Chemistry:Caldoramide
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3D model (JSmol)
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| C37H59N5O6 | |
| Molar mass | 669.908 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Caldoramide is a pentapeptide[1] isolated from the cyanobacteria Caldora penicillata.[2] It has cytotoxic effects on cancer cells and has been the subject of extensive oncological research.[3] It is structurally analogous to belamide A and dolastatin 15. Its appearance is that of a powdery, white, substance.[3]
Structure
The N-terminus for Caldoramide is N,N-dimethylvaline which is attached to a valine which is attached to an N-Me-valine connected to an N-Me-isoleucine which is attached to the C-terminus. The molecule can also be written as N,N-diMe-Val-Val-N-Me-Val-N-Me-Ile-3-O-Me-4-benzylpyrrolinone.[3]
Extraction
Freeze-dried samples of Caldora penicillata had EtOAc−MeOH and H2O−EtOH applied to them in order to extract Caldoramide. The extracts were partitioned with n-BuOH and H2O and then fractions were taken based on solubility in either EtOAc or BuOH. Caldoramide was extracted from the BuOH soluble fraction.[3]
Pharmacological activity
Caldoramide has been found to be cytotoxic against HCT116 colorectal cancer cell lines.[3]
See also
References
- ↑ "Synthesis and anticancer activity of the proposed structure of caldoramide, an N-peptidyltetramate from the cyanobacterium Caldora penicillata". Tetrahedron 74 (38): 5138–5142. 2018. doi:10.1016/j.tet.2018.04.004.
- ↑ "Hoshinoamides A and B, Acyclic Lipopeptides from the Marine Cyanobacterium Caldora penicillata". Journal of Natural Products 81 (11): 2545–2552. November 2018. doi:10.1021/acs.jnatprod.8b00643. PMID 30387355. https://pubs.acs.org/doi/10.1021/acs.jnatprod.8b00643.
- ↑ 3.0 3.1 3.2 3.3 3.4 "Caldoramide, a Modified Pentapeptide from the Marine Cyanobacterium Caldora penicillata". Journal of Natural Products 79 (7): 1867–71. July 2016. doi:10.1021/acs.jnatprod.6b00203. PMID 27380142.
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