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US 7,736,624 B2Granted
Methods and compositions for diagnostic and therapeutic targeting of COX-2
OwnerLawrence J. Marnett, Md. Jashim Uddin +1inventors
InventorsLawrence J. Marnett, Md. Jashim Uddin, Brenda C. Crews
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Abstract
The presently disclosed subject matter provides compositions that selectively bind cyclooxygenase-2 and comprise a therapeutic and/or diagnostic moiety. Also provided are methods for using the disclosed compositions for diagnosing (i.e., by imaging) a target cell and/or treating a disorder associated with a cyclooxygenase-2 biological activity.
Claims21
A cyclooxygenase-2-selective therapeutic and/or diagnostic agent of the following structural formula:
- wherein:
- R1=C1 to C6 alkoxy, C1 to C6 branched alkoxy, or halo-substituted versions thereof;
- R2=benzoyl or halo-substituted benzoyl;
- X is an active agent selected from the group consisting of a chemotherapeutic agent;
- a fluorophore selected from the group consisting of dansyl chloride, dabsyl chloride, nitrobenzodiazolamine (NBD), fluorescein and derivatives thereof, rhodamine and derivatives thereof;
- a cyanine dye;
- and a near infrared (NIR) dye;
- and
- A is an alkylamide tether selected from the group consisting of an alkyldiamide tether, an alkylamidodiester tether, an alkyldiamidomonoester tether, an alkylamidosulfonamide tether, an alkylamidothiourea tether, an alkyldiamidosulfonamide tether, and an aminoalkyldiamide tether;
- B is —NH;
- and
- n is 1.
9 more elements
A method for synthesizing a therapeutic and/or diagnostic agent, the method comprising:
- (a) providing a non-steroidal anti-inflammatory drug (NSAID), or a derivative thereof, comprising the following formula:
- wherein:
- R1=C1 to C6 alkoxy, C1 to C6 branched alkoxy, or halo-substituted versions thereof;
- R2=benzoyl or halo-substituted benzoyl;
- n is 1
- (b) derivatizing the carboxylic acid moiety to a secondary amide or an ester;
- and
- (c) complexing an active agent to the secondary amide or the ester to produce a therapeutic and/or diagnostic agent having the following structure:
- wherein:
- (i) X is an active agent selected from the group consisting of a chemotherapeutic agent;
- a fluorophore selected from the group consisting of dansyl chloride, dansyl chloride, nitrobenzodiazolamine (NBD), fluorescein and derivatives thereof, rhodamine and derivatives thereof;
- a cyanine dye;
- and a near infrared (NIR) dye;
- (ii) A is an alkylamide tether selected from the group consisting of an alkyldiamide tether, an alkylamidodiester tether, an alkyldiamidomonoester tether, an alkylamidosulfonamide tether, an alkylamidothiourea tether, an alkyldiamidosulfonamide tether, and an aminoalkyldiamide tether;
- (iii) B —NH;
- and
- (iv) the therapeutic and/or diagnostic agent selectively binds to cyclooxygenase-2 (COX-2).
14 more elements
Dependencies are inferred from the claim text.