Description

Hydroxy-dPEG®24-TFP ester, product number QBD-11349, is a long (76 atoms, 88.8 Å), hydroxy-terminated, single molecular weight, discrete polyethylene glycol (dPEG®) compound functionalized with a 2,3,5,6-tetrafluorophenyl (TFP) ester for conjugation to primary and secondary amines. This product can be used for modification of amine-functionalized surfaces (e.g., silica, glass), modification of proteins and peptides at accessible amine sites on the molecules, the construction of discrete PEG dendrimers, and many other applications. The free hydroxy end of the dPEG® spacer can be functionalized for further reactions or left unmodified to increase hydrophilicity or modify the charge of conjugate molecules and surfaces.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See chapter 18, Discrete PEG Reagents, pp.787-821, for a full overview of the dPEG® products.

Description

m-dPEG®24-Lipoamide, product number QBD-10804, is a long (82 atoms), amphiphilic, methyl-terminated, monodisperse PEG product functionalized with lipoic acid and designed to modify metal surfaces such as gold or silver. The primary application of this product is the stable passivation of metal surfaces through the use of lipoic acid, which forms two dative bonds with gold or silver, conjugated to a short, monodispersed PEG spacer. Because the terminal dithiolane unit forms two dative bonds with metals, it is consequently more stable on the metal surface than comparable compounds containing a single sulfhydryl group that can create a dative bond. The amphiphilic, non-antigenic, monodispersed PEG spacer imparts water solubility to and increases the hydrodynamic volume of conjugated molecules and surfaces.

m-dPEG®24-lipoamide was designed for stable passivation of gold or silver surfaces. For useful surface coating, it may prove helpful to create a mixed layer consisting of m-dPEG®24-lipoamide and another, longer dPEG® product with a lipoamido group on one end and reactive, affinity, or other functional groups on the opposite end. Thus, the shorter m-dPEG®24-lipoamide will form a uniform coating of methyl-terminated PEG above the metal surface, and the longer dPEG® product will rise above the dPEG® coating intermittently throughout the surface layer.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0), pp. 188-190, 458-497, 924-935.

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

Gastrointestinal Bioavailability of 2.0 nm Diameter Gold Nanoparticles. Candice A. Smith, Carrie A. Simpson, Ganghyeok Kim, Carly J. Carter, and Daniel L. Feldheim. ACS Nano. 2013, 7 (5) pp 3991–3996. April 21, 2013. DOI: 10.1021/nn305930e.

Description

t-boc-N-amido-dPEG®24-acid, product number QBD-10760, is composed of a boc-protected primary amine and a propionic acid group on opposite ends of an extended (76 atoms), single molecular weight, discrete PEG (dPEG®) linker. Designed for use in Boc-based peptide chemical synthesis, t-boc-N-amido-dPEG®24-acid can be used to insert a discrete PEG linker/spacer at the N-terminus of a peptide chain or to add a dPEG® onto the side chain of an amino acid such as lysine or ornithine. Insertion of t-boc-N-amido-dPEG®24-acid at the N-terminus of a peptide allows the creation of a flexible, hydrophilic bridge to the C-terminus of another peptide. The Boc protecting group cleaves easily under acidic conditions with, for example, TFA. This compound can also be used to modify amine-functionalized surfaces to passivate them with a hydrophilic spacer. Removal of the boc group with acid allows for functionalization of the surface with peptides, proteins, or small molecules.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

Description

m-dPEG®24-DBCO, product number QBD-10583, is a methoxy-terminated, discrete polyethylene glycol (dPEG®) click chemistry reagent designed for chemical modification of surfaces through strain-promoted azide-alkyne cycloaddition (SPAAC). From the terminal methyl group to the reactive site on the dibenzylcyclooctyne (DBCO) group, the dPEG® spacer is 83 atoms long.

DBCO was designed for bio-orthogonal click chemistry applications using SPAAC, also known as copper-free click chemistry, which was developed by Carolyn Bertozzi and colleagues to avoid the potential toxicity of Cu(I) that is used in Copper(I)-Promoted Azide Alkyne Cycloaddition (CuAAC) discovered by K. Barry Sharpless and colleagues. The dPEG® spacer differs from traditional PEG spacers and linkers in that it consists of a single molecular weight and chain length of PEG (i.e., it is monodispersed), which simplifies analysis of conjugates made with this compound.

Potential uses for this product include modifying alkyne-functionalized surfaces and peptides and proteins containing alkyne-functionalized amino acid side chains.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See chapter 18, Discrete PEG Reagents, pp.787-821, for a full overview of the dPEG® products.

Description

Azido-dPEG®24-OH (Azido-dPEG®24-alcohol), product number QBD-10543, is a click chemistry reagent used to modify surfaces and biomolecules or to crosslink with other surfaces or biomolecules in supramolecular construction. This product consists of an azide and a terminal hydroxy group separated by a long (72 atoms), single molecular weight, discrete-length polyethylene glycol (dPEG®) chain. The terminal azide reacts in copper(I)-catalyzed, ruthenium-catalyzed, and strain-promoted azide-alkyne cycloaddition reactions (CuAAC, RuAAC, and SPAAC, respectively). If left unmodified, the alcohol group increases the water solubility and hydrodynamic volume of molecules and surfaces to which it is conjugated. Modifying the alcohol with a reactive group such as chloride, tosylate, or mesylate allows Azido-dPEG®24-OH to function as a crosslinker through subsequent chemical manipulations.

As a click chemistry reagent, azido-dPEG®24-OH can participate in CuAAC, RuAAC, and SPAAC reactions. Because Vector Laboratories’ dPEG® products are amphiphilic, these reactions can occur almost equally well in water or organic solvents. Thus, azido-dPEG®24-OH can be used in conjugations with biomolecules where organic solvents may damage the conjugate target.

The primary alcohol group on the opposite end of the linker can be used as a neutrally charged functional group. In this function, the alcohol enhances the water solubility of the conjugate molecule. Alternatively, the alcohol group can be functionalized with reactive groups and used to modify the conjugate further.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

High-Throughput Chemical Modification of Oligonucleotides for Systematic Structure-Activity Relationship Evaluation. Daniel Zewge, Francis Gosselin, David Matthew Tellers, Ian W. Davies, Vasant Jadhav, Sandhya S. Nerurkar, Yu Yuan, Jenny Li, W. Michael Flanagan, and Denise M. Kenski. Bioconjugate Chemistry. 2014, November 14, 2014. DOI” 10.1021/bc500453q.

Description

m-dPEG®24-azide, product number QBD-10540, also known as azido-m-dPEG®24, is a monodispersed PEG product used in click chemistry applications. A non-reactive, charge-neutral methyl group and an alkyne-reactive azido group, respectively, terminate the two ends of the long (74 atoms), single molecular weight, discrete PEG (dPEG®) spacer. Both metal-catalyzed (Cu(I), Ru) azide-alkyne cycloaddition (CuAAC, RuAAC) and strain-promoted azide-alkyne cycloaddition (SPAAC) work with this product. Possible click chemistry-based applications for this product include the construction of dendrimers and hydrogels and the modification of alkyne-functionalized surfaces or biomolecules containing alkyne groups.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

Description

Azido-dPEG®24-acid, product number QBD-10514, is a click chemistry reagent consisting of an azide and a propionic acid group on opposite ends of a long (76 atoms), hydrophilic, single molecular weight polyethylene glycol spacer with a discrete chain length (dPEG®). The azide moiety acts as an alkyne partner for metal-catalyzed (i.e., Cu(I), Ru) or strain-promoted click chemistry, or as a masked amine. The propanoic acid moiety can be coupled to a primary or secondary amine through an acylation reaction.

Our dPEG® products are single molecular weight compounds. Unlike traditional, polymeric polyethylene glycol (PEG), dPEG® products contain a single molecular weight PEG chain with a discrete chain length. The use of dPEG® instead of traditional polymer PEG allows accurate characterization of conjugates without sacrificing any of the benefits of PEG.

Activation of the propionic acid moiety with an acylating agent enables conjugation of azido-dPEG®24-acid to a primary or secondary amine. Popular acylating agents include such as N-hydroxysuccinimide (NHS); 2,3,5,6-tetrafluorophenol (TFP); or 2,3,4,5,6-pentafluorophenol (PFP). Alternatively, 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) or another suitable carbodiimide can be used to couple the acid moiety directly to an amine without prior activation.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See Chapter 18, Discrete PEG Reagents, pp. 787-821, for a full overview of the dPEG® products.

Description

m-dPEG®24-MAL, product number QBD-10319, is a sulfhydryl-reactive, single molecular weight, with a discrete chain length PEG (dPEG®). This product modifies surfaces and biomolecules with free thiol groups through the maleimide reactive group. The non-immunogenic, methyl-terminated dPEG® chain has no charge but adds water solubility and hydrodynamic volume to molecules to which it is conjugated.

The reaction of the maleimide end of m-dPEG®24-MAL, product number QBD-10319, with a sulfhydryl proceeds best at pH 6.5 – 7.5. Conduct the conjugation at the lowest reasonable pH within this range. Above pH 7.5, free amines compete with free thiols at the maleimide reaction site, which creates confusing results. Moreover, at higher pH values, the maleimide ring may open to form unreactive maleamic acid.
Published uses for m-dPEG®24-MAL include the following:
modifying surface-accessible free thiols on enzymes to probe enzymatic function;
developing a virus-based drug delivery system; and,
developing probes of cellular redox reactions.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See chapter 18, Discrete PEG Reagents, pp.787-821, for a full overview of the dPEG® products.

Modulation of Cell Surface Protein Free Thiols: A Potential Novel Mechanism of Action of the Sesquiterpene Lactone Parthenolide. Jolanta Skalska, Paul S. Brookes, Sergiy M. Nadtochiy, Shannon P. Hilchey, Craig T. Jordan, Monica L. Guzman, Sanjay B. Maggirwar, Margaret M. Briehl, Steven H. Bernstein. PLoS ONE. 4 (12), e8115. December 2, 2009. DOI: 10.1371 /journal.pone.0008115.

Cell-Specific Delivery of Diverse Cargos by BacteriophageMS2 Virus-like Particles. Carlee E. Ashley Eric C. Carnes, Genevieve K. Phillips, Paul N. Durfee, Mekensey D. Buley, Christopher A. Lino, David P. Padilla, Brandy Phillips, Mark B. Carter, Cheryl L. Willman, C. Jeffrey Brinker, Jerri do Carmo Caldeira, Bryce Chackerian, Walker Wharton, and David S. Peabody.ACS Nano, 2011, 5 (7), pp 5729–5745, May 26, 2011. DOI: 10.1021/nn201397z.

Going through the barrier: coupled disulfide exchange reactions promote efficient catalysis in Quiescin sulfhydryl oxidase. Benjamin A. Israel, Vamsi K. Kodali, and Colin Thorpe. The Journal of Biological Chemistry. 2013, December 30, 2013. DOI: 10.1074/jbc.M113.536219.

2-Cys peroxiredoxins participate in the oxidation of chloroplast enzymes in the dark. Valle Ojeda, Juan Manuel, Pérez-Ruiz, and Francisco Javier Cejudo. Molecular Plant. 2018, pp 1-32. October 4, 2018. DOI: 10.1016/j.molp.2018.09.005.

Complement Activation and Cell Uptake Responses Toward Polymer-Functionalized Protein Nanocapsules. Nicholas M. Molino, Kateryna Bilotkach, Deborah A. Fraser, Dongmei Ren, and Szu-Wen Wang. Biomacromolecules, 2012, 13 (4), pp 974–981. March 14, 2012. DOI: 10.1021/bm300083e.

Redox-regulated dynamic interplay between Cox19 and the copper-binding protein Cox11 in the intermembrane space of mitochondria facilitates biogenesis of cytochrome c oxidase. Manuela Bode, Michael W. Woellhaf, Maria Bohnert, Martin van der Laan, Frederik Sommer, Martin Jung, Richard Zimmermann, Michael Schroda, Johannes M. Herrmann. Molecular Biology of the Cell. April 29, 2015. DOI: 10.1091/mbc.E14-11-1526

NTRC-dependent redox balance of 2-Cys peroxiredoxins is needed for optimal function of the photosynthetic apparatus. Juan Manuel Pérez-Ruiz, Belén Naranjo, Valle Ojeda, Manuel Guinea, and Francisco Javier Cejudo. Proceedings of the National Academy of Sciences of the United States of America. 2017, 114 (45) pp 12069-12074. 9/26/2017. DOI: 10.1073/pnas.1706003114.

A chloroplast redox relay adapts plastid metabolism to light and affects cytosolic protein quality control. Valle Ojeda, Julia Jiménez-López, Francisco José Romero-Campero, Francisco Javier Cejudo, Juan Manuel Pérez-Ruiz. Plant Physiology. 2021, kiab246. 05/26/2021. DOI: 10.1093/plphys/kiab246

Protocol for determining protein cysteine thiol redox status using western blot analysis, Bikram Datt Pant, Sunhee Oh, Hee-Kyung Lee, Raja Sekhar Nandety, Kirankumar S. Mysore, Volume 33, Issue 11, 15 December 2020, https://doi.org/10.1016/j.xpro.2021.100566

Aim32 is a dual-localized 2Fe-2S mitochondrial protein that functions in redox quality control, Danyun Zhang, Owen R. Dailey, Daniel J. Simon, James A. Wohlschlegel, Carla M. Koehler, Deepa V. Dabir, Journal of Biological Chemistry, 2021, Volume 297, Issue 4, 10/2021, DOI: 10.1016/j.jbc.2021.101135

Depletion of m-type thioredoxin impairs photosynthesis, carbon fixation, and oxidative stress in cyanobacteria. Manuel J Mallén-Ponce, María José Huertas, Ana María Sánchez-Riego, Francisco J Florencio. Plant Physiology. 2021. Volume 187, Issue 3. July 15, 2021. DOI: 10.1093/plphys/kiab321

Characterization of the Gluathione-dependent reduction of the perixiredoxin 5 homolog PfAOP from Plasmodium Falciparum. Robin Chumann, Lukas Lang, Marcel Deponte. Wiley Online Library. 2022. Volume 31, Issue 5. April 9, 2022. https://doi.org/10.1002/pro.4290

Regulation of Derlin-1-mediated degradation of NADPH oxidase partner p22phox by thiol modification. Kei Miyano, Shuichiro Okamoto, Mizuho Kajikawa, Takuya Kiyohara, Chikage Kawai, Akira Yamauchi, Futoshi Kuribayashi. Redox Biology, Volume 56, October 2022, 102479. 08/12/2022. https://doi.org/10.1016/j.redox.2022.102479

Description

m-dPEG®24-amine, product number QBD-10318, is a non-immunogenic, water-soluble chemical modification reagent. The product contains a single molecular weight, discrete-length polyethylene glycol (dPEG®) chain terminated on one end with a methyl group and on the other end with a reactive primary amine. The amino group reacts with carboxylic acids (and their active esters), aldehydes, and ketones. Reacting the amino group with aldehydes or ketones forms a labile imine (Schiff base). Reacting carboxylic acids or their active esters with m-dPEG®24-amine forms stable amide bonds. Uses for this product include passivating surfaces and coating biomolecules.

Biomolecules modified with m-dPEG®24-amine display enhanced water solubility, increased hydrodynamic volume, and reduced immunogenicity. This product reacts quickly with active esters of carboxylic acids (for example, NHS esters and TFP esters) to form amide bonds. Also, it forms amide bonds directly with carboxylic acids using the carbodiimide EDC.

Several publications in the scientific literature report the successful use of m-dPEG®24-amine. Published reports using this product include:
development of molecular pincers as protein sensors;
development and modification of luminescent Iridium (III) polypyridine complexes for use as biological labels and probes;
development of probes for continuous real-time modification of renal function; and,
development of a membrane filter system with antifouling properties for water purification.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See chapter 18, Discrete PEG Reagents, pp.787-821, for a full overview of the dPEG® products.

Molecular Pincers: Antibody-Based Homogeneous Protein Sensors. Ewa Heyduk, Benjamin Dummit, yie-Hwa Chang, and Tomasz Heyduk, Anal. Chem., 2008, 80 (13), pp 5152–5159 May 21, 2008. DOI: 10.1021/ac8004154.

Modification of Luminescent Iridium (III) Polypyridine Complexes with discrete Poly(ethylene glycol) (PEG) Pendants: Synthesis, Emissive behavior, Intracellular Uptake, and PEGylation Properties. Steve Po-Yam Li, Hua-Wei Liu, Kenneth Yin Zhang, and Kenneth Kam-Wing Lo. Chemistry A European Journal. 2010, 16 (28), pp. 8329 – 8339. July 26, 2010. DOI: 10.1002/chem.201000474.

New optical probes for the continuous monitoring of renal function. Richard B. Dorshow, Bethel Asmelash, Lori K. Chinen, Martin P. Debreczeny, Richard M. Fitch, John N. Freskos, Karen P. Galen, Kimberly R. Gaston, Timothy A. Marzan, Amruta R. Poreddy, Raghavan Rajagopalan, Jeng-Jong Shieh, William L. Neumann. Proc. SPIE 6867, Molecular Probes for Biomedical Applications II. 2008. 68670C. February 13,2008. DOI: 10.1117/12.763697.

Luminescent Iridium(III) Polypyridine PEG Complexes: Synthesis, Photophysical, and Biological Properties. Steve Po-Yam Li, Johnson Lui-Lui Tsai, and Kenneth Kam-Wing Lo. NANOMED. 2010, pp 66-71. December 5, 2010. http://dx.doi.org/10.1109/NANOMED.2010.5749807.

Design of cyclometalated iridium(III) polypyridine complexes as luminescent biological labels and probes. Kenneth Kam-Wing Lo, Kenneth Yin Zhang, and Steve Po-Yam Li. Pure Appl. Chem. 2011, 83, (4) pp 823–840. February 28, 2011. DOI: 10.1351/PAC-CON-10-08-20.

Antifouling and tunable amino functionalized porous membranes for filtration Applications. Bijay P. Tripathi, Nidhi C. Dubey, S. Choudhury and M. Stamm. Journal of Materials Chemistry. 2012, 22 (1) pp 19981-19992. August 1, 2012. DOI: 10.1039/c2jm34172g.

Cell-Specific Delivery of Diverse Cargos by BacteriophageMS2 Virus-like Particles. Carlee E. Ashley Eric C. Carnes, Genevieve K. Phillips, Paul N. Durfee, Mekensey D. Buley, Christopher A. Lino, David P. Padilla, Brandy Phillips, Mark B. Carter, Cheryl L. Willman, C. Jeffrey Brinker, Jerri do Carmo Caldeira, Bryce Chackerian, Walker Wharton, and David S. Peabody.ACS Nano, 2011, 5 (7), pp 5729–5745, May 26, 2011. DOI: 10.1021/nn201397z.

Description

Amino-dPEG®24-acid, product number QBD-10317, is a PEGylated amino acid. A primary amine group and a propionic acid group sit on opposite ends of a long (76 atoms), single molecular weight polyethylene glycol (PEG) spacer of discrete length (dPEG®). The highly hydrophilic, discrete PEG spacer (Ð = 1) increases the hydrodynamic volume and imparts water solubility to conjugates that incorporate it. Moreover, Amino-dPEG®24-acid benefitted numerous applications, including peptide synthesis, peptide modification, surface modification, oligonucleotide sequencing, drug delivery, and small molecule modification.

Specifications

Documents

References

Greg T. Hermanson, Bioconjugate Techniques, 2nd Edition, Elsevier Inc., Burlington, MA 01803, April, 2008 (ISBN-13: 978-0-12-370501-3; ISBN-10: 0-12-370501-0). Specifically see pp. 726-729 in his Chapter 18 on discrete PEG compounds for pegylation applications.

Greg T. Hermanson, Bioconjugate Techniques, 3rd Edition, Elsevier, Waltham, MA 02451, 2013, ISBN 978-0-12-382239-0; See chapter 18, Discrete PEG Reagents, pp.787-821, for a full overview of the dPEG® products.

PEG-Labeled Nucleotides and Nanopore Detection for Single Molecule DNA Sequencing by Synthesis. Shiv Kumar, Chuanjuan Tao, Minchen Chien, Brittney Hellner, Arvind Balijepalli, Joseph W. F. Robertson, Zengmin Li, James J. Russo, Joseph E. Reiner3, John J. Kasianowicz & Jingyue Ju. Scientific Reports. 2012, 2 (684), September 21, 2012. DOI: 10.1038/srep00684.

Proton-sponge activity and receptor-targeting of sequence-defined nucleic acid carriers. Ulrich Benjamin Lachelt. October 21, 2014.

ICAM-1 Targeted Catalase Encapsulated PLGA-b-PEG Nanoparticles against Vascular Oxidative Stress. Sari, E.; Tunc-Sarisozen, Y.; Mutlu, H.; Shahbazi, R.; Ucar, G.; Ulubayram, K. Journal of Microencapsulation 2015, 32 (7), 687–698. https://doi.org/10.3109/02652048.2015.1073384.