Synthesis of (E)-9-(1-pyrenyl)-4-hydroxynon-2-enal, a fluorescent probe of the (E)-4-hydroxynon-2-enal with retained biological properties.
(E)-9-(1-pyrenyl)-4-hydroxynon-2-enal (FHNE), a fluorescent probe of (E)-4-hydroxynon-2-enal (HNE) is synthesised in seven steps and in 35% overall yield, starting from commercially available 1-pyrencarboxyaldehyde. When incubated with cultured HeLa cells this fluorescent probe penetrates cells and particularly concentrates in the region surrounding the nucleus. As the parent compound, HNE it is able to induce the activation of heat shock factor (HSF) and is able to induce the binding of HSF to heat shock element (HSE).
Allevi
P
P
Departimento di Chimica e Biochimica Medica, Universita degli Studi diMilano, Italy. pietro.allevi@ unimi.it
Anastasia
M
M
Cajone
F
F
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D002467:Cell Nucleus / Q000378:metabolism; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006367:HeLa Cells; D006360:Heat-Shock Proteins / Q000378:metabolism; D006801:Humans; D015227:Lipid Peroxidation; D009682:Magnetic Resonance Spectroscopy; D011721:Pyrenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C404170:9-(1-pyrenyl)-4-hydroxynon-2-enal; D000447:Aldehydes; D005456:Fluorescent Dyes; D006360:Heat-Shock Proteins; D011721:Pyrenes; C027576:4-hydroxy-2-nonenal