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Literature DB >> 31633350

Engineering Fluorine into Verticillins (Epipolythiodioxopiperazine Alkaloids) via Precursor-Directed Biosynthesis.

Chiraz Soumia M Amrine¹, Jessica L Long¹, Huzefa A Raja¹, Steven J Kurina², Joanna E Burdette², Cedric J Pearce³, Nicholas H Oberlies¹.

Abstract

Precursor-directed biosynthesis was used to generate a series of fluorinated verticillins. The biosynthesis of these epipolythiodioxopiperazine alkaloids was monitored in situ via the droplet liquid microjunction surface sampling probe (droplet probe), and a suite of NMR and mass spectrometry data were used for their characterization. All analogues demonstrated nanomolar IC50 values vs a panel of cancer cell lines. This approach yielded new compounds that would be difficult to generate via synthesis.

Entities: CellLine Chemical Disease Gene Species

Year: 2019 PMID： 31633350 PMCID： PMC6996222 DOI： 10.1021/acs.jnatprod.9b00711

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

48 in total

Review 1. Understanding nature's strategies for enzyme-catalyzed racemization and epimerization.

Authors: Martin E Tanner
Journal: Acc Chem Res Date: 2002-04 Impact factor: 22.384

2. 11,11'-dideoxy-verticillin: a natural compound possessing growth factor receptor tyrosine kinase-inhibitory effect with anti-tumor activity.

Authors: Yi-Xiang Zhang; Yi Chen; Xiao-Ning Guo; Xiong-Wen Zhang; Wei-Min Zhao; Li Zhong; Jin Zhou; Yong Xi; Li-Ping Lin; Jian Ding
Journal: Anticancer Drugs Date: 2005-06 Impact factor: 2.248

3. The MLL1-H3K4me3 Axis-Mediated PD-L1 Expression and Pancreatic Cancer Immune Evasion.

Authors: Chunwan Lu; Amy V Paschall; Huidong Shi; Natasha Savage; Jennifer L Waller; Maria E Sabbatini; Nicholas H Oberlies; Cedric Pearce; Kebin Liu
Journal: J Natl Cancer Inst Date: 2017-01-28 Impact factor: 13.506

Review 4. Ciprofloxacin: review on developments in synthetic, analytical, and medicinal aspects.

Authors: Prabodh Chander Sharma; Ankit Jain; Sandeep Jain; Rakesh Pahwa; Mohammad Shahar Yar
Journal: J Enzyme Inhib Med Chem Date: 2010-08 Impact factor: 5.051

Review 5. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Authors: Jiang Wang; María Sánchez-Roselló; José Luis Aceña; Carlos del Pozo; Alexander E Sorochinsky; Santos Fustero; Vadim A Soloshonok; Hong Liu
Journal: Chem Rev Date: 2013-12-03 Impact factor: 60.622

Review 6. Biosynthetic gene clusters for epipolythiodioxopiperazines in filamentous fungi.

Authors: Ellen M Fox; Barbara J Howlett
Journal: Mycol Res Date: 2007-09-01

7. Cytotoxic and Antihaptotactic beauvericin analogues from precursor-directed biosynthesis with the insect pathogen Beauveria bassiana ATCC 7159.

Authors: Yuquan Xu; Jixun Zhan; E M Kithsiri Wijeratne; Anna M Burns; A A Leslie Gunatilaka; István Molnár
Journal: J Nat Prod Date: 2007-09-06 Impact factor: 4.050

8. Quantitative Assessment of the Impact of Fluorine Substitution on P-Glycoprotein (P-gp) Mediated Efflux, Permeability, Lipophilicity, and Metabolic Stability.

Authors: Martin Pettersson; Xinjun Hou; Max Kuhn; Travis T Wager; Gregory W Kauffman; Patrick R Verhoest
Journal: J Med Chem Date: 2016-05-26 Impact factor: 7.446

Engineering Fluorine into Verticillins (Epipolythiodioxopiperazine Alkaloids) via Precursor-Directed Biosynthesis.

Review 1. Understanding nature's strategies for enzyme-catalyzed racemization and epimerization.

2. 11,11'-dideoxy-verticillin: a natural compound possessing growth factor receptor tyrosine kinase-inhibitory effect with anti-tumor activity.

3. The MLL1-H3K4me3 Axis-Mediated PD-L1 Expression and Pancreatic Cancer Immune Evasion.

Review 4. Ciprofloxacin: review on developments in synthetic, analytical, and medicinal aspects.

Review 5. Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Review 6. Biosynthetic gene clusters for epipolythiodioxopiperazines in filamentous fungi.

7. Cytotoxic and Antihaptotactic beauvericin analogues from precursor-directed biosynthesis with the insect pathogen Beauveria bassiana ATCC 7159.

8. Quantitative Assessment of the Impact of Fluorine Substitution on P-Glycoprotein (P-gp) Mediated Efflux, Permeability, Lipophilicity, and Metabolic Stability.

9. Enhanced dereplication of fungal cultures via use of mass defect filtering.

10. Greensporones: resorcylic acid lactones from an aquatic Halenospora sp.

1. Semisynthetic Derivatives of the Verticillin Class of Natural Products through Acylation of the C11 Hydroxy Group.

2. Biosynthetic Plasticity Enables Production of Fluorinated Aurachins.