Description

m-dPEG®8-Lipoamide, product number QBD-10800, is a medium-length (34 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®8-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®8-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®8-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.

Description

m-dPEG®8-thiol, product number QBD-10793, is a short (26 atoms) monodisperse PEGylation reagent designed to modify gold and silver surfaces or biomolecules that contain free, surface-accessible thiols. One end of the spacer terminates with a methyl group, while the other end terminates with a sulfhydryl. The sulfhydryl group forms dative bonds with gold or silver, disulfides with free thiols, and thioether bonds with maleimide and bromoacetate groups.

This product is useful for the passivation of gold or silver surfaces. The hydrophilic, non-immunogenic dPEG® spacer eliminates non-specific interactions with the metal surfaces.

If reacted with free thiols on biomolecules, m-dPEG®8-thiol forms disulfide bonds. Moreover, the resulting conjugates display improved water solubility and increased hydrodynamic volume. Furthermore, conjugation of this product with biomolecules potentially reduces or eliminates non-specific interactions and immunogenicity.

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.

Biomarker-Mediated Disruption of Coffee-Ring Formation as a Low Resource Diagnostic Indicator. Joshua R. Trantum, David W. Wright, and Frederick R. Haselton, Langmuir, 2012, 28 (4), pp 2187–2193 December 9, 2011. DOI.org/10.1021/la203903a.

(INVITED)Quantitative detection of SARS-CoV-2 virions in aqueous mediums by IoT optical fiber sensors. Nunzio Cennamo, Girolamo D’Agostino, Laura Pasquardini, Francesco Arcadio, Chiara Perri, Nicola Coppola, Italo Francesco Angelillo, Lucia Altucci, Francesco Di Marzo, Eva Maria Parisio, Giulio Camarlinghi, Luigi Zeni. Science Direct. Volume 5. https://doi.org/10.1016/j.rio.2021.100177

Description

t-boc-N-amido-dPEG®8-acid, product number QBD-10760, is composed of a boc-protected primary amine and a propionic acid group on opposite ends of a short (28 atoms), single molecular weight, discrete PEG (dPEG®) linker. Designed for use in Boc-based peptide chemical synthesis, t-boc-N-amido-dPEG®8-acid can be used to insert a discrete PEG linker/spacer at the N-terminus of a peptide chain or to add a short dPEG® onto the side chain of an amino acid such as lysine or ornithine. Insertion of t-boc-N-amido-dPEG®8-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.

Covalently deposited dyes: a new chromogen paradigm that facilitates analysis of multiple biomarkers in situ. William A Day, Mark R Lefever, Robert L Ochs, Anne Pedata, Lauren J Behman, Julia Ashworth-Sharpe, Donald D Johnson, Eric J May, James G Grille, Esteban A Roberts, Jerry W Kosmeder, and Larry E Morrison. Laboratory Investigation. 2016, 00 pp 1-10. November 21, 2016. DOI: 10.1038/labinvest.2016.115.

Description

m-dPEG®8-MAL, product number QBD-10746, is a thiol-reactive, single molecular weight, monodisperse PEG reagent with a spacer length of 32 atoms. The terminal maleimido group reacts rapidly and specifically at pH 6.5 – 7.5 with free thiols to form thioether bonds in a click chemistry type of reaction. The non-immunogenic dPEG® product increases the water solubility and hydrodynamic volume of conjugates made with it. Moreover, this product reduces or eliminates immunogenicity and non-specific interactions caused by hydrophobicity. This product is designed to modify small molecules, biomolecules, hydrogels, and surfaces (metal, glass, silica) containing free sulfhydryl groups.

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). See all of the extensive references to the reactions of maleimides with a variety of compounds and applications, Hermanson, p.1174 (index for maleimides) and references therein.

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®8-OH (Azido-dPEG®8-alcohol), product number QBD-10542, 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 medium-length (24 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®8-OH to function as a crosslinker through subsequent chemical manipulations.

As a click chemistry reagent, azido-dPEG®8-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®8-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.

Description

m-dPEG®8-azide, product number QBD-10534, also known as azido-m-dPEG®8, 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 medium-length (26 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.

Clickable Poly(ethylene glycol)-Microsphere-Based Cell Scaffolds. Peter K. Nguyen, Christopher G Snyder, Jason D. Shields, Amanda W. Smith, Donald L. Elbert. Macromolecular Journals. 2013, 214 (8) 948-956. March 4, 2013. DOI: 10.1002/macp.201300023.

Description

Azido-dPEG®8-NHS ester, product number QBD-10503, is a water-soluble click chemistry crosslinker containing an azide group linked to an N-hydroxysuccinimidyl (NHS) ester through a single molecular weight, discrete polyethylene glycol (dPEG®) spacer. Azido-dPEG®8-NHS ester works with copper(I)-catalyzed, ruthenium-catalyzed and with copper-free (e.g., strain-promoted) click chemistry. The dPEG® spacer imparts water solubility and adds hydrodynamic volume to the conjugated product. The single molecular weight product design, with its discrete chain length, simplifies the analysis of this product.

Our single molecular weight, discrete chain length PEG (dPEG®) products are a superior alternative to traditional polyethylene glycol products. Conventional PEGylation reagents consist of a complex mixture of different chain lengths due to the polymerization processes that form them. In contrast, each dPEG® product contains a discrete chain length of PEG with only one molecular weight. Conjugates made with dPEG® products have less complicated analyses compared to conjugates prepared with traditional PEGylation reagents.

NHS esters are the most popular, most widely used way to conjugate carboxylic acids to primary or secondary amines resulting in stable amide bonds. NHS esters react quickly and efficiently in aqueous media at physiological pH values (7.0 – 7.5). However, they are prone to hydrolysis at a rate that is pH-dependent. Published research shows that 2,3,5,6-tetrafluorophenyl (TFP) esters are more hydrolytically stable and have better reactivity with amines than NHS esters.

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.

A Modular Platform for the Rapid Site-Specific Radiolabeling of Proteins with F Exemplified by Quantitative Positron Emission Tomography of Human Epidermal Growth Factor Receptor 2. Herman S. Gill, Jeff N. Tinianow, Annie Pgasawara, Judith E. Flores, Alexander N. Vanderbilt, Helga Raab, Justin M. Scheer, Richard Vandlen, Simon-P. Williams, and Jan Marik, J. Med. Chem., 2009, 52 (19), pp 5816–5825 September 9, 2009. DOI: 10.1021/jm900420c.

An Effective Targeted Nanoglobular Manganese(II) Chelate Conjugate for Magnetic Resonance Molecular Imaging of Tumor Extracellular Matrix. Mingqian Tan, Xueming Wu, Eun-Kee Jeong, Qianjin Chen, Dennis L. Parker, and Zheng-Rong Lu,Mol. Pharmaceutics, 2010, 7 (4), pp 936–943 May 19, 2010. DOI: 10.1021/mp100054m.

Constant-speed vibrational signaling along polyethylene glycol chain up to 60-Å distance. Zhiwei Lin and Igor V. Rubtsov. PNAS, 2012, 5 (109), pp 1413-1418, January 31, 2012. DOI:10.1073/pnas.1116289109.

Ballistic energy transport along PEG chains: distance dependence of the transport efficiency. Zhiwei Lin , Nan Zhang , Janarthanan Jayawickramarajah and Igor V. Rubtsov. Physical Chemistry Chemical Physics. 2012, 30 (14), pp 10445-10454. April 12, 2012. DOI: 10.1039/C2CP40187H.

Enzymatic Ligation of Large Biomolecules to DNA. Rasmus Schøler Sørensen, Anders Hauge Okholm, David Schaffert, Anne Louise Bank Kodal, Kurt V. Gothelf, and Jørgen Kjems. ACS Nano. 2013, 7 (9) pp 8098–8104. August 8, 2013. DOI: 10.1021/nn403386f.

Click Chemistry Immobilization of Antibodies on Polymer Coated Gold Nanoparticles. Chiara Finetti, Laura Sola, Margherita Pezzullo, Davide Prosperi, Miriam Colombo, Benedetta Riva, Svetlana Avvakumova, Carlo Morasso, Silvia Picciolini, and Marcella Chiari. Langmuir. 2016, 32, pp 7435-7441. July 1, 2016. DOI: 10.1021/acs.langmuir.6b01142.

Modular Assembly of Cell-targeting Devices Based on an Uncommon G-quadruplex Aptamer. Felipe Opazo, Laura Eiden, Line Hansen, Falk Rohrbach, Jesper Wengel, Jørgen Kjems, and Günter Mayer. Molecular Therapy Nucleic Acids. 2015, 4 pp e251. 9/1/2015. DOI: 10.1038/mtna.2015.25.

Description

m-dPEG®8-acid, product number QBD-10324, is a medium-length (26 atoms), methyl-capped, discrete chain length polyethylene glycol (dPEG®) spacer. The reactive end of the molecule terminates in a propionic acid group. The terminal propionic acid moiety can be coupled directly to free amines using EDC or another carbodiimide. Alternatively, the reactive end can be functionalized as an active ester that can then be conjugated to free amines. N-hydroxysuccinimide (NHS), 2,3,5,6-tetrafluorophenol (TFP), and 2,3,4,5,6-pentafluorophenol (PFP) typically are used for this functionalization.

m-dPEG®8-acid can modify amine-functionalized surfaces (carbon nanotubes, other nanoparticles, quantum dots, etc.) or free amines on biomolecules. When used to coat surfaces or modify biomolecules, m-dPEG®8-acid reduces, and often eliminates, non-specific binding and increases hydrophilicity. Please note that modification of surface amines on biomolecules with this uncharged, methyl-capped dPEG® spacer may alter the overall charge of the resulting conjugates.

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.

Surface functionalization of magnetic iron oxide nanoparticles for MRI applications –effect of anchoring group and ligand exchange protocol. Eric D. Smolensky, Hee-Yun E. Park, Thelma S. Berquo and Valerie C. Pierre. Contrast Media Mol. Imaging Journal. 2010 6 (4), pp 189-199. August 2010. DOI:10.1002/cmmi.417.

Multivalent Benzamidine Molecules for Plasmin Inhibition: Effect of Valency and Linker Length. Tanmaye Nallan Chakravarthula, Dr. Ziqian Zeng, Prof. Nathan J. Alves. ChemMedChem, Volume 17, Issue 22, (2022), 09/16/2022, https://doi.org/10.1002/cmdc.202200364

Description

m-dPEG®8-amine, product number QBD-10278, is a methyl-terminated PEG amine compound. The PEG is a water-soluble, single molecular weight PEG product with a discrete chain length (dPEG®). Carboxylic acids and their active esters react with the amino terminus to form amide bonds. Furthermore, the amino terminus reacts with aldehydes and ketones, forming reducible Schiff bonds. Uses for m-dPEG®8-amine include modification of acid-functionalized surfaces and free carboxylic acid groups on biomolecules.

In published scientific literature, the following applications have utilized m-dPEG®8-amine:
Development of probes for continuous real-time modification of renal function;
Surface functionalization of magnetic iron nanoparticles;
PEGylation of PAMAM dendrimers to modify cytotoxicity and transfection efficiency; and,
Surface coating of carbon nanotubes used for thermally controllable extraction and separation of peptides.

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.

Surface functionalization of magnetic iron oxide nanoparticles for MRI applications –effect of anchoring group and ligand exchange protocol. Eric D. Smolensky, Hee-Yun E. Park, Thelma S. Berquo and Valerie C. Pierre. Contrast Media Mol. Imaging. 2010, 6 (4), pp 189-199. August 2010. DOI:10.1002/cmmi.417.

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.

Effects of PEGylation and Acetylation of PAMAM Dendrimers on DNA Binding, Cytotoxicity and in Vitro Transfection Efficiency. Kristina Fant, Elin K. Esbjörner, Alan Jenkins, Martin C. Grossel, Per Lincoln, and Bengt Nordén. Mol. Pharmaceutics. 2010, 7 (5) pp 1734–1746. August 9, 2010. DOI: 10.1021/mp1001312.

Soft Nanotubes Derivatized with Short PEG Chains for Thermally Controllable Extraction and Seperation of Peptides. Naohiro Kameta, Wuxiao Ding, and Jiuchao Dong. ACS Omega. 2017, 2, pp 6143-6150. September 26, 2017. DOI: 10.1021/acsomega.7b00838.

Benzene tricarboxamide derivatives with lipid and ethylene glycol chains self-assemble into distinct nanostructures driven by molecular packing, Nada Aljuaid a, Mark Tully b, Jani Seitsonen c, Janne Ruokolainen c and Ian W. Hamley, ChemComm, 2021, 57, 8360, 07/27/2021, DOI: 10.1039/d1cc03437e

Description

Amino-dPEG®8-acid, product number QBD-10277, is an amino PEG acid. A primary amine and propionic acid terminate the ends of the polyethylene glycol (PEG) spacer. The single molecular weight PEG spacer is discrete (Ð = 1) and highly hydrophilic. Consequently, it increases the hydrodynamic volume and imparts water solubility to conjugates that incorporate it.

Both ends of the molecule are available for conjugation. Conjugation of only one end of the dPEG® spacer may modify the overall charge of the conjugate. Many different types of coupling reactions are effective for this purpose. However, care should be taken not to use single-step EDC coupling, as this will polymerize the dPEG® product.

Scientific publications report the use of Amino-dPEG®8-acid in modifying diverse compounds including antibodies, enzymes, carbon nanotubes, and SU-8 (an epoxy-based negative photoresist) layered atop a quartz surface. In each case, amino-dPEG®8-acid was shown to improve the performance of the conjugate compared to the unmodified material. The improved conjugate performance occurred through increased signal-to-noise ratio, reduced non-specific binding, or both.

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.

Spacer length effects on in vitro imaging and surface accessibility of fluorescent inhibitors of prostate specific membrane antigen. Tiancheng Liu, Jessie R. Nedrow-Byers, Mark R. Hopkins, Clifford E. Berkman. Bioorganic & Medicinal Chemistry Letters. 2011, 21 (23), pp 7013–7016 October 4, 2011. DOI:10.1016/j.bmcl.2011.09.115.

Short PEG-Linkers Improve the Performance of Targeted, Activatable Monoclonal Antibody-Indocyanine Green Optical Imaging Probes. Kohei Sano, Takahito Nakajima, Kiminori Miyazaki, Yuya Ohuchi, Takashi Ikegami, Peter L. Choyke and Hisataka Kobayashi. Bioconjugate Chem. 2013, 24 (5) pp 811–816. April 22, 2013. DOI: 10.1021/bc400050k.

Novel 3D LithographicallyPrepared Solid-Phase Surfaces Made from SU-8 for Next Generation Sequencing. Hong Wang, Makgorzata Witek, Daniel Park, Jianmin Huang,Francis Barany, Steven A. Soper. Miniaturized Systems for Chem and Life Sci. 2011, pp.73-75. October 6, 2011. DOI: www.rsc.org/images/LOC/2011/PDFs/Papers/026_0829.pdf

Drug loading, dispersion stability, and therapeutic efficacy in targeted drug delivery with carbon nanotubes. Elena Heister, Vera Neves, Constanze Lamprecht, S.Ravi P. Silva, Helen M. Coley, Johnjoe McFadden. Carbon. 2011, 50 (2) pp 622-632. August 31, 2011. DOI: 10.1016/j.carbon.2011.08.074.

Enzyme Catalytic Efficiency: A Function of Bio_nano Interface Reactions. Alan S Campbell, Chenbo Dong, Fanke Meng, Jeremy Hardinger, Gabriela C Perhinschi, Nianqiang Wu, and Cerasela Zoica Dinu. ACS Applied Materials and Interfaces. 2014, 6 pp 5393-5403. March 25, 2014. DOI: dx.doi.org/10.1021/am500773g.

Redirecting extracellular proteases to molecularly guide radiosensitizing drugs to tumors. Dina V. Hingorani, Jessica L. Crisp, Matthew K. Doan, Maria F. Camargo, Maryam A. Quraishi, Joseph Aguilera, Mara Gilardi, Larry A.Gross, Tao Jiang, Wei T. Li, Weg M.Ongkeko, Ezra E. W. Cohen, j. Silvio Gutkind, Stephen R. Adams, Sunil J .Advania. Biomaterials. 2020, Volume 248, July 2020, 120032. 04/11/2020. https://doi.org/10.1016/j.biomaterials.2020.120032