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[CAS NO. 129497-78-5] Verteporfin

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Catalog:	HY-B0146
Brand:	MCE
CAS:	129497-78-5

Overview

MDL	MFCD28098202
Molecular Weight	718.79
Molecular Formula	C82H84N8O16
SMILES	C[C@]1(/C2=C/C(N3)=C4C)C(C(/C=C(C(C)=C/5C=C)\NC5=C/C6=N/C(C(CCC(OC)=O)=C6C)=C\C3=C4CCC(O)=O)=N2)=CC=C(C(OC)=O)[C@H]1C(OC)=O.C[C@]7(/C8=C/C(N9)=C%10C)C(C(/C=C(C(C)=C/%11C=C)\NC%11=C/C%12=N/C(C(CCC(O)=O)=C%12C)=C\C9=C%10CCC(OC)=O)=N8)=CC=C(C(OC)=O)[C@H]7C(OC)=O

For research use only. We do not sell to patients.

101 Publications Citing Use of MCE

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[43]Transl Res. 2022 Nov 23;S1931-5244(22)00252-3.
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[45]Am J Cancer Res. 2020 Jan 1;10(1):196-210.
[46]Stem Cell Res Ther. 2021 Oct 7;12(1):523.
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[48]J Genet Genomics. 2022 Nov 29;S1673-8527(22)00250-8.
[49]Cell Biosci. 2020 Dec 22;10(1):146.
[50]FASEB J. 2023 Feb;37(2):e22783.
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[52]Genes Dis. 19 November 2021.
[53]Biomed Pharmacother. 2023 Jan 25;159:114302.
[54]Biomed Pharmacother. 2020 Jun;126:110080.
[55]J Cell Mol Med. 2020 Jul;24(14):8179-8193.
[56]Cells. 2022, 11(2), 237.
[57]Cells. 2020 Apr 18;9(4):1010.
[58]Biochim Biophys Acta Mol Basis Dis. 2020 Mar 1;1866(3):165625.
[59]Cell Commun Signal. 2022 Apr 12;20(1):52.
[60]Phytomedicine. 20 September 2022, 154466.
[61]Phytomedicine. 26 December 2021, 153913.
[62]Phytomedicine. 2020, Jul 28.
[63]J Biol Chem. 2022 Mar 2;101792.
[64]J Cell Biochem. 2020 Mar;121(3):2343-2353.
[65]Cancer Cell Int. 2022 Mar 9;22(1):113.
[66]Cancer Cell Int. 2021 Feb 19;21(1):128.
[67]Cancer Cell Int. 2019 Jul 12;19:179.
[68]Acs Biomater Sci Eng. 2022 Feb 14;8(2):598-609.
[69]Cell Death Discov. 2023 Jan 25;9(1):30.
[70]Ultrasonics. 2023 Feb 8;131:106949.
[71]Int Immunopharmacol. 2020 Mar 6;82:106366.
[72]Front Cell Neurosci. 2018 Dec 11;12:489.
[73]Mediat Inflamm. 28 Jul 2021.
[74]Mol Immunol. 2019 Mar;107:29-40.
[75]Oncol Rep. 2021 Oct;46(4):224.
[76]Oncol Rep. 2021 Jan;45(1):83-94.
[77]Exp Cell Res. 2020 Feb 1;387(1):111745.
[78]J Pharm Biomed Anal. 20 January 2022, 114473.
[79]Stem Cells Dev. 2020 Oct 15;29(20):1309-1319.
[80]Biochem Biophys Res Commun. 25 October 2022.
[81]Biochem Biophys Res Commun. 2020 Jun 30;527(3):624-630.
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[83]Biochem Biophys Res Commun. 2019 Mar 5;510(2):219-223.
[84]Cancer Manag Res. 2021,13: 4829-4840.
[85]Connect Tissue Res. 2022 Feb 7;1-16.
[86]J Oral Pathol Med. 2020 Apr;49(4):305-310.
[87]Oncol Lett. August 10, 2021.
[88]Mol Med Rep. 2020 Nov;22(5):3955-3961.
[89]Arch Med Res. 2020 Feb;51(2):124-134.
[90]Clin Exp Dermatol. 2021 Oct 8.
[91]Arch Oral Biol. 2019 Apr;100:23-32.
[92]Anim Cells Syst. 07 Nov 2022.
[93]Research Square Print. November 17th, 2022
[94]Research Square Print. October 27th, 2022.
[95]Research Square Print. September 30th, 2022.
[96]Research Square Print. 2022 Aug.
[97]Research Square Print. 2022 Jun.
[98]Research Square Preprint. 2022 May.
[99]Research Square Preprint. 2022 Jan.
[100]Research Square Preprint. 2021 Sep.
[101]bioRxiv. 2020 May.

Summary

Verteporfin (CL 318952) is a photosensitizer for photodynamic therapy to eliminate the abnormal blood vessels in the eye associated with conditions such as age-related macular degeneration. Verteporfin is a YAP inhibitor which disrupts YAP-TEAD interactions. Verteporfin induces cell apoptosis ^[1] . Verteporfinis an autophagy inhibitor that blocks autophagy at an early stage by inhibiting autophagosome formation ^[3] .

IC50 & Target

IC50: YAP-TEAD interaction

In Vitro

Verteporfin is specifically selected by PDX-cell screening. The concentrations to cause 50% growth inhibition (GI ₅₀ ) for PhLO, PhLH, and PhLK are 228 nM, 395 nM, and 538 nM, respectively, whereas GI ₅₀ for ALL-1, TCC-Y/sr, and NPhA1 are 3.93 µM, 2.11 µM, and 5.61 µM, respectively. GSH significantly reduces the sensitivity of 2 out of 3 PDX cells to verteporfin. Verteporfin reduces the mitochondrial membrane potential in PDX cells ^[1] . Verteporfin reduces the PTX-resistance on HCT-8/T cells by inhibiting YAP expression and combination therapy with verteporfin and NSC 125973 shows synergism on inhibition of YAP and cytotoxicity to HCT-8/T ^[2] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Verteporfin (10 mg/kg, c.s.c.) and BMS-354825 significantly reduces the leukemia cell ratio, and combined therapy further reduced the number of leukemia cells in the spleen ^[1] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT00135837	Novartis\|QLT Inc.	Age-Related Macular Degeneration	June 2003	Phase 4
NCT03033225	Mayo Clinic\|National Cancer Institute (NCI)	Advanced Pancreatic Carcinoma\|Locally Advanced Pancreatic Carcinoma\|Metastatic Pancreatic Carcinoma\|Pancreatic Neoplasm\|Stage II Pancreatic Cancer AJCC v8\|Stage IIA Pancreatic Cancer AJCC v8\|Stage IIB Pancreatic Cancer AJCC v8\|Stage III Pancreatic Cancer AJCC v8\|Stage IV Pancreatic Cancer AJCC v8\|Unresectable Pancreatic Carcinoma	December 6, 2016	Phase 2
NCT00007969	QLT Inc.\|National Cancer Institute (NCI)	Melanoma (Skin)	October 2000	Phase 1\|Phase 2
NCT00546936	Barnes Retina Institute\|Genentech, Inc.	Presumed Ocular Histoplasmosis (POHS)	October 2007	Phase 2
NCT02702700	Centre Hospitalier Universitaire Vaudois	Pleural Effusion, Malignant	January 2016	Phase 1
NCT02457026	Duke University\|Bausch & Lomb Incorporated	Neovascular Age-related Macular Degeneration	January 2016	Not Applicable
NCT00002647	Medical College of Wisconsin\|National Cancer Institute (NCI)	Brain and Central Nervous System Tumors\|Metastatic Cancer	May 1994	Phase 1
NCT00049959	QLT Inc.\|Novartis	Basal Cell Carcinoma\|Nevoid Basal Cell Carcinoma Syndrome\|Gorlin Syndrome		Phase 3
NCT00433017	Novartis	Macular Degeneration\|Choroidal Neovascularization	May 2007	Phase 2\|Phase 3
NCT00574093	Fondazione G.B. Bietti, IRCCS	Neovascular Age Related Macular Degeneration	January 2008	Phase 2
NCT01846273	Novartis Pharmaceuticals\|Novartis	Age-related Macular Degeneration\|Polypoidal Choroidal Vasculopathy	August 7, 2013	Phase 4
NCT00570193	Mid-Atlantic Retina Consultations, Inc.	Choroidal Neovascularization\|Macular Degeneration	December 2006	Phase 1\|Phase 2
NCT01325181	Jang Won Heo\|Novartis Korea Ltd.\|Seoul National University Hospital	Chronic Central Serous Chorioretinopathy	July 2009	Phase 1\|Phase 2
NCT01922102	Novartis Pharmaceuticals\|Novartis	Visual Impairment Due to Choroidal Neovascularization (CNV) Secondary to Pathologic Myopia (PM)	September 11, 2013	Phase 3
NCT03067051	SpectraCure AB	Recurrent Prostate Cancer	March 21, 2017	Phase 1\|Phase 2
NCT00347399	Asociación para Evitar la Ceguera en México	Age Related Macular Degeneration	March 2006	Phase 2
NCT00729846	California Retina Consultants\|Novartis	Age Related Macular Degeneration\|Choroidal Neovascularization\|Macular Edema	May 2006	Phase 2
NCT04075136	Wake Forest University Health Sciences\|Modulight	Exudative Age Related Macular Degeneration	November 2022	Phase 4
NCT00390208	Bay Area Retina Associates\|QLT Inc.	Age Related Macular Degeneration	August 2006	Phase 2
NCT00426998	Retinal Consultants Medical Group	Choroidal Neovascularization\|Macular Degeneration	April 2006	Phase 2
NCT01019668	Shin Kong Wu Ho-Su Memorial Hospital	Central Serous Chorioretinopathy	November 2008	Not Applicable
NCT01746875	Norwegian University of Science and Technology	Macular Degeneration\|Retinal Detachment	February 2014	Not Applicable
NCT00436553	Novartis	Macular Degeneration\|Choroidal Neovascularization	February 2007	Phase 3
NCT00331435	Ophthalmic PDT Study Group	Age Related Macular Degeneration	June 2006	Phase 4
NCT00211445	Manhattan Eye, Ear & Throat Hospital	Chronic Central Serous Chorioretinopathy	July 2002	Phase 2
NCT02872064	University College, London	Breast Neoplasms	January 2013	Not Applicable
NCT00403442	Vitreous -Retina- Macula Consultants of New York\|QLT Inc.	Macular Degeneration	September 2006	Phase 1
NCT01256580	Massachusetts Eye and Ear Infirmary	Choroidal Neovascularization\|Myopia\|Punctate Inner Choroidopathy (PIC)\|Multifocal Choroiditis\|Ocular Histoplasmosis Syndrome\|Central Serous Chorioretinopathy (CSC)\|Angioid Streaks\|Trauma, or Hereditary Eye Diseases	August 2010	Not Applicable
NCT00527475	Texas Retina Associates\|Novartis	Macular Degeneration	May 2007	Phase 2
NCT00359164	University of British Columbia	Macular Degeneration	July 2006	Phase 2
NCT00211419	Manhattan Eye, Ear & Throat Hospital\|Alcon Research	Maculopathy, Age-Related		Phase 1
NCT01217944	Novartis Pharmaceuticals\|Novartis	Pathological Myopia	October 2010	Phase 3
NCT03459144	Sun Yat-sen University	Polypoidal Choroidal Vasculopathy	December 1, 2012	Not Applicable
NCT00473642	Oklahoma State University Center for Health Sciences\|Novartis	Age-Related Maculopathy\|Choroidal Neovascularization	May 2007	Phase 4
NCT05589974	Helse Stavanger HF	Central Serous Chorioretinopathy	October 1, 2022
NCT00390026	St. Erik Eye Hospital	Age-Related Macular Degeneration	November 2006	Phase 3
NCT04590664	Emory University\|National Cancer Institute (NCI)	Glioblastoma\|Recurrent Glioblastoma	January 15, 2021	Phase 1\|Phase 2
NCT00674323	Novartis	Polypoidal Choroidal Vasculopathy	April 2008	Phase 4
NCT01570608	The Ludwig Boltzmann Institute of Retinology and Biomicroscopic Laser Surgery	Age Related Macular Degeneration	March 2007	Phase 3
NCT00242580	Novartis Pharmaceuticals\|QLT Inc.\|Novartis	Macular Degeneration\|Choroidal Neovascularization	September 2005	Phase 3
NCT02939274	Rogers Sciences Inc.	Metastatic Breast Cancer	October 2016	Phase 2
NCT00471406	Chonnam National University Hospital	Corneal Neovascularization		Not Applicable
NCT00134667	Eyetech Pharmaceuticals\|Pfizer	Age-Related Macular Degeneration	March 2005	Phase 4
NCT00492284	QLT Inc.	Choroidal Neovascularization\|Macular Degeneration	July 2007	Phase 2

Appearance

Solid

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility

In Vitro:

DMSO : ≥ 200 mg/mL ( 278.25 mM )

DMF : 10 mg/mL ( 13.91 mM ; ultrasonic and warming and heat to 60°C)

* "≥" means soluble, but saturation unknown.

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	1.3912 mL	6.9561 mL	13.9123 mL
5 mM	0.2782 mL	1.3912 mL	2.7825 mL
10 mM	0.1391 mL	0.6956 mL	1.3912 mL

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 5 mg/mL (6.96 mM); Clear solution
2.

Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)

Solubility: ≥ 5 mg/mL (6.96 mM); Clear solution
3.

Add each solvent one by one: 10% DMF >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 2.5 mg/mL (3.48 mM); Clear solution

* All of the co-solvents are available by MCE.

References

[1] Morishita T, et al. The photosensitizer verteporfin has light-independent anti-leukemic activity for Ph-positive acute lymphoblastic leukemia and synergistically works with BMS-354825. Oncotarget. 2016 Aug 2.
[2] Pan W, et al. Verteporfin can Reverse the NSC 125973 Resistance Induced by YAP Over-Expression in HCT-8/T Cells without Photoactivation through Inhibiting YAP Expression. Cell Physiol Biochem. 2016;39(2):481-90.
[3] Donohue E, et al. The autophagy inhibitor verteporfin moderately enhances the antitumor activity of gemcitabine in a pancreatic ductal adenocarcinoma model.J Cancer. 2013 Aug 28;4(7):585-96.

Synonyms

24H,26H-Benzo[b]porphine-9,13-dipropanoic acid, 18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-, monomethyl ester, (4R,4aS)-rel-

23H,25H-Benzo[b]porphine-9,13-dipropanoic acid, 18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-, monomethyl ester, trans-

BPD-MA

CL 318952

Verteporfin

Visudyne

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