Works (21)

Updated: July 25th, 2023 21:16

2019 journal article

Annulated bacteriochlorins for near- infrared photophysical studies

NEW JOURNAL OF CHEMISTRY, 43(19), 7209–7232.

By: H. Fujita n, H. Jing n, M. Krayer n, S. Allu n, G. Veeraraghavaiah n, Z. Wu n, J. Jiang n, J. Diers* ...

UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: June 17, 2019

2015 journal article

Extending the Short and Long Wavelength Limits of Bacteriochlorin Near-Infrared Absorption via Dioxo- and Bisimide-Functionalization

JOURNAL OF PHYSICAL CHEMISTRY B, 119(12), 4382–4395.

By: P. Vairaprakash n, E. Yang*, T. Sahin n, M. Taniguchi n, M. Krayer n, J. Diers*, A. Wang*, D. Niedzwiedzki* ...

Contributors: P. Vairaprakash n, E. Yang*, T. Sahin n, M. Taniguchi n, M. Krayer n, J. Diers*, A. Wang*, D. Niedzwiedzki* ...

MeSH headings : Carbon-13 Magnetic Resonance Spectroscopy; Molecular Structure; Photochemical Processes; Porphyrins / chemical synthesis; Porphyrins / chemistry; Proton Magnetic Resonance Spectroscopy; Spectroscopy, Near-Infrared / methods
TL;DR: Six new bacteriochlorins expanding the range of the strong near-infrared absorption (Qy band) to both shorter and longer wavelengths (∼690 to ∼900 nm) have been synthesized and characterized and have excited-state lifetimes that are sufficiently long for use in molecular-based systems for photochemical applications. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2015 journal article

Photophysical Properties and Electronic Structure of Chlorin-Imides: Bridging the Gap between Chlorins and Bacteriochlorins

JOURNAL OF PHYSICAL CHEMISTRY B, 119(24), 7503–7515.

By: K. Faries*, J. Diers*, J. Springer*, E. Yang*, M. Ptaszek n, D. Lahaye n, M. Krayer n, M. Taniguchi n ...

Contributors: K. Faries*, J. Diers*, J. Springer*, E. Yang*, M. Ptaszek n, D. Lahaye n, M. Krayer n, M. Taniguchi n ...

MeSH headings : Electrons; Fluorescence; Imides / chemistry; Molecular Structure; Photochemical Processes; Porphyrins / chemistry; Quantum Theory
TL;DR: The photophysical properties of a set of six chlorin-imides and nine synthetic chlorin analogues that extend the absorption deeper into these key spectral regions of the solar spectrum and help bridge the gap between typical chlorins and bacteriochlorins are reported. (via Semantic Scholar)
UN Sustainable Development Goal Categories
7. Affordable and Clean Energy (OpenAlex)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2014 journal article

Photophysical properties and electronic structure of retinylidene-chlorin-chalcones and analogues

Photochemical & Photobiological Sciences, 13(4), 634–650.

By: J. Springer, M. Taniguchi, M. Krayer, C. Ruzie, J. Diers, D. Niedzwiedzki, D. Bocian, J. Lindsey, D. Holten

Source: NC State University Libraries
Added: August 6, 2018

2014 journal article

Stable synthetic mono-substituted cationic bacteriochlorins mediate selective broad-spectrum photoinactivation of drug-resistant pathogens at nanomolar concentrations

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY, 141, 119–127.

By: L. Huang*, M. Krayer n, J. Roubil*, Y. Huang*, D. Holten*, J. Lindsey n, M. Hamblin*

MeSH headings : Apoptosis / drug effects; Apoptosis / radiation effects; Candida albicans / drug effects; Candida albicans / radiation effects; Cations / chemistry; Cryptococcus neoformans / drug effects; Cryptococcus neoformans / radiation effects; Drug Resistance, Bacterial / drug effects; Drug Resistance, Bacterial / radiation effects; Drug Resistance, Fungal / drug effects; Drug Resistance, Fungal / radiation effects; Fluorescent Dyes / chemistry; Gram-Negative Bacteria / drug effects; Gram-Negative Bacteria / radiation effects; Gram-Positive Bacteria / drug effects; Gram-Positive Bacteria / radiation effects; HeLa Cells; Humans; Light; Photosensitizing Agents / chemical synthesis; Photosensitizing Agents / chemistry; Photosensitizing Agents / pharmacology; Porphyrins / chemical synthesis; Porphyrins / chemistry; Porphyrins / pharmacology; Singlet Oxygen / chemistry; Singlet Oxygen / pharmacology
TL;DR: The highly active photodynamic inactivation of microbial cells may stem from the amphiphilic and cationic features of the bacteriochlorins, which were tested against a panel of pathogenic microorganisms. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2013 journal article

Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures

Chemical Science, 4(5), 2036–2053.

By: K. Reddy, J. Jiang, M. Krayer, M. Harris, J. Springer, E. Yang, J. Jiao, D. Niedzwiedzki ...

Source: NC State University Libraries
Added: August 6, 2018

2013 journal article

Photophysical Properties and Electronic Structure of Bacteriochlorin-Chalcones with Extended Near-Infrared Absorption

PHOTOCHEMISTRY AND PHOTOBIOLOGY, 89(3), 586–604.

MeSH headings : Bacteriochlorophylls / chemistry; Chalcones / chemistry; Dimethyl Sulfoxide; Electrons; Kinetics; Molecular Mimicry; Porphyrins / chemistry; Quantum Theory; Solvents; Spectroscopy, Near-Infrared; Tetrapyrroles / chemistry; Thermodynamics; Toluene
TL;DR: Insight is provided into the fundamental properties of bacteriochlorins and designs for tuning the spectral and photophysical features of these near‐infrared‐absorbing tetrapyrrole chromophores are illustrated. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2013 journal article

Synthesis and evaluation of cationic bacteriochlorin amphiphiles with effective in vitro photodynamic activity against cancer cells at low nanomolar concentration

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 17(1-2), 73–85.

author keywords: photodynamic therapy; HeLa cancer cells; bacteriochlorins; confocal microscopy; subcellular localization; apoptosis
TL;DR: Three new synthetic bacteriochlorins, each bearing a single side-chain containing one or two positive charges, were investigated for their in vitro PDT activity against HeLa human cancer cells, showing the importance of appropriate peripheral groups about a photosensitizer for effective PDT applications. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2012 journal article

Biohybrid Photosynthetic Antenna Complexes for Enhanced Light-Harvesting

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 134(10), 4589–4599.

By: J. Springer, P. Parkes-Loach*, K. Reddy n, M. Krayer n, J. Jiao*, G. Lee*, D. Niedzwiedzki, M. Harris ...

MeSH headings : Amino Acid Sequence; Light; Light-Harvesting Protein Complexes / chemistry; Models, Molecular; Molecular Sequence Data; Photosynthesis; Spectroscopy, Fourier Transform Infrared
TL;DR: The new biohybrid antennas retain the energy-transfer and self-assembly characteristics of the native antenna complexes, offer enhanced coverage of the solar spectrum, and illustrate a versatile paradigm for the construction of artificial LH systems. (via Semantic Scholar)
UN Sustainable Development Goal Categories
7. Affordable and Clean Energy (OpenAlex)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2011 journal article

De novo synthesis and photophysical characterization of annulated bacteriochlorins. Mimicking and extending the properties of bacteriochlorophylls

New Journal of Chemistry, 35(3), 587–601.

By: M. Krayer, E. Yang, J. Diers, D. Bocian, D. Holten & J. Lindsey

Source: NC State University Libraries
Added: August 6, 2018

2011 journal article

Facile synthesis of a B,D-tetradehydrocorrin and rearrangement to bacteriochlorins

New Journal of Chemistry, 35(7), 1376–1384.

By: K. Aravindu, M. Krayer, H. Kim & J. Lindsey

Source: NC State University Libraries
Added: August 6, 2018

2011 journal article

Photophysical Properties and Electronic Structure of Stable, Tunable Synthetic Bacteriochlorins: Extending the Features of Native Photosynthetic Pigments

JOURNAL OF PHYSICAL CHEMISTRY B, 115(37), 10801–10816.

Contributors: E. Yang*, C. Kirmaier*, M. Krayer n, M. Taniguchi n, H. Kim n, J. Diers*, D. Bocian*, J. Lindsey n, D. Holten*

MeSH headings : Bacteriochlorophylls / chemistry; Electrons; Pheophytins / chemistry; Photosynthesis; Porphyrins / chemical synthesis; Porphyrins / chemistry; Quantum Theory; Spectroscopy, Near-Infrared
TL;DR: The studies show how the palette of synthetic bacteriochlorins extends the properties of the native photosynthetic pigments (bacteriochlorophylls) and elucidated design principles for tuning the spectral and photophysical characteristics as required for a wide variety of photochemical applications. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2011 journal article

Synthesis and Photophysical Characterization of Stable Indium Bacteriochlorins

INORGANIC CHEMISTRY, 50(10), 4607–4618.

By: M. Krayer n, E. Yang*, H. Kim n, H. Kee*, R. Deans n, C. Sluder n, J. Diers*, C. Kirmaier* ...

MeSH headings : Acids / chemistry; Bacteria; Bacteriochlorophylls / chemistry; Bacteriochlorophylls / metabolism; Catalysis; Coordination Complexes / chemical synthesis; Coordination Complexes / metabolism; Electrons; Fluorescence; Indium / chemistry; Indium / metabolism; Kinetics; Light; Magnetic Resonance Spectroscopy; Molecular Conformation / radiation effects; Molecular Mimicry; Photochemistry / methods; Photochemotherapy; Porphyrins / chemical synthesis; Porphyrins / metabolism; Pyrroles / chemistry; Quantum Theory
TL;DR: The trends in optical properties of the indium bacteriochlorins versus free base analogues, and the effects of 5-OMe versus 5-H substituents, correlate well with frontier molecular-orbital energies and energy gaps derived from density functional theory calculations. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2010 journal article

De Novo Synthesis of Long-Wavelength Absorbing Chlorin-13,15-dicarboximides

JOURNAL OF ORGANIC CHEMISTRY, 75(5), 1659–1673.

By: M. Ptaszek n, D. Lahaye n, M. Krayer n, C. Muthiah n & J. Lindsey n

TL;DR: The synthetic versatility of the de novo route complements the existing semisynthetic route from chlorophylls and should enable fundamental spectroscopic studies and photochemical applications. (via Semantic Scholar)
UN Sustainable Development Goal Categories
6. Clean Water and Sanitation (OpenAlex)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2010 journal article

Expanded Scope of Synthetic Bacteriochlorins via Improved Acid Catalysis Conditions and Diverse Dihydrodipyrrin-Acetals

JOURNAL OF ORGANIC CHEMISTRY, 75(4), 1016–1039.

By: M. Krayer n, M. Ptaszek n, H. Kim n, K. Meneely n, D. Fan n, K. Secor n, J. Lindsey n

MeSH headings : Acetals / chemistry; Acids / chemistry; Catalysis; Crystallography, X-Ray; Metalloporphyrins / chemical synthesis; Metalloporphyrins / chemistry; Models, Molecular; Molecular Structure; Photochemistry; Porphyrins / chemical synthesis; Porphyrins / chemistry; Pyrroles / chemistry; Spectroscopy, Near-Infrared
TL;DR: Four promising acid catalysis conditions are identified and 15 new bacteriochlorins prepared herein exhibit a long-wavelength absorption band in the range 707-759 nm, providing tunable access to the near-infrared region, which expands the scope of available bacterio chlorins for fundamental studies and diverse applications. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2010 journal article

In Vitro Photodynamic Therapy and Quantitative Structure-Activity Relationship Studies with Stable Synthetic Near-Infrared-Absorbing Bacteriochlorin Photosensitizers

JOURNAL OF MEDICINAL CHEMISTRY, 53(10), 4018–4027.

By: Y. Huang, P. Mroz*, T. Zhiyentayev, S. Sharma*, T. Balasubramanian, C. Ruzie*, M. Krayer*, D. Fan* ...

MeSH headings : Cell Death / drug effects; Drug Screening Assays, Antitumor; HeLa Cells; Humans; Infrared Rays; Photochemotherapy; Photosensitizing Agents / chemistry; Photosensitizing Agents / metabolism; Photosensitizing Agents / pharmacology; Porphyrins / chemistry; Porphyrins / metabolism; Porphyrins / pharmacology; Quantitative Structure-Activity Relationship; Quantum Theory
TL;DR: Testing of 12 new stable synthetic bacteriochlorins for PDT activity described, which possess a variety of peripheral substituents and are very potent in killing cancer cells in vitro after illumination, gives them great potential as photosensitizers for treatment of cancer. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2010 journal article

Stable Synthetic Cationic Bacteriochlorins as Selective Antimicrobial Photosensitizers

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 54(9), 3834–3841.

By: L. Huang*, Y. Huang*, P. Mroz*, G. Tegos*, T. Zhiyentayev*, S. Sharma*, Z. Lu*, T. Balasubramanian* ...

MeSH headings : Anti-Infective Agents / adverse effects; Anti-Infective Agents / chemical synthesis; Anti-Infective Agents / chemistry; Anti-Infective Agents / pharmacology; Candida albicans / drug effects; Candida albicans / radiation effects; Cell Survival / drug effects; Escherichia coli / drug effects; Escherichia coli / radiation effects; HeLa Cells; Humans; Light; Microscopy, Confocal; Molecular Structure; Photosensitizing Agents / adverse effects; Photosensitizing Agents / chemical synthesis; Photosensitizing Agents / chemistry; Photosensitizing Agents / pharmacology; Porphyrins / adverse effects; Porphyrins / chemical synthesis; Porphyrins / chemistry; Porphyrins / pharmacology; Staphylococcus aureus / drug effects; Staphylococcus aureus / radiation effects
TL;DR: Supporting photochemical and theoretical characterization studies indicate that the four bacteriochlorins have comparable photophysical features in homogeneous solution and the anticipated redox characteristics do not correlate with cell-killing ability, and these results support the interpretation that the disparate biological activities observed stem from cellular binding and localization effects rather than intrinsic electronic properties. (via Semantic Scholar)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2010 journal article

Stable synthetic bacteriochlorins overcome the resistance of melanoma to photodynamic therapy

FASEB JOURNAL, 24(9), 3160–3170.

By: P. Mroz*, Y. Huang*, A. Szokalska*, T. Zhiyentayev*, S. Janjua*, A. Nifli*, M. Sherwood*, C. Ruzie n ...

author keywords: multidrug resistance; melanosomes; electron microscopy
MeSH headings : Animals; Cell Line, Tumor; Male; Melanoma / drug therapy; Mice; Mice, Inbred C57BL; Microscopy, Electron, Transmission; Microscopy, Fluorescence; Molecular Structure; Photochemotherapy / methods; Porphyrins / chemical synthesis; Porphyrins / chemistry; Porphyrins / therapeutic use
TL;DR: The extent of melanin contribution to melanoma resistance to PDT was investigated in a set of melanoma cell lines that markedly differ in the levels of pigmentation;3 new bacteriochlorins successfully overcame the resistance. (via Semantic Scholar)
UN Sustainable Development Goal Categories
3. Good Health and Well-being (Web of Science; OpenAlex)
Sources: Web Of Science, ORCID
Added: August 6, 2018

2009 journal article

Fast and Robust Route to Hydroporphyrin-Chalcones with Extended Red or Near-Infrared Absorption

ORGANIC LETTERS, 11(8), 1761–1764.

By: C. Ruzie n, M. Krayer n & J. Lindsey n

MeSH headings : Aldehydes / chemistry; Chalcones / chemical synthesis; Chalcones / chemistry; Combinatorial Chemistry Techniques; Microwaves; Molecular Structure; Photochemistry; Porphyrins / chemical synthesis; Porphyrins / chemistry; Spectrophotometry, Infrared; Spectroscopy, Near-Infrared; Stereoisomerism
TL;DR: The reaction of an acetylchlorin or diacetylbacteriochlorin with an aldehyde under microwave conditions readily affords the corresponding hydroporphyrin-chalcone, which should make such constructs valuable for fundamental spectroscopic studies as well as diverse photochemical applications in the relatively unexplored red and near-infrared spectral regions. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2009 journal article

Refined syntheses of hydrodipyrrin precursors to chlorin and bacteriochlorin building blocks

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, 13(10), 1098–1110.

By: M. Krayer n, T. Balasubramanian n, C. Ruzie n, M. Ptaszek n, D. Cramer n, M. Taniguchi n, J. Lindsey n

Contributors: M. Krayer n, T. Balasubramanian n, C. Ruzié n, M. Ptaszek n, D. Cramer n, M. Taniguchi n, J. Lindsey n

author keywords: chlorin; bacteriochlorin; bromination; dihydrodipyrrin; tetrahydrodipyrrin; McMurry cyclization; Michael addition
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

2009 journal article

Tandem dispersion and killing of bacteria from a biofilm

ORGANIC & BIOMOLECULAR CHEMISTRY, 7(3), 603–606.

By: S. Rogers n, M. Krayer n, J. Lindsey n & C. Melander n

MeSH headings : Anti-Bacterial Agents / chemistry; Anti-Bacterial Agents / pharmacology; Bacteria / drug effects; Bacteria / growth & development; Biofilms; Microbial Viability / drug effects; Photosensitizing Agents / chemistry; Photosensitizing Agents / pharmacology; Triazoles / chemistry; Triazoles / pharmacology
TL;DR: The combined effects of biofilm dispersion with a 2-aminoimidazole-triazole conjugate and bactericidal activity with a photodynamic inactivation agent suggest a novel combination therapy for treating diverse microbial infections. (via Semantic Scholar)
UN Sustainable Development Goal Categories
Sources: Web Of Science, ORCID
Added: August 6, 2018

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