80474-97-1Relevant articles and documents
New approaches towards the synthesis of 1,2,3,4-tetrahydro isoquinoline-3-phosphonic acid (TicP)
Viveros-Ceballos, José Luis,Matías-Valdez, Lizeth A.,Sayago, Francisco J.,Cativiela, Carlos,Ordó?ez, Mario
, p. 451 - 459 (2021)
Two new strategies for the efficient synthesis of racemic 1,2,3,4-tetrahydroisoquinoline-3-phosphonic acid (TicP) (±)-2 have been developed. The first strategy involves the electron-transfer reduction of the easily obtained α,β-dehydro phosphonophenylalanine followed by a Pictet–Spengler cyclization. The second strategy involves a radical decarboxylation–phosphorylation reaction on 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic). In both strategies, the highly electrophilic N-acyliminium ion is formed as a key intermediate, and the target compound is obtained in good yield using mild reaction conditions and readily available starting materials, complementing existing methodologies and contributing to the easy accessibility of (±)-2 for further research.
Syntheses and evaluation of 68Ga- and 153Sm-labeled DOTA-conjugated bisphosphonate ligand for potential use in detection of skeletal metastases and management of pain arising from skeletal metastases
Chakraborty, Sudipta,Goswami, Dibakar,Chakravarty, Rubel,Mohammed, Sahiralam Khan,Sarma, Haladhar Deb,Dash, Ashutosh
, p. 1618 - 1626 (2018/06/04)
This article reports the syntheses and evaluation of 68Ga- and 153Sm-complexes of a new DOTA (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid)-conjugated geminal bisphosphonate, DOTA-Bn-SCN-BP, for their potential uses in the early detection of skeletal metastases by imaging and palliation of pain arising from skeletal metastases, respectively. The conjugate was synthesized in high purity following an easily adaptable three-step reaction scheme. Gallium-68- and 153Sm-complexes were prepared in high yield (>98%) and showed excellent in vitro stability in phosphate-buffered saline (PBS) and human serum. Both the complexes showed high affinity for hydroxyapatite particles in in vitro binding study. In biodistribution studies carried out in normal Wistar rats, both the complexes exhibited rapid skeletal accumulation with almost no retention in any other major organ. The newly synthesized molecule DOTA-Bn-SCN-BP would therefore be a promising targeting ligand for the development of radiopharmaceuticals for both imaging skeletal metastases and palliation of pain arising out of it in patients with cancer when radiolabeled with 68Ga and 153Sm, respectively. A systematic comparative evaluation, however, showed that there was no significant improvement of skeletal accumulation of the 153Sm-DOTA-Bn-SCN-BP complex over 153Sm-DOTMP (1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylenephosphonic acid) as the later itself demonstrated optimal properties required for an agent for bone pain palliation.
Synthesis, characterization, and antibacterial properties of a hydroxyapatite adhesive block copolymer
Zhang, Qiang Matthew,Serpe, Michael J.
, p. 8018 - 8025 (2015/02/19)
A novel diblock copolymer composed of bisphosphonate and pyridine oligomers has been prepared by reversible addition-fragmentation transfer (RAFT) polymerization. Ag ion was introduced into the polymer via its coordination with the pyridine groups, followed by a reduction process to obtain Ag nanoparticles with diameters of 5-15 nm measured by transmission electron microscopy (TEM). In addition, X-ray photoelectron spectroscopy (XPS) and X-ray diffraction (XRD) proved successful introduction of Ag nanoparticles into polymer. Ag nanoparticles containing polymer exhibited excellent antibacterial properties toward Lactobacillus plantarum (L. plantarum). In order to investigate its practical application as an antibacterial coating, the synthesized polymer was tethered onto hydroxyapatite (HA, main mineral component of natural bone, teeth, and most of implants for bone repair) surfaces via interaction between the polymers bisphosphonate group and HA, forming ～4 nm thick layers. Ag nanoparticles (5-15 nm in diameter) uniformly distributed around the HA particles were fabricated following the above process. The ability of the coating to kill the bacteria L. plantarum was determined, which revealed strong antibacterial properties.
