caa a22 4500 605507155 CHVBK 20210128100630.0 cr unu---uuuuu 210128e20151001xx s 000 0 eng 10.1007/s00775-015-1299-6 doi (NATIONALLICENCE)springer-10.1007/s00775-015-1299-6 Bismuth(III) α-hydroxy carboxylates: highly selective toxicity of glycolates towards Leishmania major [Elektronische Daten] [Allan Loh, Yih Ong, Victoria Blair, Lukasz Kedzierski, Philip Andrews] 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(O t Bu)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 50.0µM. 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 non-toxic towards promastigotes and human fibroblast cells. SBIC, 2015 Bismuth nationallicence α-Hydroxycarboxylic acid nationallicence Leishmania nationallicence Glycolate nationallicence Toxicity nationallicence Loh Allan School of Chemistry, Monash University, Clayton, 3800, Melbourne, VIC, Australia aut Ong Yih School of Chemistry, Monash University, Clayton, 3800, Melbourne, VIC, Australia aut Blair Victoria School of Chemistry, Monash University, Clayton, 3800, Melbourne, VIC, Australia aut Kedzierski Lukasz Walter and Eliza Institute of Medical Research, Parkville, 3052, Melbourne, VIC, Australia aut Andrews Philip School of Chemistry, Monash University, Clayton, 3800, Melbourne, VIC, Australia aut JBIC Journal of Biological Inorganic Chemistry Springer Berlin Heidelberg 20/7(2015-10-01), 1193-1203 0949-8257 20:7<1193 2015 20 775 https://doi.org/10.1007/s00775-015-1299-6 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s00775-015-1299-6 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Loh Allan School of Chemistry, Monash University, Clayton, 3800, Melbourne, VIC, Australia aut NATIONALLICENCE 700 1- Ong Yih School of Chemistry, Monash University, Clayton, 3800, Melbourne, VIC, Australia aut NATIONALLICENCE 700 1- Blair Victoria School of Chemistry, Monash University, Clayton, 3800, Melbourne, VIC, Australia aut NATIONALLICENCE 700 1- Kedzierski Lukasz Walter and Eliza Institute of Medical Research, Parkville, 3052, Melbourne, VIC, Australia aut NATIONALLICENCE 700 1- Andrews Philip School of Chemistry, Monash University, Clayton, 3800, Melbourne, VIC, Australia aut NATIONALLICENCE 773 0- JBIC Journal of Biological Inorganic Chemistry Springer Berlin Heidelberg 20/7(2015-10-01), 1193-1203 0949-8257 20:7<1193 2015 20 775