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Photo-Controlled Release of NO and CO with Inorganic and Organometallic Complexes

Part of the Structure and Bonding book series (STRUCTURE,volume 165)

Abstract

The photochemical delivery of bioactive small molecules to physiological targets provides the opportunity to control the location, timing, and dosage of such delivery. We will discuss recent developments of the synthesis and studies of various metal complexes designed for targeted release of the bioregulatory diatomics nitric oxide and carbon monoxide. Of considerable interest are those systems where the NO or CO precursor and/or the photochemical product is luminescent such that imaging techniques allow one to identify the release location.

Keywords

  • Carbon monoxide
  • Luminescence
  • Near-infrared excitation
  • Nitric oxide
  • PhotoCORM
  • PhotoNORM
  • Photoreaction

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  • DOI: 10.1007/430_2014_164
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Fig. 1
Scheme 1
Scheme 2
Fig. 2
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Scheme 3
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Fig. 20

Abbreviations

4-vpy:

4-Vinyl pyridine

AFX:

2-Aminofluorene chromophores

BODIPY:

Boron dipyrromethane difluoride

bpy:

2,2′-Bipyridine

COP-1:

Palladium dimeric complex

CORM:

Carbon monoxide releasing moiety

COSer:

Carbon monoxide sensitive biosensor

cpYFP:

Circularly permuted yellow fluorescent protein

CrONO:

trans-CrIII(Cyclam)(ONO)2 +

Cyclam:

1,4,8,11 Tetraazacyclotetradecane

DFT:

Density functional theory

DMF:

Dimethylformamide

DMSO:

Dimethylsulfoxide

dpa:

N,N-bis(2-pyridylmethyl)amine

DPBS:

Dulbecco’s phosphate buffered saline

DPPQ:

Diphenylphosphinoquinoline

EPR:

Electron paramagnetic resonance

ES:

Excited state

FLEt:

Fluorescein ethyl ester

Fluor:

Fluorescein

FRET:

Förster resonance energy transfer

GSH:

Glutathione

H2bpb:

1,2-bis(pyridine-2-carboxamido)benzene

H2bqb:

1,2-bis(quinoline-2-carboxamido)benzene

H2IQ1:

1,2-bis(isoquinoline-1-carboxamido)benzene

H-dpaq:

2-[N,N-bis(pyridine-2-ylmethyl)]-amino-N′-quinoline-8-yl-acetamido

HO:

Heme oxygenase

I :

Incident light intensity

I a :

Intensity of light absorbed

iCORM:

Inactive CORM

Im:

Imidazole

IR:

Infrared

LDH:

Lactate dehydrogenase

LF:

Ligand field

LLL:

Tripodal polypyridine ligands

mac:

5,7-Dimethyl-6-anthracyl-cyclam

Mb:

Myoglobin

MLCT:

Metal to ligand charge transfer

NIR:

Near infrared

NMR:

Nuclear magnetic resonance

NOA:

Nitric oxide analyzer

OEP:

Octaethylporphyrinato

PaPy2QH:

N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinoline-2-carboxamide

PaPy3H:

N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-pyridine-2-carboxamide

PEG:

Polyethylene glycol

pHEMA:

Poly(2-hydroxyethyl methacrylate)

photoCORM:

Photo-activated CO releasing moiety

photoNORM:

Photo-activated NO releasing moiety

PL:

Photoluminescence

Por:

Porphyrin

PPIX:

Protoporphyrin-IX

pqa:

(2-Pyridylmethyl)(2-quinolylmethyl)amine

py:

Pyridine

QD:

Quantum dot

RBS:

Roussin’s black salts

Resf:

Resorufin

RRS:

Roussin’s red salts

RSE:

Roussin’s red esters

R-tpm:

Tris(pyrazolyl)methane

Salen:

N,N′-Ethylenebis(salicylideneiminato)dianion

Salophen:

N,N′-1,2-Phenylenebis(salicylideneiminato)dianion

SBPy2Q:

N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-quinoline-2-aldimine

SBPy3 :

N,N-bis(2-pyridylmethyl)amine-N-ethyl-2-pyridine-2-aldimine

Seln:

Selenophore

Sol:

Solvent

TD-DFT:

Time-dependent density functional theory

THF:

Tetrahydrofuran

Thnl:

Thionol

TMOS:

Tetramethylorthosilicate

Tmp:

Tris(hydroxymethyl)phosphine

tpa:

Tris(2-pyridyl)amine

TPE:

Two-photon excitation

TPP:

Tetraphenylporphyrinato

TPPTS:

Tris(sulfonatophenyl)phosphine trianion

UCNP:

Upconverting nanoparticle

UV:

Ultraviolet

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Acknowledgements

This work was supported by a grant to PCF (CHE-1058794) from the US National Science Foundation, by a fellowship to AEP from the UCSB Partnership for International Research and Education in Electron Chemistry and Catalysis at Interfaces (NSF grant OISE-0968399).

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Pierri, A.E., Muizzi, D.A., Ostrowski, A.D., Ford, P.C. (2014). Photo-Controlled Release of NO and CO with Inorganic and Organometallic Complexes. In: Lo, KW. (eds) Luminescent and Photoactive Transition Metal Complexes as Biomolecular Probes and Cellular Reagents. Structure and Bonding, vol 165. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_2014_164

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