Synthesis of Monofunctional Curcumin Derivatives, Clicked Curcumin Dimer, and a PAMAM Dendrimer Curcumin Conjugate for Therapeutic Applications

Curcumin, the primary active ingredient in the spice turmeric, was converted to reactive monofunctional derivatives (carboxylic acid/azide/alkyne). The derivatives were employed to produce a 3 + 2 azide−alkyne “clicked” curcumin dimer and a poly(amidoamine) (PAMAM) dendrimer−curcumin conjugate. The...

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Bibliographic Details
Published in:Organic letters 2007-12, Vol.9 (26), p.5461-5464
Main Authors: Shi, Wei, Dolai, Sukanta, Rizk, Samar, Hussain, Afshan, Tariq, Hussnain, Averick, Saadyah, L'Amoreaux, William, El Idrissi, Abdeslem, Banerjee, Probal, Raja, Krishnaswami
Format: Article
Language:English
Subjects:
Curcumin - chemistry
Dendrimers
Dimerization
Humans
Magnetic Resonance Spectroscopy
Polyamines - chemistry
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Summary:Curcumin, the primary active ingredient in the spice turmeric, was converted to reactive monofunctional derivatives (carboxylic acid/azide/alkyne). The derivatives were employed to produce a 3 + 2 azide−alkyne “clicked” curcumin dimer and a poly(amidoamine) (PAMAM) dendrimer−curcumin conjugate. The monofunctional curcumin derivatives retain biological activity and are efficient for labeling and dissolving amyloid fibrils. The curcumin dimer selectively destroys human neurotumor cells. The synthetic methodology developed affords a general strategy for attaching curcumin to various macromolecular scaffolds.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol702370m