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. 2010 Apr 2;12(7):1384-7.
doi: 10.1021/ol1002626.

The synthesis of a c(RGDyK) targeted SN38 prodrug with an indolequinone structure for bioreductive drug release

Baohua Huang  1 , Ankur Desai, Shengzhuang Tang, Thommey P Thomas, James R Baker Jr
Affiliations

The synthesis of a c(RGDyK) targeted SN38 prodrug with an indolequinone structure for bioreductive drug release

Baohua Huang et al. Org Lett. .

Abstract

Preparation of a novel c(RGDyK) targeted SN38 prodrug incorporating an indolequinone structure for bioreductively triggered drug release is described. This design yields a prodrug that targets surface molecules on tumor cells (alpha(v)beta(3) integrins) and releases drug under bioreductive conditions. There are three moieties in the prodrug design, namely a therapeutic drug SN38, an indolequinone structure serving as a drug releasing trigger, and an alpha(v)beta(3) integrin targeting peptide c(RGDyK). Preliminary studies showed that SN38 is released in the presence of a bioreductive enzyme (DT-diaphorase).

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Figures

Figure 1
Figure 1
The release of SN38 from prodrug 1 under DTD.
Figure 2
Figure 2
Cytotoxicity of 12 in the presence of DTD.
Scheme 1
Scheme 1
The synthesis of non-targeted SN38 prodrug
Scheme 2
Scheme 2
The modification of c(RGDyK) peptide
Scheme 3
Scheme 3
The synthesis of c(RGDyK) targeted SN38 prodrug
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