@article{feese_gracz_boyle_ghiladi_2019, title={Towards microbe-targeted photosensitizers: Synthesis, characterization and in vitro photodynamic inactivation of the tuberculosis model pathogen M. smegmatis by porphyrin-peptide conjugates}, volume={23}, ISSN={1088-4246 1099-1409}, url={http://dx.doi.org/10.1142/S1088424619501505}, DOI={10.1142/S1088424619501505}, abstractNote={ Porphyrin-peptide conjugates have a breadth of potential applications, including use in photodynamic therapy, boron neutron capture therapy, as fluorescence imaging tags for tracking subcellular localization, as magnetic resonance imaging (MRI) positive-contrast reagents and as biomimetic catalysts. Here, we have explored three general routes to porphyrin-peptide conjugates using the Cu(I)-catalyzed Huisgen-Medal-Sharpless 1,3-dipolar cycloaddition of peptide-containing azides with a terminal alkyne-containing porphyrin, thereby generating porphyrin-peptide conjugates (PPCs) comprised of a cationic porphyrin coupled to short antimicrobial peptides. In addition to characterizing the PPCs using a variety of spectroscopic (UV-vis, [Formula: see text]H- and [Formula: see text]C-NMR) and mass spectrometric methods, we evaluated their efficacy as photosensitizers for the in vitro photodynamic inactivation of Mycobacterium smegmatis as a model for the pathogen Mycobacterium tuberculosis. Difficulties that needed to be overcome for the efficient synthesis of PPCs were the limited solubility of the quaternized pyridyl porphyrin in common solvents, undesired (de)metallation and transmetallation, and chromatographic purification. Photodynamic inactivation studies of a small library of PPCs against Mycobacterium smegmatis confirmed our hypothesis that the porphyrin-based photosensitizer maintains its ability to efficiently inactivate bacteria when conjugated to a small peptide by upwards of 5–6 log units (99.999[Formula: see text]%) using white light illumination (400–700 nm, 60 mW/cm[Formula: see text], 30 min). Further, hemolysis assays revealed the lack of toxicity of the PPCs against sheep blood at concentrations employed for in vitro photodynamic inactivation. Taken together, the results demonstrated the ability of PPCs to maintain their antimicrobial photodynamic inactivation efficacy when possessing a short cationic peptides for enabling the potential targeting of pathogens in vivo. }, number={11n12}, journal={Journal of Porphyrins and Phthalocyanines}, publisher={World Scientific Pub Co Pte Lt}, author={Feese, Elke and Gracz, Hanna S. and Boyle, Paul D. and Ghiladi, Reza A.}, year={2019}, month={Dec}, pages={1414–1439} }
 @article{carpenter_feese_sadeghifar_argyropoulos_ghiladi_2012, title={Porphyrin-Cellulose Nanocrystals: A Photobactericidal Material that Exhibits Broad Spectrum Antimicrobial Activity (vol 88, pg 495, 2012)}, volume={88}, ISSN={["0031-8655"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84863678900&partnerID=MN8TOARS}, DOI={10.1111/j.1751-1097.2012.01191.x}, abstractNote={Bradley L. Carpenter, Elke Feese, Hasan Sadeghifar, Dimitris S. Argyropoulos and Reza A. Ghiladi* Department of Chemistry, North Carolina State University, Raleigh, NC Department of Forest Biomaterials, North Carolina State University, Raleigh, NC Department of Chemistry, University of Helsinki, Helsinki, Finland Department of Chemistry, Science and Research Branch, Islamic Azad University, Mazandaran, Iran}, number={4}, journal={PHOTOCHEMISTRY AND PHOTOBIOLOGY}, author={Carpenter, Bradley L. and Feese, Elke and Sadeghifar, Hasan and Argyropoulos, Dimitris S. and Ghiladi, Reza A.}, year={2012}, pages={1034–1034} }
 @article{carpenter_feese_sadeghifar_argyropoulos_ghiladi_2012, title={Porphyrin-Cellulose Nanocrystals: A Photobactericidal Material that Exhibits Broad Spectrum Antimicrobial Activity†}, volume={88}, ISSN={0031-8655}, url={http://dx.doi.org/10.1111/j.1751-1097.2012.01117.x}, DOI={10.1111/j.1751-1097.2012.01117.x}, abstractNote={Abstract}, number={3}, journal={Photochemistry and Photobiology}, publisher={Wiley}, author={Carpenter, Bradley L. and Feese, Elke and Sadeghifar, Hasan and Argyropoulos, Dimitris S. and Ghiladi, Reza A.}, year={2012}, month={Mar}, pages={527–536} }
 @article{feese_sadeghifar_gracz_argyropoulos_ghiladi_2011, title={Photobactericidal Porphyrin-Cellulose Nanocrystals: Synthesis, Characterization, and Antimicrobial Properties}, volume={12}, ISSN={1525-7797 1526-4602}, url={http://dx.doi.org/10.1021/bm200718s}, DOI={10.1021/bm200718s}, abstractNote={Adherence and survival of pathogenic bacteria on surfaces leading to concomitant transmission to new hosts significantly contributes to the proliferation of pathogens, which in turn considerably increases the threat to human health, particularly by antibiotic-resistant bacteria. Consequently, more research into effective surface disinfection and alternative materials (fabrics, plastics, or coatings) with antimicrobial and other bioactive characteristics is desirable. This report describes the synthesis and characterization of cellulose nanocrystals that were surface-modified with a cationic porphyrin. The porphyrin was appended onto the cellulose surface via the Cu(I)-catalyzed Huisgen-Meldal-Sharpless 1,3-dipolar cycloaddition having occurred between azide groups on the cellulosic surface and porphyrinic alkynes. The resulting, generally insoluble, crystalline material, CNC-Por (5), was characterized by infrared and diffusion (1)H NMR spectroscopies, gel permeation chromatography, and thermogravimetric analysis. Although only suspended, and not dissolved, in an aqueous system, CNC-Por (5) showed excellent efficacy toward the photodynamic inactivation of Mycobacterium smegmatis and Staphylococcus aureus , albeit only slight activity against Escherichia coli . The synthesis, properties, and activity of CNC-Por (5) described herein serve as a benchmark toward our overall objectives of developing novel, potent, bioactive, photobactericidal materials that are effective against a range of bacteria, with potential utilization in the health care and food preparation industries.}, number={10}, journal={Biomacromolecules}, publisher={American Chemical Society (ACS)}, author={Feese, Elke and Sadeghifar, Hasan and Gracz, Hanna S. and Argyropoulos, Dimitris S. and Ghiladi, Reza A.}, year={2011}, month={Oct}, pages={3528–3539} }
 @article{feese_ghiladi_2009, title={Highly efficient in vitro photodynamic inactivation of Mycobacterium smegmatis}, volume={64}, ISSN={1460-2091 0305-7453}, url={http://dx.doi.org/10.1093/jac/dkp278}, DOI={10.1093/jac/dkp278}, abstractNote={OBJECTIVES
Efforts to control tuberculosis (TB) have been hampered by the emergence of multiple-drug resistant strains, necessitating pursuit of alternative approaches to the current antibiotic-based treatments. Herein, we explore the feasibility of photodynamic inactivation (PDI) of mycobacteria.


METHODS
In vitro PDI studies employing Mycobacterium smegmatis as a surrogate for Mycobacterium tuberculosis were performed examining photosensitizer (PS) type, concentration and light dose. M. smegmatis was grown to a concentration of 10(8) colony forming units (cfu) per mL, resuspended in PBS-0.5% Tween-80-containing buffer, incubated with the PS for 5 min and subsequently illuminated with white light (400-700 nm) at a fluence rate of 60 mW/cm(2) for 1, 5, 15 or 30 min (equivalent to 3.4, 18, 54 or 108 J/cm(2)). The percentage survival was determined by the ratio of the colony count from illuminated and non-illuminated control cell suspensions. The PSs examined were 5,10,15,20-tetrakis(1-methyl-4-pyridinyl)porphyrin tetratosylate (TMPyP), 5,10,15,20-tetrakis(4-N,N,N-trimethylanilinium)porphyrin tetrachloride (TNMAP), methylene blue (MB), 5,10,15,20-tetrakis(4-sulphonatophenyl)porphyrin (TSPP), 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin-Pd(II) (TCPP-Pd) and phthalocyanine tetrasulphonic acid (PhCS).


RESULTS
Our best results demonstrate that PDI of M. smegmatis can achieve a noteworthy 5-6 log unit reduction in cfu (99.999% + viable cell eradication) when cationic PSs are employed in the nanomolar concentration range. Anionic PSs did not effectively mediate PDI of mycobacteria due to their inability to associate with the negatively charged mycobacterial cell membrane.


CONCLUSIONS
PDI of M. smegmatis was found to be highly efficient in reducing the number of viable cells in vitro when cationic PSs were employed.}, number={4}, journal={Journal of Antimicrobial Chemotherapy}, publisher={Oxford University Press (OUP)}, author={Feese, Elke and Ghiladi, Reza A.}, year={2009}, month={Aug}, pages={782–785} }