Molecules 2008, 13(11), 2704-2716; doi:10.3390/molecules13112704
Article

Biocatalytically Oligomerized Epicatechin with Potent and Specific Anti-proliferative Activity for Human Breast Cancer Cells

Subhalakshmi Nagarajan 1,6, Ramaswamy Nagarajan 2, Susan J. Braunhut 3, Ferdinando Bruno 4, Donna McIntosh 3, Lynne Samuelson 4 and Jayant Kumar 5,6,* email
1 Department of Chemistry, University of Massachusetts, Lowell, USA 2 Department of Plastics Engineering, University of Massachusetts, Lowell, USA 3 Department of Biological Sciences, University of Massachusetts, Lowell, USA 4 U.S Army Natick Soldier Research, Development & Engineering Center, Natick, MA, 01760, USA 5 Department of Physics, University of Massachusetts, Lowell, USA 6 Center for Advanced Materials, University of Massachusetts, Lowell, USA
* Author to whom correspondence should be addressed.
Received: 18 August 2008; in revised form: 26 September 2008 / Accepted: 7 October 2008 / Published: 1 November 2008
(This article belongs to the Special Issue Phenolics and Polyphenolics)
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Abstract: Catechins, naturally occurring flavonoids derived from wine and green tea, are known to exhibit multiple health benefits. Epigallocatechin gallate (EGCG) is one of the most widely investigated catechins, but its efficacy in cancer therapy is still inconsistent and limited. The poor stability of EGCG has contributed to the disparity in the reported anti-cancer activity and other beneficial properties. Here we report an innovative enzymatic strategy for the oligomerization of catechins (specifically epicatechin) that yields stable, water-soluble oligomerized epicatechins with enhanced and highly specific anti-proliferative activity for human breast cancer cells. This one-pot oxidative oligomerization is carried out in ambient conditions using Horseradish Peroxidase (HRP) as a catalyst yielding water-soluble oligo(epicatechins). The oligomerized epicatechins obtained exhibit excellent growth inhibitory effects against human breast cancer cells with greater specificity towards growth-inhibiting cancer cells as opposed to normal cells, achieving a high therapeutic differential. Our studies indicate that water-soluble oligomeric epicatechins surpass EGCG in stability, selectivity and efficacy at lower doses.
Keywords: Oligomeric catechins; Enzymatic oligomerization; Anti-proliferative activity; Green chemistry; Flavonoids

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MDPI and ACS Style

Nagarajan, S.; Nagarajan, R.; Braunhut, S.J.; Bruno, F.; McIntosh, D.; Samuelson, L.; Kumar, J. Biocatalytically Oligomerized Epicatechin with Potent and Specific Anti-proliferative Activity for Human Breast Cancer Cells. Molecules 2008, 13, 2704-2716.

AMA Style

Nagarajan S., Nagarajan R., Braunhut S.J., Bruno F., McIntosh D., Samuelson L., Kumar J. Biocatalytically Oligomerized Epicatechin with Potent and Specific Anti-proliferative Activity for Human Breast Cancer Cells. Molecules. 2008; 13(11):2704-2716.

Chicago/Turabian Style

Nagarajan, Subhalakshmi; Nagarajan, Ramaswamy; Braunhut, Susan J.; Bruno, Ferdinando; McIntosh, Donna; Samuelson, Lynne; Kumar, Jayant. 2008. "Biocatalytically Oligomerized Epicatechin with Potent and Specific Anti-proliferative Activity for Human Breast Cancer Cells." Molecules 13, no. 11: 2704-2716.

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