Bismuth(III) α-hydroxy carboxylates: highly selective toxicity of glycolates towards Leishmania major

Abstract

Eight bismuth(III) complexes derived from the simple α-hydroxycarboxylic acids; gluconic (H₆-glu), tartaric (H₄-tar), mandelic (H₂-man), malic (H₃-mal) and glycolic (H₂-gly) have been synthesised and characterised. The complexes are formed through direct treatment of the organic acids with Bi(NO₃)3·5H₂O ([Bi(H₂-tar)(H₃- tar)] 2, [Bi(mal)(NO₃)(H₂O)₂] 6, [Bi(gly)(NO₃)(H₂O)] 8) or Bi(OtBu)₃ ([Bi(H-tar)(H₂O)₂] 1, [Bi(man)(H-man) (H₂O)] 4, [Bi2(H-mal)₃] 5, [Bi(gly)(H-gly)] 7), or through metathesis of the sodium salts with Bi(NO₃)3·5H₂O ([Bi(H3-glu)]₃). Reactions with both glucuronic and mucic acid proved to be unsuccessful. Small crystals of [Bi(gly)4(NO₃)4(H₂O)₄]·5H₂O 8 were obtained from aqueous solution and analysed by synchrotron X-ray diffraction. The data were relatively poor but composition and connectivity were established, confirming and supporting other analyses. Those complexes which displayed sufficient solubility; 2, 4, 7 and 8, were tested for their anti-Leishmanial activity against parasite promastigotes and amastigotes, and for toxicity against human fibroblast cells. All four complexes and their parent acids showed no toxicity towards either the promastigotes or fibroblast cells. However, the two glycolate complexes showed selective toxicity towards amastigotes with complex 8 providing for a low % viability of 1.8 ± 0.9 at 50.0 μM. Graphical Abstract Novel bismuth(III) complexes derived from α-hydroxycarboxylic acids have been synthesised, characterised and assessed for their anti-leishmanial activity. The glycolate complexes are selectively toxic against parasite amastigotes, with all complexes being nontoxic towards promastigotes and human fibroblast cells.

Intrinsically Fluorescent Biocompatible Terpolymers for Detection and Removal of Bi(III) and Cell Imaging

“…The limit of detection (LOD) values of terpolymers were 1.39 × 10 –6 and 2.07 × 10 –6 M (signal/noise = 3), respectively, via addition of 1.00 × 10 –9 M Bi­(III) solutions (Figure S12a,b). Notably, the LOD values were comparable to the reported values. ,, …”

“…The strong coordination of Bi­(III) with naphthalimide blocks the PET effect, and the turn-on fluorescence is regenerated. Thus, −C O NH– and  N  in rhodamine B/pyrene, − O H and −CO O – in CAU-1-(OH) 2 MOFs, −C O N– and >N– O H in N -hydroxy-1,8-naphthalimide, and − O H and −CO O H in α-hydroxycarboxylic acids selectively bind with Bi­(III). Accordingly, 1 and 2 containing −CONH–, −CON<, −OH, and −COOCH 3 functionalities are expected to bind selectively with Bi­(III).…”

“…Although very few fluorescent probes, such as rhodamine B/ pyrene, metal–organic frameworks, N -hydroxy-1,8-naphthalimide, and α-hydroxycarboxylic acids, have been reported for sensitive detection of Bi­(III), the high-performance Bi­(III) sensing using purely aliphatic intrinsically fluorescent multifunctional terpolymers suitable for diverse applications has not been reported to date. The −C O NH– and  N  functionalities of the fluorescent rhodamine B/pyrene form coordinate bonds with Bi­(III).…”

Water-Soluble Bismuth(III) Polynuclear Tyrosinehydroximate Metallamacrocyclic Complex: Structural Parallels to Lanthanide Metallacrowns

“…Recent interest in the use of alpha-emitting 213 Bi in nuclear medicine requires efficient Bi complexation, preferably within a macrocyclic cavity [ 9 , 10 ]. It is not surprising that research on the synthesis of biologically important ligands and their water-soluble complexes has received significant attention [ 11 , 12 , 13 , 14 , 15 , 16 , 17 ]. However, the chemistry of Bi(III) explored in this purpose to date is rather scarce, and the study of bismuth complexes in aqueous solutions is often difficult.…”

A Nonlinear Optically Active Bismuth–Camphorate Coordination Polymer

“…Bismuth‐based CPs remain poorly explored, but become increasingly popular in a form of homoleptically enclosed metal centers due to their sufficiently broad range of potential applications. Therefore, some discrete complexes and CPs have been reported as potential bioactive (biocidic, antidiarrheal and antacid), or bioneutral compounds, gas sorption, luminescent and catalytic materials. In the absence of d‐ or f‐block electrons, Bi III ‐based compounds are transparent in the visible region of the electromagnetic spectrum, whose is highly desirable for its use as stable laser beam modulators, Q‐switches and mode‐lockers with the most spectrometers and devices equipped with laser source.…”