1,3-Bis[2-methyl-2-(phenylthioxomethyl)hydrazide]propanedioic acid
Elesclomol
CAS: 488832-69-5
Molecular Formula: C19H20N4O2S2
1,3-Bis[2-methyl-2-(phenylthioxomethyl)hydrazide]propanedioic acid - Names and Identifiers
| Name | Elesclomol |
| Synonyms | CS-482 STA4783 STA-4783 elesclomol Elesclomol ElescloMol (STA-4783) N1',N3'-dimethyl-N1',N3'-di(phenylcarbonothioyl)malonohydrazide 1,3-Bis[2-methyl-2-(phenylthioxomethyl)hydrazide]propanedioic acid N'~1~,N'~3~-dimethyl-N'~1~,N'~3~-bis(phenylcarbothioyl)propanedihydrazide elescloMol, N'1,N'3-diMethyl-N'1,N'3-di(phenylcarbonothioyl)Malonohydrazide |
| CAS | 488832-69-5 |
| InChI | InChI=1/C19H20N4O2S2/c1-22(18(26)14-9-5-3-6-10-14)20-16(24)13-17(25)21-23(2)19(27)15-11-7-4-8-12-15/h3-12H,13H2,1-2H3,(H,20,24)(H,21,25) |
1,3-Bis[2-methyl-2-(phenylthioxomethyl)hydrazide]propanedioic acid - Physico-chemical Properties
| Molecular Formula | C19H20N4O2S2 |
| Molar Mass | 400.52 |
| Density | 1.313 |
| pKa | 7.99±0.70(Predicted) |
| Storage Condition | -20℃ |
| Refractive Index | 1.667 |
| In vitro study | Using Affymetrix gene chip analysis, Elesclomol treated Hs294T cells at 100 nM for 6 hours significantly induced the expression of heat shock stress response genes and metallothionein genes. Elesclomol (100 nM) treatment of Ramos Burkitt's lymphoma B cells for 1 hour and 6 hours rapidly induced a 4.8-fold and 160-fold increase in Hsp70 RNA levels, respectively, consistent with intracellular ROS content, the content of ROS was increased by 20% and 385 by Elesclomol treatment for 0.5 H and 6 H, respectively, and the antioxidant N-acetylcysteine (NAC) and Tiron pretreatment inhibited the induction of HSP70. 200 nM Elesclomol treatment of HSB2 cells for 18 hours, by inducing oxidative stress, increased early and late apoptotic cells by 3.7 and 11 times, respectively, the above effects can be completely inhibited by NAC, it has no effect on normal cells. Elesclomol significantly inhibited SK-MEL-5, MCF-7, and HL-60 cell viability with IC50 of 110 nM, 24 nM, and 9 nM, respectively. Elesclomol acts on yeast cells to induce copper-dependent ROS production and toxicity. Unlike acting on specific targets in cells, Elesclomol interacts with the electron transport chain (ETC), the electron transport chain is a coherent set of biological processes that occur in the mitochondria to obtain high levels of ROS in the organelles, thus leading to cell death. |
| In vivo study | Although Elesclomol alone at a dose of 25-100 mg/kg treated nude mouse models carrying human breast cancer (MDA435, MCF7 and ZR-75-1), lung cancer (RER) or lymph cancer (U937) had no anticancer activity, but Elesclomol greatly enhances the efficacy of chemotherapy drugs, such as paclitaxel, which can cause tumor decline and also prolong the life of mice. |
1,3-Bis[2-methyl-2-(phenylthioxomethyl)hydrazide]propanedioic acid - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.497 ml | 12.484 ml | 24.968 ml |
| 5 mM | 0.499 ml | 2.497 ml | 4.994 ml |
| 10 mM | 0.25 ml | 1.248 ml | 2.497 ml |
| 5 mM | 0.05 ml | 0.25 ml | 0.499 ml |
Last Update：2024-01-02 23:10:35
1,3-Bis[2-methyl-2-(phenylthioxomethyl)hydrazide]propanedioic acid - Reference Information
| Overview | Illimo (Elesclomol) is an oxidative stress inducer that triggers cancer cell apoptosis; it can trigger cell death in metastatic melanoma cells; Mainly by inhibiting oxidative phosphorylation. Ilimo (Elesclomol) can be used as a new targeted drug, which plays an important role in the treatment of metastatic melanoma. In October 2007, Synta Pharmaceutical Company and GlaxoSmithKline (GSK) Company signed a cooperation agreement to jointly develop and sell Elesclomol, which was approved by FDA for listing in the first half of 2010. |
| function | the "first type" mitochondrial anticancer drug of ilimam can selectively cause cancer cells to wither and have no effect or only minor effect on normal cells. It has entered clinical trials. |
| Mechanism of action | Ilimo can chelate with extracellular Cu2 to form a complex, selectively transporting Cu2 into the mitochondria. In the mitochondria, Cu2 is reduced to Cu and induces mitochondria to produce a large amount of ROS to cause cancer cells to apoptosis. |
| references | [1]http://baike.baidu.com/link?url=9Hb2ZnLyr4OxXnNASII7TvtJ8bu8vrsKsi3LL5JLcNUFAUj6y5wFuciBmJPEf6ecPSrAgCNef0pH89sFJP_RfwSSgiF9TmJuFUyqORHI92dGdV-dYn-Q5STBENlWHhfa [2] Lu Li (review), Peng Fang (review). research status of targeted anti-tumor drugs [J]. medical review, 2010, 16(13):1964-1966. [3] he kai, yang Yong, Li shuping, et al. Progress in research and development of mitochondrial functional damage and anti-oxidant and anti-cancer drugs targeting mitochondria [J]. Chinese Journal of New Drugs and Clinics, 2014(8):553-558. [4] Jim Watson.Oxidants, Zhu Gongjian, Min Jianping, et al. Oxidants, antioxidants and refractory metastatic cancer [J]. Gansu Medicine, 2013, 32(5):321-329. |
| biological activity | Elesclomol (STA-4783) is a new and effective oxidative stress inducer, which causes apoptosis in tumor cells. Phase 3. |
| Target | Value |
Last Update：2024-04-09 21:32:06
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View History
1,3-Bis[2-methyl-2-(phenylthioxomethyl)hydrazide]propanedioic acid
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5-(FURAN-2-YL)-2-((4-(6-METHYLBENZO[D]THIAZOL-2-YL)PHENYLAMINO)METHYLENE)CYCLOHEXANE-1,3-DIONE
DO3A-t-Bu-ester(M-130)
2-[(phenylmethyl)thio]-3-pyridinecarboxylic acid
N-(4-氟苯基)-5,6-二甲基噻吩并[2,3-D]嘧啶-4-胺
1-[3,5-BIS(TRIFLUOROMETHYL)BENZYL]PYRID-2-ONE-3-CARBOXYLIC ACID
2(1H)-Pyridinone, 3-[3-(4-fluorophenyl)-2-methyl-1-oxo-2-propen-1-yl]-4,6-dimethyl-
L-Orn(Boc)-OMe·HCl
603067-19-2
496786-70-0
5-(FURAN-2-YL)-2-((4-(6-METHYLBENZO[D]THIAZOL-2-YL)PHENYLAMINO)METHYLENE)CYCLOHEXANE-1,3-DIONE
DO3A-t-Bu-ester(M-130)
2-[(phenylmethyl)thio]-3-pyridinecarboxylic acid