169062-92-4
Chemical Structure
Cyclomarin A
- CAS No.: 169062-92-4
- Formula:C56H82N8O11
- Molecular Weight:1043.30
InChIKey: WCNJVJCYRBJSLC-BCJYPDSRSA-N
SMILES: CC(N1C2=CC=CC=C2C([C@H]([C@@]3([H])C(N([C@H](C(N[C@H](C(N[C@@](C(N[C@H](C(N([C@H](C(N[C@@](C(N3)=O)([H])[C@H](C)/C=C(C)\C)=O)CC(C)C)C)=O)C(C)C)=O)([H])[C@@H](C4=CC=CC=C4)OC)=O)C)=O)C[C@@H](C)CO)C)=O)O)=C1)([C@@H]5CO5)C
Biological Activity: Cyclomarin A is an antibacterial agent with a Kd of 2.3 nM against Mycobacterium tuberculosis ClpC1, a Kd of 2.2 nM against ClpC2, and an IC50 of 0.004 μM against Plasmodium falciparum PfAp3Aase. Cyclomarin A binds to the N-terminal domain of ClpC1, stimulates ATPase and proteolytic activities, dysregulates proteolysis, and induces proteome imbalance; it also binds to ClpC2 and upregulates its transcription level. Cyclomarin A binds to PfAp3Aase in dimeric form, blocks the substrate-binding pathway, inhibits the growth of Plasmodium falciparum in the erythrocytic stage, and shows no activity against human cells. Cyclomarin A exhibits moderate cytotoxicity against a variety of cancer cell lines. Cyclomarin A can serve as a lead compound for the development of Homo-BacPROTAC. Cyclomarin A is applicable to research related to tuberculosis and malaria[1][2][3][4][5].
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Cyclomarin A | Cyclomarin A is an antibacterial agent with a Kd of 2.3 nM against Mycobacterium tuberculosis ClpC1, a Kd of 2.2 nM against ClpC2, and an IC50 of 0.004 μM against Plasmodium falciparum PfAp3Aase. Cyclomarin A binds to the N-terminal domain of ClpC1, stimulates ATPase and proteolytic activities, dysregulates proteolysis, and induces proteome imbalance; it also binds to ClpC2 and upregulates its transcription level. Cyclomarin A binds to PfAp3Aase in dimeric form, blocks the substrate-binding pathway, inhibits the growth of Plasmodium falciparum in the erythrocytic stage, and shows no activity against human cells. Cyclomarin A exhibits moderate cytotoxicity against a variety of cancer cell lines. Cyclomarin A can serve as a lead compound for the development of Homo-BacPROTAC. Cyclomarin A is applicable to research related to tuberculosis and malaria. | |||||||||||||||||||||
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References
- [1]. Hoi DM, et al. Clp-targeting BacPROTACs impair mycobacterial proteostasis and survival. Cell. 2023 May 11;186(10):2176-2192.e22. [Content Brief]
- [2]. Barbie P, et al. Total Synthesis of Cyclomarin A, a Marine Cycloheptapeptide with Anti-Tuberculosis and Anti-Malaria Activity. Organic letters. 2016 Jan 15;18(2):204-7. [Content Brief]
- [3]. Bürstner N, et al. Gift from Nature: Cyclomarin A Kills Mycobacteria and Malaria Parasites by Distinct Modes of Action. Chembiochem : a European journal of chemical biology. 2015 Nov;16(17):2433-6. [Content Brief]
- [4]. Maurer M, et al. Toxic Activation of an AAA+ Protease by the Antibacterial Drug Cyclomarin A. Cell Chem Biol. 2019 Aug 15;26(8):1169-1179.e4. [Content Brief]
- [5]. Taylor G, et al. ClpC2 protects mycobacteria against a natural antibiotic targeting ClpC1-dependent protein degradation. Communications biology. 2023 Mar 21;6(1):301. [Content Brief]
