Synthesis, photophysics and photochemistry of phthalocyanine-ɛ-polylysine conjugates in the presence of metal nanoparticles against Staphylococcus aureus
- Authors: Nombona, Nolwazi , Antunes, Edith M , Chidawanyika, Wadzanai J U , Kleyi, Phumelele , Tshentu, Zenixole R , Nyokong, Tebello
- Date: 2015
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/244439 , vital:51257 , xlink:href="https://doi.org/10.1016/j.molstruc.2015.02.040"
- Description: This work reports on the photodynamic activity of Zn phthalocyanine-ɛ-polylysine conjugates in the presence of gold and silver nanoparticles (NPs) towards the inactivation of Staphylococcus aureus (S. aureus). The conjugates showed high photoinactivation with ∼6% growth at a drug dose of 3 μM and fluence of 39.6 mW/cm2 for 10 min irradiation time in the presence of silver nanoparticles. The presence of silver nanoparticels from the minimal inhibition concentration (MIC50) studies showed remarkable growth inhibition for the tested conjugates even at low concentrations. The MIC50 was lowest for the conjugate of 3 with ɛ-polylysine at concentrations of less than 0.0058 μM in the presence of AgNPs. The lethal photosensitization of microorganisms has emerged as a promising treatment since bacteria have reduced possibilities of developing resistance to photodynamic therapy.
- Full Text:
- Date Issued: 2015
Photophysical and photochemical studies of sulfur containing phthalocyanine derivatives in the presence of folic acid
- Authors: Nombona, Nolwazi , Nyokong, Tebello
- Date: 2012
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/243180 , vital:51124 , xlink:href="https://doi.org/10.1016/j.ica.2012.03.051"
- Description: The syntheses of zinc and magnesium 9,16,23-tris-(5-trifluoromethyl-2-mercaptopyridine)-2-(carboxy)phthalocyaninato complexes are described for the first time. The photophysical and photochemical parameters of these molecules in the absence or presence of folic acid are compared to the corresponding oxygen bridged complexes and to 2,9,17,23-tetrakis-[(1,6-hexanedithiol)phthalocyaninato]zinc(II), [8,15,22-tris-(naptho)-2-(amidoethanethiol)phthalocyaninato]zinc(II) and zinc phthalocyanine tetrasulfonate. In the absence of folic acid, the complexes show relatively good triplet quantum yields (ranging from 0.52 to 0.88) in DMSO with reasonable triplet lifetime between 140 and 470 μs. The complexes showed high singlet oxygen quantum yield values ranging from 0.27 to 0.66 in the absence of folic acid. In the presence of folic acid, the triplet quantum yield values were between 0.37 and 0.75 and the lifetimes were significantly reduced (70–320 μs).
- Full Text:
- Date Issued: 2012
Photophysicochemical and photodynamic studies of phthalocyanines conjugated to selected drug delivery agents
- Authors: Nombona, Nolwazi
- Date: 2012
- Subjects: Phthalocyanines Photochemistry Photochemotherapy Drug delivery systems Magnesium Zinc Nanoparticles Staphylococcus aureus
- Language: English
- Type: Thesis , Doctoral , PhD
- Identifier: vital:4333 , http://hdl.handle.net/10962/d1004994
- Description: This work reports on the successful synthesis, characterisation and photophysical properties of new asymmetric metal free, magnesium and zinc phthalocyanines. The synthesis of symmetrical phthalocyanines is also reported. A selection of phthalocyanines have been conjugated, covalently linked, encapsulated or mixed with selected of drug delivery agents which include gold or silver nanoparticles, poly-L-lysine, liposomes and folic acid. The influence of delivery agent on the photophysical and photochemical properties of conjugated phthalocyanine is investigated. The studies showed that the Au nanoparticle significantly lowered the fluorescence quantum yield values of the phthalocyanines. The photodynamic activity of Zn phthalocyanine-ε-polylysine conjugates in the presence of nanoparticles towards the inactivation of Staphylococcus aureus showed high photoinactivation in the presence of silver nanoparticles. The presence of silver nanoparticels from the minimal inhibition concentration (MIC₅₀) studies showed remarkable growth inhibition for the tested conjugates even at low concentrations. The conjugate also showed no dark toxicity when evaluated using the chick choriallantoic membrane (CAM) assay. The efficiency of selected zinc phthalocyanine as photodynamic therapy (PDT) agents was investigated. The production of reactive oxygen species (ROS) and phototoxicity of the photosensitizers were assessed. Healthy fibroblast cells and breast cancer (MCF-7) cells were treated with either free phthalocyanine or phthalocyanine bound to either gold nanoparticles or encapsulated in liposomes. Cell viability studies showed the optimum phototoxic effect on non-malignant cells to be 4.5 J.cm⁻². The PDT effect of the liposome bound phthalocyanine showed extensive damage of the breast cancer cells. Gold nanoparticles only showed a modest improvement in PDT activity.
- Full Text:
- Date Issued: 2012
Spectroscopic and physicochemical behavior of magnesium phthalocyanine derivatives mono-substituted with a carboxylic acid group
- Authors: Nombona, Nolwazi , Chidawanyika, Wadzanai J U , Nyokong, Tebello
- Date: 2012
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/244450 , vital:51258 , xlink:href="https://doi.org/10.1016/j.molstruc.2011.12.051"
- Description: This work reports on the synthesis of novel unsymmetrically substituted magnesium phthalocyanine complexes containing one carboxyl group. The physicochemical behavior of these complexes were compared with those of their unmetallated and zinc counterparts. The MgPcs showed interesting absorption spectra with [8,15,22-Tris-(naphtho)-4,5-(3-carboxy-1,2-dioxyphenyl)phthalocyaninato]magnesium (II) showing a large split in the Q band whereas [8,15,22-Tris-(naphtho)-2-(carboxy) phthalocyaninato]magnesium(II) presented only a small splitting. The magnesium phthalocyanine derivatives displayed higher fluorescence quantum yields compared to unmetallated and zinc phthalocyanine counterparts. The latter gave admirable triplet and singlet oxygen quantum yields. These molecules can distinctly be employed in the field of photodynamic therapy in combination with fluorescence imaging.
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- Date Issued: 2012
Synthesis of phthalocyanine conjugates with gold nanoparticles and liposomes for photodynamic therapy
- Authors: Nombona, Nolwazi , Maduray, Kaminee , Antunes, Edith M , Karsten, Aletta , Nyokong, Tebello
- Date: 2012
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/245798 , vital:51406 , xlink:href="https://doi.org/10.1016/j.jphotobiol.2011.11.007"
- Description: The efficiency of [2,9,17,23-tetrakis-(1,6-hexanedithiol)phthalocyaninato]zinc(II) as a photodynamic therapy (PDT) agent was investigated. This compound belongs to the second generation of photosensitizers currently tested for the cellular photo-damage of cancer cells. The production of reactive oxygen species (ROS) and phototoxicity of the photosensitizer were assessed. Healthy fibroblast cells and breast cancer (MCF-7) cells were treated with either free phthalocyanine or phthalocyanine bound to either gold nanoparticles or encapsulated in liposomes. Cell viability studies showed the optimum phototoxic effect on non-malignant cells to be 4.5 J cm−2. The PDT effect of the liposome bound phthalocyanine showed extensive damage of the breast cancer cells. Gold nanoparticles only showed a modest improvement in PDT activity.
- Full Text:
- Date Issued: 2012
Photophysical behaviour of asymmetrically substituted metal free, Mg and Zn phthalocyanines in the presence of folic acid
- Authors: Nombona, Nolwazi , Chidawanyika, Wadzanai J U , Nyokong, Tebello
- Date: 2011
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/247705 , vital:51608 , xlink:href="https://doi.org/10.1016/j.poly.2010.11.033"
- Description: This work reports on the synthesis, characterisation and photophysical properties of new asymmetric metal free, magnesium and zinc phthalocyanines containing a mono carboxylic acid group for possible linking to biological molecules via an amide bond. Successful synthesis of the phthalocyanines was achieved through the statistical condensation method. The phthalocyanines were mixed with folic acid and their photophysical properties were examined. The triplet quantum yield values for all the complexes in DMSO were between 0.49 and 0.74 and in the presence of folic acid they were between 0.37 and 0.63. The lifetimes were generally good ranging from 70 to 290 μs in the absence or presence of folic acid.
- Full Text:
- Date Issued: 2011
Synthesis and photophysical studies of phthalocyanine–gold nanoparticle conjugates
- Authors: Nombona, Nolwazi , Antunes, Edith M , Litwinski, Christian , Nyokong, Tebello
- Date: 2011
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/248438 , vital:51686 , xlink:href="https://doi.org/10.1039/C1DT11151E"
- Description: This work reports on the synthesis, characterization and photophysical studies of phthalocyanine–gold nanoparticle conjugates. The phthalocyanine complexes are: tris-(5-trifluoromethyl-2-mercaptopyridine)-2-(carboxy)phthalocyanine (3), 2,9,17,23-tetrakis-[(1, 6-hexanedithiol) phthalocyaninato]zinc(II) (8) and [8,15,22-tris-(naptho)-2(amidoethanethiol) phthalocyanato] zinc(II)(10). The gold nanoparticles were characterized using transmission electron microscopy, X-ray diffraction, atomic force microscopy and UV-vis spectroscopy where the size was confirmed to be ∼5 nm. The phthalocyanine Au nanoparticle conjugates showed lower fluorescence quantum yield values with similar fluorescence lifetimes compared to the free phthalocyanines. The Au nanoparticle conjugates of 3 and 10 also showed higher triplet quantum yields of 0.69 to 0.71, respectively. A lower triplet quantum yield was obtained for the conjugate compared to free phthalocyanine for complex 8. The triplet lifetimes ranged from 70 to 92 μs for the conjugates and from 110 to 304 μs for unbound Pc complexes.
- Full Text:
- Date Issued: 2011
Symmetrically and unsymmetrically substituted carboxy phthalocyanines as sensitizers for nanoporous ZnO films
- Authors: Masilela, Nkosiphile , Nombona, Nolwazi , Loewenstein, Thomas , Nyokong, Tebello , Schlettwein, Derck
- Date: 2010
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/249126 , vital:51780 , xlink:href="https://doi.org/10.1142/S1088424610002793"
- Description: The photoelectroectrochemical studies of water soluble octacarboxylated oxotitanium (OTiOCPc), zinc (ZnOCPC), hydroxyaluminium ((OH)AlOCPc), dihydroxysilicon ((OH)2SiOCPc), hydroxygallium (OHGaOCPc) and low symmetry zinc monocarboxy (ZnMCPc) phthalocyanines were performed. The dyes were adsorbed to nanoporous ZnO electrodeposited in the presence of eosin Y as structure directing agent (SDA) on FTO substrates by refluxing or soaking the films in a solution containing the dye of interest such that a full surface coverage was achieved. High external (IPCE) and internal (APCE) quantum efficiencies of up to 50.6% and 96.7% were achieved for the OTiOCPc complex. There was a lower overall cell efficiency for cells sensitized with phthalocyanines containing hydroxyl as axial ligand ZnO/(OH)2SiOCPc, ZnO/(OH)GaOCPc and (OH)AlOCPc because of strong aggregation on the surface of the electrodes. To further suppress dye aggregation, the zinc complex of a new monocarboxylated phthalocyanine sensitizer with bulky naphtho side groups (ZnMCPc) was employed. Among the studied sensitizers, ZnMCPc gave the highest overall cell efficiency of phthalocyanine electrodeposited on ZnO of η = 0.48%.
- Full Text:
- Date Issued: 2010
The synthesis and fluorescence behaviour of phthalocyanines unsymmetrically substituted with naphthol and carboxy groups
- Authors: Nombona, Nolwazi , Antunes, Edith M , Nyokong, Tebello
- Date: 2010
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/261534 , vital:53418 , xlink:href="https://doi.org/10.1016/j.dyepig.2009.11.010"
- Description: Unsymmetrically substituted phthalocyanines 8,15,22-tris-(naphtho)-2-(carboxy)phthalocyanine, [8,15,22-tris-(naphtho)-2-(carboxy)phthalocyanato]zinc(II), 8,15,22-tris-(naphtho)-4,5-(3-carboxy-1,2-dioxyphenyl)phthalocyanine and [8,15,22-tris-(naphtho)-4,5-(3-carboxy-1,2-dioxyphenoxy)phthalocyanato]zinc(II) were prepared using the mixed phthalonitrile cyclotetramerization of 3-(1-naphthoxy) phthalonitrile with a carboxylic acid phthalonitrile. The phthalocyanines were separated using column chromatography employing a mixture of THF, ammonia and water. The novel compounds were characterized using UV–Vis, IR, 1H NMR and mass spectrometry as well as elemental analysis. Fluorescence quantum yields were found to range from 0.05 to 0.16.
- Full Text:
- Date Issued: 2010
Comparative electrocatalytic behavior of self-assembled monolayer of thiol derivatised Co (II) phthalocyanines on gold disk, ultramicro cylinder and fiber electrodes
- Authors: Nombona, Nolwazi , Geraldo, Daniela A , Hakuzimana, Jean , Schwarz, Anne , Westbroek, Philippe , Nyokong, Tebello
- Date: 2009
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/263488 , vital:53632 , xlink:href="https://doi.org/10.1007/s10800-008-9716-y"
- Description: This paper reports on the use of thiol derivatised cobalt phthalocyanines as self assembled monolayers (SAMs) on gold disk electrode, gold ultramicro-cylinder electrode (UMCE) and on gold coated fiber for the detection of L-cysteine. The complexes are peripherally and non-peripherally substituted with phenylthio substituents. The SAM modified electrodes showed enhancement of catalytic currents and overpotential reduction occurred on the gold modified electrodes with different geometries. Electrocatalytic oxidation of L-cysteine on SAM modified gold coated fiber was reported for the first time. The gold coated fiber and ultramicro cylinder electrode were less stable towards the electrocatalytic oxidation of cysteine compared to its oxidation on the gold disk. The gold disk electrode gave better catalytic performance in terms of stability and reduction of overpotential.
- Full Text:
- Date Issued: 2009
Electrochemical studies of titanium, manganese and cobalt phthalocyanines
- Authors: Nombona, Nolwazi
- Date: 2009
- Subjects: Titanium , Manganese , Cobalt , Phthalocyanines , Electrochemistry , Electrodes , Self-assembly (Chemistry)
- Language: English
- Type: Thesis , Masters , MSc
- Identifier: vital:4312 , http://hdl.handle.net/10962/d1004970 , Titanium , Manganese , Cobalt , Phthalocyanines , Electrochemistry , Electrodes , Self-assembly (Chemistry)
- Description: Syntheses, spectral, electrochemical and spectroelectrochemical studies of phenylthio and amino derivatised metallophthalocyanines complexes are reported. The complexes are immobilized onto a gold macro disk, gold ultramicroelectrode and gold coated fiber electrodes via self assembly with phenylthio MPc derivatives or onto a glassy carbon electrode via electropolymerisation with amino MPc derivatives. For the first time MPc SAMs were formed on gold coated fiber. The electrocatalytic behavior of the modified electrodes was studied for the detection of nitrite and L-cysteine, all modified electrodes showed improved electrocatalytic oxidation compared to the unmodified electrode. The MPc complexes catalyzed nitrite oxidation via a two-electron mechanism producing nitrate. Cobalt tetraaminophthalocyanine showed the best catalytic activity for nitrite oxidation in terms of overpotential lowering compared to other complexes and thus was used for nitrite detection in a food sample, the nitrite concentration was determined to be 59.13 ppm, well within the limit for cured meat products. Electrocatalytic oxidation of L-cysteine on SAM modified gold coated fiber was reported for the first time. The gold coated fiber and ultamicro cylinder electrode were less stable towards the electro-oxidation of cysteine compared to its oxidation on the gold disk. The gold disk electrode gave better catalytic performance in terms of stability and reduction of overpotential. The phenylthio cobalt phthalocyanine derivative gave the best catalytic activity for L-cysteine oxidation in terms of overpotential lowering compared to other phenylthio derivatized MPc complexes. The amount of L-cysteine in human urine was 2.4 mM, well within the urinary L-cysteine excretion range for a healthy human being.
- Full Text:
- Date Issued: 2009
The formation of self-assembled monolayers of thiophthalocyanine complexes of titanium, vanadium and manganese and their use in l-cysteine electrocatalysis
- Authors: Mbambisa, Gcineka , Nombona, Nolwazi , Nyokong, Tebello
- Date: 2009
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/263375 , vital:53622 , xlink:href="https://doi.org/10.1016/j.microc.2009.04.009"
- Description: Self-assembled monolayers (SAMs) based on octapentylthiophthalocyanine complexes of oxovanadium (IV) (OVOPThPc), titanium(IV) (OTiOPThPc), and manganese (III) acetate (AcMnOPThPc), and of tetraphenylthiophthalocyanine complexes of hydroxo manganese(III) (OHMnTPPc) and oxotitanium(IV) (OTiTPPc) are described. The oxidation of l-cysteine was observed at potentials which ranged from 0.52 V to 0.67 V. The detection limits for l-cysteine analysis were of the order of 10− 7 to 10− 6 M.
- Full Text:
- Date Issued: 2009
The synthesis, cyclic voltammetry and spectroelectrochemical studies of Co (II) phthalocyanines tetra-substituted at the α and β positions with phenylthio groups
- Authors: Nombona, Nolwazi , Nyokong, Tebello
- Date: 2009
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/264529 , vital:53742 , xlink:href="https://doi.org/10.1016/j.dyepig.2008.06.002"
- Description: Non-peripherally substituted cobalt 1,(4)-(tetraphenylthiophthalocyaninato) and peripherally substituted cobalt 2,(3)-(tetraphenylthiophthalocyaninato) complexes were synthesized. Redox processes were observed at E1/2 = −1.44 V (I), −0.39 V (II), +0.37 V (III), +0.78 V (IV) and 1.15 V (V) for the non-peripherally substituted and at E1/2 = −1.42 V (I), −0.57, −0.39 V (II), +0.27 V (III), +0.79 V (IV) and +1.10 V (V) for the peripherally substituted complexes, respectively. The couples were assigned to CoIPc−2/CoIPc−3 (I), CoIIPc−2/CoIPc−2 (II), CoIIIPc−2/CoIIPc−2 (III), and CoIIIPc−1/CoIIIPc−2 (IV) using spectroelectrochemistry. The last process (V) could not be ascertained by spectroelectrochemistry but is associated with ring oxidation. Upon reduction or oxidation, the Q band of the non-peripherally substituted complex became less red shifted compared to that of its peripherally substituted counterpart.
- Full Text:
- Date Issued: 2009
Electrochemical and electrocatalytic properties of α-substituted manganese and titanium phthalocyanines
- Authors: Nombona, Nolwazi , Tau, Prudence , Sehlotho, Nthapo , Nyokong, Tebello
- Date: 2008
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/268587 , vital:54212 , xlink:href="https://doi.org/10.1016/j.electacta.2007.11.046"
- Description: This work reports on the synthesis of manganese and titanium phthalocyanine complexes that are tetra-substituted at four non-peripheral positions with amino ligands. The complexes are investigated for the first time for their electrochemical properties using cyclic voltammetry, rotating disc electrode voltammetry and spectroelectrochemistry. Electropolymerisation on a glassy carbon electrode was performed with ease and the modified electrodes were investigated for electrocatalysis of nitrite oxidation. Nitrite oxidation to nitrate is confirmed from the transfer of a total of two electrons.
- Full Text:
- Date Issued: 2008