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Université de Fribourg

Aerobically stable and substitutionally labile α-diimine rhenium dicarbonyl complexes

Schindler, Kevin ; Crochet, Aurélien ; Zobi, Fabio

In: RSC Advances, 2021, vol. 11, p. 7511-7520

New synthetic routes to aerobically stable and substitutionally labile α-diimine rhenium(I) dicarbonyl complexes are described. The molecules are prepared in high yield from the cis–cis–trans-[Re(CO)2(tBu2bpy)Br2]− anion (2, where tBu2bpy is 4,4′- di-tert-butyl-2,2′-bipyridine), which can be isolated from the one electron reduction of the corresponding 17-electron complex (1)....

Université de Fribourg

Antiplasmodial activity and in vivo bio-distribution of chloroquine molecules released with a 4-(4-ethynylphenyl)-triazole moiety from organometallo-cobalamins

Rossier, Jeremie ; Sovari, Sara Nasiri ; Pavic, Aleksandar ; Vojnovic, Sandra ; Stringer, Tameryn ; Bättig, Sarah ; Smith, Gregory S. ; Nikodinovic-Runic, Jasmina ; Zobi, Fabio

In: Molecules, 2019, vol. 24, no. 12, p. 2310

We have explored the possibility of using organometallic derivatives of cobalamin as a scaffold for the delivery of the same antimalarial drug to both erythro- and hepatocytes. This hybrid molecule approach, intended as a possible tool for the development of multi-stage antimalarial agents, pivots on the preparation of azide- functionalized drugs which, after coupling to the vitamin, are...

Université de Fribourg

CO and CO-releasing molecules in medicinal chemistry

Zobi, Fabio

In: Future Medicinal Chemistry, 2013, vol. 5, no. 2, p. 175-188

Since the discovery that CO acts as a cytoprotective and homeostatic molecule, increasing research efforts have been devoted to the exploitation of its therapeutic effects. Both endogenous and exogenous CO improves experimental lung, vascular and cardiac injuries and protects against several inflammatory states. The technology is now in place to bring CO to clinical applications, but the use...

Université de Fribourg

Correlation of MLCTs of Group 7 fac-[M(CO)3]+ complexes (M = Mn, Re) with bipyridine, pyridinylpyrazine, azopyridine, and pyridin-2-ylmethanimine type ligands for rational photoCORM design

Kottelat, Emmanuel ; Lucarini, Fiorella ; Crochet, Aurélien ; Ruggi, Albert ; Zobi, Fabio

In: European Journal of Inorganic Chemistry, 2019, vol. 2019, no. 33, p. 3758–3768

A mathematical correlation of the MLCT absorption maxima of structurally related fac‐ [M(CO)3L2Br] complexes (M = Mn, Re; L2 = bidentate ligand) is obtained by the comparison of a total of 50 species bearing bipyridine, pyridinylpyrazine, azopyridine and pyridin‐2‐ylmethanimine L2 type ligands. The empirical relationship is first derived by the initial comparison of the MLCT absorption...

Université de Fribourg

Correlation of surface pressure and hue of planarizable push-pull chromophores at the air/water interface

Neuhaus, Frederik ; Zobi, Fabio ; Brezesinski, Gerald ; Molin, Marta Dal ; Matile, Stefan ; Zumbuehl, Andreas

In: Beilstein Journal of Organic Chemistry, 2017, vol. 13, no. 1, p. 1099–1105

It is currently not possible to directly measure the lateral pressure of a biomembrane. Mechanoresponsive fluorescent probes are an elegant solution to this problem but it requires first the establishment of a direct correlation between the membrane surface pressure and the induced color change of the probe. Here, we analyze planarizable dithienothiophene push–pull probes in a monolayer at...

Université de Fribourg

Cytotoxicity of Mn-based photoCORMs of ethynyl-α-diimine ligands against different cancer cell lines: The key role of CO-depleted metal fragments

Rossier, Jeremie ; Delasoie, Joachim ; Haeni, Laetitia ; Hauser, Daniel ; Rothen-Rutishauser, Barbara ; Zobi, Fabio

In: Journal of Inorganic Biochemistry, 2020, vol. 209, p. 111122

A series of tricarbonyl manganese complexes bearing 4-ethynyl-2,2′-bipyridine and 5- ethynyl-1,10-phenanthroline α-diimine ligands were synthetized, characterized and conjugated to vitamin B12, previously used as a vector for drug delivery, to take advantage of its water solubility and specificity toward cancer cells. The compounds act as photoactivatable carbon monoxide-releasing molecules...

Université de Fribourg

Design, synthesis and in vivo evaluation of 3-arylcoumarin derivatives of rhenium(I) tricarbonyl complexes as potent antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA)

Sovari, Sara Nasiri ; Vojnovic, Sandra ; Bogojevic, Sanja Skaro ; Crochet, Aurélien ; Pavic, Aleksandar ; Nikodinovic-Runic, Jasmina ; Zobi, Fabio

In: European Journal of Medicinal Chemistry, 2020, vol. 205, p. 112533

We have prepared a series of ten 3-arylcoumarin molecules, their respective fac- [Re(CO)3(bpy)L]+ and fac-[Re(CO)3(L⁀L)Br] complexes and tested all compounds for their antimicrobial efficacy. Whereas the 3-arylcoumarin ligands are virtually inactive against the human-associated pathogens with minimum inhibitory concentrations (MICs) > 150 μM, when coordinated to the fac-[Re(CO)3]+ core,...

Université de Fribourg

Evaluation of the potential of cobalamin derivatives bearing ru(ii) polypyridyl complexes as photosensitizers for photodynamic therapy

Jakubaszek, Marta ; Rossier, Jeremie ; Karges, Johannes ; Delasoie, Joachim ; Goud, Bruno ; Gasser, Gilles ; Zobi, Fabio

In: Helvetica Chimica Acta, 2019, vol. 102, no. 7, p. -

The current photosensitizers (PSs) for photodynamic therapy (PDT) lack selectivity for cancer cells. To tackle this drawback, in view of selective cancer delivery, we envisioned conjugating two ruthenium polypyridyl complexes to vitamin B12 (Cobalamin, Cbl) to take advantage of the solubility and active uptake of the latter. Ultimately, our results showed that the transcobalamin pathway is...

Université de Fribourg

Formation and Reactivity of [(tacn)-N-CO-Re(III)Br(CO)(2)](+) in Water : a Theoretical and Experimental Study

Zobi, Fabio ; Blacque, Olivier ; Steyl, Gideon ; Spingler, Bernhard ; Alberto, Roger

In: Inorganic Chemistry, 2009, vol. 48, no. 11, p. 4963-4970

The chemistry of [(tacn)-N-CO-Re(III)(CO)(2)Br]X (X = Cl or Br), obtained in good yield from the reaction of fac-[(tacn)Re(I)(CO)(3)]Br (1, tacn = 1,4,7- triazacyclononane) with X(2) in water, is described. The [(tacn)-N-CO-Re(III)(CO) (2)Br]X complex (2 with X = Br(-); 2a with X = BrCl(2)(-)), which we have previously communicated, is characterized by an unusual three-membered ring acyl amide...

Université de Fribourg

Heme oxygenase-1/carbon monoxide system and embryonic stem cell differentiation and maturation into cardiomyocytes

Suliman, Hagir B. ; Zobi, Fabio ; Piantadosi, Claude A.

In: Antioxidants & Redox Signaling, 2016, vol. 24, no. 7, p. 345–360

The differentiation of embryonic stem (ES) cells into energetically efficient cardiomyocytes contributes to functional cardiac repair and is envisioned to ameliorate progressive degenerative cardiac diseases. Advanced cell maturation strategies are therefore needed to create abundant mature cardiomyocytes. In this study, we tested whether the redox-sensitive heme oxygenase-1/carbon monoxide...