Dihydroergocristine Mesylate
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-03865 |
| CAS | 24730-10-7 |
| Molecular Weight | 707.84 |
| Molecular Formula | C35H45N5O8S |
| Purity | ≥96% |
Online Inquiry
Description
Dihydroergocristine Mesylate, an ergotamine derivative, has been found to be a 5-HT receptor antagonist and exhibit protective activities to the brain at some extent.
Specification
| Related CAS | 17479-19-5 (free base) |
| Storage | Store at -20°C |
| IUPAC Name | (6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-5,8-dioxo-4-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide;methanesulfonic acid |
| Canonical SMILES | CC(C)C1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CC6C(CC7=CNC8=CC=CC6=C78)N(C5)C.CS(=O)(=O)O |
| InChI | InChI=1S/C35H41N5O5.CH4O3S/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34;1-5(2,3)4/h4-7,9-12,18,20,23,25,27-29,36,44H,8,13-17,19H2,1-3H3,(H,37,41);1H3,(H,2,3,4)/t23-,25-,27-,28+,29+,34-,35+;/m1./s1 |
| InChI Key | SPXACGZWWVIDGR-SPZWACKZSA-N |
Properties
| Appearance | White Solid |
| Boiling Point | 899.3°C at 760 mmHg |
| Melting Point | 198°C (dec.) |
Reference Reading
1. [Cerebral actions of dihydroergocristine]
V Freni, F Mauceri, F Drago, V D'Agata, A A Genazzani, L Nardo, C Valerio Arzneimittelforschung . 1992 Nov;42(11A):1391-4.
Dihydroergocristine (DEC, CAS 17479-19-5) is a dihydrogenated ergot alkaloid with a potent dopaminergic activity that has been proved both in vitro and in vivo. Apart from its effect on the secretion of pituitary hormones, the following actions have been evidenced. It induces stereotyped behaviour and changes in the sleep-waking cycle, and reduces hypoxia-induced cerebral metabolic changes and emesis. The effect of DHEC on behaviour patterns has been studied in aged male rats in comparison with young animals. The acquisition of the active avoidance response in the shuttle-box test and the retention of the passive avoidance response in a step-through passive avoidance task were facilitated in aged rats by an acute treatment with DHEC. The effect on the acquisition and extinction of the pole-jumping performance after a single injection of DHEC at the beginning of the acquisition session was restricted to the first acquisition trial. A more potent effect on the acquisition of the shuttle-box response and on the retention of passive avoidance reaction was found in animals treated subchronically with DHEC. The latter animals also showed a facilitation of acquisition and an inhibition of extinction of the pole-jumping performance. In other experiments, the repeated administration of DHEC was followed by a decrease in the excessive grooming in aged rats, which is considered a sign of the lack of adaptability of these animals. A facilitation of the compensatory mechanisms in experimental models of vertigo has also been found in animals treated with DHEC.
2. In Vitro Effect and Mechanism of Action of Ergot Alkaloid Dihydroergocristine in Chemoresistant Prostate Cancer Cells
Xin Li, Lijuan Bai, Rui Zhao, Daqing Wu, Xiaowei Ma Anticancer Res . 2020 Nov;40(11):6051-6062. doi: 10.21873/anticanres.14626.
Background/aim:Chemoresistance is a major obstacle in the treatment of prostate cancer (PCa). It is imperative to develop novel strategies for overcoming chemoresistance and improving clinical outcomes. We evaluated the in vitro activity and mechanism of action of dihydroergocristine (DHECS), an ergot alkaloid approved for the treatment of dementia, in PCa cells.Materials and methods:The in vitro effects of DHECS on PCa cell cycle and viability were determined by flow cytometry and colorimetric assay. The effects of DHECS on PCa cell signaling were evaluated by quantitative PCR, western blot analysis and reporter assay.Results:DHECS was effective in inducing cell cycle arrest and apoptosis in human PCa cells. Of particular interest, DHECS demonstrated high potency against chemoresistant PCa cells. At the molecular level, DHECS affected multiple factors implicated in the regulation of cancer cell cycle and programmed cell death, including p53, mouse double minute 2 homolog (MDM2), retinoblastoma protein (RB), p21, E2F transcription factor 1 (E2F1), survivin, myeloid cell leukemia 1 (Mcl-1) and poly ADP ribose polymerase (PARP). Furthermore, DHECS may function through dopamine receptor-mediated effects on 5'-AMP-activated protein kinase (AMPK) and nuclear factor kappa B (NF-ĸB).Conclusion:DHECS has the potential to be repurposed as a novel anticancer agent for the management of chemoresistant PCa.
3. Dihydroergocristine and memory alterations of aged male rats
B Scalisi, F Drago, U Scapagnini, V D'Agata, C Valerio Pharmacol Biochem Behav . 1988 Aug;30(4):961-5. doi: 10.1016/0091-3057(88)90127-x.
The ergot alkaloid derivative dihydroergocristine (DHECS) was injected acutely or subchronically to aged male rats of the Sprague-Dawley strain, 26 months old, at the dose of 0.05 or 0.1 mg/kg. Learning and memory ability of the animals were studied with tests of avoidance behavior. The acquisition of active avoidance behavior was studied with the shuttle-box and pole-jumping tasks. In the latter, the extinction of active avoidance behavior was also studied. A step-through type of passive avoidance task was used to examine the retention of passive avoidance responses. The acquisition of the active avoidance behavior and the retention of the passive avoidance response were reduced in aged animals as compared to those of young animals. Acute treatment of old rats with DHECS was followed by a facilitation of acquisition of active avoidance behavior in the shuttle box and of retention of passive avoidance responses in the dark box. The effect on the acquisition and extinction of pole-jumping behavior after a single injection of DHECS at the beginning of the acquisition session was restricted to the first acquisition trial. A more potent effect on the acquisition of the shuttle-box behavior and on the retention of passive avoidance reaction was found in animals treated subchronically with the ergot derivative (0.05 and 0.1 mg/kg for 10 days). These rats also showed a facilitation of acquisition and an inhibition of extinction of pole jumping behavior.
Recommended Products
| BBF-05862 | Epirubicin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-00764 | Cerebroside C | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
