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P8399

Sigma-Aldrich

Psoralen

≥99% (HPLC)

Synonym(s):

6,7-Furanocoumarin, 7H-Furo[3,2-g]benzopyran-7-one, Ficusin, Furo[3,2-g]coumarin

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About This Item

Empirical Formula (Hill Notation):
C11H6O3
CAS Number:
Molecular Weight:
186.16
Beilstein/REAXYS Number:
152784
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥99% (HPLC)

form

powder

fluorescence

λex 335 nm; λem 460 nm (pH 7.0)

storage temp.

2-8°C

SMILES string

O=C1Oc2cc3occc3cc2C=C1

InChI

1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H

InChI key

ZCCUUQDIBDJBTK-UHFFFAOYSA-N

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Application

Psoralen has been used:
  • as a crosslinker for dsRNA for in- situ hybridization studies
  • in testing melanin dispersal effects in fish scale melanophores
  • to test its stimulatory effects in osteoblast a cell proliferation assay
  • as a reference standard in high-performance liquid chromatography (HPLC)

Photochemical reagent for the investigation of nucleic acid structure and function.

Biochem/physiol Actions

Psoralen belongs to the linear type furanocoumarins. It intercalates and induces interstrand cross-links in DNA. On UV exposure psoralen is excited leading to irreversible intercalation with DNA by covalent bond formation. This property of psoralen ultraviolet A light (PUVA) is exploited in treating skin diseases and cutaneous T-cell lymphoma. However, usage psoralen also leads to hepatotoxicity and cytotoxicity by the generation of psoralen photoproducts (POPs). It may be useful in treating osteoporosis

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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The mitochondrial effects of novel apoptogenic molecules generated by psoralen photolysis as a crucial mechanism in PUVA therapy
Caffieri S, et al.
Blood, 109(11), 4988-4994 (2007)
In vitro responses of fish melanophores to lyophilized extracts of Psoralea corylifolia seeds and pure psoralen
Ali SA, et al.
Pharmaceutical biology, 49(4), 422-427 (2011)
Psoralen induced liver injury by attenuating liver regenerative capability
Zhou W, et al.
Frontiers in Pharmacology, 9, 1179-1179 (2018)
Psoralen and isopsoralen ameliorate sex hormone deficiency-induced osteoporosis in female and male mice
Yuan X, et al.
BioMed Research International, 2016 (2016)
A method for in situ localization of single-strand and double-strand RNA elements contained in the hepatitis C virus genome 3?-untranslated region
Rance E, et al.
advanced techniques in biology & medicine, 4, 171-183 (2016)

Articles

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Related Content

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of multicellular organisms, apoptosis is tightly regulated through two principal pathways by a number of regulatory and effector molecules.

n proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during the synthesis (S) phase, which is followed by a second gap phase (G2) during which growth and preparation for cell division occurs. Together, these three stages comprise the interphase phase of the cell cycle. Interphase is followed by the mitotic (M) phase.

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