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| Targets |
Terrein targets multiple signaling pathways. It inhibits Akt and ERK (extracellular signal-regulated kinase). Terrein blocks NF-κB activation. It reduces melanin levels by inhibiting tyrosinase protein production via extracellular signal-regulated protein kinase (ERK) activation. ERK activation is followed by microphthalmia-associated transcription factor (MITF) down regulation, which is required for tyrosinase expression.
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| ln Vitro |
After four days of treatment with Terrein (10-100 µM), Mel-Ab cells' melanin levels were considerably lowered in a dose-dependent manner. By inhibiting the synthesis of tyrosinase via ERK activation, terrein lowers the synthesis of melanin [1]. Terrein (5–500 µM; 24 and 48 hours) decreases these cells' viability in a way that is dependent on both concentration and time [2]. Both invasive and non-invasive breast cancer cell lines experience programmed cell death when exposed to terrein (150, 250, or 500μM; 24 hours). As a result, in later studies, Terrein's ideal non-toxic values of 25 and 75 µM were employed [2]. In MDA-MB-231 cells, terrein (25 and 75 µM) dramatically lowered the MMP-2 and MMP-9 mRNA levels. In MCF-7 cells, terrein (75 µM) dramatically lowers the amounts of MMP-2 and MMP-9 mRNA [2]. In MCF-7 cells, terrein (75 µM) suppresses the expression of RhoA, RhoB, and p-Rac1. In MDA-MB-231 cells, terrein (75 µM) suppresses the expression of p-Rac1 and RhoB [2]. Pseudomonas aeruginosa PAO1 and PA14 bacteria' biofilm formation and the synthesis of virulence components such elastase, pyocyanin, and rhamnolipid are inhibited by terrein (10, 30 and 100 μM) [3].
Terrein exhibits antibacterial activities. It reduces melanin levels in a dose-dependent manner and inhibits tyrosinase protein production. Terrein inhibits melanin synthesis by reducing tyrosinase production via ERK activation. It shows antiproliferative and anti-inflammatory effects. Terrein induces G2/M cell cycle arrest. Specific IC50 values for these activities are not extensively detailed in standard reference sources. |
| ln Vivo |
Specific in vivo efficacy data for terrein are not extensively detailed in standard reference sources. Given its anti-inflammatory and antioxidant properties, it has been investigated for possible therapeutic applications in chronic inflammatory conditions and cancer research. Studies in animal models of inflammation or cancer would be required to further evaluate its in vivo activity, though such data are not widely available in the public domain.
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| Enzyme Assay |
Terrein's enzyme inhibitory activity can be assessed using in vitro kinase assays. For ERK inhibition, recombinant ERK enzyme is incubated with its substrate (e.g., myelin basic protein) and ATP in the presence of varying concentrations of terrein. The amount of phosphorylated substrate is measured using a suitable detection method (e.g., ELISA, fluorescence, or radioactive counting) to determine the IC50. For Akt inhibition, similar assays with recombinant Akt and a specific peptide substrate are performed. NF-κB activation can be studied using electrophoretic mobility shift assay (EMSA) or reporter gene assays in cell lysates.
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| Cell Assay |
Cell Viability Assay[2]
Cell Types: MCF-7 and MDA-MB-231 Cell Tested Concentrations: 5, 25, 50, 75, 100, 150, 250, 500 µM Incubation Duration: 24 and 48 hrs (hours) Experimental Results: IC50 incubation of MCF After 24 hrs (hours), the concentrations for -7 and MDA-MB-231 cells were 2.34 mM and 700 µM, respectively. After 48 hrs (hours) of incubation, the IC50 was 244.3 µM for MCF-7 cells and 244.5 µM for MDA-MB-231 cells. Apoptosis analysis[2] Cell Types: MCF-7 and MDA-MB-231 Cell Tested Concentrations: 25, 75, 150, 250, 500 µM Incubation Duration: 24 hrs (hours) Experimental Results: The percentage of apoptotic cells after 25 and 75 µM treatment was 7.52 MCF-7 cells were 15.77% and 5.82% (control was 9.94%), and MDA-MB-231 cells were 15.77% and 15.82% (control was 8.79%). RT-PCR[2] Cell Types: MCF-7 and MDA-MB-231 Cell Tested Concentrations: 25, 75 µM Incubation Duration: Experimental Results: diminished MMP-2 and MMP-9 mRNA levels in a concentration-dependent manner. Western Blot Analysis[2] Cell Types: MCF-7 and MDA-MB-231 Cell Tested Concentrations: 75 µM Incubation Duration: 6, 12 and 24 hrs (hours) Experimental Results: RhoA and RhoB protein levels were Dramatically diminished after 6 h of 75 µM treatment in MCF-7 cells. Phosphorylated (p)-Rac1 was also slightly diminished at 12 h. However, RhoC and Cdc42 levels remained unchanged. RhoB protein levels and Rac1 phosphorylation were also diminished in MDA-MB-231 cells at 12 and 24 h, respectively. The anti-melanogenic activity of terrein is evaluated in vitro using B16 mouse melanoma cells. Cells are treated with terrein at various concentrations for a defined period (e.g., 48-72 hours) in the presence or absence of melanocyte-stimulating hormone (α-MSH). Melanin content is measured spectrophotometrically at 405 nm after cell lysis. Tyrosinase activity is assessed by measuring the oxidation of L-DOPA to dopachrome at 475 nm. Protein expression of tyrosinase, TRP-1, TRP-2, and MITF is analyzed by Western blot. Cell viability is assessed using MTT assay to distinguish anti-melanogenic effects from cytotoxicity. |
| Animal Protocol |
Specific in vivo animal experimental protocols for terrein are not extensively detailed in standard reference sources. For evaluating its anti-inflammatory properties, animal models such as carrageenan-induced paw edema in rats or DSS-induced colitis in mice could be used. Terrein would be administered orally or intraperitoneally at various doses, and inflammation markers (e.g., paw swelling, histological scores, cytokine levels) would be measured to assess efficacy.
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| ADME/Pharmacokinetics |
Terrein is soluble in water (1-1.10 mg/mL) and DMSO. It should be stored at -20°C and protected from light. Its SMILES string is OC1C(C(=O)C=C1\C=C\C)O. Specific pharmacokinetic parameters such as half-life, bioavailability, and plasma protein binding are not extensively detailed in standard reference sources.
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| Toxicity/Toxicokinetics |
The toxicity profile of terrein is not extensively documented. As a natural fungal metabolite with diverse biological activities, its safety profile would need to be established through standard toxicological studies. Terrein is classified as a combustible solid. Specific LD50 values and organ-specific toxicity data are not readily available in the public domain.
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| References |
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| Additional Infomation |
Terine is a polyol. It has been reported to be found in Aspergillus stellaria, Streptomyces, and other organisms with relevant data.
Terrein (CAS# 582-46-7) is a bioactive fungal metabolite with a purity of ≥98% (HPLC). It has been extensively studied for its diverse biological activities including anti-inflammatory, anti-oxidative, and anti-melanogenic effects. Terrein shows potential in agricultural research as an elicitor of plant defenses against pathogens. Its inhibition of melanin synthesis makes it a valuable tool for studying pigmentation pathways. |
| Molecular Formula |
C8H10O3
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| Molecular Weight |
154.165
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| Exact Mass |
154.063
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| CAS # |
582-46-7
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| PubChem CID |
6436830
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.449g/cm3
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| Boiling Point |
327.2ºC at 760mmHg
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| Flash Point |
165.9ºC
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| Index of Refraction |
1.713
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| LogP |
-0.6
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
11
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| Complexity |
228
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C/C=C/C1=CC(=O)[C@@H]([C@H]1O)O
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| InChi Key |
MHOOPNKRBMHHEC-HZIBQTDNSA-N
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| InChi Code |
InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1
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| Chemical Name |
(4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
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| Synonyms |
NSC 291308; Terrain; (+)Terrein
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.4863 mL | 32.4317 mL | 64.8635 mL | |
| 5 mM | 1.2973 mL | 6.4863 mL | 12.9727 mL | |
| 10 mM | 0.6486 mL | 3.2432 mL | 6.4863 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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