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Title: Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues
Authors: Kamiyama, H.
Kubo, Y.
Sato, H.
Yamamoto, N. 
Fukuda, T.
Ishibashi, F.
Iwao, M.
Keywords: Anti-HIV-1 activity
Entry inhibiting activity
Lamellarin sulfates
Structure-activity relationships
Issue Date: 15-Dec-2011
Citation: Kamiyama, H., Kubo, Y., Sato, H., Yamamoto, N., Fukuda, T., Ishibashi, F., Iwao, M. (2011-12-15). Synthesis, structure-activity relationships, and mechanism of action of anti-HIV-1 lamellarin α 20-sulfate analogues. Bioorganic and Medicinal Chemistry 19 (24) : 7541-7550. ScholarBank@NUS Repository.
Abstract: Lamellarin α and six different types of lamellarin α 20-sulfate analogues were synthesized and their structure-activity relationships were investigated using a single round HIV-1 vector infection assay. All lamellarin sulfates having pentacyclic lamellarin core exhibited anti-HIV-1 activity at a 10 μM concentration range regardless of the number and position of the sulfate group. On the other hand, non-sulfated lamellarin α and ring-opened lamellarin sulfate analogues did not affect HIV-1 vector infection in similar concentrations. The lamellarin sulfates utilized in this study did not exhibit unfavorable cytotoxic effect under the concentrations tested (IC 50 > 100 μM). Confocal laser scanning microscopic analysis indicated that hydrophilic lamellarin sulfates were hardly incorporated in the cell. HIV-1 Env-mediated cell-cell fusion was suppressed by lamellarin sulfates. These results suggested that lamellarin sulfates have a novel anti-HIV-1 activity besides the previously reported integrase activity inhibition, possibly at a viral entry step of HIV-1 replication. © 2011 Elsevier Ltd. All rights reserved.
Source Title: Bioorganic and Medicinal Chemistry
ISSN: 09680896
DOI: 10.1016/j.bmc.2011.10.030
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