Synthesis of natural phaeosphaeride A derivatives and an in vitro evaluation of their anti-cancer potential

Victoria V Abzianidze; Daria S Prokofieva; Leonid A Chisty; Ksenia P Bolshakova; Alexander O Berestetskiy; Taras L Panikorovskii; Alexander S Bogachenkov; Alvin A Holder

doi:10.1016/j.bmcl.2015.10.048

Synthesis of natural phaeosphaeride A derivatives and an in vitro evaluation of their anti-cancer potential

Bioorg Med Chem Lett. 2015 Dec 1;25(23):5566-9. doi: 10.1016/j.bmcl.2015.10.048. Epub 2015 Oct 19.

Authors

Victoria V Abzianidze¹, Daria S Prokofieva², Leonid A Chisty², Ksenia P Bolshakova³, Alexander O Berestetskiy³, Taras L Panikorovskii⁴, Alexander S Bogachenkov⁵, Alvin A Holder⁶

Affiliations

¹ Chemical Modeling Laboratory, Research Institute of Hygiene, Occupational Pathology and Human Ecology, Federal Medical Biological Agency, p/o Kuz'molovsky, Saint Petersburg 188663, Russian Federation. Electronic address: [email protected].
² Chemical Modeling Laboratory, Research Institute of Hygiene, Occupational Pathology and Human Ecology, Federal Medical Biological Agency, p/o Kuz'molovsky, Saint Petersburg 188663, Russian Federation.
³ All-Russian Institute of Plant Protection, Federal Agency of Scientific Organizations, Pushkin, Saint Petersburg 196608, Russian Federation.
⁴ Department of Crystallography, Institute of Earth Sciences, Saint Petersburg State University, University Emb., 7/9., Saint Petersburg 199034, Russian Federation.
⁵ Department of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetsky Pr., 26, Saint Petersburg 198504, Russian Federation.
⁶ Department of Chemistry and Biochemistry, Old Dominion University, 4541 Hampton Boulevard, Norfolk, VA 23529, United States. Electronic address: [email protected].

PMID: 26508550
DOI: 10.1016/j.bmcl.2015.10.048

Abstract

Derivatives of phaeosphaeride A (PPA) were synthesised and characterised; then anti-cancer studies were carried out on the A549 cancer cell line. It was found that the acetyl derivative (compound 3) displayed comparable in vitro cytotoxicity to that of PPA (EC50=49±7 μM and EC50=46±5 μM, respectively), while chloroacetyl derivative 6 (EC50=33±7 μM) was found to have better efficacy towards the A549 cancer cell line.

Keywords: A549 cancer cell line; Anti-cancer agents; In vitro studies; Natural products; Phaeosphaeride A; X-ray crystallography.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry
Bridged Bicyclo Compounds, Heterocyclic / pharmacology
Cell Line, Tumor
Cell Survival / drug effects
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Humans
Molecular Structure

Substances

Bridged Bicyclo Compounds, Heterocyclic
phaeosphaeride A