Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors

Sarcophine (1) is a bioactive cembranoid diterpene isolated from the Red Sea soft coral Sarcophyton glaucum. Previous semisynthesis attempts resulted in decreased or complete loss of 1’s anticancer activity. Sarcophine and analogues showed antimigratory activity against breast and prostate cancer ce...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2011-08, Vol.19 (16), p.4928-4934
Main Authors: Hassan, Hossam M., Sallam, Asmaa A., Mohammed, Rabab, Hifnawy, Mohamed S., Youssef, Diaa T.A., El Sayed, Khalid A.
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemistry
4-Butyrolactone - pharmacology
4-Butyrolactone - therapeutic use
Animals
Anthozoa - chemistry
anticarcinogenic activity
Antimigratory
Antineoplastic agents
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antineoplastic Agents - therapeutic use
Biological and medical sciences
Breast cancer
breast neoplasms
Breast Neoplasms - drug therapy
Carbamoylation
Cell Line, Tumor
Cell Migration Assays
Cell Migration Inhibition - drug effects
Cell Proliferation - drug effects
Cembranoids
corals
Diterpenes - chemical synthesis
Diterpenes - chemistry
Diterpenes - pharmacology
Diterpenes - therapeutic use
Drug Screening Assays, Antitumor
Etherification
Female
General aspects
Humans
Indian Ocean
Male
Medical sciences
metastasis
Pharmacology. Drug treatments
Prostate cancer
prostatic neoplasms
Prostatic Neoplasms - drug therapy
Sarcophyton
Sarcophyton glaucum
Semisynthesis
Structure-Activity Relationship
structure-activity relationships
Wound-healing
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Summary:Sarcophine (1) is a bioactive cembranoid diterpene isolated from the Red Sea soft coral Sarcophyton glaucum. Previous semisynthesis attempts resulted in decreased or complete loss of 1’s anticancer activity. Sarcophine and analogues showed antimigratory activity against breast and prostate cancer cell lines. This encouraged further semisynthestic optimizations to improve its activity and establish a preliminary structure–activity relationship. Eight new and five known semisynthetic analogues were generated. These compounds were evaluated for their ability to inhibit growth, proliferation, and migration of the prostate and breast metastatic cancer cell lines PC-3 and MDA-MB-231, respectively. Most analogues exhibited enhanced antimigratory activity.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2011.06.060