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Merck

SML0534

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
UNSPSC Code:
12352200
PubChem Substance ID:
329825538
NACRES:
NA.77
MDL number:
MFCD11982858

Product Name

Verteporfin, ≥94% (HPLC)

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

assay

≥94% (HPLC)

form

powder

storage condition

desiccated
protect from light

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

−20°C

Quality Level

100

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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.
Verteporfin is a photosensitizer for photodynamic therapy.

Other Notes

Light sensitive

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000389501
0000389501
0000493153
0000493155
0000493155

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Overexpression of TAZ promotes cell proliferation, migration and epithelial-mesenchymal transition in ovarian cancer.
Chen G, et al.
Oncology Letters, 12(3), 1821-1825 (2016)
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
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
Yukari Mae et al.
Molecular and clinical oncology, 13(3), 10-10 (2020-08-06)
Photodynamic therapy (PDT) induces photochemical reactions, resulting in the destruction of tumor cells via singlet (S1) oxygen production. This cellular destruction occurs specifically in tumor cells, following selective accumulation of a photosensitizer and its excitation by a specific wavelength. Verteporfin
YAP1 and AR interactions contribute to the switch from androgen-dependent to castration-resistant growth in prostate cancer.
Kuser-Abali G, et al.
Nature Communications, 6, 8126-8126 (2015)
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