ORCID Profile
0000-0001-7547-5850
Current Organisations
University of Western Australia
,
Curtin University
,
Sir Charles Gairdner Hospital
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Publisher: Elsevier BV
Date: 03-2015
DOI: 10.1016/J.EJMECH.2015.02.033
Abstract: A series of mercaptoundecahydrododecaborate (B12H11SH(2-), BSH) bearing mono- and dicarboxyalkyl derivatives was prepared, characterized, and their reactivity towards amidation and esterification in DMF was evaluated. Symmetrical alkylation of BSH was achieved by treatment with primary haloalkyl carboxylic acids in aqueous acetonitrile to produce S,S-bis(carboxyalkyl)sulfonium-undecahydro-closo-dodecaborate tetramethylammonium salts. Unsymmetrically substituted sulfonium salts were obtained through a similar treatment of cyanoethylthioether-undecahydro-closo-dodecaborate tetramethylammonium salt with haloalkyl carboxylic acid. Selective removal of the remaining cyanoethyl group upon treatment with tetramethylammonium hydroxide yielded S-carboxyalkyl-thioether-undecahydro-closo-dodecaborate ditetramethylammonium salts. N,N'-dicyclohexylcarbodiimide (DCC) activated amidation of S,S-bis(carboxyalkyl)sulfonium-undecahydro-closo-dodecaborate or S-carboxyalkyl-thioether-undecahydro-closo-dodecaborate tetramethylammonium salts with propargylamine provided the opportunity to install terminal acetylene groups for further conjugation. These compounds acted as powerful building blocks for the synthesis of a broad range of 1,4-disubstituted 1,2,3-triazole products in high yields, utilizing the Cu(I)-mediated click cycloaddition reaction. The synthesis of BSH-lipid with a two-tailed moiety was also achieved, by esterification of S,S-bis(carboxyethyl)sulfoniumundecahydro-closo-dodecaborate(1-) tetramethylammonium salt with 1,2-O-distearoyl-sn-3-glycerol, which may prove useful in the liposomal boron delivery system. The bio-compatibility of the azide-alkyne click reaction was then utilized by performing this reaction in cell culture. The distribution of BSH in HeLa cells could be visualized by treating the cells first with a BSH-alkyne compound and then with Alexa Fluor 488(®) azide dye. The BSH-dye conjugate, which did not wash out, revealed the distribution of boron in the HeLa cells. Cytotoxicity assays of these BSH derivatives revealed that the synthesized BSH-conjugated triazoles possessed low cytotoxicity in HeLa cancer cells. Of these compounds, BSH conjugated triazole 15 induced a significant increase in the level of boron accumulation in HeLa cells.
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3CC41173G
Abstract: Deboronation and cage rearrangement of the closo-1,12-carborane salt [1,12-(PPh2Me)2-1,12-C2B10H10]I2 occurs in refluxing methanol to give the zwitterionic nido-7,9-carborane 7,9-(PPh2Me)2-7,9-C2B9H9. Notably, deboronation and cage substitution of the isomeric closo-1,7-carborane salt [1,7-(PPh2Me)2-1,7-C2B10H10]I2 takes place in methanol to afford the salt [10-OMe-7,9-(PPh2Me)2-7,9-C2B9H9]I.
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3CC46903D
Abstract: The first tumour-cell selective mitochondrial agents containing Gd III which can deliver greater than 10 10 Gd atoms per tumour cell are reported.
Publisher: CSIRO Publishing
Date: 2007
DOI: 10.1071/CH07232
Abstract: The first ex les of gold(i) complexes containing monodentate diphenylphosphine-1,12-carborane and bidentate 1,12-bis(diphenylphosphine)-1,12-carborane ligands are reported.
Publisher: Wiley
Date: 31-01-2023
DOI: 10.1002/JLCR.4013
Abstract: Since first becoming commercially available in 2018, the PET radiopharmaceutical [ 18 F]PSMA‐1007 has been used widely for the diagnosis and staging of prostate cancer. A pharmacopoeia monograph first became available in 2021, prescribing a radiochemical purity specification of %, based on analytical results from both TLC (for [ 18 F]fluoride impurity alone) and HPLC (for all other 18 F‐impurities). Though this monograph has provided clarity for the quality control testing of [ 18 F]PSMA‐1007, it prescribes a HPLC method using phosphate buffer mobile phase that may present a risk of precipitation of phosphate salts in the HPLC system. The method also requires specialised hardware not immediately available to all laboratories. This work describes the development of a simple, rapid reversed‐phase HPLC method utilising 0.1 M ammonium formate mobile phase for the accurate assessment of both [ 18 F]fluoride impurity and overall radiochemical purity in a single test. This method is especially useful for assessment of product stability over time. A more accurate TLC method for [ 18 F]fluoride impurity is also described.
Publisher: International Union of Crystallography (IUCr)
Date: 30-04-2009
Publisher: Elsevier BV
Date: 07-2020
Publisher: Elsevier BV
Date: 11-2017
Publisher: Royal Society of Chemistry (RSC)
Date: 2007
DOI: 10.1039/B700689F
Abstract: The first ex les of arylphosphonium salts containing a dicarba-closo-dodecaborane(12) (closo-carborane) are reported in contrast to the 1,12-carborane derivative, the 1,2- and 1,7-isomers undergo a facile deboronation reaction in polar solvents to afford the corresponding nido-carborane phosphonium zwitterions.
Publisher: Wiley
Date: 02-04-2014
Abstract: Methods used to prepare functionalized carboranes generally require heating to high temperatures, and thus limits the range of derivatives which can be prepared directly from alkynes. We show here that by using a homogeneous silver(I) catalyst it is now possible to prepare carboranes in good to excellent yield at temperatures below 40 °C, including at room temperature. The process is general and provides an important new synthetic strategy for the preparation of functionalized boron clusters.
Publisher: Wiley
Date: 26-01-2011
Publisher: Elsevier
Date: 2013
Publisher: Elsevier BV
Date: 11-2009
Publisher: IEEE
Date: 09-2014
Publisher: Elsevier BV
Date: 09-2017
DOI: 10.1016/J.NUCMEDBIO.2017.05.010
Abstract: Deferoxamine (DFO) is a siderophore that bacteria use to scavenge iron and could serve as a targeting vector to image bacterial infection where current techniques have critical limitations. [ A library of DFO derivatives was synthesized by functionalizing the terminal amine group of DFO using three different carbamate-forming reactions. Uptake of [ The work reported shows that it is possible to functionalize DFO-type siderophores and retain active uptake of the
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C4DT00444B
Abstract: The first ex les of indoleamine-2,3-dioxygenase-1 (IDO1) inhibitors containing a carborane cage are reported.
Location: Australia
No related grants have been discovered for Joseph Ioppolo.