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SML1218

Sigma-Aldrich

Pheophorbide-a

≥90% (HPLC)

Synonyme(s) :

pheophorbide a, (3S,4S,21R)-9-Ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid, Deacetyl-2-vinylbacteriopheophorbide, Pheophorbide a5

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About This Item

Formule empirique (notation de Hill):
C35H36N4O5
Numéro CAS:
15664-29-6
Poids moléculaire :
592.68
Numéro MDL:
MFCD00210345
Code UNSPSC :
12161501
ID de substance PubChem :
329825726

Pureté

≥90% (HPLC)

Forme

powder

Conditions de stockage

protect from light

Couleur

blue, to dark brown to black

Solubilité

DMSO: 0.5 mg/mL, clear (warmed)

Température de stockage

−20°C

Chaîne SMILES 

O=C([C@@H]1C(OC)=O)C(C(N/2)=C1C([C@@H](CCC(O)=O)[C@@H]/3C)=NC3=C/4)=C(C)C2=C\C5=N/C(C(C)=C5CC)=C\C6=C(C=C)C(C)=C4N6

InChI

1S/C35H36N4O5/c1-8-19-15(3)22-12-24-17(5)21(10-11-28(40)41)32(38-24)30-31(35(43)44-7)34(42)29-18(6)25(39-33(29)30)14-27-20(9-2)16(4)23(37-27)13-26(19)36-22/h8,12-14,17,21,31,36,39H,1,9-11H2,2-7H3,(H,40,41)/b22-12-,23-13-,24-12-,25-14-,26-13-,27-14-,32-30-/t17-,21-,31+/m0/s1

Clé InChI

NSFSLUUZQIAOOX-QEWKCGBTSA-N

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Application

Pheophorbide-a has been used as a photosensitizer:
  • for the photodynamic therapy (PDT) in oral cancer cell lines
  • to test its effect on inducing oxidative stress and death in L. amazonensis
  • to test its effect on the viability of HeLa cells

Actions biochimiques/physiologiques

Pheophorbide-a, due to its photosensitizing effect, may serve as a promising bioactive compound to treat leishmaniasis. It is a metabolite of chlorophyll and possesses immunostimulation functionality. Pheophorbide-a is a photosensitizer for the photodynamic therapy. It is an ATP Binding Cassette Subfamily G Member 2 (ABCG2) transporter specific substrate. Overexpression of ATP-binding cassette (ABC) transporters in cancer cells is associated with the multidrug resistance phenotype.

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)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Dan Dan Xu et al.
Photodiagnosis and photodynamic therapy, 10(3), 278-287 (2013-09-03)
The introduction of photodynamic therapy (PDT) to the treatment of advanced prostate cancer can accomplish the eradication of local neoplasm and distant metastases with minimized damage to the adjacent structures. The evidence of PDT efficacy for androgen-refractory prostate cancer will
Charles A Barnes et al.
Journal of agricultural and food chemistry, 60(42), 10456-10460 (2012-09-26)
Efflux pumps are vital bacterial components, and research has demonstrated that some plant compounds such as pheophorbide a (php) possess efflux pump inhibitor (EPI) activity. This study determined the quantity of php present in feces as an indicator of EPI
Hyo-Eun Yoon et al.
Oncology reports, 31(1), 137-144 (2013-11-21)
Pheophorbide a (Pa), a chlorophyll derivative, is a photosensitizer that can induce significant antitumor effects in several types of tumor cells. The present study investigated the mechanism of Pa-mediated photodynamic therapy (Pa-PDT) in the human skin cancer cell lines A431
Nathielle Miranda et al.
Journal of photochemistry and photobiology. B, Biology, 174, 342-354 (2017-08-19)
Leishmaniasis is a disease caused by hemoflagellate protozoa, affecting millions of people worldwide. The difficulties of treating patients with this parasitosis include the limited efficacy and many side effects of the currently available drugs. Therefore, the search for new compounds

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