Aciculitin

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]

Aciculitins A-C

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.[2] 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. [1]

Aciculitin D exhibits cytotoxicity against human colon tumor cell line HCT-116 with IC50 value of 0.51 µM.[2] Aciculitin D also exhibits cytotoxicity against HeLa, human cervical cells with IC50 value of 0.57 µM. [2]

Further reading

Otero‐Gonzáiez, A. J., Magalhaes, B. S., Garcia‐Villarino, M., López‐Abarrategui, C., Sousa, D. A., Dias, S. C., & Franco, O. L. (2010). Antimicrobial peptides from marine invertebrates as a new frontier for microbial infection control. The FASEB journal, 24(5), 1320-1334. https://www.ncbi.nlm.nih.gov/pubmed/20065108

References
  1. Bewley, Carole A; He, Haiyin; Williams, David H; Faulkner, John (8 May 1996). "Aciculitins A−C: Cytotoxic and Antifungal Cyclic Peptides from the Lithistid Sponge Aciculites orientalis". Journal of the American Chemical Society. 118 (18): 4314–4321. doi:10.1021/ja953628w.
  2. Sugawara, Kenji; Kanki, Daichi; Watanabe, Ryuichi; Matsushima, Ryoji; Ise, Yuji; Yokose, Hisayoshi; Morii, Yasuhiro; Yamawaki, Nobuhiro; Ninomiya, Akihiro; Okada, Shigeru; Matsunaga, Shigeki (2022-07-30). "Aciculitin D, a cytotoxic heterodetic cyclic peptide from a Poecillastra sp. marine sponge". Tetrahedron. 119: 132859. doi:10.1016/j.tet.2022.132859. ISSN 0040-4020. S2CID 249353432.


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