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A series of Mn(i) photo-activated carbon monoxide-releasing molecules with benzimidazole coligands: synthesis, structural characterization, CO releasing properties and biological activity evaluation.

ABSTRACT: Five Mn(i) photo-activated carbon monoxide-releasing molecules (photo-CORMs) with benzimidazole coligands, namely [MnBr(CO)₃L1] (1, L1 = 2-(2-pyridyl)benzimidazole), [Mn(CO)₂L1(PPh₃)₂](ClO₄) (2), [MnBr(CO)₃L2] (3, L2 = 2,2'-bisbenzimidazole), [MnBr(CO)₃L3]·CH₃OH (4, L3 = 2,6-bis(benzimidazole-2'-yl)pyridine) and fac-[MnBr(CO)₃L4] (5, L4 = 2,4-bis(benzimidazole-2'-yl) pyridine) were synthesized by reactions of MnBr(CO)₅ with complexes L1-L4, respectively, and characterized via single crystal X-ray diffraction, elemental analysis, ¹H-NMR, ¹³C-NMR, IR, UV-vis and fluorescence spectroscopy. The CO-release properties of 1-5 were investigated using the myoglobin assay and CO detection, and the results show that all of the complexes could release CO rapidly upon exposure to 365 nm UV light. Comparing their half-lives of CO release, we found that increasing the degree of unsaturation and conjugation of the ligand frame could be advantageous for prolonging the time of CO-release, and that the luminescence intensity of 1-5 could gradually be enhanced. The cellular fluorescence imaging tests demonstrate that these Mn(i) photo-CORMs can be taken up by human liver cells (HL-7702) and liver cancer cells (SK-Hep1), and exhibit good capabilities for bioimaging. A cell viability assay for SK-Hep1 shows that the anticancer activity of 3 is better than that of other complexes.

SUBMITTER: Hu M

PROVIDER: S-EPMC9065806 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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A series of Mn(i) photo-activated carbon monoxide-releasing molecules with benzimidazole coligands: synthesis, structural characterization, CO releasing properties and biological activity evaluation.

Hu Mixia M Yan YaLi Y Zhu Baohua B Chang Fei F Yu Shiyong S Alatan Gaole G

RSC advances 20190702 36

Five Mn(i) photo-activated carbon monoxide-releasing molecules (photo-CORMs) with benzimidazole coligands, namely [MnBr(CO)3L1] (1, L1 = 2-(2-pyridyl)benzimidazole), [Mn(CO)2L1(PPh3)2](ClO4) (2), [MnBr(CO)3L2] (3, L2 = 2,2'-bisbenzimidazole), [MnBr(CO)3L3]·CH3OH (4, L3 = 2,6-bis(benzimidazole-2'-yl)pyridine) and fac-[MnBr(CO)3L4] (5, L4 = 2,4-bis(benzimidazole-2'-yl) pyridine) were synthesiz ...[more]

PMID: 35515566

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Project description:Due to the beneficial effects of carbon monoxide as a cell-protective and anti-inflammatory agent, CO-releasing molecules (CORMs) offer some promising potential applications in medicine. In this context, we synthesized a set of acyloxy-cyclohexadiene-Fe(CO)3 complexes, all displaying a N-methyl-pyridinium triflate moiety in the ester side chain, as mitochondria-targeting esterase-triggered CORM prodrugs. Whereas the compounds in which the acyloxy substituent is attached to the 2-position of the diene-Fe(CO)3 unit (A series) spontaneously release CO upon dissolution in phosphate buffer, which remarkably is partly suppressed in the presence of porcine liver esterase (PLE), the 1-substituted isomers (B series) show the expected PLE-induced release of CO (up to 3 equiv.). The biological activity of Mito-CORMs 2/3-B and their isophorone-derived analogs 2/3-A', which also displayed PLE-induced CO release, was assessed by using human umbilical vein endothelial cells (HUVEC). Whereas Mito-CORMs 2/3-B were not cytotoxic up to 500 μM (MTT assay), Mito-CORMs 2/3-A' caused significant toxicity at concentrations above 50 μM. The anti-inflammatory potential of both Mito-CORM variants was demonstrated by concentration-dependent down-regulation of the pro-inflammatory markers VCAM-1, ICAM-1 and CXCL1 as well as induction of HO-1 in TNFα-stimulated human umbilical vein endothelial cells (HUVECs; western blotting and qPCR). Energy phenotyping by seahorse real-time cell metabolic analysis, revealed opposing shifts of metabolic potentials in cells treated either with Mito-CORMs 2/3-B (increased mitochondrial respiration and glycolytic activity) or Mito-CORMs 2/3-A' (suppressed mitochondrial respiration and increased glycolytic activity). Thus, the Mito-CORMs represent valuable tools for the safe and targeted delivery of CO to mitochondria as a subcellular compartment to induce positive anti-inflammatory effects with only minor shifts in cellular energy metabolism. Also, due to their water solubility, these compounds provide a promising starting point for further pharmacological studies.

Dataset Information

A series of Mn(i) photo-activated carbon monoxide-releasing molecules with benzimidazole coligands: synthesis, structural characterization, CO releasing properties and biological activity evaluation.

Publications

A series of Mn(i) photo-activated carbon monoxide-releasing molecules with benzimidazole coligands: synthesis, structural characterization, CO releasing properties and biological activity evaluation.

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