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SML0534

Sigma-Aldrich

Verteporfin

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

Synonyme(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

Formule empirique (notation de Hill):
C41H42N4O8
Numéro CAS:
Poids moléculaire :
718.79
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

Verteporfin, ≥94% (HPLC)

Niveau de qualité

Pureté

≥94% (HPLC)

Forme

powder

Conditions de stockage

desiccated
protect from light

Solubilité

DMSO: 2 mg/mL, clear (warmed)

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Autres remarques

Light sensitive

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
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
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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