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| ln Vitro |
Variegated cystine-induced DNA damage triggers the ATM/53-dependent signaling pathway, which in turn helps GES-1 cells enter G2 arrest [4].
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| ln Vivo |
p21WAF1/CIP1 is inhibited by meterocystine (ip; 3 mg/kg once daily for 14 days) [3].
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
In rats given a single ip injection of 6.4 mg/animal (14)C-sterigmatocystin in DMSO, 5.6% of the activity was found in the urine, 67% in the feces and GI tract and 11% in the liver after 12 hours. These levels declined slightly after 24 hr. In fasted or non-fasted rats given 1.4 mg/animal (3)H-sterigmatocystin orally, the highest activity after 16 hr was found in the feces and GI tract; lesser amounts were found in the urine, blood, expired air, liver and kidneys. Metabolism / Metabolites In Vervet monkeys the major urinary metabolite was identified as sterigmatocystin-beta-d-glucuronide, which accounted for 75% of the oral dose administered. Sterigmatocystin was covalently bound to calf thymus DNA by incubation with phenobarbital-induced rat liver microsomes. The adduct was identified as 1,2-dihydro-2-(N7-guanyl)-1-hydroxysterigmatocystin. The structure and stereochemistry of this adduct indicated that the exo-sterigmatocystin-1,2-oxide was the metabolite that reacted with DNA, and the quantitative yield of adduct indicated that this metabolite was a major product of the in vitro metabolism of sterigmatocystin. The species sensitivity to sterigmatocystin toxicity was in the order: monkey greater than rat greater than mouse. It was postulated that these differences were due to species differences in liver sterigmatocystin distribution, sterigmatocystin 2,3-epoxide formation from sterigmatocystin and drug-metabolizing enzymes in the liver microsome. /Sterigmatocystin is/ activated by /a/ human P450 enzyme, CYP3A4. /From table/ |
| Toxicity/Toxicokinetics |
Non-Human Toxicity Values
LD50 Monkey (vervet) ip 32 mg/kg bw dissolved in dimethylsulfoxide. LD50 Rat (male) oral (10 days) 166 mg/kg bw when the cmpd was dissolved in dimethylformamide. LD50 Rat (female) oral (10 days) 120 mg/kg bw, when it was dissolved in wheat-germ oil. LD50 Rat (male) ip 60-65 mg/kg bw, depending on the solvent used. LD50 Mouse oral 800 mg/kg |
| References |
[1]. Kusunoki M, et al. Long-term administration of the fungus toxin, sterigmatocystin, induces intestinal metaplasia and increases the proliferative activity of PCNA, p53, and MDM2 in the gastric mucosa of aged Mongolian gerbils. Environ Health Prev Med. 2011 Jul;16(4):224-31.
[2]. Schroeder HW, et al. Production of sterigmatocystin by some species of the genus Aspergillus and its toxicity to chicken embryos. Appl Microbiol. 1975 Oct;30(4):589-91. [3]. Tong YF, et al. Cyclin-Dependent Kinase Inhibitor p21WAF1/CIP1 Facilitates the Development of CardiacHypertroph. Cell Physiol Biochem. 2017;42(4):1645-1656. [4]. Zhang D, et al. Sterigmatocystin-induced DNA damage triggers G2 arrest via an ATM/p53-related pathway in human gastric epithelium GES-1 cells in vitro. PLoS One. 2013 May 21;8(5):e65044. |
| Additional Infomation |
Sterigmatocystin can cause cancer according to an independent committee of scientific and health experts.
Sterigmatocystin is an organic heteropentacyclic compound whose skeleton comprises a xanthene ring system ortho-fused to a dihydrofuranofuran moiety. The parent of the class of sterigmatocystins. It has a role as a metabolite. It is functionally related to a dihydrodemethylsterigmatocystin. Sterigmatocystin has been reported in Aspergillus amstelodami, Aspergillus multicolor, and other organisms with data available. A carcinogenic mycotoxin produced in high yields by strains of the common molds, Aspergillus versicolor, A. nidulans, and an unidentified species of Bipolaris. It causes necrosis of the liver and kidney and has an inhibitory effect on orotic acid incorporation into nuclear RNA. |
| Molecular Formula |
C18H12O6
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|---|---|
| Molecular Weight |
324.28
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| Exact Mass |
324.063
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| CAS # |
10048-13-2
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| PubChem CID |
5280389
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| Appearance |
Pale-yellow crystals
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
569.7±50.0 °C at 760 mmHg
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| Melting Point |
246ºC with decomp
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| Flash Point |
215.9±23.6 °C
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| Vapour Pressure |
0.0±1.6 mmHg at 25°C
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| Index of Refraction |
1.686
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| LogP |
1.62
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
24
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| Complexity |
562
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| Defined Atom Stereocenter Count |
2
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| SMILES |
O=C1C2=C(OC3=C1C(O)=CC=C3)C4=C(O[C@]5([H])[C@@]4([H])C=CO5)C=C2OC
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| InChi Key |
UTSVPXMQSFGQTM-DCXZOGHSSA-N
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| InChi Code |
InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
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| Chemical Name |
(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one
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| Synonyms |
NSC-201423; Sterigmatocystine; Sterigmatocystin
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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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 : ~25 mg/mL (~77.09 mM)
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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 | 3.0838 mL | 15.4188 mL | 30.8375 mL | |
| 5 mM | 0.6168 mL | 3.0838 mL | 6.1675 mL | |
| 10 mM | 0.3084 mL | 1.5419 mL | 3.0838 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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