A Photoprotective Effect by Cation‐π‐Interaction? Quenching of Singlet Oxygen by an Indole Cation‐π Model System
We investigated the effect of the cation‐π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of sing...
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| Published in | Photochemistry and photobiology Vol. 96; no. 6; pp. 1200 - 1207 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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United States
Blackwell Publishing Ltd
01.11.2020
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| Subjects | |
| Online Access | Get full text |
| ISSN | 0031-8655 1751-1097 1751-1097 |
| DOI | 10.1111/php.13287 |
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| Abstract | We investigated the effect of the cation‐π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of singlet oxygen by the indole units in the presence of sodium cations (i.e. indole units subject to a cation‐π interaction) and in the absence of this interaction. We found that the cation‐π interaction significantly decreases the total rate of removal of singlet oxygen (kT) for the model system, that is, (kT = 2.4 ± 0.2) × 108 m−1 s−1 without sodium cation vs (kT = 6.9 ± 0.9) × 107 m−1 s−1 upon complexation of sodium cation to the crown ether. Furthermore, we found that the indole moieties undergo type I photooxidation processes with triplet excited methylene blue; this effect is also inhibited by the cation‐π interaction. The chemical rate of reaction of the indole groups with singlet oxygen is also slower upon complexation of sodium cation in our model system, although we were unable to obtain an exact ratio due to differences of the chemical reaction rates of the two indole moieties.
The cation‐π interaction between a sodium cation and an indole moiety significantly decreases the total rate of removal of singlet oxygen (kT) in an indole‐crown model system. A type I photooxidation of the indole group is also inhibited by the cation‐π interaction. These results imply that there may be a photoprotective effect by the cation‐π interaction for tryptophan. |
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| AbstractList | We investigated the effect of the cation-π interaction on the susceptibility of a tryptophan model system towards interaction with singlet oxygen, i.e. Type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of singlet oxygen by the indole units in the presence of sodium cations (i.e. indole units subject to a cation-π interaction) and in the absence of this interaction. We found that the cation-π interaction significantly decreases the total rate of removal of singlet oxygen (
k
T
) for the model system, i.e. (
k
T
= 2.4±0.2)×10
8
M
−1
sec
−1
without sodium cation vs. (
k
T
= 6.9±0.7)×10
7
M
−1
sec
−1
upon complexation of sodium cation to the crown ether. Furthermore, we found that the indole moieties undergo Type I photooxidation processes with triplet excited Methylene Blue; this effect is also inhibited by the cation-π interaction. The chemical rate of reaction of the indole groups with singlet oxygen is also slower upon complexation of sodium cation in our model system, although we were unable to obtain an exact ratio due to differences of the chemical reaction rates of the two indole moieties.
The cation-π interaction between a sodium cation and an indole moiety significantly decreases the total rate of removal of singlet oxygen (
k
T
) in an indole-crown model system. A Type I photooxidation of the indole group is also inhibited by the cation-π interaction. These results imply that there may be a photoprotective effect by the cation-π interaction for tryptophan. We investigated the effect of the cation-π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of singlet oxygen by the indole units in the presence of sodium cations (i.e. indole units subject to a cation-π interaction) and in the absence of this interaction. We found that the cation-π interaction significantly decreases the total rate of removal of singlet oxygen (k ) for the model system, that is, (k = 2.4 ± 0.2) × 10 m s without sodium cation vs (k = 6.9 ± 0.9) × 10 m s upon complexation of sodium cation to the crown ether. Furthermore, we found that the indole moieties undergo type I photooxidation processes with triplet excited methylene blue; this effect is also inhibited by the cation-π interaction. The chemical rate of reaction of the indole groups with singlet oxygen is also slower upon complexation of sodium cation in our model system, although we were unable to obtain an exact ratio due to differences of the chemical reaction rates of the two indole moieties. We investigated the effect of the cation‐π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of singlet oxygen by the indole units in the presence of sodium cations (i.e. indole units subject to a cation‐π interaction) and in the absence of this interaction. We found that the cation‐π interaction significantly decreases the total rate of removal of singlet oxygen (kT) for the model system, that is, (kT = 2.4 ± 0.2) × 108 m−1 s−1 without sodium cation vs (kT = 6.9 ± 0.9) × 107 m−1 s−1 upon complexation of sodium cation to the crown ether. Furthermore, we found that the indole moieties undergo type I photooxidation processes with triplet excited methylene blue; this effect is also inhibited by the cation‐π interaction. The chemical rate of reaction of the indole groups with singlet oxygen is also slower upon complexation of sodium cation in our model system, although we were unable to obtain an exact ratio due to differences of the chemical reaction rates of the two indole moieties. The cation‐π interaction between a sodium cation and an indole moiety significantly decreases the total rate of removal of singlet oxygen (kT) in an indole‐crown model system. A type I photooxidation of the indole group is also inhibited by the cation‐π interaction. These results imply that there may be a photoprotective effect by the cation‐π interaction for tryptophan. We investigated the effect of the cation‐π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of singlet oxygen by the indole units in the presence of sodium cations (i.e. indole units subject to a cation‐π interaction) and in the absence of this interaction. We found that the cation‐π interaction significantly decreases the total rate of removal of singlet oxygen ( k T ) for the model system, that is, ( k T = 2.4 ± 0.2) × 10 8 m −1 s −1 without sodium cation vs ( k T = 6.9 ± 0.9) × 10 7 m −1 s −1 upon complexation of sodium cation to the crown ether. Furthermore, we found that the indole moieties undergo type I photooxidation processes with triplet excited methylene blue; this effect is also inhibited by the cation‐π interaction. The chemical rate of reaction of the indole groups with singlet oxygen is also slower upon complexation of sodium cation in our model system, although we were unable to obtain an exact ratio due to differences of the chemical reaction rates of the two indole moieties. We investigated the effect of the cation-π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of singlet oxygen by the indole units in the presence of sodium cations (i.e. indole units subject to a cation-π interaction) and in the absence of this interaction. We found that the cation-π interaction significantly decreases the total rate of removal of singlet oxygen (kT ) for the model system, that is, (kT = 2.4 ± 0.2) × 108 m-1 s-1 without sodium cation vs (kT = 6.9 ± 0.9) × 107 m-1 s-1 upon complexation of sodium cation to the crown ether. Furthermore, we found that the indole moieties undergo type I photooxidation processes with triplet excited methylene blue; this effect is also inhibited by the cation-π interaction. The chemical rate of reaction of the indole groups with singlet oxygen is also slower upon complexation of sodium cation in our model system, although we were unable to obtain an exact ratio due to differences of the chemical reaction rates of the two indole moieties.We investigated the effect of the cation-π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of singlet oxygen by the indole units in the presence of sodium cations (i.e. indole units subject to a cation-π interaction) and in the absence of this interaction. We found that the cation-π interaction significantly decreases the total rate of removal of singlet oxygen (kT ) for the model system, that is, (kT = 2.4 ± 0.2) × 108 m-1 s-1 without sodium cation vs (kT = 6.9 ± 0.9) × 107 m-1 s-1 upon complexation of sodium cation to the crown ether. Furthermore, we found that the indole moieties undergo type I photooxidation processes with triplet excited methylene blue; this effect is also inhibited by the cation-π interaction. The chemical rate of reaction of the indole groups with singlet oxygen is also slower upon complexation of sodium cation in our model system, although we were unable to obtain an exact ratio due to differences of the chemical reaction rates of the two indole moieties. We investigated the effect of the cation‐π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type II photooxidation. The model system consists of two indole units linked to a lariat crown ether to measure the total rate of removal of singlet oxygen by the indole units in the presence of sodium cations (i.e. indole units subject to a cation‐π interaction) and in the absence of this interaction. We found that the cation‐π interaction significantly decreases the total rate of removal of singlet oxygen (kT) for the model system, that is, (kT = 2.4 ± 0.2) × 108 m−1 s−1 without sodium cation vs (kT = 6.9 ± 0.9) × 107 m−1 s−1 upon complexation of sodium cation to the crown ether. Furthermore, we found that the indole moieties undergo type I photooxidation processes with triplet excited methylene blue; this effect is also inhibited by the cation‐π interaction. The chemical rate of reaction of the indole groups with singlet oxygen is also slower upon complexation of sodium cation in our model system, although we were unable to obtain an exact ratio due to differences of the chemical reaction rates of the two indole moieties. |
| Author | Selke, Matthias Monsour, Charlotte G. Arevalo, Gary E. Garcia, Arman C. Cagan, David A. McCurdy, Alison |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32472700$$D View this record in MEDLINE/PubMed |
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| Copyright | 2020 American Society for Photobiology 2020 American Society for Photobiology. Copyright © 2020 American Society for Photobiology |
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| Snippet | We investigated the effect of the cation‐π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type... We investigated the effect of the cation-π interaction on the susceptibility of a tryptophan model system toward interaction with singlet oxygen, that is, type... We investigated the effect of the cation-π interaction on the susceptibility of a tryptophan model system towards interaction with singlet oxygen, i.e. Type II... |
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| SubjectTerms | Cations Chemical reactions Complexation Crown ethers Indoles Methylene blue Oxygen Photooxidation Singlet oxygen Sodium Tryptophan |
| Title | A Photoprotective Effect by Cation‐π‐Interaction? Quenching of Singlet Oxygen by an Indole Cation‐π Model System |
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