671791-76-7

Basic information

• Product Name: E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin
• Synonyms: E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin
• CAS NO: 671791-76-7
• Molecular Weight: 1135.23
• Mol File: 671791-76-7.mol

Chemical Properties

• CAS DataBase Reference: E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin(CAS DataBase Reference)
• NIST Chemistry Reference: E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin(671791-76-7)
• EPA Substance Registry System: E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin(671791-76-7)

Safety Data

• Hazardous Substances Data: 671791-76-7(Hazardous Substances Data)

Upstream product

• 850256-24-5 E/Z-1-(4-{2-[(2-aminooxyethyl)methylamino]ethoxy}phenyl)-1-(4-hydroxyphenyl)-2-phenylbutene 
• 850256-37-0 doxorubicin-5-formylsalicylamide 
• 671791-56-3 1-(4-methoxymethoxyphenyl)-1-(4-methoxyphenyl)-2-phenylbutan-1-ol 
• 110025-28-0 (E/Z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol 
• 61002-54-8 4-hydroxy-4'-methoxybenzophenone 
• 850256-19-8 E/Z-1-(4-hydroxyphenyl)-1-(4-methoxyphenyl)-2-phenylbutene 
• 115499-97-3 4-(methoxymethoxy)-4'-methoxybenzophenone 
• 147323-02-2 E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene 
• 850256-41-6 doxaliform 

Relevant articles and documents

Antiestrogen binding site and estrogen receptor mediate uptake and distribution of 4-hydroxytamoxifen-targeted doxorubicin-formaldehyde conjugate in breast cancer cells

The anthracycline antitumor drug, doxorubicin (DOX), has long been used as a broad spectrum chemotherapeutic. The literature now documents the role of formaldehyde in the cytotoxic mechanism, and anthracycline-formaldehyde conjugates possess substantially

Design, Synthesis, and Biological Evaluation of Doxorubicin-Formaldehyde Conjugates Targeted to Breast Cancer Cells

The anthracycline antitumor drug doxorubicin (DOX) has been utilized for decades as a broad-spectrum chemotherapeutic. Recent literature evidence documents the role of formaldehyde in the cytotoxic mechanism, and anthracycline-formaldehyde conjugates possess substantially enhanced activity in vitro and in vivo. Targeting a doxorubicin-formaldehyde conjugate specifically to cancer cells may provide a more efficacious chemotherapeutic. The design and 11-step synthesis of doxorubicin-formaldehyde conjugates targeted to the estrogen receptor, which is commonly overexpressed in breast cancer cells, are reported. The formaldehyde is incorporated in a masked form as an N-Mannich linkage between doxorubicin and salicylamide. The salicylamide triggering molecule, previously developed to release the doxorubicin-formaldehyde active metabolite, is tethered via derivatized ethylene glycols to an E and Z mixture of 4-hydroxytamoxifen. The targeting group, E/Z-4-hydroxytamoxifen, was selected for its ability to tightly bind the estrogen receptor and antiestrogen binding sites. The targeted doxorubicin-formaldehyde conjugates' estrogen receptor binding and in vitro growth inhibition were evaluated as a function of tether length. The lead compound, DOX-TEG-TAM, bearing a triethylene glycol tether, binds the estrogen receptor with a binding affinity of 2.5% relative to E/Z-4-hydroxytamoxifen and inhibits the growth of four breast cancer cell lines with 4-fold up to 140-fold enhanced activity relative to doxorubicin.