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Key role of glutamic acid for the cytotoxic activity of the cyclotide cycloviolacin O2
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Medical Sciences, Clinical Pharmacology. (Rolf Larsson)
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2006 (English)In: Cellular and Molecular Life Sciences (CMLS), ISSN 1420-682X, E-ISSN 1420-9071, Vol. 63, no 2, 235-245 p.Article in journal (Refereed) Published
Abstract [en]

Cyclotides are cyclic plant proteins with potent cytotoxic effects. Here we systematically probed the importance of surface-exposed charged amino acid residues of the cyclotide cycloviolacin O2, using a strategy involving chemical modifications. We show that the single glutamic acid plays a key role for the cytotoxicity: methylation of this residue produced a 48-fold decrease in potency. Virtually no change in potency was observed when masking the single arginine residue using 1,2-cyclohexanedione, while acetylation of the two lysine residues reduced the potency 3-fold. The derivative with modifications at both arginine and lysine residues showed a 7-fold loss of potency. In addition, we show that the activity is dependent on an intact disulfide network and that the short sequences between the six cysteine residues, that is, the backbone loops, are devoid of cytotoxic activity.

Place, publisher, year, edition, pages
2006. Vol. 63, no 2, 235-245 p.
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Medical and Health Sciences
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URN: urn:nbn:se:uu:diva-102028DOI: 10.1007/s00018-005-5486-4PubMedID: 16389447OAI: oai:DiVA.org:uu-102028DiVA: diva2:213873
Available from: 2009-04-29 Created: 2009-04-29 Last updated: 2017-12-13Bibliographically approved

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