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[ CAS No. 117-39-5 ] {[proInfo.proName]}

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Chemical Structure| 117-39-5
Chemical Structure| 117-39-5
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Product Citations

Product Citations      Expand+

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski , et al. DOI:

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

Purchased from AmBeed: ; ; ; ; ; ; 117-39-5 ; ; ; ; 62-44-2 ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ;

Scott, Jared Lee ; DOI:

Abstract: Breast cancer (BC) is the second greatest contributor to the death of women, second only to heart disease, and is the most common type of cancer. BC treatments involve the administration of adjuvant chemotherapies which often have side effects that prevent patients from completing the full course of drugs or the refusal to take these potentially lifesaving treatments. Many chemotherapy drugs are developed from plants, and some plant extracts can exhibit significant anticancer activities while also having less toxic side effects. However, these potential "plant therapeutics" suffer from poor oral bioavailability. The Apiaceae plant family consists of several species that are used as culinarily spices including anise, celery, cumin, and coriander, all of which have demonstrated antioxidant, chemopreventive, and anticancer activities. One method to improve the systemic distribution of anticancer phytochemicals is their encapsulation in naturally produced membrane bound nanoparticles known as exosomes. Exosomes are produced by most eukaryotic organisms, as well as some prokaryotes, and are involved in cell-to-cell communication through the delivery of proteins, nucleic acids, and small molecules from one cell to another. Exosomes are found in many extracellular fluids including blood, urine, and milk. Bovine milk exosomes represent a scalable source of exosomes that are already present in the human diet and have been explored as a drug delivery system that can increase effectiveness and improve bioavailability. To enhance the loading potential and anticancer bioactivity of Apiaceae phytochemicals, an acid hydrolysis (AH) of the glycoside compounds present in ethanolic spice extracts was performed on eight ethanolic spice extracts. The antiproliferative effects of AH extracts and exosomal formulations were assayed with three model types of BC cells. Cumin was characterized in greater detail as these extracts had the highest concentration of terpenoids and alkaloids while also having significant concentrations of phenolics and responded well to AH with increased antiproliferative activity and exosomal loading. Extracts and exosomal formulations exhibited broad antiproliferative effects with lower IC50s in the extracts delivered with exosomes. The phytochemical contents of AH-cumin extracts and exosomal formulations were assayed with HPLC-DAD, LC-MS/MS, and GC-MS, while the potential anticancer mechanisms of these treatments were investigated in triple negative BC (TNBC). AHcumin extracts were determined to have numerous phenolic compounds, many of which have known anticancer mechanisms, in addition to several alkaloids and lipid compounds, some of which have activities that could contribute to the anticancer effects observed. Mechanistically, AH-cumin extracts and exosomal formulations were shown to interact with multidrug resistance proteins and inhibit lipid metabolism in TNBC cells. These results indicate that acid hydrolyzed cumin extracts delivered through exosome nanoparticles represent a possible avenue towards the development of novel treatments for TNBC, the hardest type of BC to treat.

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Product Details of [ 117-39-5 ]

CAS No. :117-39-5 MDL No. :MFCD00006828
Formula : C15H10O7 Boiling Point : -
Linear Structure Formula :(HO)2C6H3C9H2O(O)(OH)3 InChI Key :REFJWTPEDVJJIY-UHFFFAOYSA-N
M.W : 302.24 Pubchem ID :5280343
Synonyms :
Sophoretin;C.I. 75720;Xanthaurine.;Quertine;Quercetol;Quercetine;NSC 9219;NCI-C60106;Meletin;Kvercetin;NSC 9221
Chemical Name :2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one

Calculated chemistry of [ 117-39-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 7.0
Num. H-bond donors : 5.0
Molar Refractivity : 78.04
TPSA : 131.36 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 1.54
Log Po/w (WLOGP) : 1.99
Log Po/w (MLOGP) : -0.56
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 1.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.16
Solubility : 0.211 mg/ml ; 0.000698 mol/l
Class : Soluble
Log S (Ali) : -3.91
Solubility : 0.0374 mg/ml ; 0.000124 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.173 mg/ml ; 0.000573 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.23

Safety of [ 117-39-5 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P301+P310+P330-P405-P501 UN#:2811
Hazard Statements:H301 Packing Group:Ⅲ
GHS Pictogram:

Applications of [ 117-39-5 ]

Quercetin (CAS: 117-39-5) can be used in the preparation of Isoquercitrin (CAS: 482-35-9). Isoquercetin serves as an antineoplastic agent, a bone density conservation agent, an osteogenesis regulator, an antioxidant, a histamine antagonist, an antipruritic drug, and a geroprotector.

Application In Synthesis of [ 117-39-5 ]

* 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 [ 117-39-5 ]

[ 117-39-5 ] Synthesis Path-Downstream   1~3

  • 1
  • (S)-tert-butyl 2-(((4-Nitrophenoxy)carbonyl)amino)propanoate [ No CAS ]
  • [ 117-39-5 ]
  • [ 1791-13-5 ]
  • C31H36N2O13 [ No CAS ]
  • C31H36N2O13 [ No CAS ]
  • 2
  • (S)-tert-butyl 2-(((4-Nitrophenoxy)carbonyl)amino)propanoate [ No CAS ]
  • [ 117-39-5 ]
  • [ 1791-13-5 ]
  • [ 1138406-34-4 ]
  • [ 1138406-36-6 ]
  • 3
  • [ 7431-83-6 ]
  • [ 117-39-5 ]
  • [ 554-91-6 ]
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