Description

DBCO-acid, product number QBD-11814, is an aza-dibenzocyclooctyne (DBCO) product used for strain-promoted azide-alkyne cycloaddition (SPAAC, also known as “”copper free click chemistry””). The DBCO moiety reacts selectively with azides via SPAAC to form stable triazole linkages. Esterification of the terminal carboxylic acid with N-hydroxysuccinimide (NHS) or 2,3,5,6-tetrafluorophenol (TFP) allows for reaction with a primary amine. Insoluble in water, DBCO-acid is slightly soluble to sparingly soluble in most organic solvents. Vector Laboratories recommends dimethylsulfoxide (DMSO), N,N’-dimethylformamide (DMF), or N,N’-dimethylacetamide (DMAC) as solvents for this product. DBCO-acid is relatively insensitive to bases and can be used in the presence of aqueous bases. This product is acid sensitive and should not be subjected to pH <5 during reaction or workup.

The published discovery in 2004 of SPAAC, also known as “”copper free click chemistry,”” by Carolyn Bertozzi and coworkers improved the click chemistry toolbox. Toxic copper catalysts were eliminated, making the reaction truly bioorthogonal. By removing the copper(I) catalyst from the reaction, living cells can be labeled with reagents designed for SPAAC. Since the original publication, multiple improvements in strained cyclooctyne reagents resulted in the development of DBCO as a nearly perfect azide partner for SPAAC.

To use DBCO-acid in aqueous media or in cells, it should be conjugated to a water-soluble dPEG® product. Vector Laboratories offers numerous products for this purpose, including amino alcohols and amino acids. We also offer many DBCO-based dPEG® products already prepared for use.

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

Amino-dPEG®24-amido-dPEG®24-acid, product number QBD-10907, is a PEGylated amino acid consisting of a primary amine group on one end and a propionic acid group sit on opposite ends of a long (152 atoms, 178.9 Å), single molecular weight polyethylene glycol (PEG) spacer with a discrete chain length (dPEG®). The dPEG® spacer consists of two dPEG®24 chains joined by an amide bond, giving the spacer the effective length of a dPEG48 linker. 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-amido-dPEG®24-acid may benefit 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.

Description

CBZ-N-amido-dPEG®24-amido-dPEG®24-acid, product number QBD-11304, is a benzyloxycarbonyl (Cbz) N-protected amino-dPEG®-acid that provides a very long (152 atoms, 178.7 Å), single molecular weight discrete PEG (dPEG®) spacer. It can be used in peptide synthesis as well as in many other reactions. Removal of the Cbz protecting group often is orthogonal to the removal of other protecting groups. The carboxylic acid end of the dPEG® linker can be conjugated to free amines, such as the side chain of lysines, using a carbodiimide like EDC, or by activation with an acylating agent like NHS or TFP.

The Cbz protecting group (also called the Z protecting group) is one of the most popular protecting groups for amines. It is stable to base and mildly acidic conditions. It can be cleaved by a variety of methods. The most popular cleavage technique is hydrogenolysis using palladium black or palladium on carbon.

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

Fmoc-N-amido-dPEG®24-amido-dPEG®24-acid, product number QBD-11301, is one of a broad line of products designed for use in peptide synthesis. The long (152 atoms), flexible, discrete PEG (dPEG®) spacer is functionalized with a propionic acid group on one end and Fmoc-protected amine on the other. The spacer length is effectively forty-eight ethylene oxide units (i.e., PEG48). The compound can be added to the N-terminus of a growing peptide chain or to a primary-amine-functionalized side chain of an amino acid such as lysine. The non-immunogenic dPEG®24-amido-dPEG®24 spacer increases the hydrodynamic volume and imparts water solubility to the conjugate molecule.

QBD-11301 permits our customers to insert a dPEG® spacer into a peptide chain using familiar Fmoc chemistry using solid phase or solution phase chemistry. However, due to the spacer’s length, it likely will work better in solution-phase syntheses. The dPEG® compound can be inserted at either end of the peptide chain or in the middle of two amino acid sequences to provide a flexible linker between distinct functional peptides. Additionally, the dPEG® spacer can be used to provide spacing in a synthetic construct where steric hindrance is a problem. The amphiphilic nature of dPEG® products means that the construct gains hydrodynamic volume and water solubility while remaining soluble in organic solvent. The Fmoc protecting group is removed easily with a solution of piperidine in N,N-dimethylformamide (DMF).

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®36-acid, product number QBD-10907, is a PEGylated amino acid. A primary amine group and a propionic acid group sit on opposite ends of a long (111 atoms, 132.7 Å), single molecular weight polyethylene glycol (PEG) spacer with a discrete chain 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®36-acid may benefit 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. Reiner, John J. Kasianowicz & Jingyue Ju. Scientific Reports. 2012, 2 (684). September 21, 2012. DOI: 10.1038/srep00684.

Description

CBZ-N-amido-dPEG®36-acid, product number QBD-10906, is a benzyl carbamate (Cbz) N-protected amino-dPEG®-acid that provides a long (111 atoms, 132.7 Å), single molecular weight discrete PEG (dPEG®) spacer. It can be used in peptide synthesis to modify the side chain of lysine and in other forms of supramolecular construction. The Cbz protecting group is stable to acidic and basic conditions and is most easily removed using palladium black or palladium on carbon with hydrogen. This makes Cbz removal orthogonal to most other peptide synthesis deprotection reactions.

CBZ-N-amido-dPEG®36-acid works well in solution-phase synthesis. Carbodiimide activation, with or without an acylating agent, permits conjugation of the acid terminus of the dPEG® product to free amines. Other synthetic processes (e.g., surface modification, supramolecular construction) requiring the attachment or insertion of a medium-length PEG linker or spacer can employ CBZ-N-amido-dPEG®36-acid profitably also.

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

“Fmoc-N-amido-dPEG®36-acid, product number QBD-10903, is one of a broad line of products designed for use in peptide synthesis. The long (112 atoms), flexible, discrete PEG (dPEG®) spacer is functionalized with a propionic acid group on one end and Fmoc-protected amine on the other. The compound can be added to the N-terminus of a growing peptide chain or to a primary-amine-functionalized side chain of an amino acid such as lysine. The non-immunogenic dPEG®36 spacer increases the hydrodynamic volume and imparts water solubility to the conjugate molecule.

QBD-10903 permits our customers to insert a dPEG® spacer into a peptide chain using familiar Fmoc chemistry using solid phase or solution phase chemistry. However, due to the spacer’s length, it may work better in solution-phase syntheses. The dPEG® compound can be inserted at either end of the peptide chain or in the middle of two amino acid sequences to provide a flexible linker between distinct functional peptides. Additionally, the dPEG® spacer can be used to provide spacing in a synthetic construct where steric hindrance is a problem. The amphiphilic nature of dPEG® products means that the construct gains hydrodynamic volume and water solubility while remaining soluble in organic solvent. The Fmoc protecting group is removed easily with a solution of piperidine in N,N-dimethylformamide (DMF).”

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.

Lipo-Oligomer Nanoformulations for Targeted Intracellular Protein Delivery. Peng Zhang, Benjamin Steinborn, Ulrich Lachelt, Stefan Zahler, and Ernst Wagner. Biomacromolecules. 2017, June 26, 2017. DOI: 10.1021/acs.biomac.7b00666.

Flexible antibodies with nonprotein hinges. Daniel J. Capon, Naoki Kaneko, Takayuki Yoshimori, Takashi Shimada, Florian M. Wurm, Peter K. Hwang, Xiaohe Tong, Staci A. Adams, Graham Simmons, Taka-Aki Sato and Koichi Tanaka. The Japan Academy, Series B. 2011, 87 (9) pp 603-616. November 11, 2011. DOI: 10.2183/pjab.87.603.

A Systematic Analysis of Peptide Linker Length and Liposomal Polyethylene Glycol Coating on Cellular Uptake of Peptide-Targeted Liposomes. Jared F. Stefanick, Jonathan D. Ashley, Tanyel Kiziltepe, and Basar Bilgicer. ACS Nano. 2013, 7 (4) pp 2935–2947. February 19, 2013. DOI: 10.1021/nn305663e.

Enhanced Cellular Uptake of Peptide-Targeted Nanoparticles through Increased Peptide Hydrophilicity and Optimized Ethylene Glycol Peptide-Linker Length. Jared F. Stefanick, Jonathan D. Ashley, and Basar Bilgicer. ACS Nano. 2013, 7 (9) pp 8115–8127. August 29, 2013. DOI: 10.1021/nn4033954.

PEG-Peptide Conjugates. Ian W Hamley. Biomacromolecules. 2014, 15 (5) pp 1543-1559. April 1, 2014. DOI: 10.1021/bm500246w.

Evaluation of Nonpeptidic Ligand Conjugates for SPECT Imaging of Hypoxic and Carbonic Anhydrase IX-Expressing Cancers. Peng-Cheng Lv, Karson S. Putt, and Philip S. Low. Bioconjugate Chemistry. 2016, 27, pp 1762-1769. June 30, 2016. DOI: 10.1021/acs.bioconjchem.6b00271.

Bioresponsive nanocarries for targeted intracellular delivery of proteins and peptides. Ruth Elisabeth and Johanna Roder. Dissertation zur Erlangung des Doktorgrades der Fakultat fur Chemie und Pharmazie der Ludwig-Maximilians-Universitat Munchen. 2016, pp 1-128.

Efficient capture of circulating tumor cells with low molecular weight folate receptor-specific ligands. Yingwen Hu, Danyang Chen, John V Napoleon, Madduri Srinivasarao, Sunil Singhal, Cagri A Savran, Philip S Low. Scientific Reports. 2022. May 20, 2022. https://doi.org/10.1038/s41598-022-12118-3

Description

t-boc-N-amido-dPEG®36-acid, product number QBD-10902, is composed of a boc-protected primary amine and a propionic acid group on opposite ends of an extended (111 atoms, 132.7 Å), single molecular weight, discrete PEG (dPEG®) linker. Designed for use in Boc-based peptide chemical synthesis, t-boc-N-amido-dPEG®36-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®36-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

Thiol-dPEG®12-acid, product number QBD-10850, is a single molecular weight, discrete-length polyethylene glycol (dPEG®) PEGylation reagent. One end of the medium-length (39 atoms, 46.8 Å) dPEG® linker terminates in a sulfhydryl (thiol) group, while a propionic acid moiety terminates the opposite end. The thiol end of the molecule forms dative bonds with gold, thioether bonds with maleimide and bromoacetate groups, and disulfide bonds with other sulfhydryl groups. The propionic acid group reacts with amines to form amide bonds. Alternatively, if it is left unreacted, the propionic acid group provides a negative charge to the conjugated molecule or modified surface.

Numerous scientific publications attest to the benefits of Thiol-dPEG®12-acid, including the following applications:
Assaying protease by using fluorescence quenching with gold nanoparticles;
Enhancing transfection efficiency;
Modulating glucose transport with gold nanoparticles;
Developing multiplexed bioassays on semiconductor gold nanocrystals;
Developing spectroscopy applications; and,
Detecting cancer through a FRET-based, NIR-activated system that uses gold nanoparticles.

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.

Gold nanoparticle-based fluorescence quenching via metal coordination for assaying protease activity. Se Yeon Park, So Min Lee, Gae Baik, Kim and Young-Pil Kim. Gold Bull. 2012, 45 pp 213–219. October 25, 2012. DOI 10.1007/s13404-012-0070-9.

Systemically probing the bottom-up synthesis of AuPAMAM conjugates for enhanced transfection efficiency. Elizabeth R. Figueroa, Stephen Yan, Nicolette K. Chamberlain-Simon, Adam Y. Lin, Aaron E. Foster, and Rebekah A. Drezek. Journal of Nanobiotechnology. 2016, 14 (24). March 31, 2016. DOI: 10.1186/s12951-016-0178-9.

Modulating the Glucose Transport by Engineering Gold Nanoparticles. Sanjib Bhattacharyya, Krishna Kattel, and Franklin Kim. Journal of Nanomedicine and Biotherapeutic Discovery. 2016, 6 (1) pp 1-5. April 30, 2016. DOI: 10.4172/2155-983X.1000141.

Use of semiconductor nanocrystals to encode microbeads for multiplexed analysis of biological samples. Mikhail A Berestovoy, Regina S Bilan, Victor Krivenkov, Igor Nabiev, and Alyona Sukhanova. IOP Science. 2017, 784 (1) pp 1742-6596. March 15, 2017. DOI: 10.1088/1742-6596/784/1/012012.

Spectroscopy Based Approaches for Detection of Ions, Alpha-L-Fucosidase, and Singlet Oxygen. Eric Waidely. University of Miami Scholarly Repository. 2017, pp 1-113. May 3, 2017. http://scholarlyrepository.miami.edu/oa_dissertations/1842.

Near-Infrared-Activated Fluorescence Resonance Energy Transfer-Based Nanocomposite to Sense MMP2-Overexpressing Oral Cancer Cells. Yung-Chieh Chan, Ming-Hsien Chan, Chieh-Wei Chen, Ru-Shi Liu, Michael Hsiao, and Din Ping Tsai. ACS Omega. 2018,3 (2) pp. 1627-1634. February 8, 2018. DOI: 10.1021/acsomega.7b01494.

Signal enhancement of optical immunosensing by gold nanoparticles. Yuan Xintong. Nanyang Technological University, School of Material Science and Engineering Thesis for the degree of Master of Engineering. 2015, pp 1-74.

Biofunctionalized Polyelectrolyte Microcapsules Encoded with Fluorescent Semiconductor Nanocrystals for Highly Specific Targeting and Imaging of Cancer Cells. Galina Nifontova, Daria Kalenichenko, Maria Baryshnikova, Fernanda Ramos Gomes, Frauke Alves, Alexander Karaulov, Igor Nabiev, and Alyona Sukhanova. Advances on Applications of Optics and Photonics – Selected Papers from the 4th International Conference on Applications of Optics and Photonics, AOP2019. November 8, 2019. DOI: 10.3390/photonics6040117

NEW FRONTIERS FOR TRIPLE NEGATIVE BREAST CANCER DETECTION AND TREATMENT: FROM MECHANICAL BIOMARKERS TO SPECIFIC NANOPARTICLE ENTRY FOR ROBOTICALLY CONTROLLED LASER-INDUCED HYPERTHERMIA. Vanessa Uzonwanne. Worchester Polytechnic Institute. 2022. May 22, 2022.

SCORe: SARS-CoV-2 Omicron Variant RBD-Binding DNA Aptamer for Multiplexed Rapid Detection and Pseudovirus Neutralization. Lucy F. Yang, Nataly Kacherovsky, Joey Liang, Stephen J. Salipante, and Suzie H. Pun. Anal. Chem. 2022, 94, 37, 12683–12690. https://doi.org/10.1021/acs.analchem.2c01993

Description

Methoxytrityl-S-dPEG®12-acid, product number QBD-10846, permits the introduction of a protected thiol-dPEG® spacer/linker onto a molecule by reaction with a free amine. The dPEG®12 linker is functionalized with a methoxytrityl (Mmt)-protected thiol group one end and an amine-reactive propionic acid moiety on the other. The Mmt protecting group is easily removed under relatively mild conditions using dilute trifluoroacetic acid (TFA) with a scavenger.

QBD-10846 permits our customers to insert a medium-length (39 atoms, 46.8 Å) dPEG® into a peptide chain using familiar solid phase or solution phase chemistry. The dPEG® can be inserted at the N-terminus of a peptide chain or on any amino acid side chain with an exposed free amine. In addition, the dPEG® spacer can be used simply to provide additional distance in a synthetic construct where steric hindrance is a problem. The amphiphilic nature of dPEG® means that the construct will gain some degree of water solubility while remaining soluble in organic solvent. The Mmt protecting group removes relatively easily with a dilute solution of TFA that also contains a scavenger such as triethylsilane (TES) or triisopropylsilane (TIPS). Once the thiol group is deprotected, it can be reacted with another thiol to form a disulfide bond or with any thiol-reactive group such as maleimide, bromoacetamide, alkene (thiol-ene reaction) or alkyne (thiol-yne reaction).

Upon activation, Methoxytrityl-S-dPEG®12-acid reacts with any free amine, whether on a peptide, surface, or other molecule. This allows for a broad range of applications where this product can be employed to convert an amine to a thiol.

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.

Gold Nanoparticles Functionalized with Peptides for Specific Affinity Aggregation Assays of Estrogen Receptors and Their Agonists. Yoshiyuki Takatsuji, Shinya Ikeno and Tetsuya Haruyama. Sensors. 2012, 12 (4), pp 4952-4961. April 18, 2012. DOI: 10.3390/s120404952.