Description

DM-Nitrophen tetrasodium salt (CAS 291517-40-3) is a high-purity, water-soluble caged compound widely utilized in photochemical and biochemical research. With the molecular formula C₁₈H₁₉N₃Na₄O₁₂, this tetrasodium salt derivative of DM-Nitrophen serves as a photolabile chelator for rapid release of Ca²⁺ upon UV irradiation (300-400 nm). Its IUPAC name, tetrasodium;2-[[2-[bis(carboxylatomethyl)amino]-2-(4,5-dimethoxy-2-nitrophenyl)ethyl]-(carboxylatomethyl)amino]acetate, reflects its tetra-anionic structure with four sodium counterions. This product is particularly valuable for studying calcium signaling dynamics, neurotransmitter release, and muscle contraction mechanisms with millisecond temporal precision. Supplied as a lyophilized powder with >95% purity (HPLC), it exhibits excellent stability in aqueous buffers when protected from light. The compound’s unique dimethoxy-nitrophenyl chromophore provides efficient two-photon uncaging capabilities for advanced microscopy applications.

Properties

• CAS Number: 291517-40-3
• Complexity: 673
• IUPAC Name: tetrasodium;2-[[2-[bis(carboxylatomethyl)amino]-2-(4,5-dimethoxy-2-nitro-phenyl)ethyl]-(carboxylatomethyl)amino]acetate
• InChI: InChI=1S/C18H23N3O12.4Na/c1-32-13-3-10(11(21(30)31)4-14(13)33-2)12(20(8-17(26)27)9-18(28)29)5-19(6-15(22)23)7-16(24)25;;;;/h3-4,12H,5-9H2,1-2H3,(H,22,23)(H,24,25)(H,26,27)(H,28,29);;;;/q;4*+1/p-4
• InChI Key: KCTLZBKLHCBAMY-UHFFFAOYSA-J
• Exact Mass: 561.05595018
• Molecular Formula: C18H19N3Na4O12
• Molecular Weight: 561.3
• SMILES: COC1=C(C=C(C(=C1)C(CN(CC(=O)[O-])CC(=O)[O-])N(CC(=O)[O-])CC(=O)[O-])[N+](=O)[O-])OC.[Na+].[Na+].[Na+].[Na+]
• Topological: 231
• Monoisotopic Mass: 561.05595018
• Synonyms: 291517-40-3, DM-Nitrophen tertasodium, DA-72841, Sodium 2,2′,2”,2”’-((1-(4,5-dimethoxy-2-nitrophenyl)ethane-1,2-diyl)bis(azanetriyl))tetraacetate

Application

DM-Nitrophen tetrasodium is primarily employed in photolysis studies to investigate rapid calcium-dependent processes in cellular systems. Researchers utilize this caged compound to precisely control calcium ion release in neurons, cardiomyocytes, and other excitable cells. Its fast uncaging kinetics make it ideal for studying synaptic transmission and intracellular signaling cascades. The compound has been successfully applied in two-photon microscopy experiments for spatially restricted calcium uncaging. Additionally, it serves as a critical tool in muscle physiology research to examine excitation-contraction coupling mechanisms.

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