Synthetic aminopyrrolic receptors have apoptosis inducing activity

Seong Hyun Park, Yoon Pyo Choi, Jinhong Park, Andrew Share, Oscar Francesconi, Cristina Nativi, Wan Namkung, Jonathan L. Sessler, Stefano Roelens, Injae Shin

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

We report two synthetic aminopyrrolic compounds that induce apoptotic cell death. These compounds have been previously shown to act as receptors for mannosides. The extent of receptor-induced cell death is greater in cells expressing a high level of high-mannose oligosaccharides than in cells producing lower levels of high-mannose glycans. The ability of synthetic receptors to induce cell death is attenuated in the presence of external mannosides. The present results provide support for the suggestion that the observed cell death reflects an ability of the receptors to bind mannose displayed on the cell surface. Signaling pathway studies indicate that the synthetic receptors of the present study promote JNK activation, induce Bax translocation to the mitochondria, and cause cytochrome c release from the mitochondria into the cytosol, thus promoting caspase-dependent apoptosis. Such effects are also observed in cells treated with mannose-binding ConA. The present results thus serve to highlight what may be an attractive new approach to triggering apoptosis via modes of action that differ from those normally used to promote apoptosis.

Original languageEnglish
Pages (from-to)7284-7292
Number of pages9
JournalChemical Science
Volume6
Issue number12
DOIs
Publication statusPublished - 2015 Jan 1

Fingerprint

Artificial Receptors
Cell death
Mannose
Mannosides
Apoptosis
Mitochondria
Caspases
Cytochromes c
Oligosaccharides
Polysaccharides
Chemical activation
Cells

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Park, S. H., Choi, Y. P., Park, J., Share, A., Francesconi, O., Nativi, C., ... Shin, I. (2015). Synthetic aminopyrrolic receptors have apoptosis inducing activity. Chemical Science, 6(12), 7284-7292. https://doi.org/10.1039/c5sc03200h
Park, Seong Hyun ; Choi, Yoon Pyo ; Park, Jinhong ; Share, Andrew ; Francesconi, Oscar ; Nativi, Cristina ; Namkung, Wan ; Sessler, Jonathan L. ; Roelens, Stefano ; Shin, Injae. / Synthetic aminopyrrolic receptors have apoptosis inducing activity. In: Chemical Science. 2015 ; Vol. 6, No. 12. pp. 7284-7292.
@article{964423d8fe1f4d3a9354a87cba2e5274,
title = "Synthetic aminopyrrolic receptors have apoptosis inducing activity",
abstract = "We report two synthetic aminopyrrolic compounds that induce apoptotic cell death. These compounds have been previously shown to act as receptors for mannosides. The extent of receptor-induced cell death is greater in cells expressing a high level of high-mannose oligosaccharides than in cells producing lower levels of high-mannose glycans. The ability of synthetic receptors to induce cell death is attenuated in the presence of external mannosides. The present results provide support for the suggestion that the observed cell death reflects an ability of the receptors to bind mannose displayed on the cell surface. Signaling pathway studies indicate that the synthetic receptors of the present study promote JNK activation, induce Bax translocation to the mitochondria, and cause cytochrome c release from the mitochondria into the cytosol, thus promoting caspase-dependent apoptosis. Such effects are also observed in cells treated with mannose-binding ConA. The present results thus serve to highlight what may be an attractive new approach to triggering apoptosis via modes of action that differ from those normally used to promote apoptosis.",
author = "Park, {Seong Hyun} and Choi, {Yoon Pyo} and Jinhong Park and Andrew Share and Oscar Francesconi and Cristina Nativi and Wan Namkung and Sessler, {Jonathan L.} and Stefano Roelens and Injae Shin",
year = "2015",
month = "1",
day = "1",
doi = "10.1039/c5sc03200h",
language = "English",
volume = "6",
pages = "7284--7292",
journal = "Chemical Science",
issn = "2041-6520",
publisher = "Royal Society of Chemistry",
number = "12",

}

Park, SH, Choi, YP, Park, J, Share, A, Francesconi, O, Nativi, C, Namkung, W, Sessler, JL, Roelens, S & Shin, I 2015, 'Synthetic aminopyrrolic receptors have apoptosis inducing activity', Chemical Science, vol. 6, no. 12, pp. 7284-7292. https://doi.org/10.1039/c5sc03200h

Synthetic aminopyrrolic receptors have apoptosis inducing activity. / Park, Seong Hyun; Choi, Yoon Pyo; Park, Jinhong; Share, Andrew; Francesconi, Oscar; Nativi, Cristina; Namkung, Wan; Sessler, Jonathan L.; Roelens, Stefano; Shin, Injae.

In: Chemical Science, Vol. 6, No. 12, 01.01.2015, p. 7284-7292.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthetic aminopyrrolic receptors have apoptosis inducing activity

AU - Park, Seong Hyun

AU - Choi, Yoon Pyo

AU - Park, Jinhong

AU - Share, Andrew

AU - Francesconi, Oscar

AU - Nativi, Cristina

AU - Namkung, Wan

AU - Sessler, Jonathan L.

AU - Roelens, Stefano

AU - Shin, Injae

PY - 2015/1/1

Y1 - 2015/1/1

N2 - We report two synthetic aminopyrrolic compounds that induce apoptotic cell death. These compounds have been previously shown to act as receptors for mannosides. The extent of receptor-induced cell death is greater in cells expressing a high level of high-mannose oligosaccharides than in cells producing lower levels of high-mannose glycans. The ability of synthetic receptors to induce cell death is attenuated in the presence of external mannosides. The present results provide support for the suggestion that the observed cell death reflects an ability of the receptors to bind mannose displayed on the cell surface. Signaling pathway studies indicate that the synthetic receptors of the present study promote JNK activation, induce Bax translocation to the mitochondria, and cause cytochrome c release from the mitochondria into the cytosol, thus promoting caspase-dependent apoptosis. Such effects are also observed in cells treated with mannose-binding ConA. The present results thus serve to highlight what may be an attractive new approach to triggering apoptosis via modes of action that differ from those normally used to promote apoptosis.

AB - We report two synthetic aminopyrrolic compounds that induce apoptotic cell death. These compounds have been previously shown to act as receptors for mannosides. The extent of receptor-induced cell death is greater in cells expressing a high level of high-mannose oligosaccharides than in cells producing lower levels of high-mannose glycans. The ability of synthetic receptors to induce cell death is attenuated in the presence of external mannosides. The present results provide support for the suggestion that the observed cell death reflects an ability of the receptors to bind mannose displayed on the cell surface. Signaling pathway studies indicate that the synthetic receptors of the present study promote JNK activation, induce Bax translocation to the mitochondria, and cause cytochrome c release from the mitochondria into the cytosol, thus promoting caspase-dependent apoptosis. Such effects are also observed in cells treated with mannose-binding ConA. The present results thus serve to highlight what may be an attractive new approach to triggering apoptosis via modes of action that differ from those normally used to promote apoptosis.

UR - http://www.scopus.com/inward/record.url?scp=84946923618&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84946923618&partnerID=8YFLogxK

U2 - 10.1039/c5sc03200h

DO - 10.1039/c5sc03200h

M3 - Article

VL - 6

SP - 7284

EP - 7292

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

IS - 12

ER -

Park SH, Choi YP, Park J, Share A, Francesconi O, Nativi C et al. Synthetic aminopyrrolic receptors have apoptosis inducing activity. Chemical Science. 2015 Jan 1;6(12):7284-7292. https://doi.org/10.1039/c5sc03200h