Caldoramide

Caldoramide
Identifiers
CAS Number	1961308-67-7;
3D model (JSmol)	Interactive image;
PubChem CID	132525321;
UNII	9QZW82STF4 ;
	InChI InChI=1S/C37H59N5O6/c1-22(2)19-28(35(45)42-27(29(48-13)21-30(42)43)20-26-17-15-14-16-18-26)40(11)37(47)33(25(7)8)41(12)36(46)31(23(3)4)38-34(44)32(24(5)6)39(9)10/h14-18,21-25,27-28,31-33H,19-20H2,1-13H3,(H,38,44)/t27-,28-,31-,32-,33-/m0/s1 Key: XMIMMOXGNBQXIJ-VLQZMBLPSA-N;
	SMILES CC(C)CC(C(=O)N1C(C(=CC1=O)OC)CC2=CC=CC=C2)N(C)C(=O)C(C(C)C)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)N(C)C;
Properties
Chemical formula	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). Infobox references

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]

References

^ Wunder A, Rothemund M, Schobert R (2018). "Synthesis and anticancer activity of the proposed structure of caldoramide, an N-peptidyltetramate from the cyanobacterium Caldora penicillata". Tetrahedron. 74 (38): 5138–5142. doi:10.1016/j.tet.2018.04.004. S2CID 103025376.
^ Iwasaki A, Tadenuma T, Sumimoto S, Shiota I, Matsubara T, Saito-Nakano Y, et al. (November 2018). "Hoshinoamides A and B, Acyclic Lipopeptides from the Marine Cyanobacterium Caldora penicillata". Journal of Natural Products. 81 (11): 2545–2552. doi:10.1021/acs.jnatprod.8b00643. PMID 30387355. S2CID 53725718.
^ ^a ^b ^c ^d ^e Gunasekera SP, Imperial L, Garst C, Ratnayake R, Dang LH, Paul VJ, Luesch H (July 2016). "Caldoramide, a Modified Pentapeptide from the Marine Cyanobacterium Caldora penicillata". Journal of Natural Products. 79 (7): 1867–71. doi:10.1021/acs.jnatprod.6b00203. PMC 5215049. PMID 27380142.

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[1] Wunder A, Rothemund M, Schobert R (2018). "Synthesis and anticancer activity of the proposed structure of caldoramide, an N-peptidyltetramate from the cyanobacterium Caldora penicillata". Tetrahedron. 74 (38): 5138–5142. doi:10.1016/j.tet.2018.04.004. S2CID 103025376.

[2] Iwasaki A, Tadenuma T, Sumimoto S, Shiota I, Matsubara T, Saito-Nakano Y, et al. (November 2018). "Hoshinoamides A and B, Acyclic Lipopeptides from the Marine Cyanobacterium Caldora penicillata". Journal of Natural Products. 81 (11): 2545–2552. doi:10.1021/acs.jnatprod.8b00643. PMID 30387355. S2CID 53725718.

[Gunasekera_2016-3] Gunasekera SP, Imperial L, Garst C, Ratnayake R, Dang LH, Paul VJ, Luesch H (July 2016). "Caldoramide, a Modified Pentapeptide from the Marine Cyanobacterium Caldora penicillata". Journal of Natural Products. 79 (7): 1867–71. doi:10.1021/acs.jnatprod.6b00203. PMC 5215049. PMID 27380142.

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[2]

[3]

v t e Cyanotoxins
Neurotoxins	Anatoxin-a Guanitoxin Antillatoxin BMAA Kalkitoxin Saxitoxin
Hepatotoxins	Cylindrospermopsin Microcystins (e.g. Microcystin-LR) Nodularin
Other	Aplysiatoxin Apratoxin A Caldoramide Coibamide A Cyanobacterin Cyanopeptolin Cyclamide Debromoaplysiatoxin Lyngbyatoxin-a Microviridin Aetokthonotoxin
Category

Structure

Extraction

Pharmacological activity

See also

References