1-Acyl-5-methoxy-8-nitro-1,2-dihydroquinoline: a biologically useful photolabile precursor of carboxylic acids

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

“…246,248 Corrie and co-workers also designed a clever combination of a nitroindoline core and an absorbing “antenna”, which will be discussed later (section 8.1). 249 The compounds 130 (250) and 131 (251) have recently been proposed as PPGs.…”

“…Despite the rather low two-photon cross sections of nitroindolyl cages ( 125 , 127 , 283 , and 130 , Table 11; see also section 3.3), they have been successfully employed in several biochemical applications. 10d,250,483,494 …”

Photoinduced Release of Neurotransmitter Amino Acids from Coumarin‐Fused Julolidine Ester Cages

“…There has been growing interest in photoremovable protecting groups (PPGs), known as phototriggers or cages in biochemistry, because they allow controlled spatial and temporal release, based on sensitivity to light, of numerous chemically and biologically relevant entities. Examples are calcium ions,5,6 amino acids,7 nucleotides,8,9 peptides,10 proteins,11 neurotransmitters,12,13 and other cell‐signalling molecules 14. Their applications include the caging of several functional groups (e.g., phosphates,9 thiols,15 amines,9 alcohols,16,17 and carboxylic acids17), and it is possible to find photolabile protecting groups with a large variety of chemical structures, which have been developed to fulfil the requirements of increasingly ambitious applications 18.…”

A Photocleavable Masked Nuclear‐Receptor Ligand Enables Temporal Control of C. elegans Development

“…Compared to nitroindole and nitrodehydroquinoline derivatives previously used for masking carboxylic acids, [12] MMNA offers similar quantum efficiency (Table S1), but is commercially available and less prone to undesired oxidative degradation. Irradiation at 365 nm of MMNA-masked ( RS )-2-methylundecanoic acid or MMNA-masked dafa#4, a likely intermediate in DAF-12 ligand biosynthesis, [8b] resulted in nearly quantitative conversion into the free acids, as indicated by NMR spectroscopic analysis of the reaction mixtures (Figures 2, S2).…”

“…To develop inactive, photocleavable derivatives of DAF-12 ligands or biosynthetic precursors that could be incorporated in vivo, the properties of 5-methoxy-N-methyl-2-nitroaniline (MMNA) amides were investigated (Figure 2). Compared to the nitroindole and nitrodehydroquinoline derivatives previously used for masking carboxylic acids, [12] MMNA offers similar quantum efficiency (Table S1 in the Supporting Information) but is commercially available and less prone to undesired oxidative degradation. MMNA-masked variants of dafa#1, dafa#4 (a likely intermediate in DAF-12 ligand biosynthesis), [8b] and a simple 2-methyl-branched carboxylic acid, (RS)-2-methylundecanoic acid, were prepared.…”