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484-20-8 (Bergapten)

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Identification

Bergapten Bergapten
Name Bergapten
Formula C12H8O4
MW 216.19
CAS No. 484-20-8
EINECS 207-604-5
Smiles COC1=C(C=CC2=O)C(O2)=CC3=C1C=CO3
Synonyms 5-Methoxypsoralen; 4-Methoxy-7H-furo[3,2-g]chromen-7-one; 4-methoxy-7H-furo[3,2-g]chromen-7-one
InChI InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
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Introduction

5-Methoxypsoralen, a naturally occurring linear furocoumarin, has been successfully used in combination with ultraviolet (UV) A irradiation [psoralen plus UV (PUVA)] to manage psoriasis and vitiligo; inhibit proliferation in the human hepatocellular carcinoma cell line. IC50 value: Target: anti cancer in vitro: 5-MOP increased the activity of NATand also increased the further metabolism of AAF at 24 h in the rat stomach.

Background Information

5-Methoxypsoralen, a naturally occurring linear furocoumarin, has been successfully used in combination with ultraviolet (UV) A irradiation [psoralen plus UV (PUVA)] to manage psoriasis and vitiligo; inhibit proliferation in the human hepatocellular carcinoma cell line. IC50 value: Target: anti cancer in vitro: 5-MOP increased the activity of NATand also increased the further metabolism of AAF at 24 h in the rat stomach. In the rat colon, no statistically significant changes caused by 5-MOP were observed in NAT activity, but 5-MOP increased the further metabolism of AAF at 24 to 72 h. 5-MOP decreased the activity of NAT only at 72-h incubation in SC-M1 cells. In COLO 205 cells, however, 5-MOP decreased the activity of NAT between 24 h and 72 h [2]. 5-methoxypsoralen resulted in IL-8 inhibition at 10 microM concentration, without effects on cell proliferation. In synthesis, 5-methoxypsoralen can be taken into consideration to investigate mechanisms of neutrophil chemotactic signalling and for its potential application in modulating the excessive CF lung inflammation [3]. High concentration of 5-MOP (5 x 10(-5) M) induced a time-dependent increase of tyrosinase activity and melanin content, which was correlated to an increase of both mRNA and protein levels of tyrosinase. These results demonstrate that the 5-MOP stimulation of melanogenesis is related to increased tyrosinase synthesis [4]. Morphological analysis, cell viability assay, DNA analysis and cell-cycle analysis suggest that there are at least three modes of the suppressive effects shown by 5-MOP: (a) kills J5 cells directly; (b) induces apoptosis by arresting J5 cells at the G2/M phase in the cell cycle; (c) induces apoptosis through an independent pathway with cell-cycle arrest at 24-72 h of exposure [5]. in vivo: In patients and volunteers, PUVA 5-methoxypsoralen causes a dose-related increase in cutaneous photosensitivity. However, mean minimum phototoxic doses (MPD) were 30 to 50% greater with 5-methoxypsoralen than with 8-methoxypsoralen within individuals; this suggests lower photoactivity with 5-methoxypsoralen [1]. ......by MedChemexpress Co., Ltd.
Bergapten is a psoralen that can be photoactivated and is capable of crossing-linking DNA, covalently modifying proteins and lipids, and consequently inhibiting cell replication. ......by Target Molecule Corp.
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Protocol(Only for Reference)

Cell Experiment

Animal Experiment

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Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000013521

Storage condition

Solubility

DMSO by MedChemexpress Co., Ltd.
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Mechanism and Indication

Signaling Pathways Metabolic Enzyme/Protease Autophagy
Target Autophagy Cytochrome P450
Research Area Cancer
Indications
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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Bergapten - Phase 3 Clinical
Bergapten - Phase 3
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Safety Data of Bergapten

´╗┐Hazard Symbols : Xi
´╗┐Risk Statements : R43
Safety Statements : S36/37
RTECS : LV1300000
WGKGermany : 2
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Spectral Information

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Suppliers List

Company Price and Availability Country/Region
Andard-Mount Company Limited UNITED KINGDOM
Baoji Herbest Bio-Tech Co., Ltd. China
CHEMSCENE, LLC USA
MedChemexpress Co., Ltd. 1g/USD120(In stock);5g/USD480(In stock) USA
Selleck Chemicals LLC USA
Shanghai Haoyuan Chemexpress Co., Ltd. 1g/USD120(In stock);5g/USD480(In stock) China
Target Molecule Corp. 10mg/USD89();25mg/USD146();50mg/USD209() USA
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Related Products

Other Forms of 484-20-8

Name CAS No Formula MW

Recommended Compounds in Autophagy Cytochrome P450

Name CAS No Formula MW
Pirarubicin (Hydrochloride) 95343-20-7 C32H38ClNO12 664.1
Berberine (chloride hydrate) 141433-60-5 C20H18ClNO4 371.81
DMH-1 1206711-16-1 C24H20N4O 380.44
CB-839 1439399-58-2 C26H24F3N7O3S 571.57
H 89 (hydrochloride) 130964-39-5 C20H22BrCl2N3O2S 519.28
Shikonin 517-89-5 C16H16O5 288.3
H 89 127243-85-0 C20H20BrN3O2S 446.36
Eupatilin 22368-21-4 C18H16O7 344.32
Isoalantolactone 470-17-7 C15H20O2 232.32
Scutellarein 529-53-3 C15H10O6 286.24
Leonurine 24697-74-3 C14H21N3O5 311.33
Berbamine (hydrochloride) 6078-17-7 C37H42Cl2N2O6 681.65
Ruxolitinib (S enantiomer) 941685-37-6 C17H18N6 306.37
D-Glucosamine (Hydrochloride) 66-84-2 C6H14ClNO5 215.63
Schizandrin A 61281-38-7 C22H28O6 388.45
Schisandrol B 58546-54-6 C23H28O7 416.46
Schisandrol A 7432-28-2 C24H32O7 432.51
Anhydroicaritin 118525-40-9 C21H20O6 368.38
Bicyclol 118159-48-1 C19H18O9 390.34
Azithromycin (hydrate) 117772-70-0 C38H72N2O12 748.98

Recommended Compounds in Same Indication

Name CAS No Formula MW
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Route of Synthesis

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References

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More Information

Bergapten

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