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[ CAS No. 13406-29-6 ] {[proInfo.proName]}

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Chemical Structure| 13406-29-6
Chemical Structure| 13406-29-6
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Product Citations

Product Citations      Expand+

Keyes, Robert F. ; McAllister, Donna ; Dwinell, Michael B. , et al. DOI: PubMed ID:

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 , et al. DOI: PubMed ID:

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 [ 13406-29-6 ]

CAS No. :13406-29-6 MDL No. :MFCD00058883
Formula : C21H12F9P Boiling Point : -
Linear Structure Formula :- InChI Key :PXYCJKZSCDFXLR-UHFFFAOYSA-N
M.W : 466.28 Pubchem ID :139448
Synonyms :

Calculated chemistry of [ 13406-29-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 18
Fraction Csp3 : 0.14
Num. rotatable bonds : 6
Num. H-bond acceptors : 9.0
Num. H-bond donors : 0.0
Molar Refractivity : 100.15
TPSA : 13.59 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.08
Log Po/w (XLOGP3) : 7.26
Log Po/w (WLOGP) : 9.96
Log Po/w (MLOGP) : 7.61
Log Po/w (SILICOS-IT) : 8.61
Consensus Log Po/w : 7.5

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -7.34
Solubility : 0.0000214 mg/ml ; 0.0000000459 mol/l
Class : Poorly soluble
Log S (Ali) : -7.37
Solubility : 0.0000199 mg/ml ; 0.0000000426 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.06
Solubility : 0.0000000407 mg/ml ; 0.0000000001 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.96

Safety of [ 13406-29-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P273-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13406-29-6 ]

* 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 [ 13406-29-6 ]

[ 13406-29-6 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 402-43-7 ]
  • [ 13406-29-6 ]
  • 2
  • [ 62-53-3 ]
  • [ 13406-29-6 ]
  • [ 13406-18-3 ]
  • 3
  • [ 80-48-8 ]
  • [ 13406-29-6 ]
  • [ 120360-41-0 ]
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Technical Information

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