Metallosupramolecur Architectures of Bile Acid Derivatives: from
Metallosupramolecular Cages to Infinite Coordination Particles
Subhasis Chattopadhyaya,b,c
, Radek Mareka,c
, Ondřej Jurčeka,b,c
*
a
Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, 62500 Brno, Czech Republic;
subhasischattopadyay101@gmail.com
b
Department of Natural Drugs, Faculty of Pharmacy, Masaryk University, 61200 Brno, Czech Republic
c
CEITEC - Central European Institute of Technology, Masaryk University, Kamenice 5, 62500 Brno, Czech
Republic
Bile acids (BAs) are enantiomerically pure steroid compounds synthesized in human liver from
cholesterol. They participate in enterohepatic circulation in digestion of lipids and lipophilic
nutrients. BAs differ from each other by number and spatial orientation of hydroxyl groups
located in the steroid skeleton and contain one carboxylic acid group attached to the steroid
skeleton through an alkyl chain. These groups can be chemically modified into various
coordination sites with a control over the bend angle, topicity, and flexibility of the final ligand.
We have shown that coordination-driven self-assembly of these BA-based building units can
lead to many metallosupramolecular structures (MSS) by varying reaction conditions, i.e.,
solvent, metal salts, or metal-to-ligand ratio. Owning to the properties of the BAs, these MSS
could be promising candidates for diverse applications, from basic host-guest chemistry,
recognition to biomedical applications. Despite of these facts, BA-based coordination
metallosupramolecular structures were unexplored until recently (Figure 1a).1, 2
Figure 1. BA-based metallosupramolecular architectures.
Inspired by the discovery, we have designed and synthesized BA-based Pd6L8 and first-ever
Pd12L16 metallosupramolecular cages (Figure 1b) using tritopic pyridyl ligand and square planar
Pd2+
via molecular paneling method. Pyridyl coordinating ligands and Pd2+
salts are the most
explored combination in metallosupramolecular chemistry. Therefore, design and synthesis of
the next generation of BA-based non-pyridyl biocompatible ligands were performed. These
novel ligands upon coordination with various metal salts form infinite coordination particles3
and composite materials (Figure 1c, Figure 1d). In my presentation I will describe the basic
principles, synthesis, and structural details of these metallosupramolecular architectures which
provide insight into self-assembly of unsymmetric natural molecule-based ligands.
1. Jurček, O.; Bonakdarzadeh, P.; Kalenius, E.; Linnanto, J. M.; Groessl, M.; Knochenmuss, R.;
Ihalainen, J. A.; Rissanen, K. Angew. Chem. Int. Ed. 2015, 54 (51), 15462-15467.
2. Jurček, O.; Nonappa, Kalenius, E.; Jurček, P.; Linnanto, J. M.; Puttreddy, R.; Valkenier, H.;
Houbenov, N.; Babiak, M.; Peterek, M.; Davis, A. P.; Marek, R.; Rissanen, K. Cell Rep. Phys.
Sci. 2021, 2 (1), 100303-100323.
3. Spokoyny, A. M.; Kim, D.; Sumrein, A.; Mirkin, C. A. Chem. Soc. Rev. 2009, 38 (5), 1218-
1227.