Synthesis and two-photon photolysis of 6-(ortho-nitroveratryl)-caged IP3 in living cells

Kantevari, Srinivas; Hoang, Caroline J; Ogrodnik, Jakob; Egger, Marcel; Niggli, Ernst; Ellis-Davies, Graham C R (2006). Synthesis and two-photon photolysis of 6-(ortho-nitroveratryl)-caged IP3 in living cells. ChemBioChem, 7(1), pp. 174-80. Weinheim: Wiley-VCH 10.1002/cbic.200500345

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The synthesis of a photolabile derivative of inositol-1,4,5-trisphosphate (IP3) is described. This new caged second messenger (6-ortho-nitroveratryl)-IP3 (6-NV-IP3) has an extinction coefficient of 5000 M(-1) cm(-1) at 350 nm, and a quantum yield of photolysis of 0.12. Therefore, 6-NV-IP3 is photolyzed with UV light about three times more efficiently than the widely used P(4(5))-1-(2-nitrophenyl)ethyl-caged IP3 (NPE-IP3). 6-NV-IP3 has a two-photon cross-section of about 0.035 GM at 730 nm. This absorbance is sufficiently large for effective two-photon excitation in living cells at modest power levels. Using near-IR light (5 mW, 710 nm, 80 MHz, pulse-width 70 fs), we produced focal bursts of IP3 in HeLa cells, as revealed by laser-scanning confocal imaging of intracellular Ca2+ concentrations. Therefore, 6-NV-IP3 can be used for efficient, subcellular photorelease of IP3, not only in cultured cells but also, potentially, in vivo. It is in the latter situation that two-photon photolysis should reveal its true forte.

Item Type:

Journal Article (Original Article)


04 Faculty of Medicine > Pre-clinic Human Medicine > Institute of Physiology

UniBE Contributor:

Ogrodnik, Jakob, Egger, Marcel, Niggli, Ernst










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Date Deposited:

04 Oct 2013 14:45

Last Modified:

05 Dec 2022 14:14

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URI: (FactScience: 687)

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