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Sporopollenin exine capsules (SpECs) derived from Lycopodium clavatum provide practical antioxidant properties by retarding rancidification of an ω-3 oil (2020)
Journal Article
Thomasson, M. J., Diego-Taboada, A., Barrier, S., Martin-Guyout, J., Amedjou, E., Atkin, S. L., …Mackenzie, G. (2020). Sporopollenin exine capsules (SpECs) derived from Lycopodium clavatum provide practical antioxidant properties by retarding rancidification of an ω-3 oil. Industrial Crops and Products, 154, https://doi.org/10.1016/j.indcrop.2020.112714

In recent years the use of natural antioxidants in foodstuffs and personal care products has become increasingly important for consumers and therefore manufacturers. In this work, sporopollenin exine capsules (SpECs), extracted from spores of the com... Read More about Sporopollenin exine capsules (SpECs) derived from Lycopodium clavatum provide practical antioxidant properties by retarding rancidification of an ω-3 oil.

The role of whole genome sequencing in characterizing the mechanism of action of para-aminosalicylic acid and its resistance (2020)
Journal Article
Satta, G., Witney, A. A., Begum, N., Ortiz Canseco, J., Boa, A. N., & McHugh, T. D. (in press). The role of whole genome sequencing in characterizing the mechanism of action of para-aminosalicylic acid and its resistance. Antimicrobial agents and chemotherapy, https://doi.org/10.1128/aac.00675-20

Para-aminosalicylic acid (PAS) remains one of the drugs of last resort for the treatment of tuberculosis, but its mechanism of action is not completely understood yet. The main aim of this project was to identify new potential mechanisms of action an... Read More about The role of whole genome sequencing in characterizing the mechanism of action of para-aminosalicylic acid and its resistance.

N-cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites (2019)
Journal Article
Chandrabalan, A., McPhillie, M. J., Morice, A. H., Boa, A. N., & Sadofsky, L. R. (2019). N-cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites. European Journal of Medicinal Chemistry, 170, 141-156. https://doi.org/10.1016/j.ejmech.2019.02.074

The transient receptor potential ankyrin 1 (TRPA1) channel is a non-selective cation channel, which detects noxious stimuli leading to pain, itch and cough. However, the mechanism(s) of channel modulation by many of the known, non-reactive modulators... Read More about N-cinnamoylanthranilates as human TRPA1 modulators: Structure-activity relationships and channel binding sites.

Interconvertible geometric isomers of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors exhibit multiple binding modes (2017)
Journal Article
Boa, A. N., McConkey, G. A., Bedingfield, P. T., Burrell, D. R., Chambers, N. C., Cunningham, F., …Boa, A. N. (2017). Interconvertible geometric isomers of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors exhibit multiple binding modes. Bioorganic and Medicinal Chemistry Letters, 27(16), 3878-3882. https://doi.org/10.1016/j.bmcl.2017.06.052

Two new tricyclic β-aminoacrylate derivatives (2e and 3e) have been found to be inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) with Ki 0.037 and 0.15 μM respectively. 1H and 13C NMR spectroscopic data show that these compo... Read More about Interconvertible geometric isomers of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors exhibit multiple binding modes.

Sulfonated sporopollenin as an efficient and recyclable heterogeneous catalyst for dehydration of D-xylose and xylan into furfural (2016)
Journal Article
Wang, Y., Len, T., Huang, Y., Diego Taboada, A., Boa, A. N., Ceballos, C., …Len, C. (2017). Sulfonated sporopollenin as an efficient and recyclable heterogeneous catalyst for dehydration of D-xylose and xylan into furfural. ACS Sustainable Chemistry and Engineering, 5(1), 392-398. https://doi.org/10.1021/acssuschemeng.6b01780

The natural acidity of sporopollenin, the biopolymer coating the outer walls of pollen grains, was enhanced by the sulfonation of its surface. Modified sporopollenin displaying sulfonic acid groups has been prepared, characterized by elemental analys... Read More about Sulfonated sporopollenin as an efficient and recyclable heterogeneous catalyst for dehydration of D-xylose and xylan into furfural.

Sporopollenin, the least known yet toughest natural biopolymer (2015)
Journal Article
Mackenzie, G., Boa, A. N., Diego-Taboada, A., Atkin, S. L., & Sathyapalan, T. (in press). Sporopollenin, the least known yet toughest natural biopolymer. Frontiers in Materials, 2, 1-5. https://doi.org/10.3389/fmats.2015.00066

Sporopollenin is highly cross-linked polymer composed of carbon, hydrogen, and oxygen that is extraordinarily stable and has been found chemically intact in sedimentary rocks some 500 million years old. It makes up the outer shell (exine) of plant sp... Read More about Sporopollenin, the least known yet toughest natural biopolymer.

Sporopollenin as an efficient green support for covalent immobilization of a lipase (2015)
Journal Article
de Souza, S. P., Bassut, J., Marquez, H. V., Junior, I. I., Miranda, L. S. M., Huang, Y., …de Souza, R. O. M. A. (2015). Sporopollenin as an efficient green support for covalent immobilization of a lipase. Catalysis science & technology, 5(6), 3130-3136. https://doi.org/10.1039/c4cy01682c

Sporopollenin exine capsules (SECs), derived from the spores of Lycopodium clavatum, have been functionalised with 1,n-diamines and the resulting aminoalkyl microcapsules used to immobilize Candida antarctica lipase B (Cal B) via a glutaradehyde-base... Read More about Sporopollenin as an efficient green support for covalent immobilization of a lipase.

Protein free microcapsules obtained from plant spores as a model for drug delivery: Ibuprofen encapsulation, release and taste masking (2013)
Journal Article
Diego-Taboada, A., Maillet, L., Banoub, J. H., Lorch, M., Rigby, A. S., Boa, A. N., …Mackenzie, G. (2013). Protein free microcapsules obtained from plant spores as a model for drug delivery: Ibuprofen encapsulation, release and taste masking. Journal of Materials Chemistry B, 1(5), 707-713. https://doi.org/10.1039/c2tb00228k

Sporopollenin exine capsules (SEC) extracted from Lycopodium clavatum spores were shown to encapsulate ibuprofen as a drug model, with 97 ± 1% efficiency as measured by recovery of the loaded drug and absence of the drug on the SEC surface by scannin... Read More about Protein free microcapsules obtained from plant spores as a model for drug delivery: Ibuprofen encapsulation, release and taste masking.

Pharmacological comparison of novel synthetic fenamate analogues with econazole and 2-APB on the inhibition of TRPM2 channels (2012)
Journal Article
Chen, G., Zeng, B., Eastmond, S., Elsenussi, S. E., Boa, A. N., & Xu, S. (2012). Pharmacological comparison of novel synthetic fenamate analogues with econazole and 2-APB on the inhibition of TRPM2 channels. British Journal of Pharmacology, 167(6), 1232-1243. https://doi.org/10.1111/j.1476-5381.2012.02058.x

BACKGROUND: Fenamate analogues, econazole and 2-APB are inhibitors of TRPM2 channels, which have been used as research tools. However, these compounds have different chemical structures and therapeutic applications. Here we aimed to investigate the p... Read More about Pharmacological comparison of novel synthetic fenamate analogues with econazole and 2-APB on the inhibition of TRPM2 channels.

Sequestration of edible oil from emulsions using new single and double layered microcapsules from plant spores (2012)
Journal Article
Queneau, Y., Boa, A., Atkin, S., Beckett, S., MacKenzie, G., Huang, Y., …Mackenzie, G. (2012). Sequestration of edible oil from emulsions using new single and double layered microcapsules from plant spores. Journal of Materials Chemistry, 22(19), 9767-9773. https://doi.org/10.1039/c2jm00103a

Microcapsules were obtained conveniently from Lycopodium clavatum spores possessing either a single layered shell of sporopollenin (exine) or double layered shell of sporopollenin and cellulose with an inner layer (intine). These microcapsules were f... Read More about Sequestration of edible oil from emulsions using new single and double layered microcapsules from plant spores.

Effect of non-steroidal anti-inflammatory drugs and new fenamate analogues on TRPC4 and TRPC5 channels (2012)
Journal Article
Jiang, H., Zeng, B., Chen, G., Bot, D., Eastmond, S., Elsenussi, S. E., …Xu, S. (2012). Effect of non-steroidal anti-inflammatory drugs and new fenamate analogues on TRPC4 and TRPC5 channels. Biochemical Pharmacology, 83(7), 923-931. https://doi.org/10.1016/j.bcp.2012.01.014

Non-steroidal anti-inflammatory drugs (NSAIDs) are widely used anti-inflammatory therapeutic agents,among which the fenamate analogues play important roles in regulating intracellular Ca<sup>2+</sup> transient and ion channels. However, the eff... Read More about Effect of non-steroidal anti-inflammatory drugs and new fenamate analogues on TRPC4 and TRPC5 channels.

Effect of non-steroidal anti-inflammatory drugs and new fenamate analogues on TRPC4 and TRPC5 channels (2012)
Journal Article
Xu, S., Boa, A., Atkin, S., Elsenussi, S., Chen, G., Bot, D., …Xu, S. Z. (2012). Effect of non-steroidal anti-inflammatory drugs and new fenamate analogues on TRPC4 and TRPC5 channels. Biochemical Pharmacology, 83(7), 923-931. https://doi.org/10.1016/j.bcp.2012.01.014

Non-steroidal anti-inflammatory drugs (NSAIDs) are widely used anti-inflammatory therapeutic agents,among which the fenamate analogues play important roles in regulating intracellular Ca2+ transient and ion channels. However, the effect of NSAIDs on... Read More about Effect of non-steroidal anti-inflammatory drugs and new fenamate analogues on TRPC4 and TRPC5 channels.

Dimroth-type rearrangement of 1-benzyl- and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino)imidazoles (2011)
Journal Article
Rouse, S., Vanbaelinghem, L., Ewing, D., Boa, A., MacKenzie, G., Costanzi, S., …Mackenzie, G. (2012). Dimroth-type rearrangement of 1-benzyl- and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino)imidazoles. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 53(4), 412-415. https://doi.org/10.1016/j.tetlet.2011.11.058

An efficient route is described to an unusual exocyclic 4-β-d-ribofuranosyl-aminoimidazole nucleoside, related 4-N-benzylaminoimidazoles and imidazole analogues of precursors in the de novo biosynthesis of purines, via a regiospecific and stereoselec... Read More about Dimroth-type rearrangement of 1-benzyl- and 1-glycosyl-5-aminoimidazoles to 4-(N-substituted amino)imidazoles.

A synthesis of bredinin (Mizoribine®) from an acyclic precursor (2011)
Journal Article
Humble, R. W., Middleton, D. F., Banoub, J., Ewing, D. F., Boa, A. N., & Mackenzie, G. (2011). A synthesis of bredinin (Mizoribine®) from an acyclic precursor. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 52(47), 6223-6227. https://doi.org/10.1016/j.tetlet.2011.09.085

Bredinin (4-carbamoyl-1-β-D-ribofuranosylimidazolium-5-olate, 1) was synthesised by the formation of amalonamate from 2,3-isopropylidene-D-ribofuranosylamine and ethyl malonyl chloride, followed by a sequence involving amination, via reduction o... Read More about A synthesis of bredinin (Mizoribine®) from an acyclic precursor.

Sporopollenin capsules at fluid interfaces: Particle-stabilised emulsions and liquid marbles (2011)
Journal Article
Rocher, A., MacKenzie, G., Kibble, M., Boa, A., Binks, B., Boa, A. N., …Rocher, A. (2011). Sporopollenin capsules at fluid interfaces: Particle-stabilised emulsions and liquid marbles. Soft matter, 7(8), 4017-4024. https://doi.org/10.1039/c0sm01516d

Hollow particles of sporopollenin from spores of the plant Lycopodium clavatum have been prepared. These particles possess ionisable groups on their surface such that they become increasingly negatively charged with an increase in pH. The particles a... Read More about Sporopollenin capsules at fluid interfaces: Particle-stabilised emulsions and liquid marbles.

TRPA1 is activated by direct addition of cysteine residues to the N-hydroxysuccinyl esters of acrylic and cinnamic acids (2010)
Journal Article
Sadofsky, L. R., Boa, A. N., Maher, S. A., Birrell, M. A., Belvisi, M. G., & Morice, A. H. (2011). TRPA1 is activated by direct addition of cysteine residues to the N-hydroxysuccinyl esters of acrylic and cinnamic acids. Pharmacological research : the official journal of the Italian Pharmacological Society, 63(1), 30-36. https://doi.org/10.1016/j.phrs.2010.11.004

The nociceptor TRPA1 is thought to be activated through covalent modification of specific cysteine residues on the N terminal of the channel. The precise mechanism of covalent modification with unsaturated carbonyl-containing compounds is unclear, th... Read More about TRPA1 is activated by direct addition of cysteine residues to the N-hydroxysuccinyl esters of acrylic and cinnamic acids.

Access to a primary aminosporopollenin solid support from plant spores (2010)
Journal Article
MacKenzie, G., Atkin, S., Boa, A., Boasman, A., Löbbert, A., Barrier, S., …Mackenzie, G. (2010). Access to a primary aminosporopollenin solid support from plant spores. Green chemistry : an international journal and green chemistry resource : GC, 12(2), 234-240. https://doi.org/10.1039/b913215e

Sporopollenin, which is a naturally occurring and highly resilient organic polymer constituting the external shell of spores and pollen grains, has been converted into a primary amine form with a loading of 0.58 +/- 0.04 mmol. g(-1) by reductive amin... Read More about Access to a primary aminosporopollenin solid support from plant spores.

Synthesis and reactions of α-fluoro-α-amino amides (2008)
Journal Article
Bailey, P. D., Clayson, J., & Boa, A. N. (2009). Synthesis and reactions of α-fluoro-α-amino amides. Tetrahedron, 65(8), (1724-1736). doi:10.1016/j.tet.2008.11.061. ISSN 0040-4020

N-((S)-1-Phenylethyl)halofluoroethanamides have been investigated as precursors to N-protected α-fluoro-α-amino amides by nucleophilic displacement of halide with nitrogen nucleophiles such as potassium phthalimide, sodium succinimide, so... Read More about Synthesis and reactions of α-fluoro-α-amino amides.

Parallel kinetic resolution of racemic 1-phenylethanol using quasi-enantiomeric combinations of carboxylic acids mediated by N,N′-dicyclohexylcarbodiimide and 3,5-lutidine (2008)
Journal Article
Shaye, N., Coulbeck, E., Boa, A., Al Shaye, N., Boa, A. N., Coulbeck, E., & Eames, J. (2008). Parallel kinetic resolution of racemic 1-phenylethanol using quasi-enantiomeric combinations of carboxylic acids mediated by N,N′-dicyclohexylcarbodiimide and 3,5-lutidine. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 49(31), 4661-4665. https://doi.org/10.1016/j.tetlet.2008.05.036

The parallel kinetic resolution of racemic 1-phenylethanol using an equimolar combination of quasi-enantiomeric 2-arylpropionic and butanoic acids mediated by a N,N′-dicyclohexylcarbodiimide (DCC)/3,5-lutidine coupling is discussed. The levels of dia... Read More about Parallel kinetic resolution of racemic 1-phenylethanol using quasi-enantiomeric combinations of carboxylic acids mediated by N,N′-dicyclohexylcarbodiimide and 3,5-lutidine.

Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro (2004)
Journal Article
Ahmed, S., Davoust, E., Boa, A., Boyle, R., Ahmed, S., Davoust, E., …Boyle, R. W. (2004). Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro. Tetrahedron letters; the international organ for the rapid publication of preliminary communications in organic chemistry, 45(31), 6045-6047. https://doi.org/10.1016/j.tetlet.2004.06.021

A convenient and flexible synthesis of meso-tetraaryl porphyrins substituted with three thioglycosyl units, and also bearing one pyridyl substituent is reported. Quaternisation of the pyridine nitrogen with alkyl iodides gives access to a range of wa... Read More about Thioglycosylated cationic porphyrins––convenient synthesis and photodynamic activity in vitro.


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