Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, red-emitting chlorins
Abstract
PEGylated chlorins are soluble in water, can be excited in the near-ultraviolet, and exhibit a relatively narrow fluorescence band in the red spectral region.
- Authors:
-
- North Carolina State Univ., Raleigh, NC (United States). Dept. of Chemistry
- Washington Univ., St. Louis, MO (United States). Dept. of Chemistry
- NIRvana Sciences, Research Triangle Park, NC (United States)
- Univ. of California, Riverside, CA (United States). Dept. of Chemistry
- Publication Date:
- Research Org.:
- Energy Frontier Research Centers (EFRC) (United States). Photosynthetic Antenna Research Center (PARC)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES)
- OSTI Identifier:
- 1388778
- Grant/Contract Number:
- SC0001035
- Resource Type:
- Accepted Manuscript
- Journal Name:
- New Journal of Chemistry
- Additional Journal Information:
- Journal Volume: 40; Journal Issue: 9; Related Information: PARC partners with Washington University in St. Louis (lead); University of California, Riverside; University of Glasgow, UK; Los Alamos National Laboratory; University of New Mexico; New Mexico Corsortium; North Carolina State University; Northwestern University; Oak Ridge National Laboratory; University of Pennsylvania; Sandia National Laboratories; University of Sheffield, UK; Journal ID: ISSN 1144-0546
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Liu, Mengran, Chen, Chih-Yuan, Mandal, Amit Kumar, Chandrashaker, Vanampally, Evans-Storms, Rosemary B., Pitner, J. Bruce, Bocian, David F., Holten, Dewey, and Lindsey, Jonathan S. Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, red-emitting chlorins. United States: N. p., 2016.
Web. doi:10.1039/C6NJ01154C.
Liu, Mengran, Chen, Chih-Yuan, Mandal, Amit Kumar, Chandrashaker, Vanampally, Evans-Storms, Rosemary B., Pitner, J. Bruce, Bocian, David F., Holten, Dewey, & Lindsey, Jonathan S. Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, red-emitting chlorins. United States. https://doi.org/10.1039/C6NJ01154C
Liu, Mengran, Chen, Chih-Yuan, Mandal, Amit Kumar, Chandrashaker, Vanampally, Evans-Storms, Rosemary B., Pitner, J. Bruce, Bocian, David F., Holten, Dewey, and Lindsey, Jonathan S. Thu .
"Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, red-emitting chlorins". United States. https://doi.org/10.1039/C6NJ01154C. https://www.osti.gov/servlets/purl/1388778.
@article{osti_1388778,
title = {Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, red-emitting chlorins},
author = {Liu, Mengran and Chen, Chih-Yuan and Mandal, Amit Kumar and Chandrashaker, Vanampally and Evans-Storms, Rosemary B. and Pitner, J. Bruce and Bocian, David F. and Holten, Dewey and Lindsey, Jonathan S.},
abstractNote = {PEGylated chlorins are soluble in water, can be excited in the near-ultraviolet, and exhibit a relatively narrow fluorescence band in the red spectral region.},
doi = {10.1039/C6NJ01154C},
journal = {New Journal of Chemistry},
number = 9,
volume = 40,
place = {United States},
year = {Thu Jul 21 00:00:00 EDT 2016},
month = {Thu Jul 21 00:00:00 EDT 2016}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 25 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Photodynamic therapy with mTHPC and polyethylene glycol-derived mTHPC: a comparative study on human tumour xenografts
journal, February 1999
- Ris, H-B; Krueger, T.; Giger, A.
- British Journal of Cancer, Vol. 79, Issue 7-8
Soluble precipitable porphyrins for use in targeted molecular brachytherapy
journal, January 2008
- Yao, Zhen; Borbas, K. Eszter; Lindsey, Jonathan S.
- New J. Chem., Vol. 32, Issue 3
Water Proton Relaxivity, Superoxide Dismutase-like Activity, and Cytotoxicity of a Manganese(III) Porphyrin Having Four Poly(ethylene glycol) Tails
journal, May 2014
- Hitomi, Yutaka; Ekawa, Tomoyuki; Kodera, Masahito
- Chemistry Letters, Vol. 43, Issue 5
Synthesis and applications of heterobifunctional poly(ethylene oxide) oligomers
journal, January 2008
- Thompson, M. S.; Vadala, T. P.; Vadala, M. L.
- Polymer, Vol. 49, Issue 2
Investigation of MALDI-TOF Mass Spectrometry of Diverse Synthetic Metalloporphyrins, Phthalocyanines and Multiporphyrin Arrays
journal, April 1999
- Srinivasan, N.; Haney, Carol A.; Lindsey, Jonathan S.
- Journal of Porphyrins and Phthalocyanines, Vol. 03, Issue 04
Properties of Polyethylene Glycol Supported Tetraarylporphyrin in Aqueous Solution and Its Interaction with Liposomal Membranes
journal, October 2008
- Nawalany, Kinga; Kozik, Bartlomiej; Kepczynski, Mariusz
- The Journal of Physical Chemistry B, Vol. 112, Issue 39
Effects of Substituents on Synthetic Analogs of Chlorophylls. Part 4: How Formyl Group Location Dictates the Spectral Properties of Chlorophylls b , d and f
journal, January 2015
- Yuen, Jonathan M.; Harris, Michelle A.; Liu, Mengran
- Photochemistry and Photobiology, Vol. 91, Issue 2
Refined Synthesis of 2,3,4,5-Tetrahydro-1,3,3-trimethyldipyrrin, a Deceptively Simple Precursor to Hydroporphyrins
journal, September 2005
- Ptaszek, Marcin; Bhaumik, Jayeeta; Kim, Han-Je
- Organic Process Research & Development, Vol. 9, Issue 5
Near-IR Emissive Chlorin–Bacteriochlorin Energy-Transfer Dyads with a Common Donor and Acceptors with Tunable Emission Wavelength
journal, October 2013
- Yu, Zhanqian; Ptaszek, Marcin
- The Journal of Organic Chemistry, Vol. 78, Issue 21
Synthesis of 1-Formyldipyrromethanes
journal, May 2006
- Ptaszek, Marcin; McDowell, Brian E.; Lindsey, Jonathan S.
- The Journal of Organic Chemistry, Vol. 71, Issue 11
In-vivo photodynamic activity of mTHPC poly(ethylene glycol) conjugates (SC102)
conference, December 1997
- Grahn, Michael F.; McGuinness, Anita; de Jode, Martin L.
- BiOS Europe '97, SPIE Proceedings
Refined syntheses of hydrodipyrrin precursors to chlorin and bacteriochlorin building blocks
journal, October 2009
- Krayer, Michael; Balasubramanian, Thiagarajan; Ruzié, Christian
- Journal of Porphyrins and Phthalocyanines, Vol. 13, Issue 10
Sparsely substituted chlorins as core constructs in chlorophyll analogue chemistry. Part 3: Spectral and structural properties
journal, April 2007
- Taniguchi, Masahiko; Ptaszek, Marcin; McDowell, Brian E.
- Tetrahedron, Vol. 63, Issue 18
Rational Synthesis of Meso-Substituted Chlorin Building Blocks
journal, January 2001
- Strachan, Jon-Paul; O'Shea, Donal F.; Balasubramanian, Thiagarajan
- The Journal of Organic Chemistry, Vol. 66, Issue 2
A New Route for Installing the Isocyclic Ring on Chlorins Yielding 13 1 -Oxophorbines
journal, September 2006
- Laha, Joydev K.; Muthiah, Chinnasamy; Taniguchi, Masahiko
- The Journal of Organic Chemistry, Vol. 71, Issue 18
A novel chlorin–PEG–folate conjugate with higher water solubility, lower cytotoxicity, better tumor targeting and photodynamic activity
journal, October 2013
- Li, Donghong; Li, Pengxi; Lin, Huiyun
- Journal of Photochemistry and Photobiology B: Biology, Vol. 127
Modification of the Peripheral Substituents in Chlorophylls a and b and Their Derivatives (Review)
journal, April 2004
- Pavlov, V. Yu.; Ponomarev, G. V.
- Chemistry of Heterocyclic Compounds, Vol. 40, Issue 4
A simple method for chemoselective phenol alkylation
journal, October 2007
- Liu, Pingli; Huang, Liang; Faul, Margaret M.
- Tetrahedron Letters, Vol. 48, Issue 41
Rational Synthesis of Meso-Substituted Chlorin Building Blocks
journal, May 2000
- Strachan, Jon-Paul; O'Shea, Donal F.; Balasubramanian, Thiagarajan
- The Journal of Organic Chemistry, Vol. 65, Issue 10
Near-infrared absorbing dyes
journal, September 1992
- Fabian, Juergen; Nakazumi, Hiroyuki; Matsuoka, Masaru
- Chemical Reviews, Vol. 92, Issue 6
Synthesis and cellular studies of PEG-functionalized meso-tetraphenylporphyrins
journal, January 2007
- Sibrian-Vazquez, Martha; Jensen, Timothy J.; Vicente, M. Graça H.
- Journal of Photochemistry and Photobiology B: Biology, Vol. 86, Issue 1
Thermodynamics of Hydrophobic Interactions: Entropic Recognition of a Hydrophobic Moiety by Poly(Ethylene Oxide)–Zinc Porphyrin Conjugates
journal, October 2007
- Iwamoto, Hiroya; Mizutani, Tadashi; Kano, Koji
- Chemistry – An Asian Journal, Vol. 2, Issue 10
Progress towards synthetic chlorins with graded polarity, conjugatable substituents, and wavelength tunability
journal, April 2015
- Ra, Doyoung; Gauger, Kelly A.; Muthukumaran, Kannan
- Journal of Porphyrins and Phthalocyanines, Vol. 19, Issue 04
Amphiphilic, hydrophilic, or hydrophobic synthetic bacteriochlorins in biohybrid light-harvesting architectures: consideration of molecular designs
journal, July 2014
- Jiang, Jianbing; Reddy, Kanumuri Ramesh; Pavan, M. Phani
- Photosynthesis Research, Vol. 122, Issue 2
9-Acylation of 1-Acyldipyrromethanes Containing a Dialkylboron Mask for the α-Acylpyrrole Motif
journal, November 2004
- Zaidi, Syeda Huma H.; Muthukumaran, Kannan; Tamaru, Shun-ichi
- The Journal of Organic Chemistry, Vol. 69, Issue 24
Synthesis of Meso-Substituted Chlorins via Tetrahydrobilene- a Intermediates
journal, November 2001
- Taniguchi, Masahiko; Ra, Doyoung; Mo, Guoning
- The Journal of Organic Chemistry, Vol. 66, Issue 22
Polarity-tunable and wavelength-tunable bacteriochlorins bearing a single carboxylic acid or NHS ester. Use in a protein bioconjugation model system
journal, January 2015
- Jiang, Jianbing; Chen, Chih-Yuan; Zhang, Nuonuo
- New Journal of Chemistry, Vol. 39, Issue 1
Synthesis of perylene–porphyrin building blocks and rod-like oligomers for light-harvesting applications
journal, January 2002
- Loewe, Robert S.; Tomizaki, Kin-ya; Youngblood, W. Justin
- J. Mater. Chem., Vol. 12, Issue 12
Strongly Conjugated Hydroporphyrin Dyads: Extensive Modification of Hydroporphyrins’ Properties by Expanding the Conjugated System
journal, August 2014
- Yu, Zhanqian; Pancholi, Chirag; Bhagavathy, Ganga Viswanathan
- The Journal of Organic Chemistry, Vol. 79, Issue 17
Near-infrared tunable bacteriochlorins equipped for bioorthogonal labeling
journal, January 2015
- Jiang, Jianbing; Taniguchi, Masahiko; Lindsey, Jonathan S.
- New Journal of Chemistry, Vol. 39, Issue 6
De Novo Synthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World
journal, June 2015
- Lindsey, Jonathan S.
- Chemical Reviews, Vol. 115, Issue 13
A compact water-soluble porphyrin bearing an iodoacetamido bioconjugatable site
journal, January 2008
- Borbas, K. Eszter; Kee, Hooi Ling; Holten, Dewey
- Org. Biomol. Chem., Vol. 6, Issue 1
Hydrophilic tetracarboxy bacteriochlorins for photonics applications
journal, January 2014
- Jiang, Jianbing; Vairaprakash, Pothiappan; Reddy, Kanumuri Ramesh
- Org. Biomol. Chem., Vol. 12, Issue 1
Synthetic studies relevant to biosynthetic research on vitamin B12. Part 1. Syntheses of C-methylated chlorins based on 1-pyrrolines (3,4-dihydropyrroles)
journal, January 1984
- Battersby, Alan R.; Fookes, Christopher J. R.; Snow, Roger J.
- Journal of the Chemical Society, Perkin Transactions 1
A theoretical and experimental study of light absorption and scattering by in vivo skin
journal, July 1980
- Dawson, J. B.; Barker, D. J.; Ellis, D. J.
- Physics in Medicine and Biology, Vol. 25, Issue 4
PEGylated meso-arylporpholactone metal complexes as optical cyanide sensors in water
journal, January 2014
- Worlinsky, Jill L.; Halepas, Steven; Brückner, Christian
- Org. Biomol. Chem., Vol. 12, Issue 23
A chromatic explosion: the development and future of multiparameter flow cytometry
journal, December 2008
- Chattopadhyay, Pratip K.; Hogerkorp, Carl-Magnus; Roederer, Mario
- Immunology, Vol. 125, Issue 4
Deep-Red Emissive BODIPY–Chlorin Arrays Excitable with Green and Red Wavelengths
journal, April 2015
- Meares, Adam; Satraitis, Andrius; Santhanam, Nithya
- The Journal of Organic Chemistry, Vol. 80, Issue 8
Synthesis of a novel amphiphilic porphyrin carrying water-soluble polyether side chains of controlled chain length. Formation of a cofacial molecular assembly in aqueous media
journal, January 1988
- Aida, Takuzo; Takemura, Akihiko; Fuse, Masahiro
- Journal of the Chemical Society, Chemical Communications, Issue 5
Fast and Robust Route to Hydroporphyrin−Chalcones with Extended Red or Near-Infrared Absorption
journal, April 2009
- Ruzié, Christian; Krayer, Michael; Lindsey, Jonathan S.
- Organic Letters, Vol. 11, Issue 8
Phosphorescent Pd Porphyrin−Dendrimers: Tuning Core Accessibility by Varying the Hydrophobicity of the Dendritic Matrix
journal, March 2002
- Rozhkov, Vladimir; Wilson, David; Vinogradov, Sergei
- Macromolecules, Vol. 35, Issue 6
Bioconjugatable, PEGylated hydroporphyrins for photochemistry and photomedicine. Narrow-band, near-infrared-emitting bacteriochlorins
journal, January 2016
- Zhang, Nuonuo; Jiang, Jianbing; Liu, Mengran
- New Journal of Chemistry, Vol. 40, Issue 9
Quantifying spillover spreading for comparing instrument performance and aiding in multicolor panel design
journal, February 2013
- Nguyen, Richard; Perfetto, Stephen; Mahnke, Yolanda D.
- Cytometry Part A, Vol. 83A, Issue 3
Synthetic Chlorins Bearing Auxochromes at the 3- and 13-Positions
journal, July 2009
- Laha, Joydev K.; Muthiah, Chinnasamy; Taniguchi, Masahiko
- The Journal of Organic Chemistry, Vol. 74, Issue 14
PEG — A versatile conjugating ligand for drugs and drug delivery systems
journal, October 2014
- Kolate, Atul; Baradia, Dipesh; Patil, Sushilkumar
- Journal of Controlled Release, Vol. 192
Synthetic bacteriochlorins bearing polar motifs (carboxylate, phosphonate, ammonium and a short PEG). Water-solubilization, bioconjugation, and photophysical properties
journal, January 2015
- Jiang, Jianbing; Yang, Eunkyung; Reddy, Kanumuri Ramesh
- New Journal of Chemistry, Vol. 39, Issue 7
A deep profiler's guide to cytometry
journal, July 2012
- Bendall, Sean C.; Nolan, Garry P.; Roederer, Mario
- Trends in Immunology, Vol. 33, Issue 7
How green is green chemistry? Chlorophylls as a bioresource from biorefineries and their commercial potential in medicine and photovoltaics
journal, January 2015
- Ryan, Aoife A.; Senge, Mathias O.
- Photochemical & Photobiological Sciences, Vol. 14, Issue 4
(α-Ethoxyvinyl)tributyltin; An Efficient Reagent for the Nucleophilic Acetylation of Organic Halides via Palladium Catalysis
journal, February 1987
- Kosugi, Masanori; Sumiya, Takashi; Obara, Yukimasa
- Bulletin of the Chemical Society of Japan, Vol. 60, Issue 2
Meso-Tetra(hydroxyphenyl)porphyrins, a new class of potent tumour photosensitisers with favourable selectivity
journal, November 1986
- Berenbaum, M. C.; Akande, S. L.; Bonnett, R.
- British Journal of Cancer, Vol. 54, Issue 5
Synthetic Chlorins Bearing Auxochromes at the 3- and 13-Positions
journal, May 2006
- Laha, Joydev K.; Muthiah, Chinnasamy; Taniguchi, Masahiko
- The Journal of Organic Chemistry, Vol. 71, Issue 11
Strategies toward the synthesis of amphiphilic porphyrins
journal, September 2014
- Pisarek, Sabina; Maximova, Ksenia; Gryko, Dorota
- Tetrahedron, Vol. 70, Issue 38
Spectral Signatures of Photosynthesis. I. Review of Earth Organisms
journal, February 2007
- Kiang, Nancy Y.; Siefert, Janet
- Astrobiology, Vol. 7, Issue 1
Design and synthesis of water-soluble bioconjugatable trans-AB-porphyrins
journal, December 2008
- Muresan, Ana Z.; Lindsey, Jonathan S.
- Tetrahedron, Vol. 64, Issue 50
A Scalable Synthesis of Meso-Substituted Dipyrromethanes
journal, November 2003
- Laha, Joydev K.; Dhanalekshmi, Savithri; Taniguchi, Masahiko
- Organic Process Research & Development, Vol. 7, Issue 6
Dendritic Phosphorescent Probes for Oxygen Imaging in Biological Systems
journal, May 2009
- Lebedev, Artem Y.; Cheprakov, Andrei V.; Sakadžić, Sava
- ACS Applied Materials & Interfaces, Vol. 1, Issue 6
PEG Encapsulation of Porphyrins for Cell Imaging and Photodynamic Therapy
journal, May 2013
- Liu, Jinjun; Zhang, Licui; Du, Xiaojuan
- Letters in Organic Chemistry, Vol. 10, Issue 5
Cytometry: Today’s technology and tomorrow’s horizons
journal, July 2012
- Chattopadhyay, Pratip K.; Roederer, Mario
- Methods, Vol. 57, Issue 3
The Breaking and Mending of meso -Tetraarylporphyrins: Transmuting the Pyrrolic Building Blocks
journal, March 2016
- Brückner, Christian
- Accounts of Chemical Research, Vol. 49, Issue 6
Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility
journal, May 2006
- Borbas, K. Eszter; Mroz, Pawel; Hamblin, Michael R.
- Bioconjugate Chemistry, Vol. 17, Issue 3
Synthetic approaches for the conjugation of porphyrins and related macrocycles to peptides and proteins
journal, January 2011
- Giuntini, Francesca; Alonso, Cristina M. A.; Boyle, Ross W.
- Photochemical & Photobiological Sciences, Vol. 10, Issue 5
Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation
journal, December 2015
- Herzberger, Jana; Niederer, Kerstin; Pohlit, Hannah
- Chemical Reviews, Vol. 116, Issue 4
Polymeric Conjugates for Drug Delivery
journal, December 2011
- Larson, Nate; Ghandehari, Hamidreza
- Chemistry of Materials, Vol. 24, Issue 5
Design, Synthesis, and Photophysical Characterization of Water-Soluble Chlorins
journal, April 2008
- Borbas, K. Eszter; Chandrashaker, Vanampally; Muthiah, Chinnasamy
- The Journal of Organic Chemistry, Vol. 73, Issue 8
Brilliant violet fluorophores: A new class of ultrabright fluorescent compounds for immunofluorescence experiments
journal, April 2012
- Chattopadhyay, Pratip K.; Gaylord, Brent; Palmer, Adrian
- Cytometry Part A, Vol. 81A, Issue 6
Click chemistry: the emerging role of the azide-alkyne Huisgen dipolar addition in the preparation of substituted tetrapyrrolic derivatives
journal, July 2011
- Dumoulin, Fabienne; Ahsen, Vefa
- Journal of Porphyrins and Phthalocyanines, Vol. 15, Issue 07n08
Homogeneous detection of nucleic acids by transient-state polarized fluorescence
journal, September 1993
- Devlin, R.; Studholme, R. M.; Dandliker, W. B.
- Clinical Chemistry, Vol. 39, Issue 9
Works referencing / citing this record:
Attempted syntheses of N-confused hydroporphyrins through modified Lindsey routes
journal, April 2019
- Xiong, Ruisheng; Arkhypchuk, Anna I.; Eszter Borbas, K.
- Journal of Porphyrins and Phthalocyanines, Vol. 23, Issue 04n05