PERYLENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H12
Molecular Weight	252.3093
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1=CC2=CC=CC3=C2C(=C1)C4=CC=CC5=CC=CC3=C45

InChI

InChIKey=CSHWQDPOILHKBI-UHFFFAOYSA-N

InChI=1S/C20H12/c1-5-13-6-2-11-17-18-12-4-8-14-7-3-10-16(20(14)18)15(9-1)19(13)17/h1-12H

HIDE SMILES / InChI

Molecular Formula	C20H12
Molecular Weight	252.3093
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Perylene diimide G-quadruplex DNA binding selectivity is mediated by ligand aggregation.	2002-02-11	11814817
Improved procedure for the quality control of Hypericum perforatum L.	2002-01-17	11793812
Biodistribution of hypericin in orthotopic transitional cell carcinoma bladder tumors: implication for whole bladder wall photodynamic therapy.	2002-01-10	11774272
Analysis of agricultural commodities and foods for Alternaria mycotoxins.	2002-01-05	11767150
Separation of hypericins and hyperforins in extracts of Hypericum perforatum L. using non-aqueous capillary electrophoresis with reversed electro-osmotic flow.	2002-01-01	11682223
Transferrin-mediated targeting of hypericin embedded in sterically stabilized PEG-liposomes.	2002-01	11743662
Hypericin and hypocrellin induced apoptosis in human mucosal carcinoma cells.	2001-12-01	11748006
Photogeneration of singlet oxygen (1O2) and free radicals (Sen-, O2-) by tetra-brominated hypocrellin B derivative.	2001-12	11811528
CD and melting curves structural studies of the tandem DNA complex formed with oligonucleotides carrying photoactive and sensitizing groups in the nick region.	2001-12	11790149
Saint John's wort: an in vitro analysis of P-glycoprotein induction due to extended exposure.	2001-12	11739235
Development of a simple, rapid and reproducible HPLC assay for the simultaneous determination of hypericins and stabilized hyperforin in commercial St. John's wort preparations.	2001-12	11600308
Butylamino-demethoxy-hypocrellins and photodynamic therapy decreases human cancer in vitro and in vivo.	2001-11-29	11731224
Inhibition of c-erbB-2 expression an activity in human ovarian carcinoma cells by hypericin.	2001-11-29	11724334
Blepharismins, produced by the protozoan, Blepharisma japonicum, form ion-permeable channels in planar lipid bilayer membranes.	2001-11-23	11728465
Simple and accurate computations of solvatochromic shifts in pi --> pi* transitions of aromatic chromophores.	2001-11-14	11697965
Cleavage of telomeric G-quadruplex DNA with perylene-EDTA*Fe(II).	2001-11-13	11695914
[Experimental cultivation of Hypericum perforatum L. in Bratislava].	2001-11	11797201
Photosensitization mechanism of active species by the complex of hypocrellin B with aluminum ion.	2001-11	11767418
Chelation of hypocrellin B with zinc ions with electron paramagnetic resonance (EPR) evidence of the photodynamic activity of the resulting chelate.	2001-11	11767412
Evolution of absorption, fluorescence, laser and chemical properties in the series of compounds perylene, benzo(ghi)perylene and coronene.	2001-11	11765794
A study of hypericin-induced teratogenicity during organogenesis using a whole rat embryo culture model.	2001-11	11704142
Induction of apoptosis by Hypericin through activation of caspase-3 in human carcinoma cells.	2001-11	11605021
Over-expression of the cercosporin facilitator protein, CFP, in Cercospora kikuchii up-regulates production and secretion of cercosporin.	2001-10-16	11682184
Catalytic inhibition of human DNA topoisomerase IIalpha by hypericin, a naphthodianthrone from St. John's wort (Hypericum perforatum).	2001-10-15	11597574
Design of multidye systems for FRET-based applications.	2001-09-21	11563049
Photodynamic therapy of murine fibrosarcoma with topical and systemic administration of hypericin.	2001-09	11695874
A systematic review and meta-analysis of Hypericum perforatum in depression: a comprehensive clinical review.	2001-09	11552767
St John's wort, hypericin, and imipramine: a comparative analysis of mRNA levels in brain areas involved in HPA axis control following short-term and long-term administration in normal and stressed rats.	2001-09	11526469
Synthesis of a novel hypocrellin B derivative and its photogeneration of semiquinone anion radical.	2001-08-30	11535411
EPR investigation of the free radicals generated during the photosensitization of TiO2 colloid by hypocrellin B.	2001-08	11697194
Tumor-specific and photodependent cytotoxicity of hypericin in the human LNCaP prostate tumor model.	2001-08	11547559
Tumor cell toxicity of hypericin and related analogs.	2001-08	11547558
Toward hypericin-derived potential photodynamic therapy agents.	2001-08	11547557
The structure of hypericin in solution. Searching for hypericin's 1,6 tautomer.	2001-08	11547556
Synthesis, characterization and photodynamic activity of amino-substituted hypocrellin derivatives.	2001-08	11547555
Spectroscopic study of visible-light effects on hypericin-lens proteins systems.	2001-08	11547554
Photosensitization of hypomycin B--a novel perylenequinonoid pigment with only one intramolecular hydrogen bond.	2001-08	11547553
Photobleaching of hypocrellin B and its butylamino-substituted derivative in solutions.	2001-08	11547552
Interaction of hypericin with serum albumins: surface-enhanced Raman spectroscopy, resonance Raman spectroscopy and molecular modeling study.	2001-08	11547551
In vitro study of the photocytotoxicity of some hypericin analogs on different cell lines.	2001-08	11547550
Identification of a vibrational frequency corresponding to H-atom translocation in hypericin.	2001-08	11547549
Hypericin derivatives: substituent effects on radical-anion formation.	2001-08	11547548
Effect of structural modification on photodynamic activity of hypocrellins.	2001-08	11547547
Different pathways mediate cytochrome c release after photodynamic therapy with hypericin.	2001-08	11547546
Cellular photodestruction induced by hypericin in AY-27 rat bladder carcinoma cells.	2001-08	11547545
Anti-cancer activities of hypericin in the dark.	2001-08	11547544
Variability in the content of the constituents of Hypericum perforatum L. and some commercial extracts.	2001-07	11548855
[Hyperici herba (Hypericum perforatum L].	2001	11769089
Intracellular localisation of hypericin in human glioblastoma and carcinoma cell lines.	2001	11702633
Final report on the safety assessment of Hypericum perforatum extract and Hypericum perforatum oil.	2001	11558639

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:15:22 GMT 2025` Edited by `admin` on `Mon Mar 31 19:15:22 GMT 2025`
Record UNII	5QD5427UN7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PERYLENE

Systematic Name

English

NSC-6512

Preferred Name

English

PERILENE

Common Name

English

PERYLENE [HSDB]

Common Name

English

PERYLENE [IARC]

Common Name

English

PERYLENE [MI]

Common Name

English

PERI-DINAPHTHALENE

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

205-900-9