Luminescent fac-[Re(CO)₃(phen)] carboxylato complexes with non-steroidal anti-inflammatory drugs: synthesis and mechanistic insights into the in vitro anticancer activity of fac-[Re(CO)₃(phen)(aspirin)]

Abstract

Luminescent fac-[Re(CO)3(phen)(aspirin)]: insights into in vitro anticancer activity and confocal microscopy imaging in HeLa cells.

Insight into the Biological Activity of Organometallic Acetylsalicylic Acid (Aspirin) Derivatives

“…An approximately 14 % increase in the sub‐G1 phase of HeLa cells was observed, which is a sign of pro‐apoptotic activity. Pro‐apoptotic activity of rhenium derivative 33 was further substantiated by the Annexin V and Caspase‐3/7 assay . Antiproliferative activity of 33 seems not to be directly linked to COX‐2 inhibition in the concentration range of 10 to 100 μM; the compound was not superior to the inhibitory activity of aspirin.…”

“…In 2019 Kowalski and co‐workers reported the synthesis and biological activity studies of fac ‐[Re(CO) 3 (phen)(aspirin)] complex 33 with phen=1,10‐phenanthroline (Figure ) . Compound 33 showed orange luminescence stemming from the metal‐to‐ligand charge‐transfer ( 3 MLCT) triplet excited state.…”

“…Accordingly, inside the cell, compound 33 dissociates to produce the luminescent the fac ‐[Re(CO) 3 (phen)] + cation and the ASA anion. The positively charged organometallic cation is preferentially localized in mitochondria, but also in other subcellular compartments such as the Golgi apparatus and the endoplasmic reticulum (Figure ) …”

Ru(II) Complexes Bearing O, O-Chelated Ligands Induced Apoptosis in A549 Cells through the Mitochondrial Apoptotic Pathway

“…Liu and Dhar et al reported that a novel Pt(IV) prodrug of cisplatin, asplatin, with the ligation of aspirin ( c , c , t -[PtCl 2 (NH 3 ) 2 (OH) (aspirin)]), demonstrated significantly higher cytotoxicity than cisplatin towards tumor cells and nearly completely overcame the drug resistance of cisplatin-resistant cells [ 20 – 22 ]. Recently, Kowalski reported a new rhenium compound with AS as the ligand, fac -[Re(CO) 3 (phen)(aspirin)], which exhibited activity against HeLa human cancer cells, and this anticancer activity could be linked to ROS production, and cell cycle disturbance followed by triggering an apoptotic pathway of cell death [ 23 ]. Similar exciting antitumor effect has also been found in other metal-based complexes of SA.…”

Top-down mass spectrometry reveals multiple interactions of an acetylsalicylic acid bearing Zeise’s salt derivative with peptides

“…Coordination of NSAIDs to metal centers aims at obtaining antiproliferative activity through a dual mode of action: inhibition of COX and, e.g., ROS generation by the metal. Complexes of Ru II , Os II , Cu II , Re II , Fe II , Co II and Zn II with indomethacin, naproxen, diclofenac and ibuprofen have been reported [3][4][5][6][7][8][9][10][11]. Examples of ASA derivatives involve Ir III [12], Pt IV [13], Ag I [14,15] and various metal carbonyls [16][17][18].…”