Verteporfin

For research use only.

Catalog No.S1786 Synonyms: CL 318952, Visudyne

57 publications

Verteporfin  Chemical Structure

CAS No. 129497-78-5

Verteporfin (CL 318952, Visudyne) is a small molecule that inhibits TEAD–YAP association and YAP-induced liver overgrowth. It is also a potent second-generation photosensitizing agent derived from porphyrin. Verteporfin is an autophagy inhibitor. Verteporfin inhibits cell proliferation and induces apoptosis.

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Selleck's Verteporfin has been cited by 57 publications

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Biological Activity

Description Verteporfin (CL 318952, Visudyne) is a small molecule that inhibits TEAD–YAP association and YAP-induced liver overgrowth. It is also a potent second-generation photosensitizing agent derived from porphyrin. Verteporfin is an autophagy inhibitor. Verteporfin inhibits cell proliferation and induces apoptosis.
Targets
VDA [1]
(Endothelial cells)
YAP/TEAD interaction [3]
In vitro

Verteporfin is about four times more efficient in absorbing light at wavelengths that penetrate tissues best (i.e., around 700 nm) and thus provides a much higher cytotoxic effect than hematoporphyrin (10 times more in human adherent cell lines). Verteporfin is lipophilic and is more readily taken up by malignant or activated cells, compared with normal or resting cells. Verteporfin binds with LDL to form a complex, which is then taken up into proliferating cells (e.g., neovascular endothelial cells) probably via LDL receptors and endocytosis. Verteporfin therapy achieves complete angiographic occlusion of the neovascular compartment by thrombosis of vascular channels, following selective endothelial damage. Verteporfin therapy selectively induces reproducible and isolated choriocapillary occlusion without alteration of overlying photoreceptors or ganglion cells, as shown by light and electron microscopy. [1] Verteporfin conbined with light rapidly exhibits apoptotic changes reflected by caspase-3 and caspase-9 activation and PARP cleavage in HL-60 cells, changes that are blocked by the general caspase inhibitor ZVAD.fmk. [2]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
HL-60 MUXGeY5kfGmxbjDhd5NigQ>? MYD+NVAxKG6pL33M M4TIWGROW09? NVi0VG01cW6lcnXhd4V{KESQQTDmdoFodWWwdHH0bY9vKGyndnXsdy=> NF3Bb3EyODZyN{exNC=>
HL-60 NVn4UZNC[3m2b4TvfIlkcXS7IHHzd4F6 NVXXS3J1hjFyMDDu[{9uVA>? Ml7USG1UVw>? MUXpcohq[mm2czDj[YxtKH[rYXLpcIl1gQ>? NYXBb|JSOTB4MEe3NVA>
Jurkat Mk[yRZBweHSxc3nzJIF{e2G7 NWm1[WtnhjJ6MDDuUS=> MoLiSG1UVw>? MoPIbY5lfWOnczDhJGJkdC1{LXTldIVv\GWwdDDhdI9xfG:|aYO= NVfhbHZ[OTF{NEW0NVU>
RIF-1 NHTpem5HfW6ldHnvckBie3OjeR?= MlzhNUDPxGdxbXy= MoS1SG1UVw>? M1i5b4Rm[3KnYYPld{BwgHmpZX6gZ49ve3WvcITpc44> M2TqN|EzPjF3N{G4
RIF-1 M3LwPIN6fG:2b4jpZ4l1gSCjc4PhfS=> NWXtN4F[OSEQvHevcYw> NVfzfJZSTE2VTx?= NV3idXhR\GWlcnXhd4UhfG9iMkCgxtEhPSViY3XscEB{fXK4aY\hcC=> NGHacmoyOjZzNUexPC=>
SVEC4-10 MULGeY5kfGmxbjDhd5NigQ>? Mk\yNlAxKG6pL33s MoL0SG1UVw>? NYOwOnFJcW6mdXPld{BucWO{b4T1ZpVt\SCmZYDvcJlu\XKrenH0bY9v MXGxOlQ3PzFyNh?=
SVEC4-10 NVHtc21jTnWwY4Tpc44h[XO|YYm= NFfueo8zODBibnevcYw> NH\ZU5VFVVOR MWPpcoR2[2W|IIP0doV{eyCjY4TpckBncWKncjDmc5Ju[XSrb36= MY[xOlQ3PzFyNh?=
ARPE-19 NWX4VIxN[3m2b4TvfIlkcXS7IHHzd4F6 NFThZYt,OC5zIN88[{9udA>? NWrKcJR4TE2VTx?= Mn33d4hwf3NiYTDkc5NmNWSncHXu[IVvfCC2b4jpZ4l1gQ>? Mn:zNVY6QDd7MEW=
ARPE-19 NGjDRm9HfW6ldHnvckBie3OjeR?= M4XIbVAvODFizsznM41t MoDGSG1UVw>? MXfpcoNz\WG|ZYOgWmVITiCjbnSgdoVlfWOnczDQSWRHKGW6cILld5Nqd25? MlP5NVY6QDd7MEW=
Y-79 MUXHdo94fGhiaX7obYJqfG:{eTDhd5NigQ>? NYnrUpNbhjFizsznM41t NIDNSlVFVVOR NWPTNpJ{\GWlcnXhd4V{KHKndHnuc4Jt[XO2b33hJINmdGxicILvcIln\XKjdHnvci=> NETxOFEyQDV5OUe2OC=>
WERI-Rb1 MYjHdo94fGhiaX7obYJqfG:{eTDhd5NigQ>? M2TRW54yKM7:Zz;tcC=> MnnXSG1UVw>? M2K0XoRm[3KnYYPld{Bz\XSrbn;icIF{fG:vYTDj[YxtKHC{b3zp[oVz[XSrb36= NUi5dpd3OTh3N{m3OlQ>
RB247C3 M3:wdWdzd3e2aDDpcohq[mm2b4L5JIF{e2G7 M{fPXJ4yKM7:Zz;tcC=> Mm\0SG1UVw>? MnS3[IVkemWjc3XzJJJmfGmwb3LsZZN1d22jIHPlcIwheHKxbHnm[ZJifGmxbh?= MYSxPFU4QTd4NB?=
RB355 M4fnUmdzd3e2aDDpcohq[mm2b4L5JIF{e2G7 MnnxglEh|rypL33s NIXWelRFVVOR MnH0[IVkemWjc3XzJJJmfGmwb3LsZZN1d22jIHPlcIwheHKxbHnm[ZJifGmxbh?= M{LEdFE5PTd7N{[0
RB383 Mn;JS5Jwf3SqIHnubIljcXSxcomgZZN{[Xl? MX\+NUDPxGdxbXy= NVPGTZgyTE2VTx?= MWLk[YNz\WG|ZYOgdoV1cW6xYnzhd5RwdWFiY3XscEBxem:uaX\ldoF1cW:w MnzDNVg2Pzl5NkS=
hFibro MVnjfZRwfG:6aXPpeJkh[XO|YYm= M3XNO|AvPSEEtXevcYw> M3TiZWROW09? NUTCU5Nv\GWlcnXhd4V{KH[rYXLpcIl1gSCkeTC4Okw2LQ>? M4TrZ|I{PDRzMUG0
pTMC MWjjfZRwfG:6aXPpeJkh[XO|YYm= MnzZNE42KML3Zz;tcC=> MmTqSG1UVw>? Mn3Z[IVkemWjc3XzJJZq[WKrbHn0fUBjgSB7Mj65KS=> NX\VcJB1OjN2NEGxNVQ>
hTMC MYnjfZRwfG:6aXPpeJkh[XO|YYm= MVGwMlUhyrWpL33s NH;zO4pFVVOR MXLk[YNz\WG|ZYOgeoli[mmuaYT5JIJ6KDh6Lkml Mn7ENlM1PDFzMUS=
ARPE-19 MXLjfZRwfG:6aXPpeJkh[XO|YYm= M4jsXFAvPSEEtXevcYw> MoS2SG1UVw>? NXvTXIhp\GWlcnXhd4V{KH[rYXLpcIl1gSCkeTC1OU42LQ>? M1\LPVI{PDRzMUG0
Panc-1 NH\3RWxIem:5dHigbY5pcWKrdH;yfUBie3OjeR?= MWOxNEDPxE1? NV\1Z5ZiTE2VTx?= MXvpcohq[mm2czDj[YxtKHC{b3zp[oVz[XSrb36= NYX1TGNtOjRyNkmwOlk>
MIA PaCa-2 MkPRS5Jwf3SqIHnubIljcXSxcomgZZN{[Xl? NWjEWWR{OTBizszN MWHEUXNQ NFuwXmZqdmirYnn0d{Bk\WyuIIDyc4xq\mW{YYTpc44> Mm\iNlQxPjlyNkm=
BxPC-3 NUjWNnFGT3Kxd4ToJIlvcGmkaYTvdpkh[XO|YYm= NYXJe2FnOTBizszN MUXEUXNQ M4T5bIlvcGmkaYTzJINmdGxicILvcIln\XKjdHnvckBkd22ybHX0[Yx6 MlvvNlQxPjlyNkm=
SU86.86 Ml7MS5Jwf3SqIHnubIljcXSxcomgZZN{[Xl? NF\WcokyOCEQvF2= M3PxUGROW09? M{fYcYlvcGmkaYTzJINmdGxicILvcIln\XKjdHnvckBkd22ybHX0[Yx6 NITOSoMzPDB4OUC2PS=>
MCF-7 NVLXeYp4SXW2b4DoZYd6KGG|c3H5 MVuxNEDPxE1? M1i4TWROW09? NH;1RVBqdmirYnn0d{Bo\W2laYThZolv\S2rbnT1Z4VlKGG3dH;wbIFogQ>? NYnKWWRVOjRyNkmwOlk>
WERI NHTWbHFIem:5dHigbY5pcWKrdH;yfUBie3OjeR?= MUn+NVAh|rypL33s M4q4NGROW09? NVPub3dQcW6qaXLpeJMh\3Kxd4ToJI9nKHKndHnuc4Jt[XO2b33hJINmdGy| Ml;DNlQ5OzdzNEK=
WERI NEHRXopHfW6ldHnvckBie3OjeR?= NUTJOnB7hjFyIN88[{9udA>? MlfqSG1UVw>? M{XkSIJtd2OtczDj[YxtKGO7Y3zlJJBzd2e{ZYPzbY9v Mm\xNlQ5OzdzNEK=
Y-79 MV\GeY5kfGmxbjDhd5NigQ>? NU\oSml5hjFyIN88[{9udA>? MkHrSG1UVw>? MnHBZoxw[2u|IHPlcIwh[3mlbHWgdJJw\3Knc4Ppc44> MWKyOFg{PzF2Mh?=
Y-79 M2HFPGZ2dmO2aX;uJIF{e2G7 MVP+NVAh|rypL33s MnrpSG1UVw>? NVPjRpVT[W[oZXP0d{B[SVBvVFXBSEBxem:2bz3vcoNw\2WwZTDwZZRpf2G7 NEjMbYQzPDh|N{G0Ni=>
Y-79 MYTGeY5kfGmxbjDhd5NigQ>? Ml;TglExKM7:Zz;tcC=> M{L0UGROW09? NHXncllld3ewLYLl[5Vt[XSnczDwcJVzcXCxdHXuZ5khdWG{a3XyJG9EXC12 M3TnblI1QDN5MUSy

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
p-S6(S240/244) / p-4EBP1(S65); 

PubMed: 28202507     


KLE, EFE184 and NOU-1 were treated with Verteporfin (0.1 μM, 0.3 μM). After 36h, cell lysates were western blotted with indicated antibodies. Bands are from one of three independent experiments.

c-Myc / Bcl-2; 

PubMed: 29416644     


In CAL27 cell lines, the expression of BCL-2 and C-MYC proteins decreased with the increase of Verteporfin concentration. The presented columns are given as the means ± SD. *p < 0.05, **P < 0.01, ***p < 0.001.

ECAD / Vimentin / Sox2 / CD44 / CD133; 

PubMed: 30467925     


Yes-associated protein 1 (YAP1), E-cadherin, vimentin (epithelial-mesenchymal transition [EMT] pathway), SOX2 CD44 and CD133 (autophagy markers) were detected by western blot in control, verteporfin (1 μmol/L) and verteporfin + 231-taxol (0.5 μmol/L) resistance groups.

beta-catenin; 

PubMed: 28202507     


KLE, EFE184, NOU-1 and SKUT-2 were treated with 3 μM Verteporfin. After 24h, cell lysates were western blotted with indicated antibodies. Bands are from one of three independent experiments.

28202507 29416644 30467925
Growth inhibition assay
Cell viability; 

PubMed: 28042502     


A: Cell viability was determined by MTS assay after the UM cells were exposed to verteporfin for 72 hours. B: After treated with various concentrations of verteporfin for 24 hours, the UM cells (e.g., 92.1, Mel 270, Omm 1, Omm 2.3) were seeded in drug-free soft agar culture for 14 days. Colonies were counted. 

28042502
Immunofluorescence
YAP1; 

PubMed: 30254296     


Treatment of U343 cells with 5 μM VP between 1-8 h in both 21% and 1% O2 induced morphological changes. Scale bar represents 10 µm. VP: Verteporfin

Calreticulin; 

PubMed: 30254296     


Calreticulin (CRT) significantly increased in VP-treated (5 µM, 2 h) U87 cells in both 21% and 1% O2 indicating likely ER stress.

p-YAP(Y357); 

PubMed: 28404908     


Confocal images of HEC-1-B cells and organoids which were subjected to immunofluorescence detection of A. YAP and B. phospho-YAP after VP treatment. YAP and phospho-YAP are conjugated with goat anti-mouse and goat anti-rabbit Alexa flour secondary antibodies respectively. (A) Upper panel bar=63x and lower panel bar = 20x. (B) Upper panel bar=63x and lower panel bar = 20x.

30254296 28404908
In vivo Verteporfin can be used for angiographic visualization of choroidal vessels and CNV, which demonstrates that the photosensitizer accumulates rapidly in experimental CNV in monkeys. Verteporfin accumulates rapidly in the established vasculature of the choroid, RPE, and photoreceptors of rabbit eyes. Verteporfin reaches maximal tissue levels within 3 hours of intravenous injection, followed by a rapid decline within 24 hours in mice. Verteporfin is metabolized to a less active form in vivo and is cleared very rapidly, predominantly in the feces and a very small proportion excreted in urine. Verteporfin therapy effectively and selectively prevents fluorescein dye leakage from experimentally induced CNV in monkeys. [1]

Protocol

Solubility (25°C)

In vitro DMSO 100 mg/mL (139.12 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 718.79
Formula

C41H42N4O8

CAS No. 129497-78-5
Storage powder
in solvent
Synonyms CL 318952, Visudyne
Smiles COC(=O)CCC1=C(C)C2=CC3=NC(=CC4=C(C)C(=C([NH]4)C=C5N=C(C=C1[NH]2)C(=C5C)CCC(O)=O)C=C)C6=CC=C(C(C(=O)OC)C36C)C(=O)OC

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT03797547 Active not recruiting Other: AFLIBERCEPT Myopic Choroidal Neovascularisation Poitiers University Hospital June 22 2018 --
NCT01846273 Completed Drug: Ranibizumab|Drug: Verteporfin PDT|Drug: Sham PDT Age-related Macular Degeneration|Polypoidal Choroidal Vasculopathy Novartis Pharmaceuticals|Novartis August 7 2013 Phase 4
NCT00423189 Terminated Drug: Ranibizumab (Lucentis)|Drug: 0.5mg ranibizumab Age-Related Macular Degeneration David M. Brown M.D.|Novartis Pharmaceuticals|Greater Houston Retina Research January 2007 Phase 4
NCT00403442 Terminated Device: Verteporfin Therapy/ Drug: Bevacizumab Macular Degeneration Vitreous -Retina- Macula Consultants of New York|QLT Inc. September 2006 Phase 1

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID