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Facile synthesis and biological evaluation of chrysin derivatives (2021)
Journal Article
Omonga, N., Zia, Z., Ghanbour, H., Ragazzon-Smith, A., Foster, H., Hadfield, J., & Ragazzon, P. (2021). Facile synthesis and biological evaluation of chrysin derivatives. Journal of Chemical Research, 45(11-12), 1083-1092. https://doi.org/10.1177/17475198211057467

In this paper, novel synthetic methods, including microwave O-alkylation, were used to produce several chrysin derivatives. These compounds were purified, characterised and tested on different cell lines and bacterial strains. From this family, 7-(2,... Read More about Facile synthesis and biological evaluation of chrysin derivatives.

Syntheses of Combretastatin A‐4 and related stilbenes by using aqueous conditions (2021)
Journal Article
Barnes, N., Ahmed Mal Ullah, A., Ragazzon, P., Charafi, N., & Hadfield, J. (2021). Syntheses of Combretastatin A‐4 and related stilbenes by using aqueous conditions. ChemistrySelect, 6(28), 7082-7086. https://doi.org/10.1002/slct.202101960

Combretastatin A‐4 (CA4) is a potent anti‐mitotic and vascular disrupting agent. Organic chemists have been working to optimize the synthesis of CA4 for the past 3 decades, with methods requiring hazardous solvents and harsh reaction conditions. Here... Read More about Syntheses of Combretastatin A‐4 and related stilbenes by using aqueous conditions.

A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors (2020)
Journal Article
Barnes, N., Parker, A., Mal Ullah, A., Ragazzon, P., & Hadfield, J. (2020). A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors. Bioorganic and Medicinal Chemistry, 28(19), 115684. https://doi.org/10.1016/j.bmc.2020.115684

A series of combretastatin derivatives were designed and synthesised by a two-step stereoselective synthesis by use of Wittig olefination followed by Suzuki cross-coupling. Interestingly, all new compounds (2a-2i) showed potent cell-based antiprolife... Read More about A 2-step synthesis of Combretastatin A-4 and derivatives as potent tubulin assembly inhibitors.

Microwave assisted synthesis of novel bis-flavone dimers as new anticancer agents (2018)
Journal Article
Ragazzon, P., McGown, A., Ragazzon-Smith, A., Hadfield, J., & Potgetier, H. (2018). Microwave assisted synthesis of novel bis-flavone dimers as new anticancer agents. Letters in Organic Chemistry, 16(1), 66-75. https://doi.org/10.2174/1570178615666180621094529

In this study we describe a microwave based click chemistry method used to prepare a family of novel bis-flavone dimers. The substituted 7-hydroxy and 4’-hydroxy flavonoids were linked through a triazole ring. The compounds were easily synthesized an... Read More about Microwave assisted synthesis of novel bis-flavone dimers as new anticancer agents.

Tubulin-binding dibenz[c,e]oxepines: Part 2 Structural variation and biological evaluation as tumour vasculature disrupting agents (2017)
Journal Article
Hadfield, J., Rossington, S., Wallace, T., Shnyder, S., & Williams, K. (2017). Tubulin-binding dibenz[c,e]oxepines: Part 2 Structural variation and biological evaluation as tumour vasculature disrupting agents. Bioorganic and Medicinal Chemistry, 25(5), 1630-1642. https://doi.org/10.1016/j.bmc.2017.01.027

5,7-Dihydro-3,9,10,11-tetramethoxybenz[c,e]oxepin-4-ol 1, prepared from a dibenzyl ether precursor via Pd-catalysed intramolecular direct arylation, possesses broad-spectrum in vitro cytotoxicity towards various tumour cell lines, and induces vascul... Read More about Tubulin-binding dibenz[c,e]oxepines: Part 2 Structural variation and biological evaluation as tumour vasculature disrupting agents.

Expanding the scope of the Babler-Daubin oxidation : 1,3-oxidative transposition of secondary allylic alcohols (2016)
Journal Article
Killoran, P., Rossington, S., Wilkinson, J., & Hadfield, J. (2016). Expanding the scope of the Babler-Daubin oxidation : 1,3-oxidative transposition of secondary allylic alcohols. Tetrahedron Letters, 57(35), 3954-3957. https://doi.org/10.1016/j.tetlet.2016.07.076

We report the catalytic chromium-mediated oxidation of secondary allylic alcohols to give α,β-unsaturated aldehydes with exclusive (E)-stereoselectivity. This facile procedure employs catalytic PCC (5 mol%) and periodic acid (H5IO6) as a co-oxidant.... Read More about Expanding the scope of the Babler-Daubin oxidation : 1,3-oxidative transposition of secondary allylic alcohols.

Three-dimensional imaging and uptake of the anticancer drug combretastatin in cell spheroids and photoisomerization in gels with multiphoton excitation (2015)
Journal Article
Scherer, K., Bisby, R., Botchway, S., Hadfield, J., Haycock, J., & Parker, A. (2015). Three-dimensional imaging and uptake of the anticancer drug combretastatin in cell spheroids and photoisomerization in gels with multiphoton excitation. Journal of Biomedical Optics, 20(7), 78003. https://doi.org/10.1117/1.JBO.20.7.078003

The uptake of E-combretastatins, potential pro-drugs of the anticancer Z-isomers, into multicellular spheroids has been imaged by intrinsic fluorescence in three dimensions using two-photon excited fluorescence lifetime imaging with 625 nm ultrafast... Read More about Three-dimensional imaging and uptake of the anticancer drug combretastatin in cell spheroids and photoisomerization in gels with multiphoton excitation.

Anticancer phototherapy using activation of E-combretastatins by two-photon–induced isomerization (2014)
Journal Article
Hadfield, J., Bisby, R., Scherer, K., Botchway, S., & Parker, A. (2014). Anticancer phototherapy using activation of E-combretastatins by two-photon–induced isomerization. Journal of Biomedical Optics, 20(5), 1004-1. https://doi.org/10.1117/1.JBO.20.5.051004

The photoisomerization of relatively nontoxic E-combretastatins to clinically active Z-isomers is shown to occur in solution through both one- and two-photon excitations at 340 and 625 nm, respectively. The photoisomerization is also demonstrated t... Read More about Anticancer phototherapy using activation of E-combretastatins by two-photon–induced isomerization.

Spectroscopy and fluorescence lifetime imaging in live cells of a cyano-substituted combretastatin (2014)
Journal Article
combretastatin. Biomedical Spectroscopy and Imaging, 3, 211-218. https://doi.org/10.3233/BSI-140067

Fluorescence lifetime imaging has been used to observe the real-time uptake in live mammalian cells of a combretastatin-type drug analogue that is a substituted stilbene with a cyano group at the bridging olefinic bond. Fluorescence spectra in a ran... Read More about Spectroscopy and fluorescence lifetime imaging in live cells of a cyano-substituted combretastatin.

Novel cyanocombretastatins as potent tubulin polymerisation inhibitors (2012)
Journal Article
Jalily, P., Hirst, N., Hadfield, J., & Rossington, S. (2012). Novel cyanocombretastatins as potent tubulin polymerisation inhibitors. Bioorganic and Medicinal Chemistry Letters, 22(21), 6731-6734. https://doi.org/10.1016/j.bmcl.2012.08.089

A series of novel cyanocombretastatins bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted phenyl rings, were synthesised and their antitumour activity was evaluated. The Z-cyanocombretastatins were synthesised in a one-ste... Read More about Novel cyanocombretastatins as potent tubulin polymerisation inhibitors.

A practical radiosynthesis of a tritium-labelled fluoro combretastatin (2012)
Journal Article
Hadfield, J., Hirst, N., Mcgown, A., Lawrence, N., & Gaukroger, K. (2012). A practical radiosynthesis of a tritium-labelled fluoro combretastatin. Journal of Labelled Compounds and Radiopharmaceuticals, 55(8), 303-306. https://doi.org/10.1002/jlcr.2939

Zybrestat (combretastatin A-4 disodium diphosphate) is currently in clinical trials as an antivascular anticancer agent. A similar fluorinated agent has shown promise as an antivascular agent and a radiolabelled version would enable further understan... Read More about A practical radiosynthesis of a tritium-labelled fluoro combretastatin.

Time-resolved nanosecond fluorescence lifetime imaging and picosecond infrared spectroscopy of combretastatin A-4 in solution and in cellular systems (2012)
Journal Article
Bisby, R., Botchway, S., Greetham, G., Hadfield, J., Mcgown, A., Parker, A., …Towrie, M. (2012). Time-resolved nanosecond fluorescence lifetime imaging and picosecond infrared spectroscopy of combretastatin A-4 in solution and in cellular systems. Measurement Science and Technology, 23, 084001. https://doi.org/10.1088/0957-0233/23/8/084001

Fluorescence lifetime images of intrinsic fluorescence obtained with two-photon excitation at 630 nm are shown following uptake of a series of E-combretastatins into live cells, including human umbilical vein endothelial cells (HUVECs) that are the t... Read More about Time-resolved nanosecond fluorescence lifetime imaging and picosecond infrared spectroscopy of combretastatin A-4 in solution and in cellular systems.

Fluorescence lifetime imaging of E-combretastatin uptake and distribution in live mammalian cells (2011)
Journal Article
and distribution in live mammalian cells. European Journal of Cancer, 48(12), 1896-1903. https://doi.org/10.1016/j.ejca.2011.11.025

To investigate within live mammalian cells the uptake and disposition of combretastatins, fluorescence lifetime imaging was used with two-photon excitation (2PE). Combretastatin A4 (CA4) and analogues are potential anticancer drugs due to their abili... Read More about Fluorescence lifetime imaging of E-combretastatin uptake and distribution in live mammalian cells.

Tubulin-binding Dibenz[c,e]oxepines as Colchinol analogues for targeting tumour vasculature (2010)
Journal Article
targeting tumour vasculature. Organic and Biomolecular Chemistry, 9(1), 219-231. https://doi.org/10.1039/c0ob00500b

Various methoxy- and hydroxy-substituted dibenz[c,e]oxepines were prepared via the copper(I)-induced coupling of ether-tethered arylstannanes or the dehydrative cyclisation of 1,1'- biphenyl-2,2'-dimethanols, assembled using the Ullmann cross-coupl... Read More about Tubulin-binding Dibenz[c,e]oxepines as Colchinol analogues for targeting tumour vasculature.

Analogues of Y27632 increase gap junction communication and suppress the formation of transformed NIH3T3 colonies (2009)
Journal Article
Hampson, L., He, X., Hadfield, J., Kemp, T., Butler, J., Mcgown, A., …Hampson, I. (2009). Analogues of Y27632 increase gap junction communication and suppress the formation of transformed NIH3T3 colonies. British Journal of Cancer, 101(5), 829-839. https://doi.org/10.1038/sj.bjc.6605208

Constitutive activation of RhoA-dependent RhoA kinase (ROCK) signalling is known to promote cellular transformation and the ROCK inhibitor Y-27632 has the ability to suppress focus formation of RhoA transformed NIH3T3 cells. METHODS: Sixty-four novel... Read More about Analogues of Y27632 increase gap junction communication and suppress the formation of transformed NIH3T3 colonies.

Synthesis and evaluation of double bond substituted combretastatins (2005)
Journal Article
Hadfield, J., Gaukroger, K., Hirst, N., Weston, A., Lawrence, N., & McGown, A. (2005). Synthesis and evaluation of double bond substituted combretastatins. European Journal of Medicinal Chemistry, 40(6), 529-541. https://doi.org/10.1016/j.ejmech.2004.12.008

A series of combretastatins substituted with epoxides, amides and small alkyl groups has been synthesised and evaluated for cytotoxicity and their ability to inhibit the assembly of tubulin. The methyl and ethyl substituted phenols 36, 44 have shown... Read More about Synthesis and evaluation of double bond substituted combretastatins.

Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit? (2003)
Journal Article
Gaukroger, K., Hadfield, J., Lawrence, N., Nolan, S., & McGown, A. (2003). Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit?. Organic and Biomolecular Chemistry, 1(17), 3033-3037. https://doi.org/10.1039/b306878a

A series of combretastatins possessing both a trimethoxy unit and other substituents on ring A has been synthesised and tested for cytotoxicity and their ability to interact with the protein tubulin. All previous studies have indicated that the trime... Read More about Structural requirements for the interaction of combretastatins with tubulin: how important is the trimethoxy unit?.

Novel syntheses of cis and trans isomers of combretastatin A-4 (2001)
Journal Article
Gaukroger, K., Hadfield, J., Hepworth, L., Lawrence, N., & McGown, A. (2001). Novel syntheses of cis and trans isomers of combretastatin A-4. Journal of Organic Chemistry, 66(24), 8135-8138. https://doi.org/10.1021/jo015959z

A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decar... Read More about Novel syntheses of cis and trans isomers of combretastatin A-4.

Linked parallel synthesis and MTT bioassay screening of substituted chalcones (2001)
Journal Article
Lawrence, N., Rennison, D., McGown, A., Ducki, S., Gul, L., Hadfield, J., & Khan, N. (2001). Linked parallel synthesis and MTT bioassay screening of substituted chalcones. Journal of Combinatorial Chemistry, 3(5), 421-426. https://doi.org/10.1021/cc000075z

A 644-membered library of chalcones was prepared by parallel synthesis using the Claisen-Schmidt base-catalyzed aldol condensation of substituted acetophenones and benzaldehydes. The cytotoxicity of these chalcones was conveniently determined upon th... Read More about Linked parallel synthesis and MTT bioassay screening of substituted chalcones.