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New Alloferon Analogues: Synthesis and Antiviral Properties
Author(s) -
Kuczer Mariola,
Majewska Anna,
Zahorska Renata
Publication year - 2013
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.12020
Subject(s) - peptide , stereochemistry , vero cell , chemistry , cytotoxic t cell , structure–activity relationship , cell culture , biochemistry , biology , in vitro , genetics
We have extended our study on structure/activity relationship studies of insect peptide alloferon (H‐His‐Gly‐Val‐Ser‐Gly‐His‐Gly‐Gln‐His‐Gly‐Val‐His‐Gly‐OH) by evaluating the antiviral effects of new alloferon analogues. We synthesized 18 alloferon analogues: 12 peptides with sequences shortened from N‐ or C‐ terminus and 6 N ‐terminally modified analogues H‐X 1 ‐Gly‐Val‐Ser‐Gly‐His‐Gly‐Gln‐His‐Gly‐Val‐His‐Gly‐OH, where X 1 = Phe ( 13 ), Tyr ( 14 ), Trp ( 15 ), Phg ( 16 ), Phe(p‐Cl) ( 17 ), and Phe(p‐OMe) ( 18 ). We found that most of the evaluated peptides inhibit the replication of Human Herpesviruses or Coxsackievirus B2 in Vero, HEp‐2 and LLC‐MK 2 cells. Our results indicate that the compound [3‐13]‐alloferon ( 1 ) exhibits the strongest antiviral activity (IC 50 = 38 μ m ) among the analyzed compound. Moreover, no cytotoxic activity against the investigated cell lines was observed for all studied peptides at concentration 165 μ m or higher.