Discovery of Amantamide, a Selective CXCR7 Agonist from Marine Cyanobacteria

CXCR7 plays an emerging role in several physiological processes. A linear peptide, amantamide (1), was isolated from marine cyanobacteria, and the structure was determined by NMR and mass spectrometry. The total synthesis was achieved by solid-phase method. After screening two biological target libr...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 6; pp. 1622 - 1626
Main Authors Liang, Xiao, Luo, Danmeng, Yan, Jia-Lei, Rezaei, Mohammad A, Salvador-Reyes, Lilibeth A, Gunasekera, Sarath P, Li, Chenglong, Ye, Tao, Paul, Valerie J, Luesch, Hendrik
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.03.2019
Amer Chemical Soc
Subjects
Amides - chemistry
Amides - pharmacology
Chemistry
Chemistry, Organic
Cyanobacteria - chemistry
Molecular Structure
Peptides - chemistry
Physical Sciences
Receptors, CXCR - antagonists & inhibitors
Receptors, CXCR - chemistry
Science & Technology
RECEPTOR
DESIGN
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Summary:CXCR7 plays an emerging role in several physiological processes. A linear peptide, amantamide (1), was isolated from marine cyanobacteria, and the structure was determined by NMR and mass spectrometry. The total synthesis was achieved by solid-phase method. After screening two biological target libraries, 1 was identified as a selective CXCR7 agonist. The selective activation of CXCR7 by 1 could provide the basis for developing CXCR7-targeted therapeutics and deciphering the role of CXCR7 in different diseases.
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X.L., structure elucidation, further purification through hydrolysis-re-esterification, cell-based biological experiments, experimental design and manuscript writing; D.L., structure elucidation; J.Y., total synthesis; M.R., molecular modeling; L.A.S. and S.P.G., natural product isolation; C.L., supervision of molecular modeling; T.Y., supervision of total synthesis; V.J.P., sample collection and identification and manuscript editing; H.L., supervision of experimental design and conduction and manuscript editing. All authors have given approval to the final version of the manuscript.
Author Contributions
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b00163