Abstract

2-Hydroxymethylene-8-dimethylamino quinoline-(DMAQ) derived photosensitive probes were prepared and tested under 366 nm and 730 nm 150 fs pulsed (“two-photon”) irradiation conditions. Brief bursts of photolysis of 250 μM solution of the kainate derivative of 2f generated sufficient kainate in a small spot to excite large inward currents and somatic spiking in Purkinje neurons.

© 2016 Optical Society of America

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  1. G. Bort, T. Gallavardin, D. Ogden, and P. I. Dalko, “From one-photon to two-photon probes: “caged” compounds, actuators, and photoswitches,” Angew. Chem. Int. Ed. Engl. 52(17), 4526–4537 (2013).
    [Crossref] [PubMed]
  2. H.-M. Lee, D. R. Larson, and D. S. Lawrence, “Illuminating the chemistry of life: design, synthesis, and applications of “caged” and related photoresponsive compounds,” ACS Chem. Biol. 4(6), 409–427 (2009).
    [Crossref] [PubMed]
  3. M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
    [Crossref] [PubMed]
  4. N. I. Kiskin and D. Ogden, “Two-photon excitation and photolysis by pulsed laser illumination modelled by spatially non-uniform reactions with simultaneous diffusion,” Eur. Biophys. J. 30(8), 571–587 (2002).
    [Crossref] [PubMed]
  5. M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
    [Crossref] [PubMed]
  6. P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
    [Crossref] [PubMed]
  7. Y. Zhu, C. M. Pavlos, J. P. Toscano, and T. M. Dore, “8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope,” J. Am. Chem. Soc. 128(13), 4267–4276 (2006).
    [Crossref] [PubMed]
  8. M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
    [Crossref] [PubMed]
  9. C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
    [Crossref] [PubMed]
  10. M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, “Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates,” J. Org. Chem. 65(1), 164–168 (2000).
    [Crossref] [PubMed]
  11. S. Clavaguera, S. I. Khan, and Y. Rubin, “Unexpected de-arylation of a pentaaryl fullerene,” Org. Lett. 11(6), 1389–1391 (2009).
    [Crossref] [PubMed]
  12. M. Lu, O. D. Fedoryak, B. R. Moister, and T. M. Dore, “Bhc-diol as a photolabile protecting group for aldehydes and ketones,” Org. Lett. 5(12), 2119–2122 (2003).
    [Crossref] [PubMed]
  13. F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
    [Crossref] [PubMed]
  14. N. I. Kiskin, R. Chillingworth, J. A. McCray, D. Piston, and D. Ogden, “The efficiency of two-photon photolysis of a “caged” fluorophore, o-1-(2-nitrophenyl)ethylpyranine, in relation to photodamage of synaptic terminals,” Eur. Biophys. J. 30(8), 588–604 (2002).
    [Crossref] [PubMed]

2015 (1)

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

2014 (1)

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

2013 (1)

G. Bort, T. Gallavardin, D. Ogden, and P. I. Dalko, “From one-photon to two-photon probes: “caged” compounds, actuators, and photoswitches,” Angew. Chem. Int. Ed. Engl. 52(17), 4526–4537 (2013).
[Crossref] [PubMed]

2012 (2)

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

2011 (1)

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

2009 (3)

H.-M. Lee, D. R. Larson, and D. S. Lawrence, “Illuminating the chemistry of life: design, synthesis, and applications of “caged” and related photoresponsive compounds,” ACS Chem. Biol. 4(6), 409–427 (2009).
[Crossref] [PubMed]

M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
[Crossref] [PubMed]

S. Clavaguera, S. I. Khan, and Y. Rubin, “Unexpected de-arylation of a pentaaryl fullerene,” Org. Lett. 11(6), 1389–1391 (2009).
[Crossref] [PubMed]

2006 (1)

Y. Zhu, C. M. Pavlos, J. P. Toscano, and T. M. Dore, “8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope,” J. Am. Chem. Soc. 128(13), 4267–4276 (2006).
[Crossref] [PubMed]

2003 (1)

M. Lu, O. D. Fedoryak, B. R. Moister, and T. M. Dore, “Bhc-diol as a photolabile protecting group for aldehydes and ketones,” Org. Lett. 5(12), 2119–2122 (2003).
[Crossref] [PubMed]

2002 (2)

N. I. Kiskin, R. Chillingworth, J. A. McCray, D. Piston, and D. Ogden, “The efficiency of two-photon photolysis of a “caged” fluorophore, o-1-(2-nitrophenyl)ethylpyranine, in relation to photodamage of synaptic terminals,” Eur. Biophys. J. 30(8), 588–604 (2002).
[Crossref] [PubMed]

N. I. Kiskin and D. Ogden, “Two-photon excitation and photolysis by pulsed laser illumination modelled by spatially non-uniform reactions with simultaneous diffusion,” Eur. Biophys. J. 30(8), 571–587 (2002).
[Crossref] [PubMed]

2000 (1)

M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, “Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates,” J. Org. Chem. 65(1), 164–168 (2000).
[Crossref] [PubMed]

Acher, F. C.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

Auger, C.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Blanchard-Desce, M.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

Bort, G.

G. Bort, T. Gallavardin, D. Ogden, and P. I. Dalko, “From one-photon to two-photon probes: “caged” compounds, actuators, and photoswitches,” Angew. Chem. Int. Ed. Engl. 52(17), 4526–4537 (2013).
[Crossref] [PubMed]

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

Cais, O.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Chillingworth, R.

N. I. Kiskin, R. Chillingworth, J. A. McCray, D. Piston, and D. Ogden, “The efficiency of two-photon photolysis of a “caged” fluorophore, o-1-(2-nitrophenyl)ethylpyranine, in relation to photodamage of synaptic terminals,” Eur. Biophys. J. 30(8), 588–604 (2002).
[Crossref] [PubMed]

Clavaguera, S.

S. Clavaguera, S. I. Khan, and Y. Rubin, “Unexpected de-arylation of a pentaaryl fullerene,” Org. Lett. 11(6), 1389–1391 (2009).
[Crossref] [PubMed]

Corrie, J. E. T.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Cowell, J. K.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Crawford, D. J.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Dalko, P. I.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

G. Bort, T. Gallavardin, D. Ogden, and P. I. Dalko, “From one-photon to two-photon probes: “caged” compounds, actuators, and photoswitches,” Angew. Chem. Int. Ed. Engl. 52(17), 4526–4537 (2013).
[Crossref] [PubMed]

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

Davis, M. J.

M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
[Crossref] [PubMed]

Dhimane, H.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

Doan, B.-T.

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

Dore, T. M.

M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
[Crossref] [PubMed]

Y. Zhu, C. M. Pavlos, J. P. Toscano, and T. M. Dore, “8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope,” J. Am. Chem. Soc. 128(13), 4267–4276 (2006).
[Crossref] [PubMed]

M. Lu, O. D. Fedoryak, B. R. Moister, and T. M. Dore, “Bhc-diol as a photolabile protecting group for aldehydes and ketones,” Org. Lett. 5(12), 2119–2122 (2003).
[Crossref] [PubMed]

Dunkel, P.

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

Fedoryak, O. D.

M. Lu, O. D. Fedoryak, B. R. Moister, and T. M. Dore, “Bhc-diol as a photolabile protecting group for aldehydes and ketones,” Org. Lett. 5(12), 2119–2122 (2003).
[Crossref] [PubMed]

Ferroud, C.

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

Gallavardin, T.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

G. Bort, T. Gallavardin, D. Ogden, and P. I. Dalko, “From one-photon to two-photon probes: “caged” compounds, actuators, and photoswitches,” Angew. Chem. Int. Ed. Engl. 52(17), 4526–4537 (2013).
[Crossref] [PubMed]

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

Hodgson, A. C. C.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Khan, S. I.

S. Clavaguera, S. I. Khan, and Y. Rubin, “Unexpected de-arylation of a pentaaryl fullerene,” Org. Lett. 11(6), 1389–1391 (2009).
[Crossref] [PubMed]

Kiskin, N. I.

N. I. Kiskin and D. Ogden, “Two-photon excitation and photolysis by pulsed laser illumination modelled by spatially non-uniform reactions with simultaneous diffusion,” Eur. Biophys. J. 30(8), 571–587 (2002).
[Crossref] [PubMed]

N. I. Kiskin, R. Chillingworth, J. A. McCray, D. Piston, and D. Ogden, “The efficiency of two-photon photolysis of a “caged” fluorophore, o-1-(2-nitrophenyl)ethylpyranine, in relation to photodamage of synaptic terminals,” Eur. Biophys. J. 30(8), 588–604 (2002).
[Crossref] [PubMed]

Kragor, C. H.

M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
[Crossref] [PubMed]

Larson, D. R.

H.-M. Lee, D. R. Larson, and D. S. Lawrence, “Illuminating the chemistry of life: design, synthesis, and applications of “caged” and related photoresponsive compounds,” ACS Chem. Biol. 4(6), 409–427 (2009).
[Crossref] [PubMed]

Lawrence, D. S.

H.-M. Lee, D. R. Larson, and D. S. Lawrence, “Illuminating the chemistry of life: design, synthesis, and applications of “caged” and related photoresponsive compounds,” ACS Chem. Biol. 4(6), 409–427 (2009).
[Crossref] [PubMed]

Lee, H.-M.

H.-M. Lee, D. R. Larson, and D. S. Lawrence, “Illuminating the chemistry of life: design, synthesis, and applications of “caged” and related photoresponsive compounds,” ACS Chem. Biol. 4(6), 409–427 (2009).
[Crossref] [PubMed]

Lu, M.

M. Lu, O. D. Fedoryak, B. R. Moister, and T. M. Dore, “Bhc-diol as a photolabile protecting group for aldehydes and ketones,” Org. Lett. 5(12), 2119–2122 (2003).
[Crossref] [PubMed]

Masuda, Y.

M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, “Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates,” J. Org. Chem. 65(1), 164–168 (2000).
[Crossref] [PubMed]

McCray, J. A.

N. I. Kiskin, R. Chillingworth, J. A. McCray, D. Piston, and D. Ogden, “The efficiency of two-photon photolysis of a “caged” fluorophore, o-1-(2-nitrophenyl)ethylpyranine, in relation to photodamage of synaptic terminals,” Eur. Biophys. J. 30(8), 588–604 (2002).
[Crossref] [PubMed]

Moister, B. R.

M. Lu, O. D. Fedoryak, B. R. Moister, and T. M. Dore, “Bhc-diol as a photolabile protecting group for aldehydes and ketones,” Org. Lett. 5(12), 2119–2122 (2003).
[Crossref] [PubMed]

Murata, M.

M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, “Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates,” J. Org. Chem. 65(1), 164–168 (2000).
[Crossref] [PubMed]

Ogden, D.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

G. Bort, T. Gallavardin, D. Ogden, and P. I. Dalko, “From one-photon to two-photon probes: “caged” compounds, actuators, and photoswitches,” Angew. Chem. Int. Ed. Engl. 52(17), 4526–4537 (2013).
[Crossref] [PubMed]

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

N. I. Kiskin and D. Ogden, “Two-photon excitation and photolysis by pulsed laser illumination modelled by spatially non-uniform reactions with simultaneous diffusion,” Eur. Biophys. J. 30(8), 571–587 (2002).
[Crossref] [PubMed]

N. I. Kiskin, R. Chillingworth, J. A. McCray, D. Piston, and D. Ogden, “The efficiency of two-photon photolysis of a “caged” fluorophore, o-1-(2-nitrophenyl)ethylpyranine, in relation to photodamage of synaptic terminals,” Eur. Biophys. J. 30(8), 588–604 (2002).
[Crossref] [PubMed]

Oyama, T.

M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, “Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates,” J. Org. Chem. 65(1), 164–168 (2000).
[Crossref] [PubMed]

Palma-Cerda, F.

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Pavlos, C. M.

Y. Zhu, C. M. Pavlos, J. P. Toscano, and T. M. Dore, “8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope,” J. Am. Chem. Soc. 128(13), 4267–4276 (2006).
[Crossref] [PubMed]

Petit, M.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

Piston, D.

N. I. Kiskin, R. Chillingworth, J. A. McCray, D. Piston, and D. Ogden, “The efficiency of two-photon photolysis of a “caged” fluorophore, o-1-(2-nitrophenyl)ethylpyranine, in relation to photodamage of synaptic terminals,” Eur. Biophys. J. 30(8), 588–604 (2002).
[Crossref] [PubMed]

Reddie, K. G.

M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
[Crossref] [PubMed]

Reynolds, S. J.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Roger, T.

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

Rubin, Y.

S. Clavaguera, S. I. Khan, and Y. Rubin, “Unexpected de-arylation of a pentaaryl fullerene,” Org. Lett. 11(6), 1389–1391 (2009).
[Crossref] [PubMed]

Scherman, D.

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

Sicard, C.

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

Slimi, R.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

Swift, K. A. D.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Toscano, J. P.

Y. Zhu, C. M. Pavlos, J. P. Toscano, and T. M. Dore, “8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope,” J. Am. Chem. Soc. 128(13), 4267–4276 (2006).
[Crossref] [PubMed]

Tran, C.

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

Vyklicky, L.

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Watanabe, S.

M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, “Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates,” J. Org. Chem. 65(1), 164–168 (2000).
[Crossref] [PubMed]

Wilson, H. C.

M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
[Crossref] [PubMed]

Zhu, Y.

M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
[Crossref] [PubMed]

Y. Zhu, C. M. Pavlos, J. P. Toscano, and T. M. Dore, “8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope,” J. Am. Chem. Soc. 128(13), 4267–4276 (2006).
[Crossref] [PubMed]

ACS Chem. Biol. (1)

H.-M. Lee, D. R. Larson, and D. S. Lawrence, “Illuminating the chemistry of life: design, synthesis, and applications of “caged” and related photoresponsive compounds,” ACS Chem. Biol. 4(6), 409–427 (2009).
[Crossref] [PubMed]

Angew. Chem. Int. Ed. Engl. (2)

G. Bort, T. Gallavardin, D. Ogden, and P. I. Dalko, “From one-photon to two-photon probes: “caged” compounds, actuators, and photoswitches,” Angew. Chem. Int. Ed. Engl. 52(17), 4526–4537 (2013).
[Crossref] [PubMed]

M. Petit, G. Bort, B.-T. Doan, C. Sicard, D. Ogden, D. Scherman, C. Ferroud, and P. I. Dalko, “X-ray photolysis to release ligands from caged reagents by an intramolecular antenna sensitive to magnetic resonance imaging,” Angew. Chem. Int. Ed. Engl. 50(41), 9708–9711 (2011).
[Crossref] [PubMed]

Eur. Biophys. J. (2)

N. I. Kiskin and D. Ogden, “Two-photon excitation and photolysis by pulsed laser illumination modelled by spatially non-uniform reactions with simultaneous diffusion,” Eur. Biophys. J. 30(8), 571–587 (2002).
[Crossref] [PubMed]

N. I. Kiskin, R. Chillingworth, J. A. McCray, D. Piston, and D. Ogden, “The efficiency of two-photon photolysis of a “caged” fluorophore, o-1-(2-nitrophenyl)ethylpyranine, in relation to photodamage of synaptic terminals,” Eur. Biophys. J. 30(8), 588–604 (2002).
[Crossref] [PubMed]

J. Am. Chem. Soc. (1)

Y. Zhu, C. M. Pavlos, J. P. Toscano, and T. M. Dore, “8-Bromo-7-hydroxyquinoline as a photoremovable protecting group for physiological use: mechanism and scope,” J. Am. Chem. Soc. 128(13), 4267–4276 (2006).
[Crossref] [PubMed]

J. Org. Chem. (2)

M. J. Davis, C. H. Kragor, K. G. Reddie, H. C. Wilson, Y. Zhu, and T. M. Dore, “Substituent effects on the sensitivity of a quinoline photoremovable protecting group to one- and two-photon excitation,” J. Org. Chem. 74(4), 1721–1729 (2009).
[Crossref] [PubMed]

M. Murata, T. Oyama, S. Watanabe, and Y. Masuda, “Palladium-catalyzed borylation of aryl halides or triflates with dialkoxyborane: A novel and facile synthetic route to arylboronates,” J. Org. Chem. 65(1), 164–168 (2000).
[Crossref] [PubMed]

Neuropharmacology (1)

F. Palma-Cerda, C. Auger, D. J. Crawford, A. C. C. Hodgson, S. J. Reynolds, J. K. Cowell, K. A. D. Swift, O. Cais, L. Vyklicky, J. E. T. Corrie, and D. Ogden, “New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups,” Neuropharmacology 63(4), 624–634 (2012).
[Crossref] [PubMed]

Org. Biomol. Chem. (1)

P. Dunkel, C. Tran, T. Gallavardin, H. Dhimane, D. Ogden, and P. I. Dalko, “Quinoline-derived two-photon sensitive quadrupolar probes,” Org. Biomol. Chem. 12(48), 9899–9908 (2014).
[Crossref] [PubMed]

Org. Lett. (4)

M. Petit, C. Tran, T. Roger, T. Gallavardin, H. Dhimane, F. Palma-Cerda, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Substitution effect on the one- and two-photon sensitivity of DMAQ “caging” groups,” Org. Lett. 14(24), 6366–6369 (2012).
[Crossref] [PubMed]

C. Tran, T. Gallavardin, M. Petit, R. Slimi, H. Dhimane, M. Blanchard-Desce, F. C. Acher, D. Ogden, and P. I. Dalko, “Two-photon “caging” groups: effect of position isomery on the photorelease properties of aminoquinoline-derived photolabile protecting groups,” Org. Lett. 17(3), 402–405 (2015).
[Crossref] [PubMed]

S. Clavaguera, S. I. Khan, and Y. Rubin, “Unexpected de-arylation of a pentaaryl fullerene,” Org. Lett. 11(6), 1389–1391 (2009).
[Crossref] [PubMed]

M. Lu, O. D. Fedoryak, B. R. Moister, and T. M. Dore, “Bhc-diol as a photolabile protecting group for aldehydes and ketones,” Org. Lett. 5(12), 2119–2122 (2003).
[Crossref] [PubMed]

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Figures (5)

Fig. 1
Fig. 1 8-DMAQ derivatives as light sensitive probes.
Fig. 2
Fig. 2 Synthesis of 5-(p-cyanophenyl)-8-DMAQ-OAc (2a), 5-(p-methoxyphenyl)-8-DMAQ-OAc (2b), 5-(p-dimethylaminophenyl)-8-DMAQ-OAc (2c).
Fig. 3
Fig. 3 Synthesis of 5-phenyl-8-DMAQ-OAc (2d) and 5-diphenylaminophenyl-8-DMAQ-OAc (2e).
Fig. 4
Fig. 4 UV absorption spectra of 5-benzoyl-8-DMAQ-OAc derivatives in acetonitrile/TRIS (20 mM) 1/1 at 293 K.
Fig. 5
Fig. 5 OP photolysis of 5-benzoyl-8-DMAQ-OAc derivatives (2a-f) at 366 nm. The remaining fraction was determined by HPLC and the reported fittings correspond to an exponential decay.

Tables (1)

Tables Icon

Table 1 Photophysical properties of chromophores 2a-f. a Measured at 366 nm; b Qu values were determined according to Eq. (1).

Equations (3)

Equations on this page are rendered with MathJax. Learn more.

Q u = [ ε (λexc) I 0(λexc) t 90% ] 1
C= 1.17 t  δ u  T  τ  V F ( P λ h c π  ω 2 ) 2
C= 4.68  δ u  T λ  V S τ π n ( P λ h c ) 2

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