Psoralen - CAS 66-97-7

Psoralen - CAS 66-97-7 Catalog number: BADC-00311

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Psoralen is a photoactive probe that has been used to investigate nucleic acid structure and function. It intercalates into DNA and, when activated by ultraviolet radiation, can create covalent interstrand crosslinks, inducing apoptosis.

Category
ADCs Cytotoxin
Product Name
Psoralen
CAS
66-97-7
Catalog Number
BADC-00311
Molecular Formula
C11H6O3
Molecular Weight
186.16
Psoralen

Ordering Information

Catalog Number Size Price Quantity
BADC-00311 100 mg $199
BADC-00311 1 g $299
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Description
Psoralen is a photoactive probe that has been used to investigate nucleic acid structure and function. It intercalates into DNA and, when activated by ultraviolet radiation, can create covalent interstrand crosslinks, inducing apoptosis.
Synonyms
Ficusin; Furocoumarin
IUPAC Name
furo[3,2-g]chromen-7-one
Canonical SMILES
C1=CC(=O)OC2=CC3=C(C=CO3)C=C21
InChI
InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H
InChIKey
ZCCUUQDIBDJBTK-UHFFFAOYSA-N
Density
1.389 g/cm3
Solubility
Chloroform, slightly in ethanol and ether, practically not in water
Melting Point
159-164°C.
LogP
1.67
Vapour Pressure
5.4X10-6 mm Hg at 25 °C (est)
Toxicity (LD50)
Exposure to more than 350 PUVA treatments greatly increases the risk of squamous cell carcinoma. Exposure to fewer than 150 PUVA treatments has, at most, modest effects on squamous cell carcinoma risk. Even high-dose exposure to PUVA does not greatly increase basal cell carcinomaa risk. The risks of squamous cell carcinom in long-term PUVA-treated patients should be considered in determining the risk of this therapy relative to other treatments for severe psoriasis. Psoralen ultraviolet B radiation (PUVB) can contribute to blue vitiligo. Psoralen can generate a very unique type of DNA damage, namely ICL (interstrand cross-link). An ICL can severely block DNA replication and transcription and cause programmed cell death. It is proposed that PUVA therapy conditions are more favorable for the formation of immunosuppressive rather than membrane-damaging psoralen photooxidation products. Psoralen inhibited the viability of normal human liver L02 cells in vitro by inducing S-phase arrest. In addition, psoralen upregulated cyclin E1 and p27 protein levels in these cells.
In Vitro
Psoralen was able to inhibit the growth of SMMC-7721 cells in a dose- and time-dependent manner and had a strong proapoptotic effect on these cells. It show a dose-dependent increase in caspase-3 activity, and elevated levels of p53 and Bax proteins in psoralen-treated cells, that coincided with dose-dependent decrease in Bcl-2 expression.
In Vivo
The acute oral median lethal dose of psoralen in ICR mice was determined to be 1,673 mg/kg. C57BL/6 mice were administered psoralen intragastrically at doses of 400 mg/kg or 800 mg/kg, and were sacrificed 24 h after treatment. Changes in various hepatotoxicity indicators demonstrated that psoralen can cause mild liver injury in mice. Psoralen inhibited the viability of normal human liver L02 cells in vitro by inducing S-phase arrest. In addition, psoralen in both the mouse livers and L02 cells upregulated cyclin E1 and p27 protein levels. The 2/3 partial hepatectomy mouse model was used to further explore the effects of psoralen on the liver regeneration and hepatocellular cycle arrest in vivo. The results showed that the decrease of liver regenerative and self-healing capabilities induced by hepatocellular cycle arrest may play an important role in the hepatotoxicity of psoralen. The further mechanism researches indicated that psoralen-induced hepatotoxicity was associated with inhibition of mTOR signalling pathway and mitochondrial injury; furthermore, MHY, an mTOR activator, partly alleviated the inhibition of mTOR and S-phase cycle arrest induced by psoralen in L02 cells.
Clinical Trial Information
NCT NumberTitleCondition Or DiseasePhaseStart DateSponsorStatus
NCT00005092Chemotherapy, Radiation Therapy, and Peripheral Stem Cell Transplantation in Treating Patients With Hematologic CancerLeukemiaPhase 1March 1999M.D. Anderson Cancer CenterCompleted
Application
ADCs Cytotoxin
Appearance
Solid powder
Purity
97 %. (HPLC).
Quantity
Milligrams-Grams
Quality Standard
Enterprise Standard
Shelf Life
Stable under recommended storage conditions
Shipping
Room temperature
Storage
Store at +4 °C, in dark place.
Pictograms
Irritant
Signal Word
Warning
Boiling Point
362.00to363.00°C.at760.00mmHg
1.Detection of Misdistribution of Tyrosinase from Melanosomes to Lysosomes and Its Upregulation under Psoralen/Ultraviolet A with a Melanosome-Targeting Tyrosinase Fluorescent Probe.
Zhou J1, Shi W1, Li L1, Gong Q1, Wu X1, Li X1, Ma H1. Anal Chem. 2016 Apr 19;88(8):4557-64. doi: 10.1021/acs.analchem.6b00742. Epub 2016 Apr 5.
Tyrosinase is regarded as an important biomarker of melanoma cancer, and its metabolism is closely related to some severe skin diseases such as vitiligo. Since tyrosinase is mainly located in the melanosomes of melanocytes, a probe that can specifically detect and image tysosinase in melanosomes would be in urgent demand to study the behavior of the enzyme in cells, but unfortunately, no melanosome-targeting tyrosinase fluorescent probe has been reported so far to the best of our knowledge. In this work, we have developed such a new probe, Mela-TYR, which bears morpholine as a melanosome-targeting group and 4-aminophenol as a tyrosinase reaction group. The probe exhibits not only a highly sensitive and selective off-on response to tyrosinase via oxidization cleavage, but also an accurate targeting ability toward the acidic organelles of melanosomes and lyososomes, which is validated by colocalization experiments with mCherry-tagged melanosomes as well as DND-99 (a commercial dye).
2.Psoralen reverses the P-glycoprotein-mediated multidrug resistance in human breast cancer MCF-7/ADR cells.
Jiang J1, Wang X1, Cheng K1, Zhao W1, Hua Y1, Xu C1, Yang Z1. Mol Med Rep. 2016 Apr 8. doi: 10.3892/mmr.2016.5098. [Epub ahead of print]
The resistance of cancer to chemotherapeutic agents is a major obstacle during chemotherapy. Clinical multidrug resistance (MDR) is commonly mediated by membrane drug efflux pumps, including ATP‑binding cassette subfamily B member 1, also termed P-glycoprotein (P-gp). P-gp is a membrane transporter encoded by the MDR1 gene. The current study aimed to investigate the impact of psoralen on the expression and function of P‑gp. The 10% inhibitory concentration (IC10) of psoralen, and its capacity to reduce MDR in adriamycin (ADR)‑resistant MCF‑7/ADR cells were determined using MTT assay. The ability of psoralen to modulate the transport activity of P‑gp in MCF‑7/ADR cells was evaluated by measuring the accumulation and efflux of rhodamine 123 (Rh 123) and adriamycin with flow cytometry. The present study evaluated the mRNA level of MDR1 in MCF‑7 and MCF‑7/ADR cells treated with psoralen using reverse transcription-quantitative polymerase chain reaction.
3.[Effects of P and K fertilizer on content of coumarin and yield of Glehnia littoralis].
Sun CS, Zheng K, Li W, Chen GL, Yu R, Yu JG. Zhongguo Zhong Yao Za Zhi. 2015 Sep;40(18):3543-8.
By a orthogonal experiment, the influence of different ratio of phosphorus and potassium fertilizers on imperatorin, isoimperatorin and psoralen contents and yield of Glehnia littoralis were studied. The results showed that root dry weight and the yield of G. littoralis increased when reasonably applied phosphorus fertilizer combined with potassium fertilizer within a certain range. And the influence of phosphorus fertilizer was greater than that of potassium fertilizer. The optimal value of root dry weight and yield achieved at both P2O5 360 kg x hm(-2), K2O 270 kg x hm(-2) and P2O5 360 kg x hm(-2), K2O 180 kg x hm(-2). The effects of different phosphorus and potassium treatments on the content of imperatorin, isoimperatorin and psoralen in G. littoralis were determined, which shows that the content increased with the moderate increase of phosphorus and potassium. And the effects of phosphorus fertilizer were more significantly. The isoimperatorin content achieved the largest value at P2O5 360 kg x hm(-2), K2O 270 kg x hm(-2), also a larger content of imperatorin and psoralen.
4.Psoralen reverses the P-glycoprotein-mediated multidrug resistance in human breast cancer MCF-7/ADR cells.
Jiang J1, Wang X1, Cheng K1, Zhao W1, Hua Y1, Xu C1, Yang Z1. Mol Med Rep. 2016 Apr 8. doi: 10.3892/mmr.2016.5098. [Epub ahead of print]
The resistance of cancer to chemotherapeutic agents is a major obstacle during chemotherapy. Clinical multidrug resistance (MDR) is commonly mediated by membrane drug efflux pumps, including ATP‑binding cassette subfamily B member 1, also termed P-glycoprotein (P-gp). P-gp is a membrane transporter encoded by the MDR1 gene. The current study aimed to investigate the impact of psoralen on the expression and function of P‑gp. The 10% inhibitory concentration (IC10) of psoralen, and its capacity to reduce MDR in adriamycin (ADR)‑resistant MCF‑7/ADR cells were determined using MTT assay. The ability of psoralen to modulate the transport activity of P‑gp in MCF‑7/ADR cells was evaluated by measuring the accumulation and efflux of rhodamine 123 (Rh 123) and adriamycin with flow cytometry. The present study evaluated the mRNA level of MDR1 in MCF‑7 and MCF‑7/ADR cells treated with psoralen using reverse transcription-quantitative polymerase chain reaction.

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