Supramolecular Self-Assembly of Histidine-Capped-Dialkoxy-Anthracene: A Visible-Light-Triggered Platform for Facile siRNA Delivery

Sachin P Patil; Basem A Moosa; Shahad Alsaiari; Kholod Alamoudi; Aws Alshamsan; Abdulaziz AlMalik; Karim Adil; Mohamed Eddaoudi; Niveen M Khashab

doi:10.1002/chem.201601442

Supramolecular Self-Assembly of Histidine-Capped-Dialkoxy-Anthracene: A Visible-Light-Triggered Platform for Facile siRNA Delivery

Chemistry. 2016 Sep 19;22(39):13789-13793. doi: 10.1002/chem.201601442. Epub 2016 Jul 28.

Authors

Sachin P Patil¹, Basem A Moosa¹, Shahad Alsaiari¹, Kholod Alamoudi¹, Aws Alshamsan², Abdulaziz AlMalik³, Karim Adil⁴, Mohamed Eddaoudi⁴, Niveen M Khashab¹

Affiliations

¹ Smart Hybrid Materials (SHMs) Laboratory, King Abdullah University of Science and Technology (KAUST), Thuwal, Makkah, 23955-6900, Kingdom of Saudi Arabia.
² Department of Pharmaceutics, College of Pharmacy and King Abdullah Institute of Nanotechnology, King Saud University, Kingdom of Saudi Arabia.
³ Center of Excellence in Nanomedicine, King Abdulaziz City for Science and Technology (KACST), Riyadh, Kingdom of Saudi Arabia.
⁴ Functional Materials Design, Discovery and Development Research, King Abdullah University of Science and Technology (KAUST), Thuwal, Makkah, 23955-6900, Kingdom of Saudi Arabia.

PMID: 27356263
DOI: 10.1002/chem.201601442

Abstract

Supramolecular self-assembly of histidine-capped-dialkoxy-anthracene (HDA) results in the formation of light-responsive nanostructures. Single-crystal X-ray diffraction analysis of HDA shows two types of hydrogen bonding. The first hydrogen bond is established between the imidazole moieties while the second involves the oxygen atom of one amide group and the hydrogen atom of a second amide group. When protonated in acidic aqueous media, HDA successfully complexes siRNA yielding spherical nanostructures. This biocompatible platform controllably delivers siRNA with high efficacy upon visible-light irradiation leading up to 90 % of gene silencing in live cells.

Keywords: hydrogen bonding; photoresponsive; self-assembly; siRNA delivery; supramolecular chemistry.

MeSH terms

Anthracenes / chemistry*
Crystallography, X-Ray
Gene Transfer Techniques*
HeLa Cells
Histidine / analogs & derivatives*
Humans
Hydrogen Bonding
Light
Models, Molecular
Proto-Oncogene Proteins c-bcl-2 / genetics
RNA Interference*
RNA, Small Interfering / administration & dosage*
RNA, Small Interfering / genetics

Substances

Anthracenes
Proto-Oncogene Proteins c-bcl-2
RNA, Small Interfering
Histidine