4-Hydroxytamoxifen(Afimoxifene)

For research use only.

Catalog No.S7827 Synonyms: Afimoxifene

5 publications

4-Hydroxytamoxifen(Afimoxifene) Chemical Structure

CAS No. 68392-35-8

4-Hydroxytamoxifen (Afimoxifene) is the active metabolite of tamoxifen and a selective estrogen receptor (ER) modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer. It activates on-target modification frequency for intein-Cas9 variants.

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Selleck's 4-Hydroxytamoxifen(Afimoxifene) has been cited by 5 publications

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  • CDK4/6 inhibitor resistance promotes diminished ER expression and activity. (a and b) Proliferation of MCF-7 and MR cells in the presence of different concentrations of ICI (a) or 4-hydroxytamoxifen (4-OHT) (b) was measured by the alamarBlue assay and plotted as % inhibition of proliferation against log concentration of inhibitor. Each data point represents the average value±s.d. of six replicates obtained in three independent experiments.

    Oncogene, 2016, 36(16):2255-2264. 4-Hydroxytamoxifen(Afimoxifene) purchased from Selleck.

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Biological Activity

Description 4-Hydroxytamoxifen (Afimoxifene) is the active metabolite of tamoxifen and a selective estrogen receptor (ER) modulator that is widely used in the therapeutic and chemopreventive treatment of breast cancer. It activates on-target modification frequency for intein-Cas9 variants.
In vitro

4-OHT is a potent activator of ER and has been shown to have a higher affinity for estrogen receptors compared to tamoxifen. It has significant dose and time-dependent direct effects to alter the contractile function of isolated adult rat cardiac myocytes[1]. 4-HT activates on-target modification frequency for intein-Cas9 variants [3].

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
MCF7 cells MVzQdo9tcW[ncnH0bY9vKGG|c3H5 M2W1ZWlvcGmkaYTpc44hd2ZiZYP0do9o\W5vc4TpcZVt[XSnZDDNR2YuPyClZXzsJJBzd2yrZnXyZZRqd25uIFnDOVA:OC53IH7N MXu5OVQ5QDF5
MCF7 cells M2HSUWZ2dmO2aX;uJIF{e2G7 NYfDUW5{UW6qaXLpeI9zgSClb37j[Y51emG2aX;uJIFo[Wmwc4SgUWNHNTdiYoLlZZN1KHS3bX;yJINmdGy|IIXzbY5oKE2FRj23JIF{e2G7LDDJR|UxRThwNTDuUS=> Ml;YNVI5OjV7M{W=
MCF7 cells MXvQdo9tcW[ncnH0bY9vKGG|c3H5 MnLKO|IhcA>? M4DxTGFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4Sg[ZN1em:pZX6gdoVk\XC2b4Kg[IVx\W6mZX70JIh2dWGwIF3DSlch[2WubIOgZYZ1\XJiN{KgbJJ{KGK7IF3UWEBie3OjeTygTWM2OD1yLkGwO{DPxE1? NV7HW3d6OTh6M{WxO|Y>
MCF7 cells MmrXVJJwdGmoZYLheIlwdiCjc4PhfS=> M3nZN|I1KGh? M{jZc2FvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4SgbJVu[W5iTVPGO{Bk\WyuczDh[pRmeiB{NDDodpMh[nliTWTTJIF{e2G7LDDJR|UxRThwNTDuUS=> NXq0TWJvOTh{N{KyOVY>
T47D:C:4:2 cells M2PDSmZ2dmO2aX;uJIF{e2G7 MWrFd5Rzd2enbnnjJIFkfGm4aYT5JIF1KHerbHSgeJlx\SCHUjDhcJBp[SCneIDy[ZN{\WRiaX6gWFQ4TDqFOkS6NkBk\WyuczDjc4V5eHKnc4Ppcoch\XO2cn;n[Y4hemW|cH;ud4Uh\WynbXXueEBjgSCmdXXsJIx2[2moZYLhd4UhemWyb4L0[ZIh\2WwZTDhd5NigQ>? NWLReJFIOjB|M{SzOlg>
MDA-MB-231 cells M2TxN2Z2dmO2aX;uJIF{e2G7 NEjyfFY{KGSjeYO= M{\5PWN6fG:|dHH0bYMh[WO2aY\peJkh[WejaX7zeEBpfW2jbjDNSGEuVUJvMkOxJINmdGy|IHHmeIVzKDNiZHH5d{BjgSCvaXPyc5RqfGW{IHHzd4F6 NUS5VFRsOjB3OUi1OVU>
PC3 cells MXfQdo9tcW[ncnH0bY9vKGG|c3H5 MlSyOFghcA>? MU\BcpRqeHKxbHnm[ZJifGm4ZTDhZ5Rqfmm2eTDh[4FqdnO2IHHu[JJw\2WwIILlZ4VxfG:{LXTl[olkcWWwdDDoeY1idiCSQ{OgZ4VtdHNiaX7jeYJifGWmIIfpeIghOC54IH7NJI9nKGW|dILh[IlwdCCjbnSgNE44KG6PIH;mJJRme3Sxc4Tldo9v\SCjZoTldkA1QCCqcoOgZpkhe3WuZn;ybI9l[W2rbnWgRkBie3OjeTygS2k2OD15LkW4OVc5KM7:TR?= MYmyNVUyOzJ5NR?=
DU145 cells NXexeWF3WHKxbHnm[ZJifGmxbjDhd5NigQ>? NHTTRY81QCCq MnfKRY51cXC{b3zp[oVz[XSrdnWgZYN1cX[rdImgZYdicW6|dDDhcoRzd2enbjDy[YNmeHSxcj3k[YZq[2mnboSgbJVu[W5iRGWxOFUh[2WubIOgbY5kfWKjdHXkJJdqfGhiMD62JI5OKG:oIHXzeJJi\GmxbDDhcoQhOC55IH7NJI9nKHSnc4Tvd5Rmem:wZTDh[pRmeiB2ODDodpMh[nlic4Xs[o9zcG:mYX3pcoUhSiCjc4PhfUwhT0l3ME2xNE44OTV{IN88US=> MVWyNVUyOzJ5NR?=
LNCAP cells NHXMUJZRem:uaX\ldoF1cW:wIHHzd4F6 MlrKOFghcA>? MlHTRY51cXC{b3zp[oVz[XSrdnWgZYN1cX[rdImgZYdicW6|dDDoeY1idiCOTlPBVEBk\WyuczDlfJBz\XO|aX7nJIFv\HKxZ3XuJJJm[2WydH;yJIlv[3WkYYTl[EB4cXSqIECuOkBvVSCxZjDld5Rz[WSrb3ygZY5lKDBwNzDuUUBw\iC2ZYP0c5N1\XKxbnWgZYZ1\XJiNEigbJJ{KGK7IIP1cIZwemixZHHtbY5mKEJiYYPzZZktKEeLNUC9PE4{OTd4NDFOwG0> MmG0NlE2OTN{N{W=
T47D cells NFz1ZppEgXSxdH;4bYNqfHliYYPzZZk> MXq1JIRigXN? NF3T[2hEgXSxdH;4bYNqfHliYXfhbY5{fCCqdX3hckBVPDeGIHPlcIx{KGGodHXyJFUh\GG7czygTWM2OD1yLkKxJO69VQ>? MVeyN|g3PDl{OB?=
MDA-MB-231 cells M{XEXHBzd2yrZnXyZZRqd25iYYPzZZk> MYCyOEBp Mn[2RY51cXC{b3zp[oVz[XSrdnWgZYN1cX[rdImgZYdicW6|dDDoeY1idiCPRFGtUWIuOjNzIHPlcIx{KGGodHXyJFI1KGi{czDifUBOXFRiYYPzZZktKEmFNUC9NVAvPCEQvF2= MX[yOFE5QTB3NR?=
MCF7 cells NE\QbodHfW6ldHnvckBie3OjeR?= M3roVlExKM7:TR?= MX62JIg> NEfVbm5WeHKnZ4XsZZRqd25ib3[gSXJidHCqYTDwdo91\WmwIHzleoVteyCrbjDoeY1idiCPQ1[3JINmdGy|IHH0JFExKHWPIHHmeIVzKDZiaILzJIJ6KFenc4Tldo4h[myxdDDt[ZRpd2R? M{C0O|I1OzN{NkOw
SKOV3 cells MoLKSpVv[3Srb36gZZN{[Xl? NYTTSYVFPDhiaB?= NGDRWVhCdnSrY3HuZ4VzKGGpYXnud5QhcHWvYX6gV2tQXjNiY3XscJMhd3[ncnX4dJJme3OrbnegVE1oeCCjc4Pld5Nm\CCjczDj[YxtKH[rYXLpcIl1gSCjZoTldkA1QCCqcoOgZpkhW1KEIHHzd4F6NCCLQ{WwQVcvPDZizszN MYGyOFk1PjF2NR?=
MDA-MB-231 cells NHLiTYxHfW6ldHnvckBie3OjeR?= NFr6cIY1QCCq NIjUVGhCdnSrY3HuZ4VzKGGpYXnud5QhcHWvYX6gSXIueG:|aYTpeoUhVUSDLV3CMVI{OSClZXzsd{Bie3Onc4Pl[EBieyClZXzsJJZq[WKrbHn0fUBi\nSncjC0PEBpenNiYomgV3JDKGG|c3H5MEBKSzVyPUWuOEDPxE1? NFzxblUzPDl2NkG0OS=>
MCF7 cells MoXDSpVv[3Srb36gZZN{[Xl? NXXlTm1lPDhiaB?= NIPOVphCdnSrY3HuZ4VzKGGpYXnud5QhcHWvYX6gSXIueG:|aYTpeoUhVUOINzDj[YxteyCjc4Pld5Nm\CCjczDj[YxtKH[rYXLpcIl1gSCjZoTldkA1QCCqcoOgZpkhW1KEIHHzd4F6NCCLQ{WwQVkvOiEQvF2= NWnX[GlWOjR7NE[xOFU>
MDA-MB-231 cells MX;GeY5kfGmxbjDhd5NigQ>? NXfvbVJQPDhiaB?= NEDEUoJCdnSrY3HuZ4VzKGGpYXnud5QhcHWvYX6gSXIudmWpYYTpeoUhVUSDLV3CMVI{OSClZXzsd{Bie3Onc4Pl[EBieyClZXzsJJZq[WKrbHn0fUBi\nSncjC0PEBpenNiYomgV3JDKGG|c3H5MEBKSzVyPU[uNkDPxE1? NXi2OHQxOjR7NE[xOFU>
MCF7 cells NHfw[VBHfW6ldHnvckBie3OjeR?= NXrLW4RjOjVyIITvJFUxOCCwTR?= NYG5eVNDPSCmYYnz MlSwRY51cWOjbnPldkBi\2GrboP0JIh2dWGwIFXSMZBwe2m2aY\lJG1ETjdiY3XscJMh[XO|ZYPz[YQh[XNiaX7obYJqfGmxbjDv[kBme3S{YXTpc4wucW6mdXPl[EBk\WyuIIDyc4xq\mW{YYTpc44h[XRiMkWwJJRwKDVyMDDuUUBi\nSncjC1JIRigXN? NFK2fJUzPDl2NkG0OS=>
MCF7 cells NUXmPYFTS3m2b4TvfIlkcXS7IHHzd4F6 NXTlN493PDhiaB?= Mk\5R5l1d3SxeHnjbZR6KGGpYXnud5QhcHWvYX6gUWNHPyClZXzsd{Bi\nSncjC0PEBpenNiYomgUXRVKGG|c3H5MEBKSzVyPUGzMlYh|ryP MXWyOVYyQDV7NR?=
DU145 cells M1rn[nBzd2yrZnXyZZRqd25iYYPzZZk> MYm3NkBp MYjBcpRqeHKxbHnm[ZJifGm4ZTDhZ5Rqfmm2eTDh[4FqdnO2IHj1cYFvKESXMUS1JINmdGy|IHHzd4V{e2WmIHHzJIlvcGmkaYTpc44hd2ZiY3XscEB3cWGkaXzpeJkh[W[2ZYKgO|IhcHK|IHL5JG1VXCCjc4PhfUwhUUN3ME2xOU4{KM7:TR?= M37C[|I2QTl|Mk[5
african green monkey Vero cells NGnEZ5dRem:uaX\ldoF1cW:wIHHzd4F6 NHvUZnI4OiCq M2\XfWFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4SgZYZzcWOjbjDndoVmdiCvb37r[ZkhXmW{bzDj[YxteyCjc4Pld5Nm\CCjczDpcohq[mm2aX;uJI9nKGOnbHygeoli[mmuaYT5JIFnfGW{IEeyJIhzeyCkeTDNWHQh[XO|YYmsJGlEPTB;MUWuNUDPxE1? MXSyOVk6OzJ4OR?=
BT-20 cells Mkn6VJJwdGmoZYLheIlwdiCjc4PhfS=> M4m1UWlvcGmkaYTvdpkh[WO2aY\peJkh[WejaX7zeEBxem:uaX\ldoF1cW:wIH;mJGJVNTJyIHPlcIx{KGmwIIDy[ZNmdmOnIH;mJHRRTSCjdDCxNIUuPSCPIHPvcoNmdnS{YYTpc44> NIPoW4kzPzZ7Nkix
Ishikawa endometrial cells MlW0SpVv[3Srb36gZZN{[Xl? NHT6dGlCdnSjZ3;ubZN1KGGldHn2bZR6KGG|IHnubIljcXSrb36gc4YhOSCwTTCxO{1j\XSjLXXzeJJi\GmxbDDzeIlufWyjdHXkJIFtc2GuaX7lJJBpd3OyaHH0ZZNmKGmwZIXjeIlwdiCrbjDJd4hqc2G5YTDlcoRwdWW2cnnhcEBk\WyuczygTWM2OD1yLkWxJO69VQ>? MUexOVM5ODJyOB?=
MCF-7-2a cells M3rPN2Z2dmO2aX;uJIF{e2G7 NILqTGtKdmirYnn0bY9vKG:oIHXzeJJi\GmxbDDpcoR2[2WmIHXzeJJw\2WwIILlZ4VxfG:{IITyZY5{[3KrcITpc45idCCjY4TpeoF1cW:wIHnuJG1ETi15LULhJINmdGy|LDDJR|UxRTBwMEC3JO69VQ>? NEXXOVYyOjZ5MkK0PS=>
Calu-1 cells MY\GeY5kfGmxbjDhd5NigQ>? MXOzNEBucW6| M3vFUGlvcGmkaYTpc44hd2ZiUFzENUBqdiCqdX3hckBE[Wy3LUGgZ4VtdHNiYYPz[ZN{\WRiYYOg[IVkemWjc3WgbY4heGixc4DoZZRq\HmuYoX0ZY5wdC2dZEndJJBzd2S3Y4Tpc44h[W[2ZYKgN|AhdWmwczDifUBu[XO|IIPw[YN1em:vZYTybYMh[W6jbInzbZMtKEmFNUC9OE45KM7:TR?= MUCxPVE{Pjl5NR?=
MCF12A cells M2e4fXBzd2yrZnXyZZRqd25iYYPzZZk> NUCzdnA6PDhiaB?= M2S3OmFvfGmycn;sbYZmemG2aY\lJIFkfGm4aYT5JIFo[Wmwc4Sg[ZN1em:pZX6gdoVk\XC2b4Kt[IVncWOrZX70JIh2dWGwIF3DSlEzSSClZXzsd{BqdmO3YnH0[YQhf2m2aDCwMlAxOyCwTTDv[kBme3S{YXTpc4wh[W6mIECuNFEhdk1ib3[geIV{fG:|dHXyc45mKGGodHXyJFQ5KGi{czDifUB{fWyob4Loc4RidWmwZTDCJIF{e2G7IHnuJJBz\XOnbnPlJI9nKDVnIH\leIFtKGKxdnnu[UB{\XK3bTygS2k2OD1|LkOxNVMyKM7:TR?= NHW1bYozOTVzM{K3OS=>
MCF7:WS8 cells MlnZSpVv[3Srb36gZZN{[Xl? MmnERYN1cX[jdHnvckBw\iCqdX3hckBGWiCrbjDoeY1idiCPQ1[3PndUQCClZXzsd{BmgHC{ZYPzbY5oKGW|dILv[4VvKHKnc4DvcpNqfmViZXzlcYVvfCCkeTDseYNq\mW{YYPlJJJmeG:{dHXyJIdmdmViYYPzZZk> MmX3NlA{OzR|Nki=
HEK293 cell NX\HPVVPTnWwY4Tpc44h[XO|YYm= NVjz[VBjOzBibXnudy=> NF7WWnFKdmirYnn0bY9vKG:oIFfGVE11[WepZXSgbJVu[W5iUFzENkBmgHC{ZYPz[YQhcW5iaIXtZY4hUEWNMkmzJINmdGy|IHHzd4V{e2WmIHHzJIRm[3KnYYPlJIlvKHCqb4PwbIF1cWS7bHL1eIFvd2xvW3S5YUBxem:mdXP0bY9vKGGodHXyJFMxKG2rboOgZpkhdWG|czDzdIVkfHKxbXX0dolkKGGwYXz5d4l{NCCLQ{WwQVAvODR2IN88US=> NF\QbW0yQTF|Nkm3OS=>
MCF12A cells NX7kS|B2WHKxbHnm[ZJifGmxbjDhd5NigQ>? NGjNPZk1QCCq NYK5VG51SW62aYDyc4xq\mW{YYTpeoUh[WO2aY\peJkh[WejaX7zeEBme3S{b3flckBz\WOncITvdk1l\W[rY3nlcpQhcHWvYX6gUWNHOTKDIHPlcIx{KGmwY4XiZZRm\CC5aYToJFAvODZibl2gc4Yh\XO2cnHkbY9tKGGwZDCwMlA4KG6PIH;mJJRme3Sxc4Tldo9v\SCjZoTldkA1QCCqcoOgZpkhe3WuZn;ybI9l[W2rbnWgRkBie3OjeTDpckBxemW|ZX7j[UBw\iCoZYThcEBjd3[rbnWgd4VzfW1iYX7kJG52W2W{dX2sJGdKPTB;Mz64PVA1PSEQvF2= M1m1RlIyPTF|Mke1
HEK293 cells M13Zb2Z2dmO2aX;uJIF{e2G7 MY\B[49vcXO2IHHjeIl3cXS7IHH0JIh2dWGwIHXzeJJw\2WwIILlcIF1\WRicnXj[ZB1d3JiZ3HtcYEh\XiycnXzd4VlKGmwIFjFT|I6OyClZXzsd{BjgSCudXPp[oVz[XOnIILldI9zfGW{IHflcoUh[XO|YYmsJGdKPTB;MT6zOUDPxE1? M1HBOVI2OzB3Nki4
rat GH3 cells MlfNSpVv[3Srb36gZZN{[Xl? NWLaNnFLPDhiaB?= MnXtRY51[WexbnnzeEBi[3Srdnn0fUBifCCHUjDpckBz[XRiR1izJINmdGy|IHHzd4V{e2WmIHHzJIlvcGmkaYTpc44hd2ZiZYP0doFlcW:uLXnu[JVk\WRicILvcIFkfGmwIHflcoUh\XiycnXzd4lwdiCjdDCxNEcuPiCPIHHmeIVzKDR6IHjyd{BjgSCUVD3QR3Ih[W6jbInzbZM> MVSyOFgxPTF7OR?=
MCF7:WS8 cells M33HdWZ2dmO2aX;uJIF{e2G7 M{\NWFQ5KGh? M3LOWWFod26rc4SgZYN1cX[rdImgZZQhTVJiaX6gbJVu[W5iTVPGO|pYWzhiY3XscJMh[XO|ZYPz[YQh[XNiR2LFRlEh\2WwZTDlfJBz\XO|aX;uJIF1KDFyJz22JG0h[W[2ZYKgOFghcHK|IHL5JHJVNVCFUjDhcoFtgXOrcx?= MUGyOFgxPTF7OR?=
rat GH3 cells MkLVSpVv[3Srb36gZZN{[Xl? NHK1WnY1QCCq Mnr4RY51[WexbnnzeEBi[3Srdnn0fUBifCCHUjDpckBz[XRiR1izJINmdGy|IHHzd4V{e2WmIHHzJIlvcGmkaYTpc44hd2ZiZYP0doFlcW:uLXnu[JVk\WRicILvcIFkfGmwIHflcoUh\XiycnXzd4lwdiCjdDCxNEcuOTBidH:gNVAoNTZiTTDh[pRmeiB2ODDodpMh[nliUmStVGNTKGGwYXz5d4l{ MUeyOFgxPTF7OR?=

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
p-ERK / ERK / p-MEK / MEK1 / MEK2 / p21 / Cyclin D1 ; 

PubMed: 26163823     


LNCaP-Raf:ER cells were treated with increasing doses of 4-hydroxytamoxifen for 2 days. The bottom panel indicates densitometry of MEK1 and MEK2 signals. Data (mean ± standard error) are from two independent experiments. Pearson’s r = 0.823 for MEK1 and −0.673 for MEK2. 

26163823
Growth inhibition assay
Cell viability; 

PubMed: 26014809     


Dose-dependent effect of 4-hydroxytamoxifen on survival of T47D, MCF-7 and BT-474 cell lines after 96 h of treatment. Control samples were treated with appropriate concentrations of DMSO. Viability was assayed by MTT method.

26014809

Protocol

Cell Research:

[1]

- Collapse
  • Cell lines: Adult Rat and Mouse Cardiac Myocytes
  • Concentrations: 0, 0.5, 1, 3, 5, and 10 µM
  • Incubation Time: 15-45 min
  • Method:

    For sarcomere length measurements, cells are covered in Tyrode’s containing 4OHT, allowed to reach 36 ± 1°C, and then stimulated at 0.2 Hz.


    (Only for Reference)
Animal Research:

[2]

- Collapse
  • Animal Models: Sprague-Dawley rats
  • Dosages: 21 mg/kg, 54 μmol/kg
  • Administration: oral administration
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 77 mg/mL (198.7 mM)
Water Insoluble
Ethanol Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 387.51
Formula

C26H29NO2

CAS No. 68392-35-8
Storage powder
in solvent
Synonyms Afimoxifene
Smiles CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03199963 Terminated Drug: 4-OH tamoxifen|Drug: Placebo Mammographic Breast Density BHR Pharma LLC August 21 2017 Phase 3

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Estrogen/progestogen Receptor Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID