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Tyrosinase‐catalyzed oxidation of rhododendrol produces 2‐methylchromane‐6,7‐dione, the putative ultimate toxic metabolite: implications for melanocyte toxicity

Overview of attention for article published in Pigment Cell & Melanoma Research, June 2014
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  • Good Attention Score compared to outputs of the same age (66th percentile)
  • Good Attention Score compared to outputs of the same age and source (75th percentile)

Mentioned by

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5 tweeters

Citations

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47 Dimensions

Readers on

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16 Mendeley
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Title
Tyrosinase‐catalyzed oxidation of rhododendrol produces 2‐methylchromane‐6,7‐dione, the putative ultimate toxic metabolite: implications for melanocyte toxicity
Published in
Pigment Cell & Melanoma Research, June 2014
DOI 10.1111/pcmr.12275
Pubmed ID
Authors

Ito S, Ojika M, Yamashita T, Wakamatsu K, Ito, Shosuke, Ojika, Makoto, Yamashita, Toshiharu, Wakamatsu, Kazumasa, Shosuke Ito, Makoto Ojika, Toshiharu Yamashita, Kazumasa Wakamatsu

Abstract

RS-4-(4-Hydroxyphenyl)-2-butanol (rhododendrol, RD) was used as a skin-whitening agent until it was reported to induce leukoderma in July 2013. To explore the mechanism underlying its melanocyte toxicity, we characterized the tyrosinase-catalyzed oxidation of RD using spectrophotometry and HPLC. Oxidation of RD with mushroom tyrosinase rapidly produced RD-quinone, which was quickly converted to 2-methylchromane-6,7-dione (RD-cyclic quinone) and RD-hydroxy-p-quinone through cyclization and addition of water molecule, respectively. RD-quinone and RD-cyclic quinone were identified as RD-catechol and RD-cyclic catechol after NaBH4 reduction. Autoxidation of RD-cyclic catechol produced superoxide radical. RD-quinone and RD-cyclic quinone quantitatively bound to thiols such as cysteine and GSH. These results suggest that the melanocyte toxicity of RD is caused by its tyrosinase-catalyzed oxidation through production of RD-cyclic quinone which depletes cytosolic GSH and then binds to essential cellular proteins through their sulfhydryl groups. The production of ROS through autoxidation of RD-cyclic catechol may augment the toxicity.

Twitter Demographics

The data shown below were collected from the profiles of 5 tweeters who shared this research output. Click here to find out more about how the information was compiled.

Mendeley readers

The data shown below were compiled from readership statistics for 16 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Japan 1 6%
Unknown 15 94%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 5 31%
Researcher 3 19%
Student > Master 2 13%
Professor 2 13%
Other 1 6%
Other 3 19%
Readers by discipline Count As %
Chemistry 5 31%
Biochemistry, Genetics and Molecular Biology 4 25%
Agricultural and Biological Sciences 3 19%
Pharmacology, Toxicology and Pharmaceutical Science 1 6%
Unspecified 1 6%
Other 2 13%

Attention Score in Context

This research output has an Altmetric Attention Score of 3. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 07 July 2014.
All research outputs
#6,614,349
of 13,118,813 outputs
Outputs from Pigment Cell & Melanoma Research
#177
of 616 outputs
Outputs of similar age
#63,195
of 187,737 outputs
Outputs of similar age from Pigment Cell & Melanoma Research
#7
of 28 outputs
Altmetric has tracked 13,118,813 research outputs across all sources so far. This one is in the 49th percentile – i.e., 49% of other outputs scored the same or lower than it.
So far Altmetric has tracked 616 research outputs from this source. They receive a mean Attention Score of 4.3. This one has gotten more attention than average, scoring higher than 71% of its peers.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 187,737 tracked outputs that were published within six weeks on either side of this one in any source. This one has gotten more attention than average, scoring higher than 66% of its contemporaries.
We're also able to compare this research output to 28 others from the same source and published within six weeks on either side of this one. This one has done well, scoring higher than 75% of its contemporaries.