Description

Bis-dPEG®11-DBCO, product number QBD-11372, is a homobifunctional click chemistry crosslinker consisting of two dibenzylcyclooctyne (DBCO) groups separated by a medium-length (39 atoms, 44.2 Å), single molecular weight, discrete polyethylene glycol (dPEG®) spacer. The DBCO groups react with azide groups via the bioorthogonal click chemistry reaction known as strain-promoted azide-alkyne cycloaddition (SPAAC), also known as copper-free click chemistry. This product is particularly useful for click chemistry reactions where the presence or use of copper(I) [Cu(I)] is undesirable. Any two molecules containing accessible azide groups can be crosslinked with this compound. Applications for Bis-dPEG®11-DBCO include crosslinking biomolecules that have been modified to include azide groups and construction of complex supramolecular structures.

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

Bis-Bromoacetamido-dPEG®11, product number QBD-11338, is a thiol-reactive, homobifunctional crosslinker, with the two reactive ends separated by a medium-length (44 atoms, 47.5 Å), single molecular weight, discrete polyethylene glycol (dPEG®) spacer. Both ends of the dPEG® spacer terminate with bromoacetyl groups that connect to the dPEG® crossbridge through amide bonds.

Bromoacetyl-functionalized reagents are useful alternatives to maleimide-functionalized reagents. The bromoacetyl group reacts with sulfhydryl groups at pH 8 or higher. Maleimide groups are chemoselective for thiols at pH 6.5 – 7.5 and lose selectivity at higher pH values. Bromoacetyl-thiol reaction rates are somewhat slower than maleimide-thiol reaction rates.

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

Bromoacetamido-dPEG®11-azide, product number QBD-11204, crosslinks free thiols with click chemistry alkyne partners across a medium-length (39 atoms, 46.0 Å) single molecular weight, discrete PEG (dPEG®) bridge.

The medium-length dPEG® linker is amphiphilic and adds hydrodynamic volume and water solubility to conjugate molecules. The flexible, non-immunogenic spacer can reduce or eliminate renal clearance and help shield conjugates from opsonization through the increased hydrodynamic volume the dPEG® linker imparts.

The bromoacetate moiety reacts chemoselectively with free thiols at pH >8.0. The bromoacetate group is an alternative to the maleimide group and is used in situations where the target molecule needs to be at a high pH. The azide group reacts with a suitable alkyne partner via metal-catalyzed (Cu, Ru) or strain-promoted (copper-free) click chemistry. Moreover, Bromoacetamido-dPEG®11-azide is stable, unlike MAL-PEG-azide constructs, which are somewhat unstable.

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

Amino-dPEG®11-ONH-t-boc, product number QBD-11112, is a PEGylation reagent that is useful as a building block or modifier. The medium-length (38 atoms, 43.8 Å), single molecular weight discrete PEG (dPEG®) spacer is functionalized with a primary amine and a boc-protected oxyamine at opposite ends of the dPEG® chain. The amine reacts with carboxylic acids and their active esters (NHS, TFP, PFP, etc.) to form stable amide bonds. The oxyamine group reacts with aldehydes and ketones to form non-labile oxime bonds, following removal of the boc protecting group with formic acid or trifluoroacetic acid. The flexible dPEG® spacer increases conjugate molecules’ hydrodynamic volume and increases their water solubiliby. Uses for this compound include building novel crosslinkers and designing water-soluble payload delivery systems.

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 pp. 276-335 for general description and use of heterobifunctional crosslinkers, and the specific sample protocol for SPDP and LC-SPDP on pp. 286-288. See Greg’s extensive index on pp. 1192-1193 for references to a number and range of applications and their respective protocols.

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

MAL-dPEG®11-Lipoamide, product number QBD-10819, is a heterobifunctional crosslinker functionalized with a maleimidopropyl group and a lipoic acid moiety on opposite ends of a medium-length (49 atoms, 59.3 Å), single molecular weight, discrete PEG (dPEG®) crosslinker. The lipoic acid moiety forms dative bonds with gold, silver, and other metals and can be used to coat or passivate metal surfaces. The maleimide group forms stable thioether bonds with free thiols and can be used to immobilize a sulfhydryl-containing biomolecule such as a peptide or antibody fragment to a metal surface through the dPEG®-lipoamide linkage. The flexible, non-immunogenic, hydrophilic dPEG® linker adds water solubility and increases the conjugate’s hydrodynamic volume.

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.

Focal adhesion regulation through microcontact printing of protein nanoparticles on self-assembled monolayers for cell guidance. Albert Martinez Moreno. DUGiDocs. 2016, June 1, 2016. DOI: http://hdl.handle.net/10256/12960.

Description

Aminooxy-dPEG®11-azide.HCl, product number QBD-10538, is a click chemistry crosslinker functionalized with an oxyamine moiety on one end of a medium-length (38 atoms), single molecular weight, discrete PEG (dPEG®) linker, and an azide group on the other end. The azide end of the linker reacts with aliphatic or cyclic alkynes through copper-catalyzed (CuAAC), ruthenium-catalyzed (RuAAC), or strain-promoted, copper-free (SPAAC) click chemistry to form a triazole ring. The molecule’s aminooxy end (sold as an HCl salt) reacts with aldehydes and ketones to form biocompatible, stable oxime bonds that are important in many bioconjugation and supramolecular construction processes.

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.

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®11-amine, product number QBD-10524, is a carbonyl-reactive, biocompatible crosslinking reagent that can participate in multiple types of reactions. The product consists of azide and amine groups on opposite ends of a medium-length (36 atoms), single molecular weight, discrete polyethylene glycol (dPEG®) chain. Alkynes react with the azido group in metal-catalyzed or strain-promoted click chemistry to yield triazole derivatives. Moreover, the azide group functions as a masked amine that reduces to a primary amine via a suitable reducing agent. Furthermore, Azido-dPEG®11-amine can participate in a Staudinger ligation with appropriate phosphine derivatives to create a water-soluble product.

The amphiphilic dPEG® product adds hydrodynamic volume and imparts water solubility to any compound to which it is conjugated. Also, because the terminal azide group functions in multiple different types of reactions, Azido-dPEG®11-amine can act as either a heterobifunctional, click chemistry crosslinker or a monoprotected homobifunctional crosslinking reagent. As a heterobifunctional click chemistry reagent, the azide group reacts with alkynes to form triazoles. The amino terminus of the molecule then can react with carboxylic acids, aldehydes, or ketones to crosslink the conjugate to another molecule. As a monoprotected homobifunctional crosslinker, the amine end reacts first with carboxylic acids (or their active esters), aldehydes, or ketones, leaving the azide end of the molecule free. The reduction of the azido group with a suitable reducing agent, such as triphenylphosphine, yields a free amine that can be conjugated similarly to the conjugation of the first amine group. Reacting the amine groups with aldehydes or ketones results in labile Schiff bases that should be reduced to secondary amines for bond stability.

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.

Structure-Based Design of a Heptavalent Anthrax Toxin Inhibitor. Amit Joshi, Sandesh Kate, Vincent Poon, Dhananjoy Mondal, Mohan B. Boggara, Arundhati Saraph, Jacob T. Martin, Ryan McAlpine, Ryan Day, Angel E. Garcia, Jeremy Mogridge, and Ravi S. Kane. Biomacromolecules, 2011, 12 (3), pp 791–796 February 8, 2011. DOI: 10.1021/bm101396u.

Detection of SK2 Channels on Hippocampal Neurons. Jamie L. Maciaszek University of Connecticut (2012) DigitalCommons@Uconn Master’s Theses Paper 237 April 20, 2012. http://digitalcommons.uconn.edu/gs_theses/237.

Description

Bis-MAL-dPEG®11, product number 10397, is a medium-length, homobifunctional, crosslinking reagent that links two molecules (e.g., peptides, proteins) together via the thiol-maleimide reaction (also known as the thiol-Michael addition). The ends of the molecule are both functionalized with maleimidopropionate groups. The two reactive ends are separated by a single molecular weight, discrete polyethylene glycol (dPEG®) spacer.

The thiol-maleimide reaction, a type of click chemistry reaction, is an extremely popular way to conjugate molecules. The maleimide functional group rapidly reacts with sulfhydryl groups, and the reaction is chemoselective for sulfhydryls in the pH range of 6.5 – 7.5.

The polyethylene glycol (PEG) spacer between the two maleimide groups is a single molecular weight compound with a discrete chain length (thus the tradename dPEG®). This product is not made from a disperse polymer but is instead a single compound. Applications for this product include, among many others, studying cell internalization of crosslinked proteins; developing FRET immunoassays; and anchoring biomolecules to surfaces.

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.

Kinetics of endophilin N-BAR domain dimerization and membrane interactions. Benjamin R. Capraro, Zheng Shi, Tingting Wu, Zhiming Chen, Joanna M. Dunn, Elizabeth Rhoades, Tobias Baumgart. Journal of Biological Chemistry. 2013, 288 (11) March 12, 2013. DOI: 10.1074/jbc.M112.435511.

Enhanced Fluorescence resonance energy transfer immunoassay with improved sensitivity based on the Fab’-based immunoconjugates. Yoshiyuki Ohiro, Hiroshi Ueda, Norio Shibata, Teruyuki Nagamune. Analytical Biochemistry. 2007, 360 (2) pp 266-272. January 15, 2007. DOI: 10.1016/j.ab.2006.10.025.

X-ray Photoelectron Spectroscopy and Differential Capacitance Study of Thiol-Functional Polysiloxane Films on Gold Supports. Patrick A. Johnson and Rastislav Levicky. Langmuir. 2004, 20 (22) pp 9621-9627. September 28, 2004. DOI: 10.1021/la048458s.

Polymercaptosiloxane Anchor Films for Robust Immobilization of Biomolecules to Gold Supports. Patrick A. Johnson and Rastislav Levicky. Langmuir . 2003, 19 (24) pp10288-10294. October 30, 2003. DOI: 10.1021/la035102s.

Unfolding Mechanisms and Conformational Stability of the Dimeric Endophilin N-BAR Domain. Rui Jin, Michael Grasso, Mingyang Zhou, Ronen Marmorstein, and Tobias Baumgart. ACS Omega. 2021, Volume 6 Issue 32. 08/04/2021. DOI: 10.1021/acsomega.1c01905.

Description

Diamido-dPEG®11-diamine, product number QBD-10361, is a water-soluble, homobifunctional, single molecular weight, discrete chain length polyethylene glycol (dPEG®) crosslinker that is 49 atoms (57.1 Å) long. Both ends of the crosslinker terminate with amino groups that react with activated carboxylates or their active esters to form stable amide bonds. Aldehydes and ketones react to form labile Schiff bases that are reducible to secondary amines for improved bond stability. This molecule is useful for modifying carboxylic acid-functionalized surfaces, small molecules with reactive carbonyl groups, and carbohydrates containing reducing sugars.

The use of Diamido-dPEG®11-diamine appears in several patents. Moreover, researchers at the Karolinska Institutet, Stockholm, Sweden, reported the use of Diamido-dPEG®11-diamine in an investigation of γ-secretase and its role in Alzheimer’s Disease. Furthermore, Diamido-dPEG®11-diamine may prove useful in the following applications:
Crosslinking peptides or other small biomolecules using available carboxylic acids, aldehydes, or ketones;
Introducing a dPEG® amine onto reducing sugars of a glycoprotein’s carbohydrate coat;
Passivating nanoparticle surfaces coated with carboxylic acids or their active esters; and,
Adding a medium-length dPEG® amine at the carboxyl terminus of a peptide.

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.

Visualizing Active Enzyme Complexes Using a Photoreactive Inhibitor for Proximity Ligation – Application on y-Secretase. Sophia Schedin-Weiss, Mitsuhiro Inoue, Yasuhiro Teranishi, Natsuko Goto Yamamoto, Helena Karlstrom, Bengt Winblad, Lars O. Tjernberg. PLoS ONE 2013, 8 (5) e63962. May 24, 2013. DOI:10.1371/journal.pone.0063962.

Teranishi, Y.; Hur, J.-Y.; Welander, H.; Frånberg, J.; Aoki, M.; Winblad, B.; Frykman, S.; Tjernberg, L. O. Affinity Pulldown of γ-Secretase and Associated Proteins from Human and Rat Brain. Journal of Cellular and Molecular Medicine 2010, 14 (11), 2675–2686. https://doi.org/10.1111/j.1582-4934.2009.00907.x.

Teranishi, Y. Identification and Investigation of Gamma-Secretase Associated Proteins from Brain. Doctoral Dissertation, Inst för neurobiologi, vårdvetenskap och samhälle / Dept of Neurobiology, Care Sciences and Society: Stockholm, Sweden, 2012.

Description

t-boc-N-amido-dPEG®11-amine, product number QBD-10172, is a diamine-functionalized, homobifunctional, monodisperse PEGylation reagent with one of the two primary amine-reactive groups protected as a tert-butyl carbamate. Both ends of the molecule react with carboxylic acids, aldehydes, and ketones. Carboxylic acids react with this product to form amide bonds, while reactions with aldehydes and ketones form Schiff bases that are reducible to secondary amines. The mono-protected end of the molecule gives the user greater control over when and where to react the primary amine following deprotection.

The free amine end of the molecule reacts with carboxylic acids or their active esters. With carboxylic acids, a carbodiimide such as EDC directly couples the amine to the acid, forming the amide. With active esters (for example, NHS or TFP esters) of carboxylic acids, the reaction runs in organic solvents or aqueous buffers using conventional chemistry. After the free amine has reacted, the protected end of the molecule is deprotected with trifluoroacetic acid (TFA) or some other suitable organic acid and then coupled to a carboxylate or active ester as above.

Scientific publications using t-boc-N-amido-dPEG®11-amine describe the following uses for this compound:
Immobilization of enzymes and antibodies;
Construction of supramolecular assemblies;
Engineering of quantum dots; and,
Development of biomolecular sensors.

Specifications

Documents

References

1. 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.

2. Oriented Immobilization of Fab Fragments by Site-Specific Biotinylation at the Conserved Nucleotide Binding Site for Enhanced Antigen Detection. Nur Mustafaoglu, Nathan J. Alves, and Basar Bilgicer. Langmuir. 2015, 31 (35) pp 9728-9736. August 14, 2015. DOI: 10.1021/acs.langmuir.5b01734.

3. Novel Nanoassemblies Composed of Squalenoyl—Paclitaxel Derivatives: Synthesis, Characterization, and Biological Evaluation, Franco Dosio, L. Harivardhan Reddy, Annalisa Ferrero, Barbara Stella, Luigi Cattel, and Patrick Couvreur. Bioconjugate Chem. 2010, 21 (7), pp 1349–1361. July 2, 2010. DOI: 10.1021/bc100154g.

4. Development of an oligo (ethylene glycol)-based SPR immunosensor for TNT detection. Yutaka Mizuta, Takeshi Onodera, Praveen Singh, Kiyoshi Matsumoto, Norio Miura, Kiyoshi Toko. Biosensors and Bioelectronics. 2008. 24 (2). Pp. 191-197. DOI:10.1016/j.bios.2008.03.042.

5. Oriented Surface Immobilization of Antibodies at the Conserved Nucleotide Binding Site for Enhanced Antigen Detection. Nathan J Alves, Tanyel Kiziltepe, and Basar Bilgicer. Langmuir. 2012, 28 (25), pp 9640-9648. May 1, 2012. DOI: 10.1021/la301887s.

6. Immobilization of Actively Thromboresistant Assemblies on Sterile Blood-Contacting Surfaces. Zheng Qu, Venkat Krishnamurthy, Carolyn A. Haller, Brent M. Dorr, Ulla M. Marzec, Sawan Hurst, Monica T. Hinds, Stephen R. Hanson, David R. Liu, and Elliot L. Chaikof. Adv. Healthcare Mater. 2013. March 23, 2013. DOI: 10.1002/adhm.201300110.

7. Oriented Surface Immobilization of Antibodies at the Conserved Nucleotide Binding Site for Enhanced Antigen Detection. Nathan J Alves, Tanyel Kiziltepe, and Basar Bilgicer. Langmuir. 2012, 28 (25) pp 9640–9648. May 21, 2012. DOI: 10.1021/la301887s.

8. Nanotube-assisted protein deactivation. Amit Joshi, Supriya Punyani, Shyam Sundhar Bale, Hoichang Yang, Theodorian Borca-Tasciuc and Ravi S. Kane. Nature Nanotechnology. 2008, 3 pp 41 – 45. December 9, 2007. doi:10.1038/nnano.2007.386

9. Biomimetic Ligands for Immunoglobulin-M Purification. Satyen Gautam. Doctoral Dissertation, National University of Singapore: Singapore, April 12, 2010. DOI: www.scholarbank.nus.edu.sg/handle/10635/22872.

10. Compact Biocompatible Quantum Dots via RAFT-Mediated Synthesis of Imidazole-Based Random Copolymer Ligand. Wenhao Liu, Andrew B. Greytak, Jungmin Lee, Cliff R. Wong, Jongnam Park, Lisa F. Marshall, Wen Jiang, Peter N. Curtin, Alice Y. Ting, Daniel G. Nocera, Dai Fukumura, Rakesh K. Jain and Moungi G. Bawendi. J. Am. Chem. Soc. 2010, 132 (2) pp 472–483. December 21, 2009. DOI: 10.1021/ja908137d.