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A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress.

Publication ,  Journal Article
Franks, AT; Wang, Q; Franz, KJ
Published in: Bioorganic & medicinal chemistry letters
November 2015

UVA radiation can damage cells and tissues by direct photodamage of biomolecules as well as by initiating metal-catalyzed oxidative stress. In order to alleviate both concerns simultaneously, we synthesized a multifunctional prochelator PC-HAPI (2-((E)-1-(2-isonicotinoylhydrazono)ethyl)phenyl (trans)-3-(2,4-dihydroxyphenyl)acrylate) that contains a trans-(o-hydroxy)cinnamate ester photocleavable protecting group that is cleaved upon UVA exposure to release a coumarin, umbelliferone, and an aroylhydrazone metal chelator, HAPI (N'-[1-(2-hydroxyphenyl)ethyliden]isonicotinoylhydrazide). While the prochelator PC-HAPI exhibits negligible affinity for iron, it responds rapidly to UVA irradiation and converts to an iron-binding chelator that inhibits iron-catalyzed formation of reactive oxygen species and protects cells from UVA damage.

Duke Scholars

Published In

Bioorganic & medicinal chemistry letters

DOI

EISSN

1464-3405

ISSN

0960-894X

Publication Date

November 2015

Volume

25

Issue

21

Start / End Page

4843 / 4847

Related Subject Headings

  • Ultraviolet Rays
  • Structure-Activity Relationship
  • Reactive Oxygen Species
  • Oxidative Stress
  • Molecular Structure
  • Medicinal & Biomolecular Chemistry
  • Isonicotinic Acids
  • Iron Chelating Agents
  • Iron
  • Humans
 

Citation

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Franks, A. T., Wang, Q., & Franz, K. J. (2015). A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress. Bioorganic & Medicinal Chemistry Letters, 25(21), 4843–4847. https://doi.org/10.1016/j.bmcl.2015.06.048
Franks, Andrew T., Qin Wang, and Katherine J. Franz. “A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress.Bioorganic & Medicinal Chemistry Letters 25, no. 21 (November 2015): 4843–47. https://doi.org/10.1016/j.bmcl.2015.06.048.
Franks AT, Wang Q, Franz KJ. A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress. Bioorganic & medicinal chemistry letters. 2015 Nov;25(21):4843–7.
Franks, Andrew T., et al. “A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress.Bioorganic & Medicinal Chemistry Letters, vol. 25, no. 21, Nov. 2015, pp. 4843–47. Epmc, doi:10.1016/j.bmcl.2015.06.048.
Franks AT, Wang Q, Franz KJ. A multifunctional, light-activated prochelator inhibits UVA-induced oxidative stress. Bioorganic & medicinal chemistry letters. 2015 Nov;25(21):4843–4847.
Journal cover image

Published In

Bioorganic & medicinal chemistry letters

DOI

EISSN

1464-3405

ISSN

0960-894X

Publication Date

November 2015

Volume

25

Issue

21

Start / End Page

4843 / 4847

Related Subject Headings

  • Ultraviolet Rays
  • Structure-Activity Relationship
  • Reactive Oxygen Species
  • Oxidative Stress
  • Molecular Structure
  • Medicinal & Biomolecular Chemistry
  • Isonicotinic Acids
  • Iron Chelating Agents
  • Iron
  • Humans