Ceratamine A
目录号 : GC35654
Ceratamine A 是从海绵 Pseudoceratina sp. 中分离出的一种抗有丝分裂杂环生物碱，能作为一种微管稳定剂。Ceratamine A 对人类癌细胞系具有细胞毒性。
Cas No.:634151-15-8
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Ceratamine A is an antimitotic heterocyclic alkaloid isolated from the marine sponge Pseudoceratina sp., acts as a microtubule-stabilizing agent. Ceratamine A exhibits cytotoxicity against human cancer cell lines[1][2][3].
[1]. Manzo E, et al. Ceratamines A and B, antimitotic heterocyclic alkaloids isolated from the marine sponge Pseudoceratina sp. collected in Papua New Guinea. Org Lett. 2003 Nov 27;5(24):4591-4. [2]. Nodwell M, et al. Synthetic approaches to the microtubule-stabilizing sponge alkaloid ceratamine A and desbromo analogues. J Org Chem. 2009 Feb 6;74(3):995-1006. [3]. Pan X, et al. Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product ceratamine A. Bioorg Med Chem Lett. 2018 Mar 1;28(5):866-868.
| Cas No. | 634151-15-8 | SDF | |
| Canonical SMILES | O=C(N(C)C=C1)C(CC2=CC(Br)=C(OC)C(Br)=C2)=C3C1=NC(NC)=N3 | ||
| 分子式 | C17H16Br2N4O2 | 分子量 | 468.14 |
| 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.1361 mL | 10.6806 mL | 21.3611 mL |
| 5 mM | 0.4272 mL | 2.1361 mL | 4.2722 mL |
| 10 mM | 0.2136 mL | 1.0681 mL | 2.1361 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。
A direct and efficient total synthesis of the tubulin-binding agents Ceratamine A and B; use of IBX for a remarkable heterocycle dehydrogenation
Org Lett 2009 May 21;11(10):2133-6.PMID:19385610DOI:10.1021/ol900709n.
The total synthesis of the tubulin-binding agents Ceratamine A and B is reported, along with des-methyl analogs, via a synthetic route that is high-yielding and operationally efficient. The synthetic route involved a Beckmann rearrangement to form an azepine ring precursor, a Knoevenagel condensation to install the benzylic side chain, and an effective imidazole annulation onto an alpha-aminoketone precursor with a protected S-methylisothiourea. Final dehydrogenation proved remarkably facile using IBX.
Synthesis and cytotoxicity of novel imidazo[4,5-d]azepine compounds derived from marine natural product Ceratamine A
Bioorg Med Chem Lett 2018 Mar 1;28(5):866-868.PMID:29433924DOI:10.1016/j.bmcl.2018.02.004.
A series of novel imidazo[4,5-d]azepine compounds derived from marine natural product Ceratamine A were designed and synthesized in 7 steps. Most compounds exhibited comparable cytotoxicity against five human cancer cell lines (HCT-116, HepG2, BGC-823, A549 and A2780) to natural product Ceratamine A. Compound 1k, bearing methoxy group at C-14, C-15 and C-16, showed the best in vitro cytotoxicity, which was better than Ceratamine A. The structure and activity relationships study showed that the benzyloxymethyl group on N-3 played an important role on the cytotoxicity.
Synthetic analogues of the microtubule-stabilizing sponge alkaloid Ceratamine A are more active than the natural product
J Med Chem 2010 Nov 11;53(21):7843-51.PMID:20945907DOI:10.1021/jm101012q.
Desbromoceratamine A (3) exhibits significantly less potent activity than the natural product Ceratamine A (1) in a cell-based assay for antimitotic activity. Synthesis of the Ceratamine A analogue 4 has shown that replacing the bromine atoms in the natural product with methyl groups generates an analogue that is more active than natural Ceratamine A (1). Further enhancement of the antimitotic activity of the ceratamine pharmacophore has been achieved in the synthetic analogue 33, which has both bromine atoms replaced with methyl groups and an additional methyl substituent on the amino nitrogen at C-2. An efficient synthetic route has been developed to 33 that should enable the first in vivo evaluation of the new ceratamine microtubule-stabilizing pharmacophore and has provided several additional analogues for structure-activity relationship evaluation.
Synthetic approaches to the microtubule-stabilizing sponge alkaloid Ceratamine A and desbromo analogues
J Org Chem 2009 Feb 6;74(3):995-1006.PMID:19128042DOI:10.1021/jo802322s.
Two synthetic approaches to the microtubule-stabilizing ceratamine alkaloids are described. The first approach involved attempts to graft an aminoimidazole moiety onto an azepine ring to form partially hydrogenated versions of the unprecedented aromatic imidazo[4,5-d]azepine core of the ceratamines. This route ultimately failed because it was not possible to aromatize the partially hydrogenated ceratamine intermediates. A second approach started with tribromoimidazole that was sequentially metalated and functionalized to efficiently generate a key imidazole intermediate containing vinyl bromide and amide functionalities. An intramolecular Buchwald vinyl amidation reaction converted this key intermediate into a bicyclic imidazo[4,5-d]azepine that was at the same oxidation state as the aromatic core of the ceratamines. The 2-amino functionality present on the imidazole ring of the ceratamines was installed using a Buchwald/Hartwig amination reaction on a 2-chloroimidazole precursor. Deprotection and aromatization resulted in the first synthesis of desbromoceratamine A (55) and desmethyldesbromoceratamine A (60). An unanticipated addition of atmospheric oxygen was encountered during deprotection of the imidazole ring in the last step of the synthesis leading to C-11 oxygenated ceratamine analogues as byproducts. Evaluation of the synthetic ceratamines in a TG3 cell-based assay for mitotic arrest revealed that the C-14 and C-16 bromine substituents in Ceratamine A (1) play a major role in the antimitotic potency of the natural product. The synthetic route to ceratamine analogues has provided sufficient quantities of desbromoceratamine A (55) for testing in mouse models of cancer.
Synthesis of antimitotic analogs of the microtubule stabilizing sponge alkaloid Ceratamine A
Org Lett 2008 Mar 20;10(6):1051-4.PMID:18278926DOI:10.1021/ol7030284.
Antimitotic analogs of the microtubule stabilizing sponge alkaloid Ceratamine A (1) have been synthesized starting from tribromoimidazole. A key step in the synthesis is the formation of the azepine ring via an intramolecular Buchwald coupling between a vinyl bromide and a N-methyl amide. This represents the first synthesis of a fully unsaturated imidazo[4,5,d]azepine. NMR data obtained for the synthetic ceratamine analogs has provided support for the structure assigned to the natural product.