Aciculitin Explained

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Aciculitins are antifungal cyclic peptides isolated from a marine sponge. There are 3 Aciculitins that are isolated from the Lithistid sponge Aciculites orientalis that differ by their homologous lipid residues.^[1]

Aciculitin D is a similar cyclic peptide to Aciculitin A-C. It was isolated from Poecillastra sp. marine sponge that is collected from the deep sea.^[2] Based on its molecular formula, Aciculitin D is the most similar to Aciculitin B structure wise since they only differ in one amino acid substitution. The structure of Aciculitin B contains one extra glutamine while the structure of Aciculitin D has one extra L-Threonine. Although the two cyclic peptides contain slightly different amino acids, they still have the same overall charge because both glutamine and L-Threonine are considered neutral amino acids.

Cytotoxicity

Aciculitin A-C exhibits cytotoxicity against human colon tumor cell line HCT-116 with IC₅₀ value of 0.5 μg/mL.

Aciculitin D exhibits cytotoxicity against human colon tumor cell line HCT-116 with IC₅₀ value of 0.51 μM. Aciculitin D also exhibits cytotoxicity against HeLa, human cervical cells with IC₅₀ value of 0.57 μM.

Further reading

• Otero-Gonzáiez . Anselmo Jesus . Magalhães . Beatriz Simas . Garcia-Villarino . Monica . López-Abarrategui . Carlos . Sousa . Daniel Amaro . Dias . Simoni Campos . Franco . Octávio Luiz . Antimicrobial peptides from marine invertebrates as a new frontier for microbial infection control . The FASEB Journal . May 2010 . 24 . 5 . 1320–1334 . 10.1096/fj.09-143388 . free . 20065108 . 23976702 .

Notes and References

1. Carole A. Bewley. Haiyin. He. David H. Williams. John. Faulkner. Journal of the American Chemical Society. 118. 18. 8 May 1996. Aciculitins A−C: Cytotoxic and Antifungal Cyclic Peptides from the Lithistid Sponge Aciculites orientalis. 10.1021/ja953628w. 4314–4321.
2. Sugawara . Kenji . Kanki . Daichi . Watanabe . Ryuichi . Matsushima . Ryoji . Ise . Yuji . Yokose . Hisayoshi . Morii . Yasuhiro . Yamawaki . Nobuhiro . Ninomiya . Akihiro . Okada . Shigeru . Matsunaga . Shigeki . Aciculitin D, a cytotoxic heterodetic cyclic peptide from a Poecillastra sp. marine sponge . Tetrahedron . July 2022 . 119 . 132859 . 10.1016/j.tet.2022.132859 . 249353432 .