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39 results on '"Woodroofe, Carolyn C."'

3. Data from Comparison of Three Transcytotic Pathways for Distribution to Brain Metastases of Breast Cancer

Author

Khan, Imran, primary, Gril, Brunilde, primary, Paranjape, Anurag N., primary, Robinson, Christina M., primary, Difilippantonio, Simone, primary, Biernat, Wojciech, primary, Bieńkowski, Michał, primary, Pęksa, Rafał, primary, Duchnowska, Renata, primary, Jassem, Jacek, primary, Brastianos, Priscilla K., primary, Metellus, Philippe, primary, Bialecki, Emilie, primary, Woodroofe, Carolyn C., primary, Wu, Haitao, primary, Swenson, Rolf E., primary, and Steeg, Patricia S., primary

Published
2023
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4. Supplementary Figure S1-S10 from Comparison of Three Transcytotic Pathways for Distribution to Brain Metastases of Breast Cancer

Author

Khan, Imran, primary, Gril, Brunilde, primary, Paranjape, Anurag N., primary, Robinson, Christina M., primary, Difilippantonio, Simone, primary, Biernat, Wojciech, primary, Bieńkowski, Michał, primary, Pęksa, Rafał, primary, Duchnowska, Renata, primary, Jassem, Jacek, primary, Brastianos, Priscilla K., primary, Metellus, Philippe, primary, Bialecki, Emilie, primary, Woodroofe, Carolyn C., primary, Wu, Haitao, primary, Swenson, Rolf E., primary, and Steeg, Patricia S., primary

Published
2023
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5. Supplementary Table 1 from Comparison of Three Transcytotic Pathways for Distribution to Brain Metastases of Breast Cancer

Author

Khan, Imran, primary, Gril, Brunilde, primary, Paranjape, Anurag N., primary, Robinson, Christina M., primary, Difilippantonio, Simone, primary, Biernat, Wojciech, primary, Bieńkowski, Michał, primary, Pęksa, Rafał, primary, Duchnowska, Renata, primary, Jassem, Jacek, primary, Brastianos, Priscilla K., primary, Metellus, Philippe, primary, Bialecki, Emilie, primary, Woodroofe, Carolyn C., primary, Wu, Haitao, primary, Swenson, Rolf E., primary, and Steeg, Patricia S., primary

Published
2023
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6. Supplementary Material and Methods from Comparison of Three Transcytotic Pathways for Distribution to Brain Metastases of Breast Cancer

Author

Khan, Imran, primary, Gril, Brunilde, primary, Paranjape, Anurag N., primary, Robinson, Christina M., primary, Difilippantonio, Simone, primary, Biernat, Wojciech, primary, Bieńkowski, Michał, primary, Pęksa, Rafał, primary, Duchnowska, Renata, primary, Jassem, Jacek, primary, Brastianos, Priscilla K., primary, Metellus, Philippe, primary, Bialecki, Emilie, primary, Woodroofe, Carolyn C., primary, Wu, Haitao, primary, Swenson, Rolf E., primary, and Steeg, Patricia S., primary

Published
2023
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7. Comparison of Three Transcytotic Pathways for Distribution to Brain Metastases of Breast Cancer

Author

Khan, Imran, primary, Gril, Brunilde, additional, Paranjape, Anurag N., additional, Robinson, Christina M., additional, Difilippantonio, Simone, additional, Biernat, Wojciech, additional, Bieńkowski, Michał, additional, Pęksa, Rafal, additional, Duchnowska, Renata, additional, Jassem, Jacek, additional, Brastianos, Priscilla K., additional, Metellus, Philippe, additional, Bialecki, Emilie, additional, Woodroofe, Carolyn C., additional, Wu, Haitao, additional, Swenson, Rolf E., additional, and Steeg, Patricia S., additional

Published
2023
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8. Perfluorinated Iridium Catalyst for Signal Amplification by Reversible Exchange Provides Metal-Free Aqueous Hyperpolarized [1-13C]-Pyruvate

Author

Ettedgui, Jessica, Blackman, Burchelle, Raju, Natarajan, Kotler, Samuel A., Chekmenev, Eduard Y., Goodson, Boyd M., Merkle, Hellmut, Woodroofe, Carolyn C., LeClair, Christopher A., Krishna, Murali C., and Swenson, Rolf E.

Abstract

Hyperpolarized (HP) carbon-13 [13C] enables the specific investigation of dynamic metabolic and physiologic processes via in vivo MRI-based molecular imaging. As the leading HP metabolic agent, [1-13C]pyruvate plays a pivotal role due to its rapid tissue uptake and central role in cellular energetics. Dissolution dynamic nuclear polarization (d-DNP) is considered the gold standard method for the production of HP metabolic probes; however, development of a faster, less expensive technique could accelerate the translation of metabolic imaging via HP MRI to routine clinical use. Signal Amplification by Reversible Exchange in SHield Enabled Alignment Transfer (SABRE-SHEATH) achieves rapid hyperpolarization by using parahydrogen (p-H2) as the source of nuclear spin order. Currently, SABRE is clinically limited due to the toxicity of the iridium catalyst, which is crucial to the SABRE process. To mitigate Ir contamination, we introduce a novel iteration of the SABRE catalyst, incorporating bis(polyfluoroalkylated) imidazolium salts. This novel perfluorinated SABRE catalyst retained polarization properties while exhibiting an enhanced hydrophobicity. This modification allows the easy removal of the perfluorinated SABRE catalyst from HP [1-13C]-pyruvate after polarization in an aqueous solution, using the ReD-SABRE protocol. The residual Ir content after removal was measured via ICP-MS at 177 ppb, which is the lowest reported to date for pyruvate and is sufficiently safe for use in clinical investigations. Further improvement is anticipated once automated processes for delivery and recovery are initiated. SABRE-SHEATH using the perfluorinated SABRE catalyst can become an attractive low-cost alternative to d-DNP to prepare biocompatible HP [1-13C]-pyruvate formulations for in vivo applications in next-generation molecular imaging modalities.

Published
2024
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9. Comparison of Three Transcytotic Pathways for Distribution to Brain Metastases of Breast Cancer

Author

Khan, Imran, primary, Gril, Brunilde, additional, Paranjape, Anurag, additional, Robinson, Christina, additional, Difilippantonio, Simone, additional, Biernat, Wojciech, additional, Bieńkowski, Michał, additional, Pęksa, Rafał, additional, Duchnowska, Renata, additional, Jassem, Jacek, additional, Brastianos, Priscilla K., additional, Metellus, Philippe, additional, Bialecki, Emilie, additional, Woodroofe, Carolyn C., additional, Wu, Haitao, additional, Swenson, Rolf, additional, and Steeg, Patricia S., additional

Published
2022
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13. Click beetle luciferase mutant and near infrared naphthyl-luciferins for improved bioluminescence imaging

Author

Hall, Mary P, Woodroofe, Carolyn C, Wood, Monika G, Que, Ivo, Van't Root, Moniek, Ridwan, Yanto, Shi, Ce, Kirkland, Thomas A, Encell, Lance P, Wood, Keith V, Löwik, Clemens, Mezzanotte, Laura, Hall, Mary P, Woodroofe, Carolyn C, Wood, Monika G, Que, Ivo, Van't Root, Moniek, Ridwan, Yanto, Shi, Ce, Kirkland, Thomas A, Encell, Lance P, Wood, Keith V, Löwik, Clemens, and Mezzanotte, Laura

Abstract

The sensitivity of bioluminescence imaging in animals is primarily dependent on the amount of photons emitted by the luciferase enzyme at wavelengths greater than 620 nm where tissue penetration is high. This area of work has been dominated by firefly luciferase and its substrate, D-luciferin, due to the system's peak emission (~ 600 nm), high signal to noise ratio, and generally favorable biodistribution of D-luciferin in mice. Here we report on the development of a codon optimized mutant of click beetle red luciferase that produces substantially more light output than firefly luciferase when the two enzymes are compared in transplanted cells within the skin of black fur mice or in deep brain. The mutant enzyme utilizes two new naphthyl-luciferin substrates to produce near infrared emission (730 nm and 743 nm). The stable luminescence signal and near infrared emission enable unprecedented sensitivity and accuracy for performing deep tissue multispectral tomography in mice.

Published
2018

15. Click beetle luciferase mutant and near infrared naphthyl-luciferins for improved bioluminescence imaging

Author

Hall, Mary P., primary, Woodroofe, Carolyn C., additional, Wood, Monika G., additional, Que, Ivo, additional, van’t Root, Moniek, additional, Ridwan, Yanto, additional, Shi, Ce, additional, Kirkland, Thomas A., additional, Encell, Lance P., additional, Wood, Keith V., additional, Löwik, Clemens, additional, and Mezzanotte, Laura, additional

Published
2018
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16. N-alkylated 6'-aminoluciferins are bioluminescent substrates for Ultra-Glo and QuantiLum luciferase: new potential scaffolds for bioluminescent assays

Author

Woodroofe, Carolyn C., Wood, Monika G., Osterman, Jean, Shultz, John W., Cali, James J., Daily, William J., Meisenheimer, Poncho L., and Klaubert, Dieter H.

Subjects
Luciferase -- Analysis, Bioluminescence -- Analysis, Biological sciences, Chemistry
Abstract

The article explains the synthesis and functions of the N-alkylated 6'-aminoluciferins, which are shown to act as the bioluminescent substrates for Ultra-Glo and QuantiLum luciferases. The strength of the bioluminescent signal is shown to be highly affected by the nature of the alkyl substituent.

Published
2008

17. Esterase-activated two-fluorophore system for ratiometric sensing of biological zinc(II)

Author

Woodroofe, Carolyn C., Won, Annie C., and Lippard, Stephen J.

Subjects
Esterases -- Research, Hydrolysis -- Research, Zinc compounds -- Chemical properties, Chemistry
Abstract

A new approach to ratiometric sensing of intracellular Zn(super 2+) based on the phenomenon of intracellular hydrolysis of esterases is described. Esterase-catalyzed hydrolysis generates a Zn(super 2+)-sensitive ZP1-like fluorophore and a Zn(super 2+)-insensitive coumarin as a calibrating fluorophore.

Published
2005

19. A novel two-fluorophore approach to ratiometric sensing of Zn(super 2+)

Author

Woodroofe, Carolyn C. and Lippard, Stephen J.

Subjects
Coumarins -- Chemical properties, Zinc compounds -- Chemical properties, Chemistry
Abstract

A small-molecule, ratiometric, two-photon compatible two-fluorophores system for sensing Zn(super 2+) in biological environments is discussed. The coumarin fluorescence was unaffected by the enhancement of Zinpyr (ZP) which was obtained by loading the cells with ZN(super 2+) and a ZnCl2-sodium pyritione solution.

Published
2003

20. Target engagement and drug residence time can be observed in living cells with BRET

Author

Robers, Matthew B., primary, Dart, Melanie L., additional, Woodroofe, Carolyn C., additional, Zimprich, Chad A., additional, Kirkland, Thomas A., additional, Machleidt, Thomas, additional, Kupcho, Kevin R., additional, Levin, Sergiy, additional, Hartnett, James R., additional, Zimmerman, Kristopher, additional, Niles, Andrew L., additional, Ohana, Rachel Friedman, additional, Daniels, Danette L., additional, Slater, Michael, additional, Wood, Monika G., additional, Cong, Mei, additional, Cheng, Yi-Qiang, additional, and Wood, Keith V., additional

Published
2015
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21. Click beetle luciferase mutant and near infrared naphthyl-luciferins for improved bioluminescence imaging.

Author

Ridwan, Yanto, Root, Moniek van't, Encell, Lance P., Wood, Keith V., Ce Shi, Ivo Que, Wood, Monika G., Woodroofe, Carolyn C., Löwik, Clemens, Mezzanotte, Laura, Hall, Mary P., and Kirkland, Thomas A.

Subjects
BEETLES, LUCIFERASES, BIOLUMINESCENCE, IMAGING systems, ENZYMES
Abstract

The sensitivity of bioluminescence imaging in animals is primarily dependent on the amount of photons emitted by the luciferase enzyme at wavelengths greater than 620 nm where tissue penetration is high. This area of work has been dominated by firefly luciferase and its substrate, D-luciferin, due to the system's peak emission (~ 600 nm), high signal to noise ratio, and generally favorable biodistribution of D-luciferin in mice. Here we report on the development of a codon optimized mutant of click beetle red luciferase that produces substantially more light output than firefly luciferase when the two enzymes are compared in transplanted cells within the skin of black fur mice or in deep brain. The mutant enzyme utilizes two new naphthyl-luciferin substrates to produce near infrared emission (730 nm and 743 nm). The stable luminescence signal and near infrared emission enable unprecedented sensitivity and accuracy for performing deep tissue multispectral tomography in mice. [ABSTRACT FROM AUTHOR]

Published
2018
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25. Luciferin analogs for improved genetic reporter assays

Author

Kovic, Yumi, primary, Rosenberg, Justin C., additional, Behney, Curran E., additional, Southworth, Tara L., additional, Branchini, Bruce R., additional, Woodroofe, Carolyn C., additional, Meisenheimer, Poncho L., additional, and Klaubert, Dieter H., additional

Published
2013
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28. Molecular engineering strategies for expanding the capabilities of fluorescent zinc (II) sensors

Author

Stephen J. Lippard., Massachusetts Institute of Technology. Dept. of Chemistry., Woodroofe, Carolyn C., 1977, Stephen J. Lippard., Massachusetts Institute of Technology. Dept. of Chemistry., and Woodroofe, Carolyn C., 1977

Abstract

Thesis (Ph. D.)--Massachusetts Institute of Technology, Dept. of Chemistry, 2004., Vita., Includes bibliographical references., (cont.) affords the two fluorophores, such that excitation of the coumarin at 445 nm and measurement of the emission at 488 nm affords information of the amount of sensor present, while excitation of the fluorescein at 505 nm and measurement of the emission at 535 nm indicates the amount of sensor in the zinc(II)-bound form. This system has been characterized and applied to the study of exogenous zinc(II) fluxes in HeLa cells. Chapter 4: Unimolecular Two-Fluorophore Ratiometric Zn²⁺ Sensing Systems. Dichlorofluorescein compounds covalently bound to zinc(II)-insensitive reporter fluorophores via a rigid cyclohexyl linker have been prepared and characterized. Based on favorable photophysical properties, a Zinpyr-1 species covalently bound to coumarin 343 has been prepared and shown to afford a ratiometric response to excess zinc(II). Chapter 5: ZPI Synthons for Functionalization of Biological Targets. Installation of a functional group prior to Mannich reaction is impractical in many cases. This chapter describes the preparation of reactive ZP1 synthons for direct functionalization of biological targets containing an amine or azide, and reports applications to the synthesis of ZPI conjugates. Appendix 1: Synthetic Approaches to Other Isomerically Pure Functionalizable Fluorophores. Crystallization approaches have been applied to separate fluorescein 5- and 6-sulfonic acid, and subsequent generation of the sulfonyl chlorides is discussed. A dibromofluoran approach to isomerically pure rhodamine carboxylates is based on a similar separation. Basic hydrolysis of the previously described 2',7'-dichlorofluorescein ..., Chapter 1: The Development and Use of Fluorescent Sensors in the Imaging of Physiological Zinc(II): A Review This chapter presents an overview of fluorescent techniques used to image chelatable zinc(II) in vivo. Many intensity-based sensors take advantage of photoinduced electron transfer quenching pathways. Peptide- and protein-based sensors offer excellent selectivity but are poorly suited to intracellular applications. Recently, ratiometric sensors in which the zinc(II) binding event interrupts or alters conjugation within the fluorophore have been described. Chapter 2: Carboxylate-Functionalized Zinpyr-1 Sensors: Synthesis, Characterization, and In Vivo Staining Patterns. A class of Zinpyr-1 sensors containing a carboxylic acid or ester at the 5- or 6-position of the fluorescein has been prepared. These sensors offer decreased background fluorescence and enhanced fluorescence response compared to the parent Zinpyr-1. The acid-functionalized sensors bear a negative charge at physiological pH, rendering them cell-impermeable. The esterified sensors are cell-permeable, but are hydrolyzed in vivo by intracellular esterases, affording a clear delineation of zinc(II)-containing damaged neurons in mechanically-injured or seizure-induced rats, rather than the punctate staining pattern obtained with Zinpyr-1. Chapter 3: Esterase-Dependent Two-Fluorophore Ratiometric Sensing of Zinc(II). This chapter describes a new approach to ratiometric sensing in which a zinc(II)-sensitive fluorescein fluorophore based on Zinpyr-1 is functionalized with a zinc(lI)-insensitive coumarin fluorophore via a flexible ester linker. The flexible linker enables intramolecular quenching of the two fluorophores. Esterase hydrolysis of the linker, by Carolyn C. Woodroofe., Ph.D.

Published
2005

29. A ligand-free solid-supported system for Sonogashira couplings: applications in nucleoside chemistry

Author

Garg, Neil K., Woodroofe, Carolyn C., Lacenere, Christopher J., Quake, Stephen R., Stoltz, Brian M., Garg, Neil K., Woodroofe, Carolyn C., Lacenere, Christopher J., Quake, Stephen R., and Stoltz, Brian M.

Abstract

A mild heterogeneous, ligand-free protocol for Sonogashira and Heck couplings has been developed and used to access several biologically important deoxynucleoside derivatives in a facile manner.

Published
2005

30. Novel Heterocyclic Analogues of Firefly Luciferin

Author

Woodroofe, Carolyn C., primary, Meisenheimer, Poncho L., additional, Klaubert, Dieter H., additional, Kovic, Yumi, additional, Rosenberg, Justin C., additional, Behney, Curran E., additional, Southworth, Tara L., additional, and Branchini, Bruce R., additional

Published
2012
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37. NanoBRETA Novel BRET Platform for the Analysis of Protein–Protein Interactions

Author

Machleidt, Thomas, Woodroofe, Carolyn C., Schwinn, Marie K., Méndez, Jacqui, Robers, Matthew B., Zimmerman, Kris, Otto, Paul, Daniels, Danette L., Kirkland, Thomas A., and Wood, Keith V.

Abstract

Dynamic interactions between proteins comprise a key mechanism for temporal control of cellular function and thus hold promise for development of novel drug therapies. It remains technically challenging, however, to quantitatively characterize these interactions within the biologically relevant context of living cells. Although, bioluminescence resonance energy transfer (BRET) has often been used for this purpose, its general applicability has been hindered by limited sensitivity and dynamic range. We have addressed this by combining an extremely bright luciferase (Nanoluc) with a means for tagging intracellular proteins with a long-wavelength fluorophore (HaloTag). The small size (19 kDa), high emission intensity, and relatively narrow spectrum (460 nm peak intensity) make Nanoluc luciferase well suited as an energy donor. By selecting an efficient red-emitting fluorophore (635 nm peak intensity) for attachment onto the HaloTag, an overall spectral separation exceeding 175 nm was achieved. This combination of greater light intensity with improved spectral resolution results in substantially increased detection sensitivity and dynamic range over current BRET technologies. Enhanced performance is demonstrated using several established model systems, as well as the ability to image BRET in individual cells. The capabilities are further exhibited in a novel assay developed for analyzing the interactions of bromodomain proteins with chromatin in living cells.

Published
2015
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38. Perfluorinated Iridium Catalyst for Signal Amplification by Reversible Exchange Provides Metal-Free Aqueous Hyperpolarized [1- 13 C]-Pyruvate.

Author

Ettedgui J, Blackman B, Raju N, Kotler SA, Chekmenev EY, Goodson BM, Merkle H, Woodroofe CC, LeClair CA, Krishna MC, and Swenson RE

Subjects
Magnetic Resonance Spectroscopy methods, Magnetic Resonance Imaging, Water, Iridium, Pyruvic Acid
Abstract

Hyperpolarized (HP) carbon-13 [ 13 C] enables the specific investigation of dynamic metabolic and physiologic processes via in vivo MRI-based molecular imaging. As the leading HP metabolic agent, [1- 13 C]pyruvate plays a pivotal role due to its rapid tissue uptake and central role in cellular energetics. Dissolution dynamic nuclear polarization (d-DNP) is considered the gold standard method for the production of HP metabolic probes; however, development of a faster, less expensive technique could accelerate the translation of metabolic imaging via HP MRI to routine clinical use. Signal Amplification by Reversible Exchange in SHield Enabled Alignment Transfer (SABRE-SHEATH) achieves rapid hyperpolarization by using parahydrogen ( p -H 2 ) as the source of nuclear spin order. Currently, SABRE is clinically limited due to the toxicity of the iridium catalyst, which is crucial to the SABRE process. To mitigate Ir contamination, we introduce a novel iteration of the SABRE catalyst, incorporating bis(polyfluoroalkylated) imidazolium salts. This novel perfluorinated SABRE catalyst retained polarization properties while exhibiting an enhanced hydrophobicity. This modification allows the easy removal of the perfluorinated SABRE catalyst from HP [1- 13 C]-pyruvate after polarization in an aqueous solution, using the ReD-SABRE protocol. The residual Ir content after removal was measured via ICP-MS at 177 ppb, which is the lowest reported to date for pyruvate and is sufficiently safe for use in clinical investigations. Further improvement is anticipated once automated processes for delivery and recovery are initiated. SABRE-SHEATH using the perfluorinated SABRE catalyst can become an attractive low-cost alternative to d-DNP to prepare biocompatible HP [1- 13 C]-pyruvate formulations for in vivo applications in next-generation molecular imaging modalities.

Published
2024
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39. Deciphering the Cellular Targets of Bioactive Compounds Using a Chloroalkane Capture Tag.

Author

Ohana RF, Kirkland TA, Woodroofe CC, Levin S, Uyeda HT, Otto P, Hurst R, Robers MB, Zimmerman K, Encell LP, and Wood KV

Subjects
Chromatography, Liquid, Drug Delivery Systems, HEK293 Cells, Histone Deacetylase Inhibitors chemistry, Histone Deacetylase Inhibitors pharmacology, Humans, Hydroxamic Acids chemistry, Hydroxamic Acids pharmacology, Protein Binding drug effects, Vorinostat, Alkanes chemistry, Chemistry Techniques, Analytical methods, Chlorine chemistry, Drug Discovery
Abstract

Phenotypic screening of compound libraries is a significant trend in drug discovery, yet success can be hindered by difficulties in identifying the underlying cellular targets. Current approaches rely on tethering bioactive compounds to a capture tag or surface to allow selective enrichment of interacting proteins for subsequent identification by mass spectrometry. Such methods are often constrained by ineffective capture of low affinity and low abundance targets. In addition, these methods are often not compatible with living cells and therefore cannot be used to verify the pharmacological activity of the tethered compounds. We have developed a novel chloroalkane capture tag that minimally affects compound potency in cultured cells, allowing binding interactions with the targets to occur under conditions relevant to the desired cellular phenotype. Subsequent isolation of the interacting targets is achieved through rapid lysis and capture onto immobilized HaloTag protein. Exchanging the chloroalkane tag for a fluorophore, the putative targets identified by mass spectrometry can be verified for direct binding to the compound through resonance energy transfer. Using the interaction between histone deacetylases (HDACs) and the inhibitor, Vorinostat (SAHA), as a model system, we were able to identify and verify all the known HDAC targets of SAHA as well as two previously undescribed targets, ADO and CPPED1. The discovery of ADO as a target may provide mechanistic insight into a reported connection between SAHA and Huntington's disease.

Published
2015
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