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Safety Information

SML0534

Sigma-Aldrich

Verteporfin

≥94% (HPLC), powder, YAP-TEA domain interaction inhibitor

Synonym(s):

(4R,4aS)-rel-18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-24H,26H-Benzo[b]porphine-9,13-dipropanoic acid monomethyl ester, Visudyne, trans-18-ethenyl-4,4a-dihydro-3,4-bis(methoxycarbonyl)-4a,8,14,19-tetramethyl-23H,25H-Benzo[b]porphine-9,13-dipropanoic acid monomethyl ester

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About This Item

Empirical Formula (Hill Notation):
C41H42N4O8
CAS Number:
129497-78-5
Molecular Weight:
718.79
MDL number:
MFCD11982858
UNSPSC Code:
12352200
PubChem Substance ID:
329825538
NACRES:
NA.77

product name

Verteporfin, ≥94% (HPLC)

Quality Level

100

Assay

≥94% (HPLC)

form

powder

storage condition

desiccated
protect from light

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

CC(C(/C=C1[C@@]2(C)C(/C(N/1)=C/3)=CC=C(C(OC)=O)[C@H]2C(OC)=O)=N/4)=C(CCC(OC)=O)C4=C\C5=C(CCC(O)=O)C(C)=C(/C=C6C(C=C)=C(C)C3=N/6)N5.CC(C(/C=C7[C@@]8(C)C(/C(N/7)=C/9)=CC=C(C(OC)=O)[C@H]8C(OC)=O)=N/%10)=C(CCC(O)=O)C%10=C\C%11=C(CCC(OC)=O)C(C)=C(/C=C%12C(C=C)

InChI

1S/2C41H42N4O8/c1-9-23-20(2)29-17-34-27-13-10-26(39(49)52-7)38(40(50)53-8)41(27,5)35(45-34)19-30-22(4)24(11-14-36(46)47)32(44-30)18-33-25(12-15-37(48)51-6)21(3)28(43-33)16-31(23)42-29;1-9-23-20(2)29-17-34-27-13-10-26(39(49)52-7)38(40(50)53-8)41(27,5)35(45-34)19-30-22(4)25(12-15-37(48)51-6)33(44-30)18-32-24(11-14-36(46)47)21(3)28(43-32)16-31(23)42-29/h2*9-10,13,16-19,38,43,45H,1,11-12,14-15H2,2-8H3,(H,46,47)/b31-16-,32-18-,34-17-,35-19-;31-16-,33-18-,34-17-,35-19-/t2*38-,41+/m00/s1

InChI key

YHNBVDZVUQFVLS-SKJZPIBWSA-N

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Application

Verteporfin has been used as a photosensitizer. It is also used as an inhibitor of YAP (Yes-associated protein)-TEA domain (TEAD) interaction.

Biochem/physiol Actions

Verteporfin has an ability to disrupt the interaction between YAP (Yes-associated protein)/TAZ (transcriptional coactivator with PDZ-binding motif) and TEA domain (TEAD) complex. It also reduces the viability of the ovarian cancer cells and almost eliminates cell migration. Therefore, verteporfin might be considered as a potent therapeutic for ovarian cancer.
Verteporfin is a photosensitizer for photodynamic therapy to eliminate the abnormal blood vessels in the eye associated with conditions such as macular degeneration. Verteporfin accumulates in abnormal blood vessels and, when stimulated by nonthermal red light with a wavelength of 693 nm in the presence of oxygen, produces highly reactive short-lived singlet oxygen and other reactive oxygen radicals, resulting in local damage to the endothelium and blockage of the vessels. Verteporfin localizes predominantly in mitochondria.

Other Notes

Light sensitive

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML0534-BULK:
SML0534-5MG:
SML0534-VAR:
SML0534-25MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Alan F Cruess et al.
Acta ophthalmologica, 87(2), 118-132 (2008-06-26)
Photodynamic therapy (PDT) with verteporfin has been used less comprehensively in the treatment of exudative age-related macular degeneration (AMD), and specifically of choroidal neovascularization (CNV), since the advent of antiangiogenic therapies. Recently, there has been a renewed interest in PDT
Kevin Tozer et al.
Ophthalmology, 120(10), 2029-2034 (2013-05-30)
To examine the outcomes of combination anti-vascular endothelial growth factor (VEGF) and photodynamic therapy (PDT) for the treatment of neovascular age-related macular degeneration (AMD) refractory to anti-VEGF monotherapy. Retrospective, interventional case series. Twenty-six eyes of 26 patients treated with anti-VEGF
Wai Man Chan et al.
Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie, 248(5), 613-626 (2010-02-18)
Verteporfin photodynamic therapy (PDT) is approved for the treatment of predominantly classic subfoveal choroidal neovascularization (CNV) due to age-related macular degeneration (AMD), as well as for subfoveal CNV due to pathologic myopia and ocular histoplasmosis syndrome. Verteporfin PDT addresses the
Victor C K Lo et al.
Journal of orthopaedic research : official publication of the Orthopaedic Research Society, 31(9), 1398-1405 (2013-04-30)
Photodynamic therapy (PDT) has been shown to ablate tumors within vertebral bone and yield short-term improvements in vertebral architecture and biomechanical strength, in particular when combined with bisphosphonate (BP) treatment. Longer-term outcomes of PDT combined with current treatments for skeletal
Akihiro Yamashita et al.
Stem cells translational medicine, 10(1), 115-127 (2020-08-22)
Human induced pluripotent stem cells (hiPSCs) are a promising cell source for the creation of cartilage to treat articular cartilage damage. The molecular mechanisms that translate culture conditions to the chondrogenic differentiation of hiPSCs remain to be analyzed. To analyze
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