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m-dPEG®₈-NHS ester (QBD-10260)

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Description

m-dPEG®8-NHS ester, product number QBD-10260, is a medium-length (26 atoms, 29.8 Å), methyl-terminated, discrete-length polyethylene glycol (dPEG®) spacer functionalized with an N-hydroxysuccinimidyl (NHS) ester for reactions with free amines. NHS reacts optimally with free amines at pH 7.0 – 7.5. The hydrolytic rate of the ester to the carboxylic acid increases with increasing pH. Please note that modification of surface amines on biomolecules (e.g., proteins and peptides) with this uncharged, methyl-capped dPEG® spacer may alter the overall charge of the resulting conjugates.

Many applications employ this m-dPEG®8-NHS ester. Published papers using this product include:
imaging applications;
design of a delivery mechanism for an anti-HIV therapeutic peptide;
coating of carbon nanotubes, gold nanoshells, and silica shelled quantum dots;
PK improvement of organophosphorus hydrolase in a therapeutic application;
peptide synthesis; and,
development of antibacterial, cytotoxic dendrimers.
m-dPEG®8-NHS ester, product number QBD-10260, is just one member of an comprehensive line of methyl-terminated dPEG® products. This line includes dPEG® spacers containing 2 to 49 ethylene glycol units.

Specifications

Unit Size100 mg, 1000 mg
Molecular Weight509.54; single compound
Chemical formulaC₂₂H₃₉NO₁₂
CAS756525-90-3
Purity> 97%
SpacersdPEG® Spacer is 26 atoms and 29.8 Å
ShippingAmbient
Typical solubility properties (for additional information contact Customer Support)Methylene chloride, Acetonitrile, DMAC or DMSO.
Storage and handling-20°C; Always let come to room temperature before opening; be careful to limit exposure to moisture and restore under an inert atmosphere; stock solutions can be prepared with dry solvent and kept for several days (freeze when not in use). dPEG® pegylation compounds are generally hygroscopic and should be treated as such. This will be less noticeable with liquids, but the solids will become tacky and difficult to manipulate, if care is not taken to minimize air exposure.

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.

Short polyethylene glycol chains densely bound to soft nanotube channels for inhibition of protein aggregation. N. Kameta, T. Matsuzawa, K. Yaoi, and M. Masuda. RSC Advances. 2016, 6 (43) pp 36744-36750. April 7, 2016. DOI: 10.1039/C6RA06793J.

Laser-Activated Gene Silencing via Gold Nanoshell-siRNA Conjugates,Gary B Braun, Alessia Pallaoro, Guohui Wi, Dimitris Missirlis, Joseph A. Zasadzinski, Matthew Tirrell, and Norbert O. Reich. ACS Nano. 2009, 3 (7), pp 2007–2015. June 15, 2009. DOI:10.1021/nn900469q.

Hairpin Structure of a Biarsenical- Tetracysteine Motif Determined by NMR Spectroscopy, Fatemeh Madani, Jesper Lind, Peter Damberg, Stephen R. Adams, Roger Y. Tsien, and Astrid O. Graslund. JACS. 2009, 131 (13), pp 4613–4615. March 12, 2009. DOI: 10.1021/ja809315x.

Potent D-peptide inhibitors of HIV-1 entry, Brett D. Welch, Andrew P. VanDemark, Annie Heroux, Christopher P. Hill, and Michael S. Kay. PNAS. 2007, 43 (104), pp 16828-16833. October 23, 2007. DOI: 10.1073/pnas.0708109104.

Improved pharmacokinetics and immunogenicity profile of organophosphorus hydrolase by chemical modification with polyethylene glycol. Boris N. Novikov, Janet K. Grimsley, Rory J. Kern, James R. Wild, Melinda E. Wales. Elsevier. 2010, 3 (146) pp 318-325. September 15, 2010. DOI: 10.1016/j.jconrel.2010.06.003.

Antibacterial activity and cytotoxicity of PEGylated poly(amidoamine) dendrimersw. Analette I. Lopez, Rose Y. Reins, Alison M. McDermott, Barbara W. Trautner and Chengzhi Cai. Molecular BioSystems. 2009, 10 (5), pp 1148-1156. May 28, 2009. DOI: 10.1039/b904746h.

Silica-Shelled Single Quantum Dot Micelles as Imaging Probes with Dual or Multimodality. Rumiana Bakalova, Zhivko Zhelev, Ichio Aoki, Hideki Ohba, Yusuke Imai, and Iwao Kanno. Anal. Chem. 2006, 78 (16) pp 5925–5932. July 14, 2006. DOI: 10.1021/ac060412b.

Development of Polyethylene Glycol-Conjugated Alendronate, a Novel Nitrogen-Containing Bisphosphonate Derivative: Evaluation of Absorption, Safety, and Effects After Intrapulmonary Administration in Rats. HIDEMASA KATSUMI, MIKI TAKASHIMA, JUN-ICHI SANO, KAZUSHI NISHIYAMA, NORIKO KITAMURA, TOSHIYASU SAKANE, TORU HIBI, AKIRA YAMAMOTO. Journal of Pharmaceutical Sciences. 2011, 100 (9) pp 3783-3792. May 12, 2011. DOI: 10.1002/jps.22620.

Novel Comb-Shaped PEGModification Enhances the Osteoclastic Inhibitory Effect and Bone Delivery of Osteoprotegerin After Intravenous Administration in Ovariectomized Rats. Yoshihiro Miyaji, Yuji Kasuya, Yoshitake Furuta, Atsushi Kurihara, Masayuki Takahashi, Ken-ichi Ogawara, Takashi Izumi & Osamu Okazaki & Kazutaka Higaki. Pharmaceutical Research. 2012, 29 (11) pp 3143-3155. June 23, 2012. DOI 10.1007/s11095-012-0807-4.

Laser-Activated Gene Silencing via Gold Nanoshell-siRNA Conjugates,Gary B Braun, Alessia Pallaoro, Guohui Wi, Dimitris Missirlis, Joseph A. Zasadzinski, Matthew Tirrell, and Norbert O. Reich. ACS Nano. 2009, 3 (7), pp 2007–2015. June 15, 2009. DOI:10.1021/nn900469q.

Hairpin Structure of a Biarsenical- Tetracysteine Motif Determined by NMR Spectroscopy, Fatemeh Madani, Jesper Lind, Peter Damberg, Stephen R. Adams, Roger Y. Tsien, and Astrid O. Graslund. JACS. 2009, 131 (13), pp 4613–4615. March 12, 2009. DOI: 10.1021/ja809315x.

Potent D-peptide inhibitors of HIV-1 entry, Brett D. Welch, Andrew P. VanDemark, Annie Heroux, Christopher P. Hill, and Michael S. Kay. PNAS. 2007, 43 (104), pp 16828-16833. October 23, 2007. DOI: 10.1073/pnas.0708109104.

Improved pharmacokinetics and immunogenicity profile of organophosphorus hydrolase by chemical modification with polyethylene glycol. Boris N. Novikov, Janet K. Grimsley, Rory J. Kern, James R. Wild, Melinda E. Wales. Elsevier. 2010, 3 (146) pp 318-325. September 15, 2010. DOI: 10.1016/j.jconrel.2010.06.003.

Antibacterial activity and cytotoxicity of PEGylated poly(amidoamine) dendrimersw. Analette I. Lopez, Rose Y. Reins, Alison M. McDermott, Barbara W. Trautner and Chengzhi Cai. Molecular BioSystems. 2009, 10 (5), pp 1148-1156. May 28, 2009. DOI: 10.1039/b904746h.

Silica-Shelled Single Quantum Dot Micelles as Imaging Probes with Dual or Multimodality. Rumiana Bakalova, Zhivko Zhelev, Ichio Aoki, Hideki Ohba, Yusuke Imai, and Iwao Kanno. Anal. Chem. 2006, 78 (16) pp 5925–5932. July 14, 2006. DOI: 10.1021/ac060412b.

Development of Polyethylene Glycol-Conjugated Alendronate, a Novel Nitrogen-Containing Bisphosphonate Derivative: Evaluation of Absorption, Safety, and Effects After Intrapulmonary Administration in Rats. HIDEMASA KATSUMI, MIKI TAKASHIMA, JUN-ICHI SANO, KAZUSHI NISHIYAMA, NORIKO KITAMURA, TOSHIYASU SAKANE, TORU HIBI, AKIRA YAMAMOTO. Journal of Pharmaceutical Sciences. 2011, 100 (9) pp 3783-3792. May 12, 2011. DOI: 10.1002/jps.22620.

Novel Comb-Shaped PEGModification Enhances the Osteoclastic Inhibitory Effect and Bone Delivery of Osteoprotegerin After Intravenous Administration in Ovariectomized Rats. Yoshihiro Miyaji, Yuji Kasuya, Yoshitake Furuta, Atsushi Kurihara, Masayuki Takahashi, Ken-ichi Ogawara, Takashi Izumi & Osamu Okazaki & Kazutaka Higaki. Pharmaceutical Research. 2012, 29 (11) pp 3143-3155. June 23, 2012. DOI 10.1007/s11095-012-0807-4.

Applicable patents and legal notices are available at legal notices.

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