Anticancer and anti-inflammatory sulfur-containing semisynthetic derivatives of sarcophine.

Abstract

Sarcophine (1), a cembranoid diterpene is known to inhibit the process of tumorigenesis. Sarcophine can be isolated in large amounts from the Red Sea soft coral Sarcophyton glaucum and hence is an ideal target for semisynthetic or biocatalytic modifications. Hydroxylated derivatives of 1 were reported to improve its anticancer activity. Despite the promising results and ready availability, there are limited attempts towards further diversifying the library of sarcophine derivatives. Hence, the current study targets the epoxide ring to generate sulfur-containing derivatives of sarcophine by reacting it with ammonium thiocyanate and Lawesson's reagent. Structure elucidation of the products was based on extensive 1D and 2D NMR and high resolution mass spectrometry, in addition to mechanistic considerations. The effect of these derivatives on highly malignant +SA mammary epithialial cell proliferation is reported. Anti-inflammatory potential of sarcophine and its derivatives is also demonstrated.

• Authors: Swapnali Sawant, Diaa Youssef, Alejandro Mayer, Paul Sylvester, Vikram Wali, Mark Arant, Khalid El Sayed
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 54 Issue 8 Pg. 1119-23 (Aug 2006) ISSN: 0009-2363 [Print] Japan
• PMID: 16880655 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Anti-Inflammatory Agents
• Antineoplastic Agents
• sarcophine
• Sulfur
• 4-Butyrolactone

Topics

• 4-Butyrolactone (analogs & derivatives, chemical synthesis, chemistry, pharmacology)
• Animals
• Anthozoa (chemistry)
• Anti-Inflammatory Agents (chemical synthesis, chemistry, pharmacology)
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Cell Proliferation (drug effects)
• Drug Screening Assays, Antitumor
• Magnetic Resonance Spectroscopy
• Mammary Neoplasms, Animal (drug therapy)
• Mass Spectrometry
• Mice
• Molecular Structure
• Rats
• Sulfur (chemistry)