Synthesis, Electrochemistry, and Bioactivity of the Cyanobacterial Calothrixins and Related Quinones

dc.contributor.authorBernardo, Paul
dc.contributor.authorChai, Christina
dc.contributor.authorHeath, Graham
dc.contributor.authorMahon, Peter
dc.contributor.authorSmith, Geoffrey D
dc.contributor.authorWaring, Paul
dc.contributor.authorWilkes, Bronwyn
dc.date.accessioned2015-12-13T23:09:34Z
dc.date.available2015-12-13T23:09:34Z
dc.date.issued2004
dc.date.updated2015-12-12T08:19:45Z
dc.description.abstractThe calothrixins are quinone-based natural products isolated from Calothrix cyanobacteria which show potent antiproliferative properties against several cancer cell lines. Preliminary mechanistic studies suggest that the biological mode of action of the calothrixins maybe linked to their ability to undergo redox cycling. In this study we compare the bioactivities of the calothrixins with those of structurally related quinones in order to identify the structural features in the calothrixins essential for biological activity. In particular, the reduction potentials of the calothrixins and some related quinones were measured electrochemically. Our studies indicate that while there is no direct correlation between the reduction potentials and biological activities of the studied compounds, in all cases quinones with EC50 values <1.6 μM undergo reduction to their respective semiquinones readily, with their E1/2 values being more positive than -0.5 V versus the standard hydrogen electrode (SHE).
dc.identifier.issn0022-2623
dc.identifier.urihttp://hdl.handle.net/1885/87057
dc.publisherAmerican Chemical Society
dc.sourceJournal of Medicinal Chemistry
dc.subjectKeywords: antineoplastic agent; benzocarbazoledione; calothrixin a; calothrixin b; carboquone; ellipticine derivative; menadione; quinone derivative; semiquinone; unclassified drug; antineoplastic activity; article; cancer cell culture; controlled study; Cyanobacte
dc.titleSynthesis, Electrochemistry, and Bioactivity of the Cyanobacterial Calothrixins and Related Quinones
dc.typeJournal article
local.bibliographicCitation.issue20
local.bibliographicCitation.lastpage4963
local.bibliographicCitation.startpage4958
local.contributor.affiliationBernardo, Paul, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationChai, Christina, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationHeath, Graham, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationMahon, Peter, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationSmith, Geoffrey D, College of Medicine, Biology and Environment, ANU
local.contributor.affiliationWaring, Paul, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWilkes, Bronwyn, College of Physical and Mathematical Sciences, ANU
local.contributor.authoremailu4021263@anu.edu.au
local.contributor.authoruidBernardo, Paul, u4006401
local.contributor.authoruidChai, Christina, u8615775
local.contributor.authoruidHeath, Graham, u8615167
local.contributor.authoruidMahon, Peter, u4043257
local.contributor.authoruidSmith, Geoffrey D, u7200037
local.contributor.authoruidWaring, Paul, u4021263
local.contributor.authoruidWilkes, Bronwyn, u4005385
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.absfor060104 - Cell Metabolism
local.identifier.ariespublicationMigratedxPub16177
local.identifier.citationvolume47
local.identifier.doi10.1021/jm049625o
local.identifier.scopusID2-s2.0-4544386788
local.identifier.uidSubmittedByMigrated
local.type.statusPublished Version

Downloads

Back to topicon-arrow-up-solid
 
APRU
IARU
 
edX
Group of Eight Member

Acknowledgement of Country

The Australian National University acknowledges, celebrates and pays our respects to the Ngunnawal and Ngambri people of the Canberra region and to all First Nations Australians on whose traditional lands we meet and work, and whose cultures are among the oldest continuing cultures in human history.


Contact ANUCopyrightDisclaimerPrivacyFreedom of Information

+61 2 6125 5111 The Australian National University, Canberra

TEQSA Provider ID: PRV12002 (Australian University) CRICOS Provider Code: 00120C ABN: 52 234 063 906