Abeotaxane

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Chemical structure of taxchinin A, an abeotaxane

Abeotaxanes are a class of taxoid molecules with a core 5/7/6 type ring structure. This structure varies from the 6/8/6 or 6/10/6-membered core ring found in conventional taxoids such as paclitaxel or docetaxel. The core carbon skeleton of a normal natural product taxane (e.g., paclitaxel, docetaxel) has a 6-membered A ring, 8-membered B ring and a 6-membered C ring, combined with conventional side chains. It is the side chains that provide most of the activity for regular taxanes. Abeotaxanes are compounds containing 3 altered ring structures, where ring A is 5 members, ring B is 7 members and ring C is 6 members, combined with conventional side chains.

Like taxanes, abeotaxanes are

microtubules. Taxanes are highly effective anti-cancer agents and are utilized as first and second-line therapy in the treatment of many solid-tumor cancers. Since the FDA approval of paclitaxel in 1998, subsequent research has focused on the synthesis of new and improved taxanes to address the issues of multi-drug resistance and central nervous system bioavailability, as well as on improvement of the side effect profile.[citation needed
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Taxchinin A was the first naturally occurring rearranged taxoid identified as an 11(15→1)-abeotaxane. Taxchinin B was the first identified 11(15→1)-abeotaxoid with an oxetane ring. The first natural taxoid, identified to have an 11(15→1)-abeotaxane ring was brevifoliol.[1] TPI 287 (formerly ARC-100), a 11(15→1)-abeotaxane that was in phase I clinical development in 2010, has demonstrated potent activity in multi-drug resistant tumor types, including taxane-resistant tumors, as well as efficacy in crossing the blood–brain barrier.[2]

References

  1. PMID 15165147
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  2. doi:10.1002/pbc.25687
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