Click Chemistry Complexes as A platform For Biological Application: A review

Main Article Content

Sarab Alazawi
Sinan Midhat Al-Bayati
Anaam Majeed Rasheed

Abstract

The 1,2, 3-triazole moiety is the main biomolecule formed from the chemistry of clicks. Click chemistry is cycloaddition reaction including Copper or ruthenium catalyzed with azide-alkyne and resulting in five membered rings. Click chemistry and its complexes are utilized as anti-cancer, anti-microbial, anti-tuberculosis, anti-viral, anti-diabetic, anti-malarial, ant?-leishmanial and neuroprotective agents and also in fluorescent technology. Biological targets required a method containing the linker feature like 1,2, 3-triazoles moiety and a new set of 1,2,3-triazole consisting hybrids and conjugates. The present review summarizes developments over the last few years in application complexes of 1,2, 3-triazole analogue. Scientists of organic fields, clinical chemistry, photochemistry, and pharmacology will benefit from this study. This review offers essential knowledge to the interested researchers.


 


 

Article Details

How to Cite
Alazawi, S., Al-Bayati , S. M. ., & Rasheed , A. M. . (2022). Click Chemistry Complexes as A platform For Biological Application: A review. Journal of Advanced Sciences and Nanotechnology, 1(4), 121–140. https://doi.org/10.55945/joasnt.2022.1.4.121-140
Section
Articles

References

Rostovtsev V V, Green LG, Fokin V V, Sharpless KB (2002) A stepwise huisgen cycloaddition process: copper (I)?catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chemie 114:2708–2711

Zhang L, Chen X, Xue P, et al (2005) Ruthenium-catalyzed cycloaddition of alkynes and organic azides. J Am Chem Soc 127:15998–15999

Hein JE, Fokin V V (2010) Copper-catalyzed azide–alkyne cycloaddition (CuAAC) and beyond: new reactivity of copper (I) acetylides. Chem Soc Rev 39:1302–1315

Yoo EJ, Ahlquist M (2007) SH kim, I. Bae, VV Fokin, KB Sharpless, S. Chang. Angew Chem 26:1760–1763

Bock VD, Hiemstra H, Van Maarseveen JH (2006) CuI?catalyzed alkyne–azide “click” cycloadditions from a mechanistic and synthetic perspective. European J Org Chem 2006:51–68

Ornelas C, Ruiz Aranzaes J, Cloutet E, et al (2007) Click assembly of 1, 2, 3?triazole?linked dendrimers, including ferrocenyl dendrimers, which sense both oxo anions and metal cations. Angew Chemie 119:890–895

Tian L, Kong L, Zhang C (2015) Synthesis, structure and in vitro cytotoxic activity of two organotin complexes of 2-phenyl-1,2, 3-triazole-4-carboxylic acid. Main Gr Met Chem 38:83–91. https://doi.org/10.1515/mgmc-2015-0010

Serebryanskaya T V., Zolotarev AA, Ott I (2015) A novel aminotriazole-based NHC complex for the design of gold(i) anti-cancer agents: synthesis and biological evaluation. Medchemcomm 6:1186–1189. https://doi.org/10.1039/c5md00185d

Aimene Y, Eychenne R, Mallet-Ladeira S, et al (2019) Novel Re (I) tricarbonyl coordination compounds based on 2-pyridyl-1, 2, 3-triazole derivatives bearing a 4-amino-substituted benzenesulfonamide arm: synthesis, crystal structure, computational studies and inhibitory activity against carbonic anhydrase I,. J Enzyme Inhib Med Chem 34:773–782

Annunziata A, Liberti D, Bedini E, et al (2021) Square-Planar vs. Trigonal Bipyramidal Geometry in Pt (II) Complexes Containing Triazole-Based Glucose Ligands as Potential Anticancer Agents. Int J Mol Sci 22:8704

Kumar S V, Scottwell SØ, Waugh E, et al (2016) Antimicrobial properties of tris (homoleptic) ruthenium (II) 2-Pyridyl-1, 2, 3-triazole “click” complexes against pathogenic bacteria, including methicillin-resistant staphylococcus aureus (MRSA). Inorg Chem 55:9767–9777

Smitten KL, Scattergood PA, Kiker C, et al (2020) Triazole-based osmium (II) complexes displaying red/near-IR luminescence: Antimicrobial activity and super-resolution imaging. Chem Sci 11:8928–8935

Sreedharan S, Sinopoli A, Jarman PJ, et al (2018) Mitochondria-localising DNA-binding biscyclometalated phenyltriazole iridium (III) dipyridophenazene complexes: syntheses and cellular imaging properties. Dalt Trans 47:4931–4940

Yu M, Zhao Q, Shi L, et al (2008) Cationic iridium (III) complexes for phosphorescence staining in the cytoplasm of living cells. Chem Commun 2115–2117

Ishizuka T, Liu HS, Ito K, Xu Y (2016) Fluorescence imaging of chromosomal DNA using click chemistry. Sci Rep 6:1–10

Wang T, Yuan C, Dai B, et al (2017) Click?Chemistry?Mediated Rapid Microbubble Capture for Acute Thrombus Ultrasound Molecular Imaging. ChemBioChem 18:1364–1368

Xie R, Dong L, Du Y, et al (2016) In vivo metabolic labeling of sialoglycans in the mouse brain by using a liposome-assisted bioorthogonal reporter strategy. Proc Natl Acad Sci 113:5173–5178

Wang H, Gauthier M, Kelly JR, et al (2016) Targeted ultrasound?assisted cancer?selective chemical labeling and subsequent cancer imaging using click chemistry. Angew Chemie Int Ed 55:5452–5456

Shen L, Cai K, Yu J, Cheng J (2019) Novel liposomal azido mannosamine lipids on metabolic cell labeling and imaging via Cu-free click chemistry. Bioconjug Chem 30:2317–2322

Mihalik SJ, Michaliszyn SF, De Las Heras J, et al (2012) Metabolomic profiling of fatty acid and amino acid metabolism in youth with obesity and type 2 diabetes: evidence for enhanced mitochondrial oxidation. Diabetes Care 35:605–611

Neves AA, Wainman YA, Wright A, et al (2016) Imaging glycosylation in vivo by metabolic labeling and magnetic resonance imaging. Angew Chemie 128:1308–1312

Omar SAE, Scattergood PA, McKenzie LK, et al (2016) Towards water soluble mitochondria-targeting theranostic osmium (II) triazole-based complexes. Molecules 21:1382

Omar SAE, Scattergood PA, McKenzie LK, et al (2018) Photophysical and cellular imaging studies of brightly luminescent osmium (II) pyridyltriazole complexes. Inorg Chem 57:13201–13212

Oh SS, Lee BF, Leibfarth FA, et al (2014) Synthetic aptamer-polymer hybrid constructs for programmed drug delivery into specific target cells. J Am Chem Soc 136:15010–15015

Wang H, Wang R, Cai K, et al (2017) Selective in vivo metabolic cell-labeling-mediated cancer targeting. Nat Chem Biol 13:415–424

Li Z, Shen D, Hu S, et al (2018) Pretargeting and bioorthogonal click chemistry-mediated endogenous stem cell homing for heart repair. ACS Nano 12:12193–12200

Kim E, Koo H (2019) Biomedical applications of copper-free click chemistry: in vitro, in vivo, and ex vivo. Chem Sci 10:7835–7851

de Souza ICA, Faro LV, Pinheiro CB, et al (2016) Investigation of cobalt (III)-triazole systems as prototypes for hypoxia-activated drug delivery. Dalt Trans 45:13671–13674

Quarta A, Amorín M, Aldegunde MJ, et al (2019) Novel synthesis of platinum complexes and their intracellular delivery to tumor cells by means of magnetic nanoparticles. Nanoscale 11:23482–23497

D’Amora A, Cucciolito ME, Iannitti R, et al (2019) Pyridine ruthenium (III) complexes entrapped in liposomes with enhanced cytotoxic properties in PC-3 prostate cancer cells. J Drug Deliv Sci Technol 51:552–558

Yu Y, Xu Q, He S, et al (2019) Recent advances in delivery of photosensitive metal-based drugs. Coord Chem Rev 387:154–179

Gou Y, Huang G, Li J, et al (2021) Versatile delivery systems for non-platinum metal-based anticancer therapeutic agents. Coord Chem Rev 441:213975