Literature DB >> 15165138

Comparison of fascaplysin and related alkaloids: a study of structures, cytotoxicities, and sources.

Nathaniel L Segraves1, Sarah J Robinson, Daniel Garcia, Sadri A Said, Xiong Fu, Francis J Schmitz, Halina Pietraszkiewicz, Frederick A Valeriote, Phillip Crews.   

Abstract

The fascaplysin class of compounds have been further investigated from six organisms consisting of four sponge collections (Fascaplysinopsis reticulata) and two tunicate collections (Didemnum sp.). This work is an extension of an earlier communication and reports the isolation of 12 new fascaplysin derivatives: 10-bromofascaplysin (7), 3,10-dibromofascaplysin (8), homofascaplysate A (9), homofascaplysin B-1 (11), 3-bromohomofascaplysins B (12), B-1 (13), and C (15), 7,14-dibromoreticulatine (17), reticulatol (20), 14-bromoreticulatol (21), and 3-bromosecofascaplysins A (22) and B (23), along with known compounds: fascaplysin (1), reticulatine (4), 3-bromofascaplysin (6), and homofascaplysin C (14). Selected compounds were screened in a cell-based cytotoxicity assay with compounds 1, 6, and fascaplysin A (24) also screened in the NCI 60 cell line panel. A biogenetic pathway for the brominated fascaplysins and brominated related alkaloids is proposed and discussed.

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Year:  2004        PMID: 15165138     DOI: 10.1021/np049935+

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  25 in total

1.  A distinctive structural twist in the aminoimidazole alkaloids from a calcareous marine sponge: isolation and characterization of leucosolenamines A and B.

Authors:  Paul Ralifo; Karen Tenney; Frederick A Valeriote; Phillip Crews
Journal:  J Nat Prod       Date:  2007-01       Impact factor: 4.050

Review 2.  A new paradigm for the development of anticancer agents from natural products.

Authors:  Balanehru Subramanian; Alexander Nakeff; Karen Tenney; Phillip Crews; Leslie Gunatilaka; Fred Valeriote
Journal:  J Exp Ther Oncol       Date:  2006

3.  Identification of the First Marine-Derived Opioid Receptor "Balanced" Agonist with a Signaling Profile That Resembles the Endorphins.

Authors:  Tyler A Johnson; Laura Milan-Lobo; Tao Che; Madeline Ferwerda; Eptisam Lambu; Nicole L McIntosh; Fei Li; Li He; Nicholas Lorig-Roach; Phillip Crews; Jennifer L Whistler
Journal:  ACS Chem Neurosci       Date:  2016-11-22       Impact factor: 4.418

Review 4.  Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.

Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

5.  Synthesis of pyrido[1,2-a]indole malonates and amines through aryne annulation.

Authors:  Donald C Rogness; Nataliya A Markina; Jesse P Waldo; Richard C Larock
Journal:  J Org Chem       Date:  2012-03-06       Impact factor: 4.354

Review 6.  A selective account of effective paradigms and significant outcomes in the discovery of inspirational marine natural products.

Authors:  Koneni V Sashidhara; Kimberly N White; Phillip Crews
Journal:  J Nat Prod       Date:  2009-03-27       Impact factor: 4.050

7.  Kinase inhibitor screening identifies CDK4 as a potential therapeutic target for melanoma.

Authors:  T Mahgoub; A J Eustace; D M Collins; N Walsh; N O'Donovan; J Crown
Journal:  Int J Oncol       Date:  2015-07-21       Impact factor: 5.650

8.  A pyrone remodeling strategy to access diverse heterocycles: application to the synthesis of fascaplysin natural products.

Authors:  Vignesh Palani; Melecio A Perea; Kristen E Gardner; Richmond Sarpong
Journal:  Chem Sci       Date:  2020-11-27       Impact factor: 9.825

9.  HLA class I and II genotype of the NCI-60 cell lines.

Authors:  Sharon Adams; Fu-Meei Robbins; Deborah Chen; Devika Wagage; Susan L Holbeck; Herbert C Morse; David Stroncek; Francesco M Marincola
Journal:  J Transl Med       Date:  2005-03-04       Impact factor: 5.531

Review 10.  Marine Indole Alkaloids.

Authors:  Natalie Netz; Till Opatz
Journal:  Mar Drugs       Date:  2015-08-06       Impact factor: 5.118

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