Combination of quinoxaline with pentamethinium system: Mitochondrial staining and targeting
Jazyk angličtina Země Spojené státy americké Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
37716274
DOI
10.1016/j.bioorg.2023.106816
PII: S0045-2068(23)00477-7
Knihovny.cz E-zdroje
- Klíčová slova
- Fluorescence mitochondrial probe, Pentamethinium salt, Quinoxaline,
- MeSH
- chinoxaliny farmakologie MeSH
- fosfatidylcholiny MeSH
- kardiolipiny * MeSH
- protinádorové látky * farmakologie chemie MeSH
- soli MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- 4-chlorophenyl methyl sulfide MeSH Prohlížeč
- chinoxaliny MeSH
- fosfatidylcholiny MeSH
- kardiolipiny * MeSH
- protinádorové látky * MeSH
- soli MeSH
Pentamethinium indolium salts are promising fluorescence probes and anticancer agents with high mitochondrial selectivity. We synthesized two indolium pentamethinium salts: a cyclic form with quinoxaline directly incorporated in the pentamethinium chain (cPMS) and an open form with quinoxaline substitution in the γ-position (oPMS). To better understand their properties, we studied their interaction with mitochondrial phospholipids (cardiolipin and phosphatidylcholine) by spectroscopic methods (UV-Vis, fluorescence, and NMR spectroscopy). Both compounds displayed significant affinity for cardiolipin and phosphatidylcholine, which was associated with a strong change in their UV-Vis spectra. Nevertheless, we surprisingly observed that fluorescence properties of cPMS changed in complex with both cardiolipin and phosphatidylcholine, whereas those of oPMS only changed in complex with cardiolipin. Both salts, especially cPMS, display high usability in mitochondrial imaging and are cytotoxic for cancer cells. The above clearly indicates that conjugates of pentamethinium and quinoxaline group, especially cPMS, represent promising structural motifs for designing mitochondrial-specific agents.
Citace poskytuje Crossref.org
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