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Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Related Experiment Video

Updated: Dec 24, 2025

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Recognizing and stabilizing miR-21 by chiral ruthenium(II) complexes.

Yin Feng¹, Jing Shu^2,3, Liangzhong Yao¹

¹1The First Affiliated Hospital of Guangdong Pharmaceutical University, Guangzhou, 510062 China.

|April 9, 2020

Summary

Chiral ruthenium(II) complexes show potential as cancer inhibitors by targeting microRNA-21 (miR-21). These complexes bind to miR-21, downregulating its expression and impacting tumor cell behavior.

Keywords:

Chiral ruthenium(II) complexes FRET MiR-21 RNA binding property

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Last Updated: Dec 24, 2025

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes

Published on: April 10, 2015

Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor

Synthesis and Evaluation of a Ruthenium-based Mitochondrial Calcium Uptake Inhibitor

Published on: October 26, 2017

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

Area of Science:

Coordination Chemistry
Molecular Biology
Cancer Research

Background:

MicroRNA-21 (miR-21) is a key regulator in tumor proliferation, invasion, and metastasis.
Targeting miR-21 offers a potential therapeutic strategy for cancer treatment.

Purpose of the Study:

To synthesize and characterize chiral ruthenium(II) complexes as potential miR-21 inhibitors.
To investigate the binding affinity, cellular uptake, and regulatory effects of these complexes on miR-21 expression.

Main Methods:

Synthesis of chiral ruthenium(II)-alkyne complexes (Λ-1 and Δ-1) using microwave-assisted Songogashira coupling.
Assessment of isomer binding capacity to miR-21.
Evaluation of cellular uptake and nuclear localization in MDA-MB-231 cells.
Analysis of miR-21 expression levels following complex treatment.

Main Results:

Chiral ruthenium(II) complexes Λ-1 and Δ-1 were successfully synthesized.
Both isomers recognized and stabilized miR-21, with the Λ-isomer exhibiting stronger binding.
The complexes were uptaken by MDA-MB-231 cells and localized in the nucleus.
Treatment with Λ-/Δ-isomer downregulated miR-21 expression.

Conclusions:

Chiral ruthenium(II) complexes demonstrate potential as anticancer agents.
These complexes function by recognizing, stabilizing, and downregulating miR-21 expression.
Further development of these complexes could lead to novel miR-21-targeted cancer therapies.