Skip NavigationSkip to Content
Return Return to Search Results

Facile photochemical synthesis of mixed siloxyacetal glycosides as potential pH-sensitized prodrugs for selective treatment of solid tumors

  1. Author:
    Svarovsky, S. A.
    Taraban, M. B.
    Barchi, J. J.

  2. Author Address

    NCI, Med Chem Lab, Frederick, MD 21702 USA. Russian Acad Sci, Inst Chem Kinet & Combust, Siberian Div, Novosibirsk 630090, Russia Svarovsky, SA, NCI, Med Chem Lab, 376 Boyles St, Frederick, MD 21702 USA
    1. Year: 2004
  2. Journal: Organic & Biomolecular Chemistry
    1. 2
    2. 21
    3. Pages: 3155-3161
  4. Type of Article: Article
  1. Abstract:

    Photochemical reactions of a variety of acylsilanes with peracetylated free glycosides in anhydrous benzene at ambient temperature yielded novel, highly acid-sensitive siloxyacetal glycosides in 75-90% yields with complete retention of configuration at the anomeric center. Subsequent deacetylation of triisopropylsiloxy- and tert-butyldimethylsiloxy derivatives with sodium methoxide in methanol afforded deprotected siloxyacetal glycosides in nearly quantitative yields. Acid hydrolysis of trimethylsilyl siloxyacetals proceeded with a half-life of 17.5 minutes at pH 6.2 which is vastly superior to the decomposition rate of conventional acetals under similar conditions. The structure of one of the novel siloxyacetals was confirmed by X-ray crystallography. In vitro biological studies showed that glucose-derived siloxyacetals may serve as potential pH-activated prodrugs for selective treatment of solid tumors

    See More

  1. Keywords:

External Sources

  1. View record in Web of Science®
  2. WOS: 000224703400018

Library Notes

  1. No notes added.
NCI at Frederick

You are leaving a government website.

This external link provides additional information that is consistent with the intended purpose of this site. The government cannot attest to the accuracy of a non-federal site.

Linking to a non-federal site does not constitute an endorsement by this institution or any of its employees of the sponsors or the information and products presented on the site. You will be subject to the destination site's privacy policy when you follow the link.

ContinueCancel