TY - JOUR
T1 - Fluorescent Arylphosphonic Acids: Synergic Interactions between Bone and the Fluorescent Core
AU - Yücesan, Gündoğ
AU - Zorlu, Yunus
AU - Brown, Connor
AU - Keil, Claudia
AU - Ayhan, Menaf M
AU - Haase, Hajo
AU - Thompson, Richard B
AU - Lengyel, Imre
N1 - © 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2020/9/1
Y1 - 2020/9/1
N2 - Herein, we report the third generation of fluorescent probes (arylphosphonic acids) to target calcifications, particularly hydroxyapatite (HAP). In this study, we use highly conjugated porphyrin-based arylphosphonic acids and their diesters, namely 5,10,15,20-Tetrakis[ m -(diethoxyphosphoryl)phenyl] porphyrin ( m -H 8 TPPA-OEt 8 ), 5,10,15,20-Tetrakis [ m -phenylphosphonic acid] porphyrin ( m -H 8 TPPA ), in comparison with their positional isomers 5,10,15,20-Tetrakis[ p -(diisopropoxyphosphoryl)phenyl] porphyrin ( p -H 8 TPPA-iPr 8 ), 5,10,15,20-Tetrakis [ p -phenylphosphonic acid] porphyrin ( p -H 8 TPPA ) which have phosphonic acid units bonded to sp 2 carbons of the fluorescent core. The conjugation of the fluorescent core is thus extended to the (HAP) via the sp 2 bonded -PO 3 H 2 units, which generates increased fluorescence upon HAP binding. The resulting fluorescent probes are highly sensitive towards the HAP in rat bone sections. The designed probes are readily taken up by cells. Due to the lower reported toxicity of ( p -H 8 TPPA ), these probes could find applications in monitoring bone resorption or adsorption, or imaging vascular or soft tissue calcifications for breast cancer diagnosis etc.
AB - Herein, we report the third generation of fluorescent probes (arylphosphonic acids) to target calcifications, particularly hydroxyapatite (HAP). In this study, we use highly conjugated porphyrin-based arylphosphonic acids and their diesters, namely 5,10,15,20-Tetrakis[ m -(diethoxyphosphoryl)phenyl] porphyrin ( m -H 8 TPPA-OEt 8 ), 5,10,15,20-Tetrakis [ m -phenylphosphonic acid] porphyrin ( m -H 8 TPPA ), in comparison with their positional isomers 5,10,15,20-Tetrakis[ p -(diisopropoxyphosphoryl)phenyl] porphyrin ( p -H 8 TPPA-iPr 8 ), 5,10,15,20-Tetrakis [ p -phenylphosphonic acid] porphyrin ( p -H 8 TPPA ) which have phosphonic acid units bonded to sp 2 carbons of the fluorescent core. The conjugation of the fluorescent core is thus extended to the (HAP) via the sp 2 bonded -PO 3 H 2 units, which generates increased fluorescence upon HAP binding. The resulting fluorescent probes are highly sensitive towards the HAP in rat bone sections. The designed probes are readily taken up by cells. Due to the lower reported toxicity of ( p -H 8 TPPA ), these probes could find applications in monitoring bone resorption or adsorption, or imaging vascular or soft tissue calcifications for breast cancer diagnosis etc.
U2 - 10.1002/chem.202001613
DO - 10.1002/chem.202001613
M3 - Article
C2 - 32293767
VL - 26
SP - 11129
EP - 11134
JO - Chemistry-a European Journal
JF - Chemistry-a European Journal
SN - 0947-6539
IS - 49
ER -