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Self-assembled amphiphilic bipyridine and bisquinoline cisplatin analogues: synthesis and anticancer properties

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Abstract

We report the synthesis and characterisation of two amphiphilic cisplatin analogues derived from bipyridine and bisquinoline modified with two 3-oxo-3,6,9,12-tetraoxadocosyl groups. The amphiphilic cisplatin analogues readily form vesicles in water such as 200 to 400 nm in diameter for the bipyridine Pt complex and 1000 to 1300 nm in diameter for the bisquinoline Pt complex. The bisquinoline Pt complex exhibited a LD50 of ~24 µM for HeLa and HEK cells. On the other hand, the Pt-bipyridine complex exhibited no notable toxicity against HeLa and HEK cells under 121 µM. Amphiphilic cisplatin analogues of this type are paving the way for a new generation of active anticancer compounds that can be carried by lipoproteins for targeted anticancer therapies in clinical applications.

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Acknowledgements

Financial support from NSF grants CHE 0748913, NIH BBRC 5G12MD007592, NIFA 2019-38422-30214 and the Ralph & Kathleen Ponce de Leon Endowment are gratefully acknowledged. We thank Dr. Raymundo Rivas Caceres (Universidad Autonoma de Ciudad Juarez) for useful assistance in this study.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Texas at El Paso, 500 W. University Ave., El Paso, TX, 79968, USA

    Gabriel A. Gonzalez, Javier Hernandez-Ortega, Sudakha Kalagara, Bonifacio Alvarado-Tenorio & Juan C. Noveron

  2. Departamento de Ciencias Quimico-Biologicas, Instituto de Ciencias Biomedicas, Universidad Autonoma de Ciudad Juarez, C.P. 32310, Chihuahua, Mexico

    Bonifacio Alvarado-Tenorio, Alejandro Martinez-Martinez & Angel G. Diaz-Sanchez

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  1. Gabriel A. Gonzalez
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Contributions

GAG: investigation, writing original draft; SK: investigation; JHO: investigation; BAT, AMM, AGDS: characterization and investigation; JCN: conceptualization, project administration, and final draft.

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Correspondence to Juan C. Noveron.

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Gonzalez, G.A., Hernandez-Ortega, J., Kalagara, S. et al. Self-assembled amphiphilic bipyridine and bisquinoline cisplatin analogues: synthesis and anticancer properties. Med Chem Res 33, 268–275 (2024). https://doi.org/10.1007/s00044-023-03175-y

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