Abstract
An aza-cycloisodityrosine analogue of RA-VII, 3, was designed and synthesized. The key aza-cycloisodityrosine unit was prepared by copper(II)-acetate-mediated intramolecular phenylamine/arylboronic acid coupling of dipeptide followed by connection with the tetrapeptide segment to afford a hexapeptide. Subsequent macrocyclization of the hexapeptide with EDC · HCl and HOOBt under dilute conditions gave 3. Analogue 3 showed significant cytotoxic activity against human promyelocytic leukemia HL-60 cells and human colon carcinoma HCT-116 cells, but its activity was weaker than that of parent peptide RA-VII (1).
Keywords:
Aza-cycloisodityrosine; Bouvardin; Cytotoxicity; RA-VII; Rubia cordifolia.
Copyright © 2013 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents, Phytogenic / chemical synthesis
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Antineoplastic Agents, Phytogenic / chemistry*
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Antineoplastic Agents, Phytogenic / toxicity
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Aza Compounds / chemistry
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Crystallography, X-Ray
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HCT116 Cells
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HL-60 Cells
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Humans
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Molecular Conformation
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Peptides / chemical synthesis
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Peptides / chemistry*
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Peptides / toxicity
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Peptides, Cyclic / chemical synthesis
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Peptides, Cyclic / chemistry*
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Peptides, Cyclic / toxicity
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Rubia / chemistry
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Rubia / metabolism
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Tyrosine / analogs & derivatives*
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Tyrosine / chemical synthesis
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Tyrosine / chemistry
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Tyrosine / toxicity
Substances
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Antineoplastic Agents, Phytogenic
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Aza Compounds
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Peptides
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Peptides, Cyclic
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bouvardin
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Tyrosine
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isodityrosine
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RA VII