Advances in 1,3-Dipolar Cycloaddition Reaction of Azides and Alkynes: A Prototype of “Click” Chemistry

In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

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"Click" chemistry as a tool to create novel biomaterials: a short review

U Porto Journal of Engineering ◽

10.24840/10.24840/2183-6493_001.001_0004 ◽

2015 ◽

Vol 1 (1) ◽

pp. 22-34 ◽

Cited By ~ 2

Author(s):

Mariana Barbosa ◽

Cristina Martins ◽

Paula Gomes

Keyword(s):

Click Chemistry ◽

Biomedical Applications ◽

Recent Literature ◽

Click Reaction ◽

Cycloaddition Reaction ◽

Polymeric Materials ◽

Short Review ◽

Dipolar Cycloaddition ◽

Functionalization Of Polymers ◽

Grafting Modification

In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

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Synthesis of Self-assembling Cyclic Peptide-polymer Conjugates using Click Chemistry

Australian Journal of Chemistry ◽

10.1071/ch10128 ◽

2010 ◽

Vol 63 (8) ◽

pp. 1169 ◽

Cited By ~ 47

Author(s):

Robert Chapman ◽

Katrina A. Jolliffe ◽

Sébastien Perrier

Keyword(s):

Click Chemistry ◽

Self Assembly ◽

Cyclic Peptide ◽

Raft Polymerization ◽

Cycloaddition Reaction ◽

Polymer Chains ◽

Dipolar Cycloaddition ◽

Molecular Weights ◽

Polymer Conjugates ◽

Self Assembling

Self-assembling cyclic peptide-polymer conjugates were prepared by ‘clicking’ polymers (prepared by RAFT polymerization) to an azide functionalized d-alt-l cyclic octapeptide via the Huisgen 1,3-dipolar cycloaddition reaction. Due to the high graft density, the efficiency of the click chemistry conjugation reaction was found to be highly dependent on the size of the polymer. At relatively low molecular weights, as many as four polymer chains could be grafted to each 8 residue cyclic peptide ring. Evidence for the self assembly of the conjugates into peptide-polymer nanotubes was observed by TEM and IR.

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New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

Revista de Chimie ◽

10.37358/rc.08.11.2011 ◽

2008 ◽

Vol 59 (11) ◽

Author(s):

Miron Teodor Caproiu ◽

Florea Dumitrascu ◽

Mino R. Caira

Keyword(s):

Nmr Spectroscopy ◽

Elemental Analysis ◽

Cycloaddition Reaction ◽

Dipolar Cycloaddition ◽

Pyridazine Derivatives ◽

New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

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Copper-catalyzed Convenient Synthesis and SAR Studies of Substituted-1,2,3-triazole as Antimicrobial Agents

Letters in Drug Design & Discovery ◽

10.2174/1570180815666180326153322 ◽

2018 ◽

Vol 16 (1) ◽

pp. 3-10

Author(s):

Aniket P. Sarkate ◽

Kshipra S. Karnik ◽

Pravin S. Wakte ◽

Ajinkya P. Sarkate ◽

Ashwini V. Izankar ◽

...

Keyword(s):

Antimicrobial Activity ◽

Antifungal Activity ◽

Antimicrobial Agents ◽

Cycloaddition Reaction ◽

Dipolar Cycloaddition ◽

One Pot ◽

Triazole Derivatives ◽

Sar Studies ◽

Convenient Synthesis ◽

Antibacterial And Antifungal

Background:A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent.Objective:We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity.Methods:A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively.Results and Conclusion:From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.

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Modified Nucleosides, Nucleotides and Nucleic Acids via Click Azide-Alkyne Cycloaddition for Pharmacological Applications

Molecules ◽

10.3390/molecules26113100 ◽

2021 ◽

Vol 26 (11) ◽

pp. 3100

Author(s):

Daniela Perrone ◽

Elena Marchesi ◽

Lorenzo Preti ◽

Maria Luisa Navacchia

Keyword(s):

Cancer Therapy ◽

Nucleic Acids ◽

Click Chemistry ◽

Nucleoside Analogs ◽

Modified Nucleosides ◽

Biological Molecules ◽

Dipolar Cycloaddition ◽

Virus Diseases ◽

Reaction Conditions ◽

Hybrid Compounds

The click azide = alkyne 1,3-dipolar cycloaddition (click chemistry) has become the approach of choice for bioconjugations in medicinal chemistry, providing facile reaction conditions amenable to both small and biological molecules. Many nucleoside analogs are known for their marked impact in cancer therapy and for the treatment of virus diseases and new targeted oligonucleotides have been developed for different purposes. The click chemistry allowing the tolerated union between units with a wide diversity of functional groups represents a robust means of designing new hybrid compounds with an extraordinary diversity of applications. This review provides an overview of the most recent works related to the use of click chemistry methodology in the field of nucleosides, nucleotides and nucleic acids for pharmacological applications.

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