Modified cyclodextrins for the selective sequestration of fentanyl related compounds and uses thereof
Novel thioalkylcarboxylate-modified CDs and pharmaceutical compositions comprising these thioalkylcarboxylate-modified CDs are disclosed, as well as methods of using the disclosed thioalkylcarboxylate-modified CDs and pharmaceutical compositions thereof to neutralize or reduce undesired effects or symptoms associated with one or more fentanyl related compounds in a subject in need thereof. The use of the disclosed thioalkylcarboxylate-modified CDs to detect the presence of one or more fentanyl related compounds in a sample is also disclosed, which comprises contacting the sample with said thioalkylcarboxylate-modified CDs or a composition comprising these CDs.
1. A compound of Formula I:
including salts and pharmaceutically acceptable salts thereof, wherein:
R is —S—(CH 2 ) n —COOH or —S—(CH 2 ) n+1 —OH; and
n is 8, 9, or 10.
2. The compound of claim 1 , wherein R is —S—(CH 2 ) n —COOH, and the salt or pharmaceutically acceptable salt is potassium salt, and/or sodium salt.
3. A composition comprising the compound of claim 1 and optionally a carrier.
4. A pharmaceutical composition comprising the compound of claim 1 and optionally a pharmaceutically acceptable carrier.
5. A method of preparing the compound of claim 1 comprising:
a) a coupling step comprising reacting a thiol R′—H and a per-7-Br-βCD to provide a coupling β-CD product:
wherein R′ —S—(CH 2 ) n —COOH.