Synthesis of fluorinated triphenylphosphonium analogs that improve cancer cell selectivity and in vivo detection. STAR Protoc 2023 Sep 15;4(3):102437
Date
08/08/2023Pubmed ID
37552599Pubmed Central ID
PMC10424135DOI
10.1016/j.xpro.2023.102437Scopus ID
2-s2.0-85175638505 (requires institutional sign-in at Scopus site)Abstract
Triphenylphosphonium (TPP+) compounds like mito-metformin (MMe) target cancer cells by exploiting their hyperpolarized mitochondrial membrane potential. Here, we present a protocol for synthesizing TPP+ analogs with selectivity for mammalian cancer cells, reduced toxicity, and quantifiability using fluorine-19 nuclear magnetic resonance (19F-NMR). We describe steps for treating mammalian cells with mitochondria-targeted compounds, treating and preparing mouse tissue with these compounds, and 19F-NMR detection of MMe analogs in cells and tissue. TPP+-conjugated metformin analogs include para-methoxy (pMeO-MMe) and para-trifluoromethyl MMe (pCF3-MMe) and meta-trifluoromethyl MMe (mCF3-MMe).
Author List
Keyes RF, McAllister D, Dwinell MB, Smith BCAuthors
Michael B. Dwinell PhD Director, Professor in the Microbiology and Immunology department at Medical College of WisconsinRobert Keyes PhD Research Scientist II in the Biochemistry department at Medical College of Wisconsin
Brian C. Smith PhD Associate Professor in the Biochemistry department at Medical College of Wisconsin
MESH terms used to index this publication - Major topics in bold
AnimalsEndrin
Mammals
Metformin
Mice
Mitochondria
Neoplasms
Organophosphorus Compounds
