(-)-Chaetominine
(Synonyms: (-)-Chaetominine) 目录号 : GC45246
A cytotoxic alkaloid
Cas No.:918659-56-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
(-)-Chaetominine is a cytotoxic alkaloid originally isolated from Chaetomium sp. IFB-E015. It inhibits the growth of K562 leukemia and SW1116 colon cancer cells (IC50s = 20 and 28 nM, respectively). (-)-Chaetominine induces apoptosis of K562 cells via upregulation of the Bax/Bcl-2 ratio, decreasing mitochondrial membrane potential, inducing mitochondrial cytochrome C release, and activation of caspase-3 and caspase-9. It also decreases doxorubicin efflux mediated by multidrug resistance-associated protein 1 (MRP1) and restores sensitivity to doxorubicin in resistant K562 cells.
| Cas No. | 918659-56-0 | SDF | |
| 别名 | (-)-Chaetominine | ||
| Canonical SMILES | O=C1N([C@H]2C)[C@]3([H])[C@](C4=CC=CC=C4N3C2=O)(O)C[C@H]1N5C=NC(C=CC=C6)=C6C5=O | ||
| 分子式 | C22H18N4O4 | 分子量 | 402.4 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.4851 mL | 12.4254 mL | 24.8509 mL |
| 5 mM | 0.497 mL | 2.4851 mL | 4.9702 mL |
| 10 mM | 0.2485 mL | 1.2425 mL | 2.4851 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Rapid Generation of Molecular Complexity by Chemical Synthesis: Highly Efficient Total Synthesis of Hexacyclic Alkaloid (-)-Chaetominine and Its Biosynthetic Implications
Chem Rec 2019 Feb;19(2-3):523-533.PMID:30252197DOI:10.1002/tcr.201800079.
The efficiency becomes a key issue in today's natural product total synthesis. While biomimetic synthesis is one of the most elegant strategies to achieve synthetic efficiency and thus to approach the ideal synthesis, most biogenetic pathways are unknown or unconfirmed. In this account, we demonstrate, through the shortest and also the most efficient asymmetric total syntheses of the hexacyclic alkaloid (-)-Chaetominine to date, that on the basis of biogenetic thinking, one can develop quite efficient bio-inspired total synthesis, which in turn serves to suggest and chemically validate plausible biosynthetic routes for the natural product. The synthetic strategy thus developed is also inspiring for the development of other synthetic methods and efficient total synthesis of other natural products.
Synthesis of (-)-Chaetominine
Org Lett 2007 Nov 8;9(23):4913-5.PMID:17944481DOI:10.1021/ol7022483.
The tricyclic hydroxy imidazolidinone was converted to chaetominine in seven steps in 22% overall yield. The key step was the construction of the delta-lactam by heating an amino ester with a catalytic amount of DMAP in toluene at reflux.
The four-step total synthesis of (-)-Chaetominine
Chem Commun (Camb) 2014 Feb 25;50(16):1986-8.PMID:24413776DOI:10.1039/c3cc48833k.
The total synthesis of the alkaloid (-)-Chaetominine (1) has been achieved in four steps with an overall yield of 33.4%. Key features of our strategy include a one-pot cascade indole epoxidation - epoxide ring-opening cyclization - lactamization reaction sequence, and the use of a nitro group as a latent amino group for the one-pot construction of the quinazolinone ring. This constitutes a step economical, redox economical and protecting group-free total synthesis.
A straightforward total synthesis of (-)-Chaetominine
Chemistry 2009 Aug 10;15(32):7922-7929.PMID:19562787DOI:10.1002/chem.200900793.
A total synthesis of the tripeptide alkaloid (-)-Chaetominine (1) was achieved in 9.3% overall yield starting from commercially available D-tryptophan methyl ester, based on a short and straightforward (nine steps) sequence. The early stage introduction (first step) of the quinazolinone moiety and the late stage introduction (penultimate step) of the hydroxy group allowed a synthetic strategy devoid of protective groups. The key step of the process is the a-c tricyclic ring construction via an unprecedented NCS-mediated N-acyl cyclization on an indole ring to give tetrahydro-1H-pyrido[2,3-b]indole 11. In the penultimate step, oxidation of the tetracyclic intermediate 14 with oxaziridine 15 gave only one of the four possible diastereoisomers, the cis-diastereoisomer 16 resulting from the attack of the oxaziridine to the double bond face opposite to the c-d ring substituents. In the last step, the complete stereocontrol of the Et(3)SiH/TFA reduction of compound 16, probably involving a N-acyliminium ion, can be attributed to ring constrain, which forces the b-c ring junction in the more stable cis-orientation. (-)-Chaetominine (1) showed a negligible inhibitory activity on several cancer cell lines.
Rhodium-Catalyzed Asymmetric N-H Functionalization of Quinazolinones with Allenes and Allylic Carbonates: The First Enantioselective Formal Total Synthesis of (-)-Chaetominine
Chemistry 2017 Dec 22;23(72):18156-18160.PMID:29105185DOI:10.1002/chem.201705059.
An unprecedented asymmetric N-H functionalization of quinazolinones with allenes and allylic carbonates was successfully achieved by rhodium catalysis with the assistance of chiral bidentate diphosphine ligands. The high efficiency and practicality of this method was demonstrated by a low catalyst loading of 1 mol % as well as excellent chemo-, regio-, and enantioselectivities with broad functional group compatibility. Furthermore, this newly developed strategy was applied as key step in the first enantioselective formal total synthesis of (-)-Chaetominine.