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The chain length of biologically produced ( R )-3-hydroxyalkanoic acid affects biological activity and structure of anti-cancer peptides

Overview of attention for article published in Journal of Biotechnology, June 2015
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Title
The chain length of biologically produced ( R )-3-hydroxyalkanoic acid affects biological activity and structure of anti-cancer peptides
Published in
Journal of Biotechnology, June 2015
DOI 10.1016/j.jbiotec.2015.02.036
Pubmed ID
Authors

Emilia Szwej, Marc Devocelle, Shane Kenny, Maciej Guzik, Stephen O’Connor, Jasmina Nikodinovic-Runic, Jelena Radivojevic, Veselin Maslak, Annete T. Byrne, William M. Gallagher, Qun Ren Zulian, Manfred Zinn, Kevin E. O’Connor

Abstract

Conjugation of DP18L peptide with (R)-3-hydroxydecanoic acid, derived from the biopolymer polyhydroxyalkanoate, enhances its anti-cancer activity (O'Connor et al., 2013. Biomaterials 34, 2710-2718). However, it is unknown if other (R)-3-hydroxyalkanoic acids (R3HAs) can enhance peptide activity, if chain length affects enhancement, and what effect R3HAs have on peptide structure. Here we show that the degree of enhancement of peptide (DP18L) anti-cancer activity by R3HAs is carbon chain length dependent. In all but one example the R3HA conjugated peptides were more active against cancer cells than the unconjugated peptides. However, R3HAs with 9 and 10 carbons were most effective at improving DP18L activity. DP18L peptide variant DP17L, missing a hydrophobic amino acid (leucine residue 4) exhibited lower efficacy against MiaPaCa cells. Circular dichroism analysis showed DP17L had a lower alpha helix content and the conjugation of any R3HA ((R)-3-hydroxyhexanoic acid to (R)-3-hydroxydodecanoic acid) to DP17L returned the helix content back to levels of DP18L. However (R)-3-hydroxyhexanoic did not enhance the anti-cancer activity of DP17L and at least 7 carbons were needed in the R3HA to enhance activity of D17L. DP17L needs a longer chain R3HA to achieve the same activity as DP18L conjugated to an R3HA. As a first step to assess the synthetic potential of polyhydroxyalkanoate derived R3HAs, (R)-3-hydroxydecanoic acid was synthetically converted to (±)3-chlorodecanoic acid, which when conjugated to DP18L improved its antiproliferative activity against MiaPaCa cells.

Twitter Demographics

The data shown below were collected from the profile of 1 tweeter who shared this research output. Click here to find out more about how the information was compiled.

Mendeley readers

The data shown below were compiled from readership statistics for 30 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
India 1 3%
Unknown 29 97%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 8 27%
Student > Master 8 27%
Researcher 4 13%
Student > Doctoral Student 2 7%
Other 1 3%
Other 2 7%
Unknown 5 17%
Readers by discipline Count As %
Agricultural and Biological Sciences 6 20%
Chemistry 4 13%
Medicine and Dentistry 3 10%
Immunology and Microbiology 3 10%
Engineering 2 7%
Other 6 20%
Unknown 6 20%

Attention Score in Context

This research output has an Altmetric Attention Score of 1. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 31 March 2015.
All research outputs
#10,845,757
of 12,236,619 outputs
Outputs from Journal of Biotechnology
#2,623
of 2,895 outputs
Outputs of similar age
#192,234
of 230,820 outputs
Outputs of similar age from Journal of Biotechnology
#26
of 47 outputs
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We're also able to compare this research output to 47 others from the same source and published within six weeks on either side of this one. This one is in the 1st percentile – i.e., 1% of its contemporaries scored the same or lower than it.