (P815 mastocytoma, B16 melanoma, P388 leukaemia) [27][28][29]. The cytotoxicity in the abovementioned articles was determined mainly by the MTT assay, but studies of mechanism of action (interaction with ctDNA, DNA nuclease activity, effect on topoisomerase I/II, cell cycle, mitochondrial membrane potential, lipophilicity, cell morphology studies, induction of oxidative stress) are not often performed.…”