Penitrem ACAS# 12627-35-9 |
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Quality Control & MSDS
3D structure
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| Cas No. | 12627-35-9 | SDF | Download SDF |
| PubChem ID | 337313 | Appearance | Powder |
| Formula | C37H44ClNO6 | M.Wt | 634.2 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble in DMSO > 10 mM | ||
| SMILES | CC(=C)C1C(C2C3(O2)C(O1)CCC4(C3(CCC5C4(C6=C7C5OC(C8CC9C8(C1=C7C(=CC(=C1CC9=C)Cl)N6)O)(C)C)C)O)C)O | ||
| Standard InChIKey | JDUWHZOLEDOQSR-JHMXYHNCSA-N | ||
| Standard InChI | InChI=1S/C37H44ClNO6/c1-15(2)28-27(40)31-37(45-31)23(43-28)9-10-33(6)34(7)18(8-11-35(33,37)41)29-25-24-21(39-30(25)34)14-20(38)17-12-16(3)19-13-22(32(4,5)44-29)36(19,42)26(17)24/h14,18-19,22-23,27-29,31,39-42H,1,3,8-13H2,2,4-7H3/t18-,19+,22+,23-,27-,28+,29-,31-,33+,34+,35-,36?,37+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Potent and selective blocker of BKCa (KCa1.1) channels (IC50 values are 6.4 and 64.4 nM for BKCa channels containing α subunits only, and those containing α and β1 respectively). Displays no effect on native delayed rectifier K+ and KATP currents, or cloned KV1.5 channels. Blocks BKCa channels in both inside-out and cell-attached patches. Shown to enhance smooth muscle contraction in vitro and increase total peripheral resistance in vivo. |
Penitrem A Dilution Calculator
Penitrem A Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.5768 mL | 7.8839 mL | 15.7679 mL | 31.5358 mL | 39.4197 mL |
| 5 mM | 0.3154 mL | 1.5768 mL | 3.1536 mL | 6.3072 mL | 7.8839 mL |
| 10 mM | 0.1577 mL | 0.7884 mL | 1.5768 mL | 3.1536 mL | 3.942 mL |
| 50 mM | 0.0315 mL | 0.1577 mL | 0.3154 mL | 0.6307 mL | 0.7884 mL |
| 100 mM | 0.0158 mL | 0.0788 mL | 0.1577 mL | 0.3154 mL | 0.3942 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Astaxanthin and Docosahexaenoic Acid Reverse the Toxicity of the Maxi-K (BK) Channel Antagonist Mycotoxin Penitrem A.[Pubmed:27834847]
Mar Drugs. 2016 Nov 9;14(11). pii: md14110208.
Penitrem A (PA) is a food mycotoxin produced by several terrestrial and few marine Penicillium species. PA is a potent tremorgen through selective antagonism of the calcium-dependent potassium BK (Maxi-K) channels. Discovery of natural products that can prevent the toxic effects of PA is important for food safety. Astaxanthin (AST) is a marine natural xanthophyll carotenoid with documented antioxidant activity. Unlike other common antioxidants, AST can cross blood brain barriers (BBBs), inducing neuroprotective effects. Docosahexaenoic acid (DHA) is polyunsaturated omega-3 fatty acid naturally occurring in fish and algae. DHA is essential for normal neurological and cellular development. This study evaluated the protective activity of AST and DHA against PA-induced toxicity, in vitro on Schwann cells CRL-2765 and in vivo in the worm Caenorhbitidis elegans and Sprague Dawley rat models. PA inhibited the viability of Schwann cells, with an IC50 of 22.6 muM. Dose-dependent treatments with 10-100 muM DHA significantly reversed the PA toxicity at its IC50 dose, and improved the survival of Schwann cells to 70.5%-98.8%. Similarly, dose-dependent treatments with 10-20 muM AST reversed the PA toxicity at its IC50 dose and raised these cells' survival to 61.7%-70.5%. BK channel inhibition in the nematode C. elegans is associated with abnormal reversal locomotion. DHA and AST counteracted the in vivo PA BK channel antagonistic activity in the C. elegans model. Rats fed a PA-contaminated diet showed high levels of glutamate (GLU), aspartate (ASP), and gamma amino butyric acid (GABA), with observed necrosis or absence of Purkinjie neurons, typical of PA-induced neurotoxicity. Dopamine (DA), serotonin (5-HT), and norepinephrine (NE) levels were abnormal, Nitric Oxide (NO) and Malondialdehyde (MDA) levels were significantly increased, and total antioxidant capacity (TAC) level in serum and brain homogenates was significantly decreased in PA-treated rats. DHA and AST treatments effectively counteracted the toxic effects of PA and normalized most biochemical parameters in rats. DHA and AST can be useful food additives to prevent and reverse PA food-induced toxicity.
Synthetic studies toward penitrem E: enantiocontrolled construction of B-E rings.[Pubmed:25452109]
Chem Commun (Camb). 2015 Jan 21;51(6):1070-3.
Enantiocontrolled construction of B-E rings of penitrem E was accomplished from 4-iodoindole in 13 steps with an overall yield of 1.7%. Diastereoselective Tf2NH-catalyzed (2+2)-cycloaddition between silyl enol ether and methyl acrylate furnished a tetracyclic product possessing the characteristic cyclobutane ring bearing a hydroxyl group.
Mechanisms of penitrem-induced cerebellar granule neuron death in vitro: possible involvement of GABAA receptors and oxidative processes.[Pubmed:23313729]
Neurotoxicology. 2013 Mar;35:129-36.
The fungal neurotoxin Penitrem A has previously been found to cause neurological disorders in animals and humans after ingestion of contaminated food and/or feed. It penetrates the blood-brain-barrier and causes cerebellar pathology in rats, including mild effects on granule neurons. The aim of the current study was to investigate the potential toxicity of Penitrem A in rat cerebellar granule neurons in vitro, and to examine the involvement of the GABAA, AMPA and NMDA receptors, intracellular signalling pathways as well as the role of oxidative stress in Penitrem A-induced neuronal death. Cerebellar granule cells were exposed to Penitrem A, alone or together with different pharmacological agents, before cell survival was assessed with the MTT assay or formation of reactive oxygen species (ROS) was investigated with the DCF assay. Penitrem A caused a time- and concentration-dependent reduction in cell survival, as well as a concentration-dependent increase in ROS production. Co-incubation with diazepam, GABA, BAPTA-AM, vitamin E, SP600125 and cyclosporine A significantly reduced cell death. Our results show that Penitrem A is toxic to cerebellar granule neurons in vitro. Further, ROS production and the GABAA receptor are likely to be involved in the induction of neuronal death following Penitrem A exposure. A disruption of calcium homeostasis and activation of the JNK pathway may also play a role in Penitrem A neurotoxicity.
Reconstitution of biosynthetic machinery for the synthesis of the highly elaborated indole diterpene penitrem.[Pubmed:25831977]
Angew Chem Int Ed Engl. 2015 May 4;54(19):5748-52.
Penitrem A is one of the most elaborated members of the fungal indole diterpenes. Two separate penitrem gene clusters were identified using genomic and RNA sequencing data, and 13 out of 17 transformations in the penitrem biosynthesis were elucidated by heterologous reconstitution of the relevant genes. These reactions involve 1) a prenylation-initiated cationic cyclization to install the bicyclo[3.2.0]heptane skeleton (PtmE), 2) a two-step P450-catalyzed oxidative processes forming the unique tricyclic penitrem skeleton (PtmK and PtmU), and 3) five sequential oxidative transformations (PtmKULNJ). Importantly, without conventional gene disruption, reconstitution of the biosynthetic machinery provided sufficient data to determine the pathway. It was thus demonstrated that the Aspergillus oryzae reconstitution system is a powerful method for studying the biosynthesis of complex natural products.
