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Literature DB >> 27380142

Caldoramide, a Modified Pentapeptide from the Marine Cyanobacterium Caldora penicillata.

Sarath P Gunasekera¹, Lorelie Imperial, Christiana Garst¹, Ranjala Ratnayake, Long H Dang, Valerie J Paul¹, Hendrik Luesch.

Abstract

The isolation, structure determination, and biological activities of a new linear pentapeptide, caldoramide (5), from the marine cyanobacterium Caldora penicillata from Florida are described. Caldoramide (5) has structural similarities to belamide A (4), dolastatin 10 (1), and dolastatin 15 (2). We profiled caldoramide against parental HCT116 colorectal cancer cells and isogenic cells lacking oncogenic KRAS or hypoxia-inducible factors 1α (HIF-1α) and 2α (HIF-2α). Caldoramide (5) showed differential cytotoxicity for cells containing both oncogenic KRAS and HIF over the corresponding knockout cells. LCMS dereplication indicated the presence of caldoramide (5) in a subset of C. penicillata samples.

Entities: CellLine Chemical Disease Gene Species

Mesh：

Substances：

Year: 2016 PMID： 27380142 PMCID： PMC5215049 DOI： 10.1021/acs.jnatprod.6b00203

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

13 in total

1. The expression and distribution of the hypoxia-inducible factors HIF-1alpha and HIF-2alpha in normal human tissues, cancers, and tumor-associated macrophages.

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Journal: Am J Pathol Date: 2000-08 Impact factor: 4.307

Review 2. Biogenetic diversity of cyanobacterial metabolites.

Authors: Ryan M Van Wagoner; Allison K Drummond; Jeffrey L C Wright
Journal: Adv Appl Microbiol Date: 2007 Impact factor: 5.086

3. Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp.

Authors: Kanchan Taori; Valerie J Paul; Hendrik Luesch
Journal: J Am Chem Soc Date: 2008-01-19 Impact factor: 15.419

Review 4. Marine natural products.

Authors: John W Blunt; Brent R Copp; Robert A Keyzers; Murray H G Munro; Michèle R Prinsep
Journal: Nat Prod Rep Date: 2014-01-17 Impact factor: 13.423

5. Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1.

Authors: H Luesch; R E Moore; V J Paul; S L Mooberry; T H Corbett
Journal: J Nat Prod Date: 2001-07 Impact factor: 4.050

6. The discovery and development of brentuximab vedotin for use in relapsed Hodgkin lymphoma and systemic anaplastic large cell lymphoma.

Authors: Peter D Senter; Eric L Sievers
Journal: Nat Biotechnol Date: 2012-07-10 Impact factor: 54.908

Review 7. Bioactive natural products from marine cyanobacteria for drug discovery.

Authors: Lik Tong Tan
Journal: Phytochemistry Date: 2007-03-02 Impact factor: 4.072

8. Caldora penicillata gen. nov., comb. nov. (cyanobacteria), a pantropical marine species with biomedical relevance.

Authors: Niclas Engene; Ana Tronholm; Lilibeth A Salvador-Reyes; Hendrik Luesch; Valerie J Paul
Journal: J Phycol Date: 2015-08 Impact factor: 2.923

9. Multidimensional Screening Platform for Simultaneously Targeting Oncogenic KRAS and Hypoxia-Inducible Factors Pathways in Colorectal Cancer.

Authors: Michelle S Bousquet; Jia Jia Ma; Ranjala Ratnayake; Pamela A Havre; Jin Yao; Nam H Dang; Valerie J Paul; Thomas J Carney; Long H Dang; Hendrik Luesch
Journal: ACS Chem Biol Date: 2016-03-03 Impact factor: 5.100

Caldoramide, a Modified Pentapeptide from the Marine Cyanobacterium Caldora penicillata.

1. The expression and distribution of the hypoxia-inducible factors HIF-1alpha and HIF-2alpha in normal human tissues, cancers, and tumor-associated macrophages.

Review 2. Biogenetic diversity of cyanobacterial metabolites.

3. Structure and activity of largazole, a potent antiproliferative agent from the Floridian marine cyanobacterium Symploca sp.

Review 4. Marine natural products.

5. Isolation of dolastatin 10 from the marine cyanobacterium Symploca species VP642 and total stereochemistry and biological evaluation of its analogue symplostatin 1.

6. The discovery and development of brentuximab vedotin for use in relapsed Hodgkin lymphoma and systemic anaplastic large cell lymphoma.

Review 7. Bioactive natural products from marine cyanobacteria for drug discovery.

8. Caldora penicillata gen. nov., comb. nov. (cyanobacteria), a pantropical marine species with biomedical relevance.

9. Multidimensional Screening Platform for Simultaneously Targeting Oncogenic KRAS and Hypoxia-Inducible Factors Pathways in Colorectal Cancer.

10. Targeting both HIF-1 and HIF-2 in human colon cancer cells improves tumor response to sunitinib treatment.

Review 1. Marine natural product peptides with therapeutic potential: Chemistry, biosynthesis, and pharmacology.

2. Inhibition of the HIF-1 Survival Pathway as a Strategy to Augment Photodynamic Therapy Efficacy.

Review 3. Structural Diversity, Biological Properties and Applications of Natural Products from Cyanobacteria. A Review.

Review 4. New Peptides Isolated from Marine Cyanobacteria, an Overview over the Past Decade.

Review 5. The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms.

6. Genome Reduction and Secondary Metabolism of the Marine Sponge-Associated Cyanobacterium Leptothoe.