Identifying apoptotic cells with the 3-hydroxyflavone derivative F2N12S, a ratiometric fluorescent small molecule probe selective for plasma membranes: a possible general mechanism for selective uptake into apoptotic cell

Hope-Roberts, M., Horobin, R.W. and Wainwright, M. (2011) Identifying apoptotic cells with the 3-hydroxyflavone derivative F2N12S, a ratiometric fluorescent small molecule probe selective for plasma membranes: a possible general mechanism for selective uptake into apoptotic cell. Biotechnic and Histochemistry, 86(4), pp. 255-261. (doi: 10.3109/10520291003723426)

Abstract

The mechanism of selective targeting of the plasma membrane of apoptotic cells by F2N12S, a recently reported ratiometric, fluorescent small molecule probe, was analyzed using decision-rule QSAR models. Selectivity was determined by a combination of the probe's weak amphiphilicity and slow flip-flop with the increased plasma membrane fluidity of apoptotic cells. The probable chemical features required for such probes may be defined in terms of numerical structural parameters as: 3.5 < AI < similar to 5.5; log P < 5.0; HGS > 400 (where AI, log P and HGS parameters model amphiphilicity, lipophilicity and headgroup size, respectively). When HGS is <400, compounds are initially membrane selective, but subsequently are internalized.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Horobin, Dr Richard
• Authors: Hope-Roberts, M., Horobin, R.W., and Wainwright, M.
• College/School: College of Medical Veterinary and Life Sciences > School of Life Sciences
• Journal Name: Biotechnic and Histochemistry
• ISSN: 1052-0295