Citation: Yin Hao-Yan, Tang Juan, Zhang Jun-Long. Sulfur speciation defined subcellular localization of coumarin derivatives: Correlation of structural relationship to biological behaviors[J]. Chinese Chemical Letters, ;2018, 29(2): 267-270. doi: 10.1016/j.cclet.2017.10.007 shu

Sulfur speciation defined subcellular localization of coumarin derivatives: Correlation of structural relationship to biological behaviors

Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China

Corresponding author: Zhang Jun-Long, zhangjunlong@pku.edu.cn
Received Date: 29 June 2017
Revised Date: 30 September 2017
Accepted Date: 11 October 2017
Available Online: 16 February 2017

Figures(4)

Targeted-delivery is of great importance to molecular probes and drugs for cell biology study. Herein we reported 11 sulfur-containing coumarins as cell imaging probes. Different sulfur speciation of the 4 representative coumarins SC1-SC4 renders them significantly different subcellular localizations and cellular uptake pathways:SC1 containing thioether group located in lysosomes, while sulfoxide and sulfone compounds SC2 and SC3 distributed in the whole cell. Furthermore, the cationic sulfonium containing compound SC4 was internalized by clathrin-mediated endocytosis and localized at mitochondria. By analyzing the molecular parameters of all 11 coumarins, we found that different sulfur speciation affected their lipophilicity and electrostatic surface potential. These two key factors play roles in altering biological behaviors of the coumarins. The results revealed the importance of sulfur speciation on the physicochemical properties and thus subcellular localization of bioprobes. This is useful for designing new functional bioprobes.
- Fluorescent imaging,
- Sulfur speciation,
- Subcellular localization,
- Sulfonium,
- Mitochondria targeting,
- Electrostatic surface potential
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