113956-82-4Relevant articles and documents
Discovery, Total Synthesis, and SAR of Anaenamides A and B: Anticancer Cyanobacterial Depsipeptides with a Chlorinated Pharmacophore
Brumley, David A.,Chen, Qi-Yin,Gunasekera, Sarath P.,Luesch, Hendrik,Paul, Valerie J.
, p. 4235 - 4239 (2020/06/27)
New modified depsipeptides and geometric isomers, termed anaenamides A (1a) and B (1b), along with the presumptive biosynthetic intermediate, anaenoic acid (2), were discovered from a marine cyanobacterium from Guam. Structures were confirmed by total synthesis. The alkylsalicylic acid fragment and the C-terminal α-chlorinated α,β-unsaturated ester are novelties in cyanobacterial natural products. Cancer cell viability assays indicated that the C-terminal unit serves as the pharmacophore and that the double-bond geometry impacts the cytotoxicity.
APRATYRAMIDE THERAPEUTIC AGENTS AND METHODS OF TREATMENT
-
Page/Page column 46-49, (2019/06/11)
The invention is directed towards Apratyramide linear depsipeptide compounds, pharmaceutical compositions thereof, and methods of affecting wound healing, and methods of affecting the biological processes involved in wound healing (e.g., inflammation, cell proliferation, tissue granulation, remodeling of scar tissue, etc.).
Apratyramide, a Marine-Derived Peptidic Stimulator of VEGF-A and Other Growth Factors with Potential Application in Wound Healing
Cai, Weijing,Salvador-Reyes, Lilibeth A.,Zhang, Wei,Chen, Qi-Yin,Matthew, Susan,Ratnayake, Ranjala,Seo, Soo Jung,Dolles, Simon,Gibson, Daniel J.,Paul, Valerie J.,Luesch, Hendrik
, p. 91 - 99 (2018/02/06)
A novel linear depsipeptide enriched with tyrosine-derived moieties, termed apratyramide, was isolated from an apratoxin-producing cyanobacterium. The structure was determined using a combination of NMR spectroscopy, mass spectrometry, and chiral analysis of the acid hydrolyzate and confirmed by total synthesis. Apratyramide up-regulated multiple growth factors at the transcript level in human keratinocyte (HaCaT) cells and induced the secretion of vascular endothelial growth factor A (VEGF-A) from HaCaT cells, suggesting the compound's potential wound-healing properties through growth factor induction. Transcriptome analysis and sequential validation supported the hypothesis and indicated its mode of action (MOA) through the unfolded protein response (UPR) pathway, which is functionally related to wound healing and angiogenesis. The conditioned medium of HaCaT cells treated with apratyramide induced angiogenesis in vitro. An ex vivo rabbit corneal epithelial model was applied to confirm the VEGF-A induction in this wound-healing model.
