tryptophan-naphthoquinone (4c) chloride

Tryptophan-naphthoquinone (4c) chloride is a research-stage small molecule consisting of a chlorinated 1,4-naphthoquinone moiety conjugated to the amino acid tryptophan. Synthesized using microwave-assisted methods, the compound has been evaluated for its antiproliferative effects in cervical cancer models. It demonstrates potent cytotoxicity against both HPV-positive (SiHa, CaLo) and HPV-negative (C33-A) tumorigenic cell lines, with IC50 values significantly lower than its non-chlorinated counterparts. Its mechanism of action is primarily attributed to the generation of reactive oxygen species (ROS) through redox cycling of the quinone moiety, leading to oxidative stress and potential interference with DNA, RNA, and protein function. The presence of the chlorine atom at the ortho-position enhances its cytotoxic potency by shifting the redox potential toward more positive values, thereby facilitating electron transfer.

Other names

2-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)-3-(1H-indol-3-yl)propanoic acidchloride tryptophan-naphthoquinone