Non-Cytotoxic Dibenzyl and Difluoroborate Curcuminoid Fluorophores Allow Visualization of Nucleus or Cytoplasm in Bioimaging.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Marco A Obregón-MendozaRaúl G Enríquez

Abstract

Curcumin, the most important secondary metabolite isolated from Curcuma longa, is known for its numerous purported therapeutic properties and as a natural dye. Herein, based on curcumin's intrinsic fluorescence, a search for improved curcumin-based fluorophores was conducted. Within the set of semi-synthetic curcumin derivatives i.e. mono (1), di (2), tri (3), tetra (4) benzylated and dibenzyl-fluoroborate (5), the fluorescence properties of 2 and 5 in solution outstood with a two-fold quantum yield compared to curcumin. Furthermore, all benzylated derivatives showed a favorable minimal cytotoxic activity upon screening at 25 μM against human cancer and non-tumoral COS-7 cell lines, with a reduction of its cytotoxic effect related to the degree of substitution. Fluorophores 2 and 5 are versatile bioimaging tools, as revealed by Confocal Fluorescence Microscopy (CFM), and showed permeation of living cell membranes of astrocytes and astrocytomas. When 2 is excited with a 405- (blue) or 543-nm (green) laser, it is possible to exclusively and intensively visualize the nucleus. However, the fluorescence emission fades as the laser wavelength moves towards the red region. In comparison, 5 allows selective visualization of cytoplasm w...Continue Reading

References

Sep 29, 2007·Biochemical Pharmacology·Ajay GoelBharat B Aggarwal
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 8, 2008·Biochimica Et Biophysica Acta·A KunwarK I Priyadarsini
Sep 9, 2008·Biochemical Pharmacology·Preetha AnandBharat B Aggarwal
Jul 11, 2009·The AAPS Journal·Jayaraj RavindranBharat B Aggarwal
Jan 1, 2014·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Cesare Mancuso, Rosaria Santangelo
May 13, 2015·Chemical Society Reviews·Simon WanningerFrank T Edelmann
May 15, 2015·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Axel AndrésJosep M Huerta
Jun 13, 2015·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Shatadal GhoshParames C Sil
Oct 22, 2015·Organic & Biomolecular Chemistry·Kwang-Su ParkYouhoon Chong
Feb 24, 2016·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·Wei ZhangErguang Li
Oct 19, 2016·Accounts of Chemical Research·Hao ZhuXiaojun Peng
Nov 20, 2018·Chemical Communications : Chem Comm·Samira Husen Alamudi, Young-Tae Chang
Mar 8, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·William Meza-MoralesRaúl G Enríquez
Apr 26, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·William Meza-MoralesRaúl G Enríquez
Apr 27, 2019·Advanced Materials·Shoujun ZhuHongjie Dai
Jul 25, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Carolina Escobedo-MartínezRaúl G Enríquez
Jul 31, 2019·Chemical Science·Peng GaoBo Tang
Jan 10, 2020·World Health & Population

❮ Previous
Next ❯

Citations

Dec 11, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Halina Maria Ekiert, Agnieszka Szopa

❮ Previous
Next ❯

Methods Mentioned

BETA
confocal microscopy
X-ray
fluorescence microscopy
fluorescence imaging
biosensing
NMR

Software Mentioned

Plus
SHELX
MestreNova
Leica LAS X
Mercury
SAINT
2014
APEX
PARST97

Related Concepts

Related Feeds

Astrocytes

Astrocytes are glial cells that support the blood-brain barrier, facilitate neurotransmission, provide nutrients to neurons, and help repair damaged nervous tissues. Here is the latest research.

Related Papers

Analytical Sciences : the International Journal of the Japan Society for Analytical Chemistry
Keitaro UmezawaKoji Suzuki
Acta Crystallographica. Section C, Crystal Structure Communications
Joel T MagueFlorastina L Payton
© 2021 Meta ULC. All rights reserved