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Isomerism

Isomerism

Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional isomers and stereoisomers. Constitutional isomers differ in the connectivity of their constituent atoms. For example, 2-butanol and diethyl ether are constitutional isomers, as they have the same chemical formula, C4H10O, but differ in the connectivity of the carbon and oxygen atoms. Constitutional isomers have different physical and chemical...

Stereoisomerism

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...

Stereoisomers

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...

Stereoisomerism of Cyclic Compounds

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

Structural Isomerism

Structural Isomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula. Structural isomerism of coordination compounds can be divided into two subcategories, the linkage isomers and coordination-sphere isomers.
Linkage isomers occur when the coordination compound contains a ligand that can bind to the transition metal center through two different atoms. For example, the CN− ligand can bind through the carbon atom or through the nitrogen atom. Similarly, SCN− can...

Constitutional Isomers of Alkanes

Constitutional Isomers of Alkanes

Organic compounds of the same molecular formula can have different structural formulas called constitutional isomers, and the phenomenon is known as constitutional isomerism. Alkanes with four or more carbons showing multiple structures with the same molecular formula thereby exhibit constitutional isomerism.
The linear isomer of an alkane is prefixed by the term “n”; hence a linear isomer of pentane is known as n-pentane. Based on the type of branching, some of the...

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Related Experiment Video

Updated: Dec 26, 2025

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Published on: October 2, 2018

Split and Use: Structural Isomers for Diagnosis and Therapy.

Yingying Ning¹, Yi-Wei Liu¹, Zi-Shu Yang¹

¹Beijing National Laboratory for Molecular Sciences, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China.

Journal of the American Chemical Society

|March 17, 2020

Summary

This summary is machine-generated.

This study introduces a novel theranostic approach using related porphyrinoid regioisomers. One isomer enables near-infrared imaging, while the other facilitates photodynamic therapy (PDT), offering a new strategy for combined diagnosis and treatment.

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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

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Last Updated: Dec 26, 2025

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities

Published on: October 2, 2018

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Solid-phase Synthesis of [4.4] Spirocyclic Oximes

Published on: February 6, 2019

Area of Science:

* Medicinal Chemistry and Molecular Imaging
* Nanotechnology and Biomedical Engineering

Background:

* Current theranostic agents often involve complex syntheses and disparate dosage requirements for diagnosis and therapy.
* The integration of diagnostic and therapeutic functionalities into a single molecular entity presents significant challenges in medicine.

Purpose of the Study:

* To develop a novel theranostic strategy using closely related porphyrinoid regioisomers.
* To demonstrate the distinct diagnostic and therapeutic capabilities of these regioisomers and their ytterbium(III) complexes.

Main Methods:

* Synthesis of porphyrinoid regioisomers via 1,3-dipolar cycloaddition.
* Formation of ytterbium(III) complexes for diagnostic and therapeutic applications.
* In vitro and in vivo evaluation of imaging and photodynamic therapy efficacy.

Main Results:

* The *cis* isomer, as its ytterbium(III) complex, exhibits luminescence suitable for near-infrared (NIR) imaging.
* The *trans* isomer, as its ytterbium(III) complex, effectively generates singlet oxygen for photodynamic therapy (PDT) with a good quantum yield.
* Both isomers demonstrate complementary biological functions, validated through in vitro and in vivo experiments.

Conclusions:

* Closely related porphyrinoid regioisomers can be separated to perform distinct diagnostic (imaging) and therapeutic (PDT) functions.
* This study presents a new paradigm for creating paired molecular sets for effective theranostic applications.
* The findings highlight a versatile approach to switching between diagnostic and therapeutic modalities using isomeric compounds.