Synthesis, Structure, and Antiproliferative Activity of Three Gallium(III) Azole Complexes

Abstract

As part of our interest into the bioinorganic chemistry of gallium, gallium(III) complexes of the azole ligands 2,1,3-benzothiadiazole (btd), 1,2,3-benzotriazole (btaH), and 1-methyl-4,5-diphenylimidazole (L) have been isolated. Reaction of btaH or btd with GaBr3 or GaCl3 resulted in the mononuclear complexes [GaBr3(btaH)2] (1) and [GaCl3(btd)2] (2), respectively, while treatment of GaCl3 with L resulted in the anionic complex (LH)2[GaCl4] (3). All three complexes were characterized by single-crystal X-ray crystallography and IR spectroscopy, while their antiproliferative activities were investigated against a series of human and mouse cancer cell lines.

Organogallium(III) complexes as apoptosis promoting anticancer agents for head and neck squamous cell carcinoma (HNSCC) cell lines

“…Gallium(III) complexes 3, 5 and 8 induced a slightly higher population in Sub-G1 (3: 31%, 5: 19%, 8: 20% versus control: 15%) and also, like cisplatin, reduced the population in the G1 phase (3: 28%, 5: 37%, 8: 27%). Complexes 3, 5 and 8 have different effects on the cell cycle depending on the cell line, which is consistent with the literature[33]. It was observed that complexes 3, 5 and 8 did not induce significant cell cycle arrest in any cell cycle phase but rather directly provoked an increase in the number of apoptotic cells with concomitant decline of all other cell…”

Anticancer Applications and Recent Investigations of Metallodrugs Based on Gallium, Tin and Titanium

“…Cal27 and FaDu cells were treated for 24 h with IC 90 concentration of the complexes and DNA appeared as characteristic ladder-like fragments suggesting an apoptotic cell death promotion. In contrast to the Cal27 cell line, there was a slight translation of FaDu cells from the G1 phase to the apoptotic phase (Sub-G1) after treatment with compounds 3, 6, and 8, which indicates that apoptosis caused by these compounds on FaDu cells may be due to interference caused in the G1 phase of the cell cycle [28].…”

Recent Developments in the Synthesis and Applications of 1,2,5-Thia- and Selenadiazoles. A Review

“…184 bis-Imine of benzothiadiazole 164 on treatment with palladium(II) tetrafluoroborate complex with acetonitrile Pd(MeCN) 4 (BF 4 ) 2 afforded twisted coordinated complex 165 in high yield (Scheme 81). 185 The benzothiadiazole ring was also found to control the arrangement through π -π interaction in the crystal packing.…”

“…3,4-Dicyano-1,2,5-selenadiazole (184) was prepared in 96%-97% yield from diaminomaleodinitrile and selenium dioxide in acetonitrile 201 or dichloromethane (Scheme 92). 202…”

“…168 Anti-cancer activity of the complex between gallium trichloride and 2,1,3-benzothiadiazole 1 (see Scheme 80) was discovered. 184 A highly fluorescent fluorinated semi-conducting polymer dot having a benzothiadiazole unit in the backbone showed a quantum yield of up to 49% for marked MCF-7 cancer cells with specific sub-cellular labeling, making them promising probes for biological detection. 246 A series of benzo-, [1,2,5]Selenadiazole [3,4-d]pyrimidine-5,7(4H,6H)-dione 218 was claimed as a proliferative agent against the human breast adrenocarcinoma, hepatoma, and melanoma cells.…”