916331-01-6

Basic information

• Product Name: trans-3-(4-allyloxyphenyl)-1-[2,4-bis(methoxymethoxy)-6-hydroxyphenyl]prop-2-en-1-one
• Synonyms: trans-3-(4-allyloxyphenyl)-1-[2,4-bis(methoxymethoxy)-6-hydroxyphenyl]prop-2-en-1-one
• CAS NO: 916331-01-6
• Molecular Weight: 400.428
• Mol File: 916331-01-6.mol

Chemical Properties

• CAS DataBase Reference: trans-3-(4-allyloxyphenyl)-1-[2,4-bis(methoxymethoxy)-6-hydroxyphenyl]prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: trans-3-(4-allyloxyphenyl)-1-[2,4-bis(methoxymethoxy)-6-hydroxyphenyl]prop-2-en-1-one(916331-01-6)
• EPA Substance Registry System: trans-3-(4-allyloxyphenyl)-1-[2,4-bis(methoxymethoxy)-6-hydroxyphenyl]prop-2-en-1-one(916331-01-6)

Safety Data

• Hazardous Substances Data: 916331-01-6(Hazardous Substances Data)

Upstream product

• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 40663-68-1 4-(2-propenyloxy)benzaldehyde 

Downstream Products

• 916330-77-3 1,28-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13,16,19,22,25,28-decaoxaoctacosane 
• 916330-76-2 1,25-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13,16,19,22,25-nonaoxapentacosane 
• 916330-75-1 1,22-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13,16,19,22-octaoxadocosane 
• 916330-74-0 1,19-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13,16,19-heptaoxanonadecane 
• 916330-73-9 1,16-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13,16-hexaoxahexadecane 
• 916330-72-8 1,13-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10,13-pentaoxatridecane 
• 916330-71-7 1,10-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7,10-tetraoxadecane 
• 916330-70-6 1,7-bis[4-((5-benzyloxy-7-methoxymethoxy)-4H-chromen-4-on-2-yl)phenyl]-1,4,7-trioxaheptane 
• 916330-66-0 5-hydroxy-7-methoxymethoxy-2-(4-allyloxyphenyl)-4H-chromen-4-one 

Relevant articles and documents

Flavonoid dimers as bivalent modulators for P-glycoprotein-based multidrug resistance: Synthetic apigenin homodimers linked with defined-length poly(ethylene glycol) spacers increase drug retention and enhance chemosensitivity in resistant cancer cells

Much effort has been spent on searching for better P-glycoprotein- (P-gp-) based multidrug resistance (MDR) modulators. Our approach was to target the binding sites of P-gp using dimers of dietary flavonoids. A series of apigenin-based flavonoid dimers, linked by poly(ethylene glycol) chains of various lengths, have been synthesized. These flavonoid dimers modulate drug chemosensitivity and retention in breast and leukemic MDR cells with the optimal number of ethylene glycol units equal to 2-4. Compound 9d bearing four ethylene glycol units increased drug accumulation in drug-resistant cells and enhanced cytotoxicity of paclitaxel, doxorubicin, daunomycin, vincristine, and vinblastine in drug-resistant breast cancer and leukemia cells in vitro, resulting in reduction of IC50 by 5-50 times. This compound also stimulated P-gp's ATPase activity by 3.3-fold. Its modulating activity was presumably by binding to the substrate binding sites of P-gp and disrupting drug efflux.

FLAVONOID DIMERS AND METHODS OF MAKING AND USING SUCH

Multidrug resistance (MDR) is a major problem in cancer chemotherapy. The best characterized resistance mechanism is the one mediated by the over- expression of drug efflux transporters, permeability-glycoprotein (P-gp), which pump a variety of anticancer drugs out of the cells, resulting in lowered intracellular drug accumulation. A series of flavonoid dimers are developed in this invention, which are linked together by linker groups of various lengths. These flavonoid dimers are found to be efficient P-gp modulators that increase cytotoxicity of anticancer drugs in vitro and dramatically enhance their intracellular drug accumulation. It is found that the flavonoid dimers of this invention is also useful in reducing drug resistance in treating parasitic diseases.