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| Targets |
Hypericin targets multiple cellular enzymes and signaling pathways. It is an inhibitor of protein kinase C (PKC), monoamine oxidase (MAO), dopamine-beta-hydroxylase, reverse transcriptase, telomerase, and cytochrome P450. Hypericin inhibits tyrosine kinases with an IC₅₀ of 7.5 μM. It also inhibits neuronal uptake of serotonin, norepinephrine, dopamine, GABA, and L-glutamate, contributing to its antidepressant effects. Additionally, hypericin inhibits RANKL-mediated osteoclastogenesis via affecting ERK signaling.
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| ln Vitro |
The development of melanocytes (Mc), cultured cells (Kc), and cell fibers (Fb) is enhanced by hypericin (0.25–4 μM; 24 h) [2]. Treatment with hypericin (3 μM; 24 h) can cause cell transplantation.
In vitro, hypericin exhibits potent phototoxic activity against various cancer cell lines, inducing both apoptosis and necrosis in a concentration- and light dose-dependent fashion. The compound inhibits the replication of enveloped viruses by suppressing the assembly and shedding of viral particles within infected cells. Hypericin shows antitumor activity through multiple mechanisms, including PKC inhibition and induction of photosensitized apoptosis. It also inhibits RANKL-mediated osteoclastogenesis in vitro. |
| ln Vivo |
Treatment with hypericin (intravenous injection; 10 mg/kg; once) slows the growth of tumors [3].
In vivo, hypericin (SGX301) is being developed as a topical photodynamic therapy for the treatment of cutaneous T-cell lymphoma (CTCL) and other skin conditions. The compound is applied topically and activated by safe visible fluorescent light, selectively destroying diseased cells while sparing healthy tissue. In animal models, hypericin has demonstrated efficacy in suppressing wear particle-induced osteolysis. The compound also exhibits antidepressant effects in preclinical models. |
| Enzyme Assay |
Non-cellular enzyme assays for hypericin involve assessing its inhibition of various target enzymes using purified preparations. PKC activity is measured using a kinase assay with a peptide substrate and [γ-³²P]ATP, with hypericin incubated at varying concentrations. MAO activity is assessed using a fluorometric assay with kynuramine as substrate. Dopamine-beta-hydroxylase inhibition is measured using a radiometric assay with [¹⁴C]tyramine. IC₅₀ values are determined from dose-response curves for each enzyme target.
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| Cell Assay |
Cell viability assay [2]
Cell Types: fibroblasts (Fb), melanocytes (Mc) and keratinocytes (Kc). Tested Concentrations: 0.25 μM; [2]. 0.5μM; 1μM; 2μM; 3μM; 4 μM Incubation Duration: 24 hrs (hours) Experimental Results: The LD50 of Fb and Mc were 1.75 μM and 3.5 μM respectively, and the LD50 dose of Kc was greater than 4 μM. Apoptosis analysis[2] Cell Types: Fibroblasts (Fb), Melanocytes (Mc) and Keratinocytes (Kc) Tested Concentrations: 3 μM Incubation Duration: 24 hrs (hours) Experimental Results: Significant (p<0.001) an early apoptotic Fb population (64%), and a smaller, significant (p<0.05) early apoptotic Mc population (20%). In vitro cellular assays for hypericin involve treating cancer cell lines with the compound and assessing phototoxicity. Cells are incubated with varying concentrations of hypericin for 2-24 hours, then exposed to visible light (e.g., 590 nm, 1-5 J/cm²). Cell viability is measured using MTT or CellTiter-Glo® assays 24 hours post-irradiation. Apoptosis is assessed by flow cytometry using Annexin V/PI staining. ROS production is measured using fluorescent probes such as DCFH-DA. The IC₅₀ for phototoxicity is determined from dose-response curves. |
| Animal Protocol |
Animal/Disease Models: 18-20 week old female balb/c (Bagg ALBino) mouse were injected with CT26 cancer [3]
Doses: 10 mg/kg Route of Administration: intravenous (iv) (iv)injection; 10 mg/kg; Experimental Results:Compared with the control group, tumor growth was delayed Four times. In vivo animal experiments with hypericin are conducted in mouse xenograft models of cancer for PDT efficacy studies. Tumor-bearing mice are treated with topical or systemic hypericin, followed by illumination of the tumor area with visible light at specific wavelengths (590-610 nm). Tumor growth inhibition is monitored by caliper measurements. In models of cutaneous T-cell lymphoma, the compound is applied topically to skin lesions and activated by light. Pharmacokinetic and toxicological studies are also conducted in rodents. |
| ADME/Pharmacokinetics |
Hypericin has a molecular weight of 504.44 and a molecular formula of C₃₀H₁₆O₈. It is a dark red to black crystalline powder with a purity of ≥98%. The compound is typically stored at -20°C, protected from light. Hypericin is poorly soluble in water but soluble in DMSO and other organic solvents. Following topical application, systemic absorption is minimal. When administered systemically, the compound has a half-life of approximately 24-48 hours and is primarily excreted in feces.
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| Toxicity/Toxicokinetics |
Hypericin is generally well-tolerated at therapeutic doses. The primary toxicity concern is phototoxicity, as the compound can cause skin photosensitization upon exposure to light. Patients using hypericin-containing products should avoid excessive sun exposure. In preclinical studies, the compound has shown low acute toxicity with no significant organ toxicity at therapeutic doses. The compound is not approved for systemic use in most countries.
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| References | |
| Additional Infomation |
Hypericin is a polycyclic aromatic hydrocarbon with antidepressant properties. It is derived from the hydride of bianthracite. Hypericin is being investigated for the treatment of cutaneous T-cell lymphoma. It has been reported to be found in plants of the Hypericum genus (such as Hypericum perforatum and Hypericum pubescens) and other organisms with relevant data. Hypericin is an anthraquinone derivative naturally found in the yellow flowers of St. John's wort, possessing antidepressant, potential antiviral, antitumor, and immunostimulatory activities. Hypericin appears to inhibit the uptake of serotonin, norepinephrine, dopamine, gamma-aminobutyric acid (GABA), and L-glutamate by neurons, which may contribute to its antidepressant effects. Hypericin may inhibit the replication of exfoliated viruses by suppressing the assembly and shedding of viral particles within infected cells. Furthermore, this substance can exert potent phototoxic effects by triggering the apoptosis signaling pathway to produce reactive oxygen species.
Hypericin (SGX301) is being developed by Soligenix as a topical photodynamic therapy for cutaneous T-cell lymphoma. It has received Orphan Drug designation from the FDA and has completed Phase 3 clinical trials. The compound is also being investigated for the treatment of psoriasis and other skin conditions. Hypericin’s mechanism of action involves light-activated production of reactive oxygen species, leading to selective destruction of diseased cells. The compound is available from various commercial suppliers for research applications. |
| Molecular Formula |
C30H16O8
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|---|---|
| Molecular Weight |
504.45
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| Exact Mass |
504.084
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| CAS # |
548-04-9
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| Related CAS # |
Hypericin-d2;Hypericin-d10
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| PubChem CID |
3663
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| Appearance |
Brown to black solid powder
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| Density |
1.9±0.1 g/cm3
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| Boiling Point |
930.1±65.0 °C at 760 mmHg
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| Melting Point |
299-301°C
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| Flash Point |
530.1±30.8 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
2.131
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| LogP |
8.39
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
38
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| Complexity |
1090
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
YDOIFHVUBCIUHF-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,33-38H,1-2H3
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| Chemical Name |
9,11,13,16,18,20-hexahydroxy-5,24-dimethyloctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(26),2,4(25),5,8,10,12,14(28),15(27),16,18,20,23-tridecaene-7,22-dione
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| Synonyms |
SGX-301 SGX301 SGX 301 NSC 622946 NSC 407313 hypericin.
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~495.60 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.08 mg/mL (4.12 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.08 mg/mL (4.12 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.9824 mL | 9.9118 mL | 19.8236 mL | |
| 5 mM | 0.3965 mL | 1.9824 mL | 3.9647 mL | |
| 10 mM | 0.1982 mL | 0.9912 mL | 1.9824 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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