Ruthenium-centred btp glycoclusters as inhibitors for Pseudomonas aeruginosa biofilm formation

Abstract

Ruthenium-centred glycoclusters based on carbohydrate-functionalised bis(triazolyl)pyridine ligands show Pseudomonas aeruginosa biofilm inhibition, with activity that is dependent on ligand structure.

Luminescent (metallo-supramolecular) cross-linked lanthanide hydrogels from a btp (2,3-bis(1,2,3-triazol-4-yl)picolinamide) monomer give rise to strong Tb(iii) and Eu(iii) centred emissions

“…The synthesis of the monomer 2 was achieved from the amine 1 , which was formed in a seven-step synthetic procedure (see ESI†), starting from the commercial starting material 2,6-dibromopyridine, using synthetic procedures developed in our laboratory. 24–27 ‡‡One of the intermediates from this synthesis, 2,6-dibromo-4-nitropyridine, crystallised during the workup and the resulting crystals were found to be suitable for X-ray crystallographic analysis. The resulting structure showed the presences of extended intermolecular halogen bonding interactions between the two bromine atoms of the pyridine and that of and the pyridine nitrogen, as well as the nitro group.…”

“…The synthesis of the monomer 2 was achieved from the amine 1, which was formed in a seven-step synthetic procedure (see ESI †), starting from the commercial starting material 2,6dibromopyridine, using synthetic procedures developed in our laboratory. [24][25][26][27] ‡ All the intermediates were fully characterised by NMR spectroscopies, IR spectroscopy and HRMS. The final two steps in the formation of 1 involved the use of click chemistry under CuAAC conditions using CuSO 4 Á5H 2 O in a DMF : H 2 O mixture, followed by removal of a Boc protecting group to give the free amine 1, being formed in a moderate yield of 52%, as a brown precipitate, and TFA salt (The structure of 1 was further confirmed by X-ray crystallography as will be discussed further below).…”

“…23 This includes their use in the formation of luminescent coordinating polymers and metallo-gels. 24,25 Gratifyingly, the btp based ligands can sensitise the excited states of various lanthanides, including the 5 D 4 state of Tb( iii ) (resulting in green emission) resulting in the formation of complexes possessing high Tb-cantered quantum yield (up to 90%), and to a lesser extent, the 5 D 0 state Eu( iii ), which results in red emission (but much lower quantum yield) in solution. 26 We also recently incorporated btp based lanthanide complexes into polymer matrixes in a non-covalent manner.…”

Generating water/MeOH-soluble and luminescent polymers by grafting 2,6-bis(1,2,3-triazol-4-yl)pyridine (btp) ligands onto a poly(ethylene-alt-maleic anhydride) polymer and cross-linking with terbium(iii)

“…16 In particular, the btp has been employed in coordination chemistry, due to its similarity to the well-known terpy ligand. 17 Recently, Byrne et al utilised this ligand upon complexation to Ru( ii ) in antifouling 18 as well as in the formation of chiral luminescent lanthanide complexes that give rise to circularly polarised luminescence (CPL) from the lanthanide centre. 19 In addition to its favourable metal ion coordination properties, the btp motif has been shown to form dimers via self-templation.…”

Rim-differentiation vs. mixture of constitutional isomers: A binding study between pillar[5]arene-based glycoclusters and lectins from pathogenic bacteria

“…Among strategies that have been developed to competitively interfere with the recognition processes between host cells and pathogens, multivalent glycoconjugates have the potential to prevent colonization or even reverse the formation of biofilms for fighting bacterial infection. Therefore, a large number of glycoclusters have been constructed based on various scaffolds including proteins [18,19], polymers [20,21], dendrimers [22], calixarenes [23][24][25][26][27][28][29][30][31], resorcinarenes [32], cyclodextrins [33], porphyrins [34][35][36][37], fullerenes [38][39][40][41][42][43][44][45][46][47], and pillararenes [48][49][50][51], to prevent or treat diseases caused by bacteria. Pillar[n]arenes, as a novel family of macrocyclic host molecules [52][53][54], have been well-received by the supra(bio)molecular chemistry community since their first report in 2008 by Ogoshi [55].…”