Transition-Metal-Free CO-Releasing BODIPY Derivatives
Activatable by Visible to NIR Light as Promising Bioactive
Molecules

J 2016

Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules

PALAO UTIEL, Eduardo, Tomáš SLANINA, Lucie MUCHOVÁ, Tomáš ŠOLOMEK, Libor VÍTEK et. al.

Basic information

Original name

Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules

Authors

PALAO UTIEL, Eduardo (724 Spain, belonging to the institution), Tomáš SLANINA (203 Czech Republic, belonging to the institution), Lucie MUCHOVÁ (203 Czech Republic), Tomáš ŠOLOMEK (703 Slovakia, belonging to the institution), Libor VÍTEK (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of the American Chemical Society, WASHINGTON, American Chemical Society, 2016, 0002-7863

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 13.858

RIV identification code

RIV/00216224:14310/16:00087939

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1021/jacs.5b10800

UT WoS

000368323100026

Keywords in English

PHOTOREMOVABLE PROTECTING GROUPS; CARBON-MONOXIDE; DESIGN STRATEGIES; ALPHA-LACTONES; GREEN LIGHT; ET-CORMS; COMPLEXES; PHOTOCORMS; ACID; DYE

Abstract

V originále

Carbon monoxide-releasing molecules (CORMs) are chemical agents used to administer CO as an endogenous, biologically active molecule. A precise spatial and temporal control over the CO release is the major requirement for their applications. Here, we report the synthesis and properties of a new generation of transition-metalfree carbon monoxide-releasing molecules based on BODIPY chromophores (COR-BDPs) activatable by visible-to-NIR (up to 730 nm) light. We demonstrate their performance for both in vitro and in vivo experimental settings, and we propose the mechanism of the CO release based on steady-state and transient spectroscopy experiments and quantum chemical calculations.

Links

GA13-25775S, research and development project

Name: Vývoj viditelným světlem aktivovatelných skupin a fluorescenčních značek pro chemii a biologii

Investor: Czech Science Foundation

LM2011028, research and development project

Name: RECETOX ? Národní infrastruktura pro výzkum toxických látek v prostředí

Investor: Ministry of Education, Youth and Sports of the CR

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

PALAO UTIEL, Eduardo, Tomáš SLANINA, Lucie MUCHOVÁ, Tomáš ŠOLOMEK, Libor VÍTEK and Petr KLÁN. Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules. Journal of the American Chemical Society. WASHINGTON: American Chemical Society, 2016, vol. 138, No 1, p. 126-133. ISSN 0002-7863. Available from: https://dx.doi.org/10.1021/jacs.5b10800.

@article{1345773,
   author = {Palao Utiel, Eduardo and Slanina, Tomáš and Muchová, Lucie and Šolomek, Tomáš and Vítek, Libor and Klán, Petr},
   article_location = {WASHINGTON},
   article_number = {1},
   doi = {http://dx.doi.org/10.1021/jacs.5b10800},
   keywords = {PHOTOREMOVABLE PROTECTING GROUPS; CARBON-MONOXIDE; DESIGN STRATEGIES; ALPHA-LACTONES; GREEN LIGHT; ET-CORMS; COMPLEXES; PHOTOCORMS; ACID; DYE},
   language = {eng},
   issn = {0002-7863},
   journal = {Journal of the American Chemical Society},
   title = {Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules},
   url = {http://pubs.acs.org/doi/abs/10.1021/jacs.5b10800},
   volume = {138},
   year = {2016}
}

TY  - JOUR
ID  - 1345773
AU  - Palao Utiel, Eduardo - Slanina, Tomáš - Muchová, Lucie - Šolomek, Tomáš - Vítek, Libor - Klán, Petr
PY  - 2016
TI  - Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules
JF  - Journal of the American Chemical Society
VL  - 138
IS  - 1
SP  - 126-133
EP  - 126-133
PB  - American Chemical Society
SN  - 00027863
KW  - PHOTOREMOVABLE PROTECTING GROUPS
KW  - CARBON-MONOXIDE
KW  - DESIGN STRATEGIES
KW  - ALPHA-LACTONES
KW  - GREEN LIGHT
KW  - ET-CORMS
KW  - COMPLEXES
KW  - PHOTOCORMS
KW  - ACID
KW  - DYE
UR  - http://pubs.acs.org/doi/abs/10.1021/jacs.5b10800
L2  - http://pubs.acs.org/doi/abs/10.1021/jacs.5b10800
N2  - Carbon monoxide-releasing molecules (CORMs) are chemical agents used to administer CO as an endogenous, biologically active molecule. A precise spatial and temporal control over the CO release is the major requirement for their applications. Here, we report the synthesis and properties of a new generation of transition-metalfree carbon monoxide-releasing molecules based on BODIPY chromophores (COR-BDPs) activatable by visible-to-NIR (up to 730 nm) light. We demonstrate their performance for both in vitro and in vivo experimental settings, and we propose the mechanism of the CO release based on steady-state and transient spectroscopy experiments and quantum chemical calculations.
ER  -

PALAO UTIEL, Eduardo, Tomáš SLANINA, Lucie MUCHOVÁ, Tomáš ŠOLOMEK, Libor VÍTEK and Petr KLÁN. Transition-Metal-Free CO-Releasing BODIPY Derivatives Activatable by Visible to NIR Light as Promising Bioactive Molecules. \textit{Journal of the American Chemical Society}. WASHINGTON: American Chemical Society, 2016, vol.~138, No~1, p.~126-133. ISSN~0002-7863. Available from: https://dx.doi.org/10.1021/jacs.5b10800.

Detailed Information on Publication Record