Development of practical red fluorescent probe for cytoplasmic calcium ions with greatly improved cell-membrane permeability

de Silva, 1997, Signaling recognition events with fluorescent sensors and switches, Chem. Rev., 97, 1515, 10.1021/cr960386p Zlokarnik, 1998, Quantitation of transcription and clonal selection of single living cells with β-lactamase as reporter, Science, 279, 84, 10.1126/science.279.5347.84 Nagano, 2002, Bioimaging of nitric oxide, Chem. Rev., 102, 1235, 10.1021/cr010152s Terai, 2008, Fluorescent probes for bioimaging applications, Curr. Opin. Chem. Biol., 12, 515, 10.1016/j.cbpa.2008.08.007 Grynkiewicz, 1985, A new generation of Ca2+ indicators with greatly improved fluorescence properties, J. Biol. Chem., 260, 3440, 10.1016/S0021-9258(19)83641-4 Harootunian, 1991, Generation of calcium oscillations in fibroblasts by positive feedback between calcium and IP3, Science, 251, 75, 10.1126/science.1986413 Hambers, 1999, Melanin-concentrating hormone is the cognate ligand for the orphan G-protein coupled receptor SLC-1, Nature, 400, 261, 10.1038/22313 Micu, 2007, Real-time measurement of free Ca2+ changes in CNS myelin by two-photon microscopy, Nat. Med., 13, 874, 10.1038/nm1568 Skokos, 2007, Peptide-MHC potency governs dynamic interactions between T cells and dendritic cells in lymph nodes, Nat. Immunol., 8, 835, 10.1038/ni1490 Kuchibhotla, 2009, Synchronous hyperactivity and intercellular calcium waves in astrocytes in alzheimer mice, Science, 323, 1211, 10.1126/science.1169096 Berridge, 2003, Calcium signaling: dynamics, homeostasis and remodeling, Nat. Rev. Mol. Cell. Biol., 4, 517, 10.1038/nrm1155 Clapham, 2007, Calcium signaling, Cell, 131, 1047, 10.1016/j.cell.2007.11.028 Miyawaki, 1997, Fluorescent indicators for Ca2+ based on green fluorescent proteins and calmodulin, Nature, 388, 882, 10.1038/42264 Zhao, 2011, An expanded palette of genetically encoded Ca2+ indicators, Science, 333, 1888, 10.1126/science.1208592 Minta, 1989, Fluorescent indicators for cytosolic calcium based on rhodamine and fluorescein chromophores, J. Biol. Chem., 264, 8171, 10.1016/S0021-9258(18)83165-9 1999, Monitoring cell calcium, 28 The Molecular Probes Handbook: A Guide to Fluorescent Probes and Labeling Technologies, 11th ed, (I. Johnson, M.T.Z. Spence, eds.), Life Technologies, Eugene, OR (2010). Ward, 2000, Pacemaking in interstitial cells of Cajal depends upon calcium handling by endoplasmic reticulum and mitochondria, J. Physiol., 525, 355, 10.1111/j.1469-7793.2000.t01-1-00355.x Kao, 2010, Practical aspects of measuring intracellular calcium signals with fluorescent indicators, Methods Cell Biol., 99, 113, 10.1016/B978-0-12-374841-6.00005-0 Oheim, 2014, New red-fluorescent calcium indicators for optogenetics, photoactivation and multi-color imaging, Biochim. Biophys. Acta, 1843, 2284, 10.1016/j.bbamcr.2014.03.010 Bolsover, 2001, Use of fluorescent Ca2+ dyes with green fluorescent protein and its variants: problems and solutions, Biochem. J., 356, 345, 10.1042/bj3560345 Luccardini, 2009, Measuring mitochondrial and cytoplasmic Ca2+ in EGFP expressing cells with a low-affinity Calcium Ruby and its dextran conjugate, Cell Calcium, 45, 275, 10.1016/j.ceca.2008.11.007 Egawa, 2011, Development of a far-red to near-infrared fluorescence probe for calcium ion and its application to multicolor neuronal imaging, J. Am. Chem. Soc., 133, 14157, 10.1021/ja205809h Matsui, 2011, A near-infrared fluorescent calcium probe: a new tool for intracellular multicolour Ca2+ imaging, Chem. Commun., 47, 10407, 10.1039/c1cc14045k Collot, 2012, Calcium rubies: a family of red-emitting functionalizable indicators suitable for two-photon Ca2+ imaging, J. Am. Chem. Soc., 134, 14923, 10.1021/ja304018d Egawa, 2013, Red fluorescent probe for monitoring the dynamics of cytoplasmic calcium ions, Angew. Chem. Int. Ed., 52, 3874, 10.1002/anie.201210279 Hirabayashi, 2015, Analysis of chemical equilibrium of Si-substituted fluorescein and its application to develop a scaffold for red fluorescent probes, Anal. Chem., 87, 9061, 10.1021/acs.analchem.5b02331 Egawa, 2011, Development of a fluorescein analogue TokyoMagenta, as a novel scaffold for fluorescence probes in red region, Chem. Commun., 47, 4162, 10.1039/c1cc00078k K. Hirabayashi, K. Hanaoka, T. Egawa, et al. Synthesis of Practical Red Fluorescent Probe for Cytoplasmic Calcium Ions with Greatly Improved Cell-membrane Permeability Data in Brief, submitted Göbel, 2007, In vivo calcium imaging of neural network function, Physiology, 22, 358, 10.1152/physiol.00032.2007 McNeil, 1987, Glass beads load macromolecules into living cells, J.Cell Sci., 88, 669, 10.1242/jcs.88.5.669 Thomas, 2000, A comparison of fluorescent Ca2+ indicator properties and their use in measuring elementary and global Ca2+ signals, Cell Calcium, 28, 213, 10.1054/ceca.2000.0152 Hajnóczky, 1995, Decoding of cytosolic calcium oscillations in the mitochondria, Cell, 82, 415, 10.1016/0092-8674(95)90430-1 Collins, 2001, Mitochondrial Ca2+ uptake depends on the spatial and temporal profile of cytosolic Ca2+ signals, J. Biol. Chem., 276, 26411, 10.1074/jbc.M101101200 Jou, 1996, Histamine induces oscillations of mitochondrial free Ca2+ concentration in single cultured rat brain astrocytes, J. Physiol., 497, 299, 10.1113/jphysiol.1996.sp021769 Zhu, 2000, Inositol tetrakisphosphate as a frequency regulator in calcium oscillations in HeLa cells, J. Biol. Chem., 275, 6063, 10.1074/jbc.275.9.6063 Stege, 1993, Hyperthermia, intracellular free calcium and calcium ionophores, J. Radiat. Biol., 64, 459, 10.1080/09553009314551651 Improta-Brears, 1999, Estrogen-induced activation of mitogen-activated protein kinase requires mobilization of intracellular calcium, Proc. Natl. Acad. Sci. U. S. A., 96, 4686, 10.1073/pnas.96.8.4686 Ariazi, 2010, The G protein?coupled receptor GPR30 inhibits proliferation of estrogen receptor?positive breast cancer cells, Cancer Res., 70, 1184, 10.1158/0008-5472.CAN-09-3068 Dombeck, 2007, Imaging large-scale neural activity with cellular resolution in awake, mobile mice, Neuron, 56, 43, 10.1016/j.neuron.2007.08.003 Cossart, 2003, Attractor dynamics of network UP states in the neocortex, Nature, 423, 283, 10.1038/nature01614 Ikegaya, 2004, Synfire chains and cortical songs: temporal modules of cortical activity, Science, 304, 559, 10.1126/science.1093173 Mainen, 1999, Synaptic calcium transients in single spines indicate that NMDA receptors are not saturated, Nature, 399, 151, 10.1038/20187 Kovalchuk, 2000, NMDA receptor-mediated subthreshold Ca2+ signals in spines of hippocampal neurons, J. Neurosci., 20, 1791, 10.1523/JNEUROSCI.20-05-01791.2000 Mizunuma, 2014, Unbalanced excitability underlies offline reactivation of behaviorally activated neurons, Nat. Neurosci., 17, 503, 10.1038/nn.3674 Collot, 2015, CaRuby-Nano: a novel high affinity calcium probe for dual color imaging, eLIFE, 4, 10.7554/eLife.05808