Detection of boronic acid derivatives in cells using a fluorescent sensor

2015 ◽  
Vol 13 (25) ◽  
pp. 6927-6930 ◽  
Author(s):  
Yoshihide Hattori ◽  
Miki Ishimura ◽  
Youichirou Ohta ◽  
Hiroshi Takenaka ◽  
Tsubasa Watanabe ◽  
...  
Keyword(s):  
Boronic Acid ◽  
Detection Method ◽  
Fluorescent Sensor ◽  
Fluorescent Sensors ◽  
Chelating Ligands ◽  
Boronic Acid Derivatives ◽  
In Cells

To develop a detection method for boronic acid derivatives, boron-chelating ligands were synthesized as fluorescent sensors for boronic acid derivatives.

scholarly journals Development of fluorescent sensors for the detection of hydrophobic amines and glycolipids

2017 ◽  
Author(s):  
◽  
Charles W. Jr. Littlefield
Keyword(s):  
Boronic Acid ◽  
Electrostatic Interactions ◽  
Fluorescent Sensor ◽  
Acid Group ◽  
Fluorescent Sensors ◽  
Synthetic Methods ◽  
Amide Bond ◽  
Primary Amines ◽  
New Synthesis ◽  
Better Than

A novel fluorescent sensor was designed and synthesized to detect hydrophobic amines and was used to extract them from synthetically prepared vesicles. This sensor had a higher affinity for diamines than primary amines, providing a fluorescence decrease upon binding both analytes. This sensor bound longer chain amines such as decylamine and 1,10-diaminodecane, better than shorter chain amines such as octylamine. This binding is influenced by both hydrophobic effects and electrostatic interactions between the sensor and analyte, driven by the hydrophobic cavity on the sensor. The sensor also unexpectedly binds to spermine and spermidine, however, with an increase in fluorescence. The mechanism for this phenomenon is not yet understood. The sensor showed it is possible to remove hydrophobic amines from synthetic veiscles, which can be applied to biological systems. A fluorescent sensor for glycolipids was also attempted to be synthesized by several different methods, incurring a new synthesis through redesigning the synthesis. Each method provided undesired products, decomposition, or no reactivity. Initial redesigns were due to complications in solubility of the carbazole aldehyde. Elongating the ester chain enhanced the solubility, but it remained unreactive towards any of the attempted reactions. This redesigned the sensor with a protected acid group that has been tested towards amide bond formation reactions to install the boronic acid or a haloarene, which will then undergo a Miyaura Borylation to install the boronic acid. If this does not prove successful, it will require alternative synthetic methods to install the boronic acid.

scholarly journals Near infrared fluorescent sensors and their use in vivo

2017 ◽  
Author(s):  
◽  
Nicholas P. Cooley
Keyword(s):  
Boronic Acid ◽  
Near Infrared ◽  
Glucose Monitoring ◽  
Aqueous Solubility ◽  
Fluorescent Sensors ◽  
Ph Sensitive ◽  
Water Soluble ◽  
Boronic Acid Derivatives ◽  
In Vivo Sensing

In an effort to design near-infrared (NIR), water soluble glucose sensors, several pH sensitive NIR cyanine derivates were designed and synthesized to provide insight into the viability of the cyanine platform as the fluorophore core for performing minimally invasive long term glucose monitoring in vivo. Many previous efforts to build effective fluorescent sensors for glucose have provided guidance towards the architecture of binding groups and fluorescent response required to achieve this goal, but have not provided appropriate solubility, or excitation and emission characteristics for in vivo sensing. In an effort to address the aqueous solubility of the highly rigid cyanine platform, a tetra sulfonated core was chosen for this work. Though fully water soluble, pH sensitive derivates still showed some aggregation characteristics. Simple sugarbinding boronic acid derivatives showed appropriate fluorescent responses, but poor binding. Efforts to improve binding through synthesis of bis-boronic acid compounds proved elusive.

scholarly journals Development of selective high-affinity fluorescent sensors for imaging neurotransmitters and application in cells and tissue

2019 ◽  
Author(s):  
◽  
Le Zhang
Keyword(s):  
Fluorescent Sensor ◽  
Photoreceptor Cells ◽  
Fluorescent Sensors ◽  
Tirf Microscopy ◽  
Glutamatergic Neurons ◽  
High Affinity ◽  
Iminium Ion ◽  
The Difference ◽  
Fluorescence Titrations ◽  
In Cells

Herein, we develop a series of selective fluorescent sensors based on a quinolone core designed to image neurotransmitters catecholamines, serotonin and glutamate. Included are the main design strategy, synthesis, spectroscopic data (UV/Vis and fluorescence) and their applications in cells and tissue. NeuroSensor 510 (NS510) was designed and synthesized as a selective sensor for imaging norepinephrine. Formation of both an iminium ion and a boronate ester gave high affinity upon binding NS510 to norepinephrine. The sensor was able to label norepinephrine vesicles in chromaffin cells to give punctate staining. Moreover, the sensor was able to monitor norepinephrine exocytosis via correlation of total internal reflective fluorescence (TIRF) microscopy and amperometry. A NIR fluorescent sensor NS659 was developed based on the structure of NS510. Several different synthetic routes were attempted before the sensor was successfully prepared. Upon binding to serotonin, the sensor gave a relatively high affinity but with quenched fluorescence. Initial tests showed that the sensor could be used to label vesicles. Finally, a molecular sensor NS560 was developed to image glutamate. Fluorescence titrations showed that the sensor bound to glutamate to give a very large turn-on response. More importantly, the sensor should be able to differentiate glutamate from GABA due to the difference both in the emission wavelength and the fluorescence response. We tested this sensor in photoreceptor cells and observed that vesicles were labeled by this sensor. Destaining of the vesicles was observed via TIRF microscopy. Also, the sensor can label glutamate in cultured glutamatergic neurons, astrocytes and cortex brain.

Mitochondria-targeting fluorescent sensor for on-off-on response to Cu2+ and ATP in cells and zebrafish

The Analyst ◽  
2021 ◽  
Author(s):  
Wan Sun ◽  
Guofeng Liu ◽  
Mingqiong Tong ◽  
Haozhan Wang ◽  
Shuhan Liu
Keyword(s):  
Adenosine Triphosphate ◽  
Fluorescent Sensor ◽  
Biological Processes ◽  
Fluorescent Molecule ◽  
Cupric Ion ◽  
Mitochondria Targeting ◽  
In Cells

Cupric ion (Cu2+) and adenosine triphosphate (ATP) are functionally important in mitochondria and play essential roles in many important biological processes. In this work, a mitochondria-targeting fluorescent molecule Mito-A was...

Synthesis of Sugar–Boronic Acid Derivatives: A Class of Potential Agents for Boron Neutron Capture Therapy

2017 ◽  
Vol 19 (7) ◽  
pp. 1678-1681 ◽  
Author(s):  
Daniela Imperio ◽  
Erika Del Grosso ◽  
Silvia Fallarini ◽  
Grazia Lombardi ◽  
Luigi Panza
Keyword(s):  
Boron Neutron Capture Therapy ◽  
Neutron Capture ◽  
Boronic Acid ◽  
Neutron Capture Therapy ◽  
Boron Neutron Capture ◽  
Boronic Acid Derivatives

Recognition and sensing of various species using boronic acid derivatives

2012 ◽  
Vol 48 (48) ◽  
pp. 5956 ◽  
Author(s):  
Zhiqian Guo ◽  
Injae Shin ◽  
Juyoung Yoon
Keyword(s):  
Boronic Acid ◽  
Boronic Acid Derivatives

The modern role of boron as a 'magic element' in biomedical science: Chemistry perspective

2021 ◽  
Author(s):  
SAURAV CHATTERJEE ◽  
NITESH MANI Mani TRIPATHI ◽  
Anupam Bandyopadhyay
Keyword(s):  
Drug Discovery ◽  
Boronic Acid ◽  
Toxic Element ◽  
Biomedical Science ◽  
Boronic Acid Derivatives

The boron was misconstrued as a toxic element for animals, which retarded the growth of boron-containing drug discovery in the last century. Nevertheless, modern applications of boronic acid derivatives are...

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