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Formation of singlet oxygen in the thermal decomposition of 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane, a chemical source of triplet-excited ketones.
Biochem Mol Biol Int 1996; 38(4):647-51BM

Abstract

Triplet-excited carbonyl species can be generated by photoexcitation of carbonyl compounds or alternatively by thermal decomposition of 1,2-dioxetanes. Such electronically excited species are involved in the oxidative modification of biologically important molecules such as DNA. This study demonstrates that thermal decomposition of 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane (HTMD), which is a chemical source of triplet-excited ketones, is accompanied by infrared photoemission at 1270 nm characteristic for singlet oxygen monomol emission. The intensity of infrared photoemission at 1270 nm was solvent-dependent, in agreement with the reported lifetime of singlet oxygen in the employed solvents. Calibration of monomol emission with the endoperoxide of 1,4-dimethylnaphthalene (DMNO2) showed that HTMD (30 mM) produced 25 microMs of singlet oxygen. Thus, the yield of singlet oxygen production in the thermal decomposition of HTMD in carbon tetrachloride is about 0.1%.

Authors+Show Affiliations

Institut für Physiologische Chemie I, Heinrich-Heine-Universität Düsseldorf, FRG.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

8728092

Citation

Briviba, K, et al. "Formation of Singlet Oxygen in the Thermal Decomposition of 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane, a Chemical Source of Triplet-excited Ketones." Biochemistry and Molecular Biology International, vol. 38, no. 4, 1996, pp. 647-51.
Briviba K, Saha-Möller CR, Adam W, et al. Formation of singlet oxygen in the thermal decomposition of 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane, a chemical source of triplet-excited ketones. Biochem Mol Biol Int. 1996;38(4):647-51.
Briviba, K., Saha-Möller, C. R., Adam, W., & Sies, H. (1996). Formation of singlet oxygen in the thermal decomposition of 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane, a chemical source of triplet-excited ketones. Biochemistry and Molecular Biology International, 38(4), pp. 647-51.
Briviba K, et al. Formation of Singlet Oxygen in the Thermal Decomposition of 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane, a Chemical Source of Triplet-excited Ketones. Biochem Mol Biol Int. 1996;38(4):647-51. PubMed PMID: 8728092.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Formation of singlet oxygen in the thermal decomposition of 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane, a chemical source of triplet-excited ketones. AU - Briviba,K, AU - Saha-Möller,C R, AU - Adam,W, AU - Sies,H, PY - 1996/4/1/pubmed PY - 1996/4/1/medline PY - 1996/4/1/entrez SP - 647 EP - 51 JF - Biochemistry and molecular biology international JO - Biochem. Mol. Biol. Int. VL - 38 IS - 4 N2 - Triplet-excited carbonyl species can be generated by photoexcitation of carbonyl compounds or alternatively by thermal decomposition of 1,2-dioxetanes. Such electronically excited species are involved in the oxidative modification of biologically important molecules such as DNA. This study demonstrates that thermal decomposition of 3-hydroxymethyl-3,4,4-trimethyl-1,2-dioxetane (HTMD), which is a chemical source of triplet-excited ketones, is accompanied by infrared photoemission at 1270 nm characteristic for singlet oxygen monomol emission. The intensity of infrared photoemission at 1270 nm was solvent-dependent, in agreement with the reported lifetime of singlet oxygen in the employed solvents. Calibration of monomol emission with the endoperoxide of 1,4-dimethylnaphthalene (DMNO2) showed that HTMD (30 mM) produced 25 microMs of singlet oxygen. Thus, the yield of singlet oxygen production in the thermal decomposition of HTMD in carbon tetrachloride is about 0.1%. SN - 1039-9712 UR - https://www.unboundmedicine.com/medline/citation/8728092/Formation_of_singlet_oxygen_in_the_thermal_decomposition_of_3_hydroxymethyl_344_trimethyl_12_dioxetane_a_chemical_source_of_triplet_excited_ketones_ DB - PRIME DP - Unbound Medicine ER -