Polarity-tunable and wavelength-tunable bacteriochlorins bearing a single carboxylic acid or NHS ester. Use in a protein bioconjugation model system

Jiang, Jianbing; Chen, Chih-Yuan; Zhang, Nuonuo; Vairaprakash, Pothiappan; Lindsey, Jonathan S.

doi:10.1039/C4NJ01340A

Title: Polarity-tunable and wavelength-tunable bacteriochlorins bearing a single carboxylic acid or NHS ester. Use in a protein bioconjugation model system

Journal Article · Thu Jan 01 00:00:00 EST 2015 · New J. Chem.

DOI:https://doi.org/10.1039/C4NJ01340A· OSTI ID:1210428

Jiang, Jianbing; Chen, Chih-Yuan; Zhang, Nuonuo; Vairaprakash, Pothiappan; Lindsey, Jonathan S.

Cite

Export

Save

Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Photosynthetic Antenna Research Center (PARC)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

DOE Contract Number:: SC0001035

OSTI ID:: 1210428

Journal Information:: New J. Chem., Vol. 39; 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

Country of Publication:: United States

Language:: English

References (63)

The Staudinger Ligation—A Gift to Chemical Biology Köhn, Maja; Breinbauer, Rolf Angewandte Chemie International Edition, Vol. 43, Issue 24 https://doi.org/10.1002/anie.200401744	journal	June 2004
Bioorthogonal chemistry: a covalent strategy for the study of biological systems Lim, Reyna K. V.; Lin, Qing Science China Chemistry, Vol. 53, Issue 1 https://doi.org/10.1007/s11426-010-0020-4	journal	January 2010
Bioorthogonal Chemistry: Applications in Activity-Based Protein Profiling Willems, Lianne I.; van der Linden, Wouter A.; Li, Nan Accounts of Chemical Research, Vol. 44, Issue 9 https://doi.org/10.1021/ar200125k	journal	September 2011
Bioorthogonal Chemistry for Site-Specific Labeling and Surface Immobilization of Proteins Chen, Yong-Xiang; Triola, Gemma; Waldmann, Herbert Accounts of Chemical Research, Vol. 44, Issue 9 https://doi.org/10.1021/ar200046h	journal	September 2011
Staudinger Ligation as a Method for Bioconjugation van Berkel, Sander S.; van Eldijk, Mark B.; van Hest, Jan C. M. Angewandte Chemie International Edition, Vol. 50, Issue 38 https://doi.org/10.1002/anie.201008102	journal	September 2011
Bioconjugation via azide–Staudinger ligation: an overview Schilling, Christine I.; Jung, Nicole; Biskup, Moritz Chemical Society Reviews, Vol. 40, Issue 9 https://doi.org/10.1039/c0cs00123f	journal	January 2011
From Mechanism to Mouse: A Tale of Two Bioorthogonal Reactions Sletten, Ellen M.; Bertozzi, Carolyn R. Accounts of Chemical Research, Vol. 44, Issue 9 https://doi.org/10.1021/ar200148z	journal	September 2011
Synthetic approaches for the conjugation of porphyrins and related macrocycles to peptides and proteins Giuntini, Francesca; Alonso, Cristina M. A.; Boyle, Ross W. Photochemical & Photobiological Sciences, Vol. 10, Issue 5 https://doi.org/10.1039/c0pp00366b	journal	January 2011
Finding the Right (Bioorthogonal) Chemistry Patterson, David M.; Nazarova, Lidia A.; Prescher, Jennifer A. ACS Chemical Biology, Vol. 9, Issue 3 https://doi.org/10.1021/cb400828a	journal	January 2014
Polymethine dyes as spectral-fluorescent probes for biomacromolecules Tatikolov, Alexander S. Journal of Photochemistry and Photobiology C: Photochemistry Reviews, Vol. 13, Issue 1 https://doi.org/10.1016/j.jphotochemrev.2011.11.001	journal	March 2012
New Trends in Near-Infrared Fluorophores for Bioimaging Umezawa, Keitaro; Citterio, Daniel; Suzuki, Koji Analytical Sciences, Vol. 30, Issue 3 https://doi.org/10.2116/analsci.30.327	journal	January 2014
Near-infrared emitting quantum dots: Recent progress on their synthesis and characterization Pichaandi, Jothirmayanantham; van Veggel, Frank C. J. M. Coordination Chemistry Reviews, Vol. 263-264 https://doi.org/10.1016/j.ccr.2013.10.011	journal	March 2014
Tolyporphin, a novel multidrug resistance reversing agent from the blue-green alga Tolypothrix nodosa Prinsep, Michele R.; Caplan, Faith R.; Moore, Richard E. Journal of the American Chemical Society, Vol. 114, Issue 1 https://doi.org/10.1021/ja00027a072	journal	January 1992
Further tolyporphins from the Blue-Green alga Tolypothrix nodosa. Prinsep, Michèle R.; Patterson, Gregory M. L.; Larsen, Linda K. Tetrahedron, Vol. 51, Issue 38 https://doi.org/10.1016/0040-4020(95)00615-F	journal	September 1995
Tolyporphins J and K, Two Further Porphinoid Metabolites from the Cyanobacterium Tolypothrix nodosa Prinsep, Michèle R.; Patterson, Gregory M. L.; Larsen, Linda K. Journal of Natural Products, Vol. 61, Issue 9 https://doi.org/10.1021/np970566+	journal	August 1998
Revised Structure of Tolyporphin A Minehan, Thomas G.; Cook-Blumberg, Laura; Kishi, Yoshito Angewandte Chemie International Edition, Vol. 38, Issue 7 https://doi.org/10.1002/(SICI)1521-3773(19990401)38:7<926::AID-ANIE926>3.0.CO;2-W	journal	April 1999
Laser desorption ionisation-time of flight mass spectrometry of the tolyporphins, bioactive metabolites from the cyanobacterium Tolypothrix nodosa Prinsep, Michèle R.; Puddick, Jonathan Phytochemical Analysis, Vol. 22, Issue 4 https://doi.org/10.1002/pca.1278	journal	February 2011
Synthesis of Bacteriochlorins and Their Potential Utility in Photodynamic Therapy (PDT) Chen, Yihui; Li, Guolin; Pandey, Ravindra Current Organic Chemistry, Vol. 8, Issue 12 https://doi.org/10.2174/1385272043370131	journal	August 2004
Bacteriochlorophyll a and Its Derivatives: Chemistry and Perspectives for Cancer Therapy Grin, Mikhail; Mironov, Andrey; Shtil, Alexander Anti-Cancer Agents in Medicinal Chemistry, Vol. 8, Issue 6 https://doi.org/10.2174/187152008785133128	journal	August 2008
Functionalized diphenylchlorins and bacteriochlorins: their synthesis and bioconjugation for targeted photodynamic therapy and tumour cell imaging Sutton, Jonathan M.; Fernandez, Nelson; Boyle, Ross W. Journal of Porphyrins and Phthalocyanines, Vol. 04, Issue 07 https://doi.org/10.1002/1099-1409(200011)4:7<655::AID-JPP245>3.0.CO;2-8	journal	November 2000
Porphyrin, Chlorin, and Bacteriochlorin Isothiocyanates: Useful Reagents for the Synthesis of Photoactive Bioconjugates ^† Sutton, J. M.; Clarke, O. J.; Fernandez, N. Bioconjugate Chemistry, Vol. 13, Issue 2 https://doi.org/10.1021/bc015547x	journal	March 2002
1,3-Dipolar Cycloaddition Reactions of Porphyrins with Azomethine Ylides ^† Silva, Ana M. G.; Tomé,, Augusto C.; Neves, Maria G. P. M. S. The Journal of Organic Chemistry, Vol. 70, Issue 6 https://doi.org/10.1021/jo048349i	journal	March 2005
High-yielding syntheses of hydrophilic conjugatable chlorins and bacteriochlorins McCarthy, Jason R.; Bhaumik, Jayeeta; Merbouh, Nabyl Organic & Biomolecular Chemistry, Vol. 7, Issue 17 https://doi.org/10.1039/b908713c	journal	January 2009
Porphyrins and other pyrrolic macrocycles in cycloaddition reactions Tomé, Augusto C.; Neves, Maria G. P. M. S.; Cavaleiro, José A. S. Journal of Porphyrins and Phthalocyanines, Vol. 13, Issue 04n05 https://doi.org/10.1142/S1088424609000619	journal	April 2009
Synthesis and Photophysical Properties of Thioglycosylated Chlorins, Isobacteriochlorins, and Bacteriochlorins for Bioimaging and Diagnostics Singh, Sunaina; Aggarwal, Amit; Thompson, Sebastian Bioconjugate Chemistry, Vol. 21, Issue 11 https://doi.org/10.1021/bc100356z	journal	November 2010
New Halogenated Water-Soluble Chlorin and Bacteriochlorin as Photostable PDT Sensitizers: Synthesis, Spectroscopy, Photophysics, and in vitro Photosensitizing Efficacy Dąbrowski, Janusz M.; Arnaut, Luis G.; Pereira, Mariette M. ChemMedChem, Vol. 5, Issue 10 https://doi.org/10.1002/cmdc.201000223	journal	August 2010
[8π+2π] Cycloaddition of meso-Tetra- and 5,15-Diarylporphyrins: Synthesis and Photophysical Characterization of Stable Chlorins and Bacteriochlorins Pereira, Nelson A. M.; Fonseca, Sofia M.; Serra, Arménio C. European Journal of Organic Chemistry, Vol. 2011, Issue 20-21 https://doi.org/10.1002/ejoc.201100465	journal	June 2011
Biodistribution and Photodynamic Efficacy of a Water-Soluble, Stable, Halogenated Bacteriochlorin against Melanoma Dąbrowski, Janusz M.; Urbanska, Krystyna; Arnaut, Luis G. ChemMedChem, Vol. 6, Issue 3 https://doi.org/10.1002/cmdc.201000524	journal	January 2011
Multifunctional Bacteriochlorins from Selective Palladium-Coupling Reactions Yu, Zhanqian; Ptaszek, Marcin Organic Letters, Vol. 14, Issue 14 https://doi.org/10.1021/ol3015545	journal	July 2012
Galactosyl Human Serum Albumin-NMP1 Conjugate: A Near Infrared (NIR)-Activatable Fluorescence Imaging Agent to Detect Peritoneal Ovarian Cancer Metastases Alexander, Vinita M.; Sano, Kohei; Yu, Zhanqian Bioconjugate Chemistry, Vol. 23, Issue 8 https://doi.org/10.1021/bc3002419	journal	July 2012
Synthesis, Photophysical and Electrochemistry of Near-IR Absorbing Bacteriochlorins Related to Bacteriochlorophyll a Kozyrev, Andrei; Ethirajan, Manivannan; Chen, Ping The Journal of Organic Chemistry, Vol. 77, Issue 22 https://doi.org/10.1021/jo301895p	journal	October 2012
Expanded Bacteriochlorins Samankumara, Lalith P.; Wells, Sarah; Zeller, Matthias Angewandte Chemie International Edition, Vol. 51, Issue 23 https://doi.org/10.1002/anie.201201124	journal	April 2012
An insight into solvent-free diimide porphyrin reduction: a versatile approach for meso-aryl hydroporphyrin synthesis Pereira, Mariette M.; Abreu, Artur R.; Goncalves, Nuno P. F. Green Chemistry, Vol. 14, Issue 6 https://doi.org/10.1039/c2gc35126a	journal	January 2012
Oxazolochlorins. 9. meso -Tetraphenyl-2-oxabacteriochlorins and meso -Tetraphenyl-2,12/13-dioxabacteriochlorins Ogikubo, Junichi; Meehan, Eileen; Engle, James T. The Journal of Organic Chemistry, Vol. 78, Issue 7 https://doi.org/10.1021/jo400031r	journal	February 2013
Photophysics of Glycosylated Derivatives of a Chlorin, Isobacteriochlorin and Bacteriochlorin for Photodynamic Theragnostics: Discovery of a Two-photon-absorbing Photosensitizer Aggarwal, Amit; Thompson, Sebastian; Singh, Sunaina Photochemistry and Photobiology, Vol. 90, Issue 2 https://doi.org/10.1111/php.12179	journal	November 2013
De Novo Synthesis of Stable Tetrahydroporphyrinic Macrocycles: Bacteriochlorins and a Tetradehydrocorrin Kim, Han-Je; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 70, Issue 14 https://doi.org/10.1021/jo050467y	journal	July 2005
Regioselective 15-Bromination and Functionalization of a Stable Synthetic Bacteriochlorin Fan, Dazhong; Taniguchi, Masahiko; Lindsey, Jonathan S. The Journal of Organic Chemistry, Vol. 72, Issue 14 https://doi.org/10.1021/jo070785s	journal	July 2007
Expanded Scope of Synthetic Bacteriochlorins via Improved Acid Catalysis Conditions and Diverse Dihydrodipyrrin-Acetals Krayer, Michael; Ptaszek, Marcin; Kim, Han-Je The Journal of Organic Chemistry, Vol. 75, Issue 4, p. 1016-1039 https://doi.org/10.1021/jo9025572	journal	February 2010
De novo synthesis and photophysical characterization of annulated bacteriochlorins. Mimicking and extending the properties of bacteriochlorophylls Krayer, Michael; Yang, Eunkyung; Diers, James R. New Journal of Chemistry, Vol. 35, Issue 3, p. 587-601 https://doi.org/10.1039/c0nj00771d	journal	January 2011
Synthesis and Physicochemical Properties of Metallobacteriochlorins Chen, Chih-Yuan; Sun, Erjun; Fan, Dazhong Inorganic Chemistry, Vol. 51, Issue 17 https://doi.org/10.1021/ic301262k	journal	August 2012
Recent Advances in the Synthesis of Hydroporphyrins Galezowski, Michal; Gryko, Daniel Current Organic Chemistry, Vol. 11, Issue 15 https://doi.org/10.2174/138527207782023157	journal	October 2007
β-selective C-glycosidations: lewis-acid mediated reactions of carbohydrates with silyl ketene acetals Minehan, Thomas G.; Kishi, Yoshito Tetrahedron Letters, Vol. 38, Issue 39 https://doi.org/10.1016/S0040-4039(97)01602-X	journal	September 1997
Total Synthesis of the Proposed Structure of (+)-Tolyporphin AO,O-Diacetate Minehan, Thomas G.; Kishi, Yoshito Angewandte Chemie International Edition, Vol. 38, Issue 7 https://doi.org/10.1002/(SICI)1521-3773(19990401)38:7<923::AID-ANIE923>3.0.CO;2-7	journal	April 1999
Synthesis and Structure of Tolyporphin A O,O -Diacetate Wang, Wengui; Kishi, Yoshito Organic Letters, Vol. 1, Issue 7 https://doi.org/10.1021/ol9902374	journal	October 1999
Palette of lipophilic bioconjugatable bacteriochlorins for construction of biohybrid light-harvesting architectures Reddy, Kanumuri Ramesh; Jiang, Jianbing; Krayer, Michael Chemical Science, Vol. 4, Issue 5 https://doi.org/10.1039/c3sc22317e	journal	January 2013
Hydrophilic tetracarboxy bacteriochlorins for photonics applications Jiang, Jianbing; Vairaprakash, Pothiappan; Reddy, Kanumuri Ramesh Org. Biomol. Chem., Vol. 12, Issue 1 https://doi.org/10.1039/C3OB41791C	journal	January 2014
Versatile design of biohybrid light-harvesting architectures to tune location, density, and spectral coverage of attached synthetic chromophores for enhanced energy capture Harris, Michelle A.; Jiang, Jianbing; Niedzwiedzki, Dariusz M. Photosynthesis Research, Vol. 121, Issue 1 https://doi.org/10.1007/s11120-014-9993-8	journal	March 2014
Activatable Organic Near-Infrared Fluorescent Probes Based on a Bacteriochlorin Platform: Synthesis and Multicolor in Vivo Imaging with a Single Excitation Harada, Toshiko; Sano, Kohei; Sato, Kazuhide Bioconjugate Chemistry, Vol. 25, Issue 2 https://doi.org/10.1021/bc4005238	journal	January 2014
Photophysical Properties and Electronic Structure of Stable, Tunable Synthetic Bacteriochlorins: Extending the Features of Native Photosynthetic Pigments Yang, Eunkyung; Kirmaier, Christine; Krayer, Michael The Journal of Physical Chemistry B, Vol. 115, Issue 37 https://doi.org/10.1021/jp205258s	journal	September 2011
A model for the photosynthetic unit photochemical and spectral studies on pheophytin a absorbed onto small particles Cellarius, Richard A.; Mauzerall, David Biochimica et Biophysica Acta (BBA) - Biophysics including Photosynthesis, Vol. 112, Issue 2 https://doi.org/10.1016/0926-6585(66)90324-4	journal	February 1966
Reaction of Dicarbonates with Carboxylic Acids Catalyzed by Weak Lewis Acids: General Method for the Synthesis of Anhydrides and Esters Bartoli, Giuseppe; Bosco, Marcella; Carlone, Armando Synthesis, Vol. 2007, Issue 22 https://doi.org/10.1055/s-2007-990812	journal	November 2007
Investigation and Refinement of Palladium-Coupling Conditions for the Synthesis of Diarylethyne-Linked Multiporphyrin Arrays Wagner, Richard W.; Ciringh, Yangzhen; Clausen, Christian Chemistry of Materials, Vol. 11, Issue 10 https://doi.org/10.1021/cm9903529	journal	October 1999
3-Carboxy-6-chloro-7-hydroxycoumarin: A highly fluorescent, water-soluble violet-excitable dye for cell analysis Abrams, Barny; Diwu, Zhenjun; Guryev, Oleg Analytical Biochemistry, Vol. 386, Issue 2 https://doi.org/10.1016/j.ab.2008.12.018	journal	March 2009
Antibody derivatization and conjugation strategies: Application in preparation of stealth immunoliposome to target chemotherapeutics to tumor Manjappa, Arehalli S.; Chaudhari, Kiran R.; Venkataraju, Makam P. Journal of Controlled Release, Vol. 150, Issue 1 https://doi.org/10.1016/j.jconrel.2010.11.002	journal	February 2011
Brilliant violet fluorophores: A new class of ultrabright fluorescent compounds for immunofluorescence experiments Chattopadhyay, Pratip K.; Gaylord, Brent; Palmer, Adrian Cytometry Part A, Vol. 81A, Issue 6 https://doi.org/10.1002/cyto.a.22043	journal	April 2012
Dual-Purpose Polymer Labels for Fluorescent and Mass Cytometric Affinity Bioassays Majonis, Daniel; Ornatsky, Olga; Weinrich, Dirk Biomacromolecules, Vol. 14, Issue 5 https://doi.org/10.1021/bm4001662	journal	April 2013
Regioselective and Stoichiometrically Controlled Conjugation of Photodynamic Sensitizers to a HER2 Targeting Antibody Fragment Bryden, Francesca; Maruani, Antoine; Savoie, Huguette Bioconjugate Chemistry, Vol. 25, Issue 3 https://doi.org/10.1021/bc5000324	journal	February 2014
Structure covalente de la myoglobine de cheval Dautrevaux, M.; Boulanger, Y.; Han, K. European Journal of Biochemistry, Vol. 11, Issue 2 https://doi.org/10.1111/j.1432-1033.1969.tb00769.x	journal	December 1969
Putative Interhelix Ion Pairs Involved in the Stability of Myoglobin ^† Ramos, Carlos H. I.; Kay, Michael S.; Baldwin, Robert L. Biochemistry, Vol. 38, Issue 30 https://doi.org/10.1021/bi9828627	journal	July 1999
Immobilization of myoglobin from horse skeletal muscle in hydrophilic polymer networks Castro-Forero, Angelines; Jiménez, David; López-Garriga, Juan Journal of Applied Polymer Science, Vol. 107, Issue 2 https://doi.org/10.1002/app.26289	journal	January 2007
PhotochemCAD 2: A Refined Program with Accompanying Spectral Databases for Photochemical Calculations¶ Dixon, James M.; Taniguchi, Masahiko; Lindsey, Jonathan S. Photochemistry and Photobiology, Vol. 81, Issue 1 https://doi.org/10.1562/2004-11-06-TSN-361.1	journal	January 2005
Cleavage of the haem-protein link by acid methylethylketone Teale, F. W. J. Biochimica et Biophysica Acta, Vol. 35 https://doi.org/10.1016/0006-3002(59)90407-X	journal	January 1959
Investigation of MALDI-TOF Mass Spectrometry of Diverse Synthetic Metalloporphyrins, Phthalocyanines and Multiporphyrin Arrays Srinivasan, N.; Haney, Carol A.; Lindsey, Jonathan S. Journal of Porphyrins and Phthalocyanines, Vol. 03, Issue 04 https://doi.org/10.1002/(SICI)1099-1409(199904)3:4<283::AID-JPP132>3.0.CO;2-F	journal	April 1999

Similar Records

Synthetic bacteriochlorins bearing polar motifs (carboxylate, phosphonate, ammonium and a short PEG). Water-solubilization, bioconjugation, and photophysical properties

Journal Article · Thu Jan 01 00:00:00 EST 2015 · New Journal of Chemistry · OSTI ID:1210428

Jiang, Jianbing; Yang, Eunkyung; Reddy, Kanumuri Ramesh; +5 more

Production of alpha-hydroxy carboxylic acids and esters from higher sugars using tandem catalyst systems

Patent · Tue Nov 07 00:00:00 EST 2017 · OSTI ID:1210428

Orazov, Marat; Davis, Mark E.

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

Journal Article · Thu Mar 26 00:00:00 EDT 2015 · J. Phys. Chem. B · OSTI ID:1210428

Vairaprakash, Pothiappan; Yang, Eunkyung; Sahin, Tuba; +9 more

Related Subjects

solar (fuels)
photosynthesis (natural and artificial)
biofuels (including algae and biomass)
bio-inspired
charge transport
membrane
synthesis (novel materials)
synthesis (self-assembly)

Title: Polarity-tunable and wavelength-tunable bacteriochlorins bearing a single carboxylic acid or NHS ester. Use in a protein bioconjugation model system

Citation Formats

References (63)

Similar Records

Related Subjects