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Merck
CN

SML1218

Pheophorbide-a

≥90% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C35H36N4O5
CAS Number:
15664-29-6
Molecular Weight:
592.68
UNSPSC Code:
12161501
PubChem Substance ID:
329825726
MDL number:
MFCD00210345

Key Documents

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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

SMILES string

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 key

NSFSLUUZQIAOOX-QEWKCGBTSA-N

assay

≥90% (HPLC)

form

powder

storage condition

protect from light

color

blue, to dark brown to black

solubility

DMSO: 0.5 mg/mL, clear (warmed)

storage temp.

−20°C

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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

Biochem/physiol Actions

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.

Other Notes

light sensitive

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
085M4717V

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Rubén Ruiz-González et al.
Cancers, 9(2) (2017-02-22)
A combination of therapies to treat cancer malignancies is at the forefront of research with the aim to reduce drug doses (ultimately side effects) and diminish the possibility of resistance emergence given the multitarget strategy. With this goal in mind
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
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
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
Sook Moon et al.
Oncotarget, 8(21), 35184-35192 (2017-05-01)
MicroRNAs (miRNAs) regulate key biological processes, and their aberrant expression has been related to cancer development. Photodynamic therapy (PDT) has emerged as one of the most promising modalities for cancer treatment. However, the application of PDT has been limited to
View All Related Papers

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