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Chemical Structure| 855-38-9 Chemical Structure| 855-38-9
Chemical Structure| 855-38-9

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Synonyms: Tris(p-anisyl)phosphine

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Keyes, Robert F. ; McAllister, Donna ; Dwinell, Michael B. ; Smith, Brian C. ;

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 NMR (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).

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Mahmoud AbuEid ; Robert F. Keyes ; Donna McAllister ; Francis Peterson ; Ishaque Pulikkal Kadamberi ; Daniel J. Sprague , et al.

Abstract: Triphenylphosphonium (TPP+) conjugated compounds selectively target cancer cells by exploiting their hyperpolarized mitochondrial membrane potential. To date, studies have focused on modifying either the linker or the cargo of TPP+-conjugated compounds. Here, we investigated the biological effects of direct modification to TPP+ to improve the efficacy and detection of mito-metformin (MMe), a TPP+-conjugated probe we have shown to have promising preclinical efficacy against solid cancer cells. We designed, synthesized, and tested trifluoromethyl and methoxy MMe analogs (pCF3-MMe, mCF3-MMe, and pMeO-MMe) against multiple distinct human cancer cells. pCF3-MMe showed enhanced selectivity toward cancer cells compared to MMe, while retaining the same signaling mechanism. Importantly, pCF3-MMe allowed quantitative monitoring of cellular accumulation via 19F-NMR in vitro and in vivo. Furthermore, adding trifluoromethyl groups to TPP+ reduced toxicity in vivo while retaining anti-tumor efficacy, opening an avenue to de-risk these next-generation TPP+-conjugated compounds.

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Product Details of Tris(4-methoxyphenyl)phosphine

CAS No. :855-38-9
Formula : C21H21O3P
M.W : 352.36
SMILES Code : COC1=CC=C(P(C2=CC=C(OC)C=C2)C3=CC=C(OC)C=C3)C=C1
Synonyms :
Tris(p-anisyl)phosphine
MDL No. :MFCD00014896
InChI Key :UYUUAUOYLFIRJG-UHFFFAOYSA-N
Pubchem ID :70071

Safety of Tris(4-methoxyphenyl)phosphine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Tris(4-methoxyphenyl)phosphine

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 855-38-9 ]

[ 855-38-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 52522-40-4 ]
  • [ 855-38-9 ]
  • Pd5(SO2)4(P(C6H4OCH3)3)5 [ No CAS ]
 

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