Substitution Effect on the One- and Two-photon Sensitivity of DMAQ “Caging” Groups

Abstract

The systematic SAR study of a "caging" group showed a strong influence of the position of the donor dimethylamino group on the efficiency of photolysis of the DMAQ (2-hydroxymethylene-(N,N-dimethylamino)quinoline) caged acetate under one-photon near-UV or two-photon near-IR excitation. Photorelease of l-glutamate by the most efficient 8-DMAQ derivative strongly and efficiently activated glutamate receptors, generating large, fast rising responses similar to those elicited by glutamate photoreleased from the widely used MNI-caged glutamate.

Quinoline‐Derived Two‐Photon Sensitive Quadrupolar Probes

“…The synthesis of compound 1a started from the diiodofluorene 3 (Scheme 1) prepared according to Goeldner et al [4] with al ittle modification. The Suzuki-Miyaura-type coupling between the boronic ester 4a [13] prepared from commercially available fluoronitrobenzene through the Skraup-Doebner-von Miller synthesis as reported earlier [12] and the diiodofluorene 3 under standard conditions (i.e.,[ Pd(PPh 3 ) 4 ]( 10 mol %), Na 2 CO 3 (aq.,2m)i nd imethylethane (DME),8 0 8C) afforded the protected compound 5a (51 % yield), which was transformed to the desired acetate 1a by aH F/pyridined esilylation/acetylation sequence (84 %). As imilar sequence was used for the synthesis of compound 1b,b y using the boronic ester, 4b [6] and the diiodofluorene 3 (31 %), followed by deprotection and acetylation (quant.…”

“…The compounds were photolyzed at l = 366 nm under earlier described conditions. [7,12,13] Briefly,a na liquot (1 mL) of the solution was irradiated by using a6WC arl Roth lamp and the transformation was monitored over 30 minutes by following the disappearance of the starting materiala nd the appearance of the quinoline photoproduct by HPLC. No quantitative analysis of the released acetic acid was made.…”

A Quinoline-Based Ratiometric and Reversible Fluorescent Probe for Cadmium Imaging in Living Cells

“…42) Hela cells were passed and plated to ca. 70% confluence in 96-well paltes 24 h before treatment.…”

Tandem Systems for Two‐Photon Uncaging of Bioactive Molecules

“…As for 1P absorption (1PA), the 2P uncaging (2PU) sensitivity δ u (in Goeppert-Mayer (GM)) corresponding to the product of the two-photon absorption cross-section σ 2 (in GM) and Φ u has been defined as the figure of merit to quantify the efficiency of PPGs for 2PU. [17] Interest in the photorelease of neurotransmitters such as GABA or glutamate has led to the emergence of new families of PPGs such as nitrobenzyl and homobenzyl derivatives, [18][19][20] coumarins, [18,[21][22][23][24][25][26] nitroindolines [27,28] or quinolines [29][30][31] (Figure 1).…”