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In mammalian tissues, ultraweak chemiluminescence arising from biomolecule oxidation has been attributed to the radiative deactivation of singlet molecular oxygen [O-2 ((1)Delta(g))] and electronically excited triplet carbonyl products involving dioxetane intermediates. Herein, we describe evidence of the generation of O-2 ((1)Delta(g)) in aqueous solution via energy transfer from excited triplet acetone. This involves thermolysis of 3,3,4,4-tetramethyl-1,2-dioxetane, a chemical source, and horseradish peroxidase-catalyzed oxidation of 2-methylpropanal, as an enzymatic source. Both sources of excited carbonyls showed characteristic light emission at 1,270 nm, directly indicative of the monomolecular decay of O-2 ((1)Delta(g)). Indirect analysis of O2 (1Dg) by electron paramagnetic resonance using the chemical trap 2,2,6,6-tetramethylpiperidine showed the formation of 2,2,6,6-tetramethylpiperidine-1-oxyl. Using [O-18]-labeled triplet, ground state molecular oxygen [O-18(2) ((3)Sigma(g) -)], chemical trapping of O-18(2) ((1)Delta(g)) with disodium salt of anthracene-9,10-diyldiethane-2,1-diyl disulfate yielding the corresponding double-[O-18]-labeled 9,10-endoperoxide, was detected through mass spectrometry. This corroborates formation of O-2 ((1)Delta(g)). Altogether, photoemission and chemical trapping studies clearly demonstrate that chemically and enzymatically nascent excited carbonyl generates O-18(2) ((1)Delta(g)) by triplet-triplet energy transfer to ground state oxygen O-2 ((1)Delta(g)), and supports the long formulated hypothesis of O-2 ((1)Delta(g)) involvement in physiological and pathophysiological events that might take place in tissues in the absence of light.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)PRONEX/FINEP (Programa de Apoio aos Nucleos de Excelencia)PRPUSP (Pro-Reitoria de Pesquisa da Universidade de São Paulo)Instituto do Milenio-RedoxomaNAP Redoxoma (PRPUSP)Fundo Bunka de Pesquisa Banco Sumitomo Mitsui )L'OREALJohn Simon Guggenheim Memorial FoundationNational Foundation for Cancer Research, Bethesda, MD, USAUniv São Paulo, Inst Quim, Dept Bioquim, BR-05513970 São Paulo, BrazilUniv Fed Parana, Dept Bioquim & Biol Mol, Set Ciencias Biol, BR-80060000 Curitiba, Parana, BrazilCEA Grenoble, Inst Nanosci & Cryogenie, F-38054 Grenoble 9, FranceUniv Dusseldorf, Inst Biochem & Mol Biol 1, Dusseldorf, GermanyUniv Dusseldorf, Leibniz Res Inst Environm Med, Dusseldorf, GermanyUniversidade Federal de São Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Dept Ciencias Exatas & Terra, São Paulo, BrazilUniversidade Federal de São Paulo, Inst Ciencias Ambientais Quim & Farmaceut, Dept Ciencias Exatas & Terra, São Paulo, BrazilFAPESP: 2006/56530-4FAPESP: 2012/12663-1Instituto do Milenio-Redoxoma: 420011/2005-6FAPESP: 573530/2008-4NAP Redoxoma (PRPUSP): 2011.1.9352.1.8FAPESP: 2013/07937-8Web of Scienc

Excited singlet molecular O2 (1Δg) is generated enzymatically from excited carbonyls in the dark