Linear Heterobifunctional PEG Derivatives

JenKem PEG RnDJenKem Technology provides high quality heterobifunctional polyethylene glycol derivatives (PEGs) with high purity and low polydispersity.

JenKem Technology’s heterobifunctional PEG derivatives are generally employed as crosslinking agents or as spacers between two different chemical entities. The PEG moiety in the heterobifunctional PEG derivatives provides water solubility, biocompatibility, and flexibility to the linker. Applications are especially geared towards the development of antibody drug conjugates (ADC’s). Linear heterobifunctional PEG derivatives have the following general structure:

X―PEG―Y

where X and Y are two different functional reactive groups.

JenKem Technology’s multi-arm heterofunctional PEG Derivatives are also useful as linkers for Antibody-Drug Conjugates. ADCs conjugated via heterobifunctional PEGs exhibit improved water solubility and PK/PD profile. Heterobifunctional PEG products with molecular weights and functional groups not listed in our online catalog may be available by custom synthesis. Please inquire at tech@jenkemusa.com about pricing and availability of custom synthesis PEGs. For global distribution, please visit link. To order directly from JenKem Technology:

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PEG PRODUCT PURITY REACTIVITY DETAILS
HO-PEG-CM ≥95% Hydroxyl PEG Carboxyl (Hydroxyl PEG Acetic Acid, HO-PEG-CM, HO-PEG-COOH). COOH group is stable and can be activated [1, 2]
HO-PEG-SCM ≥95% Hydroxyl PEG Succinimidyl Carboxymethyl Ester (HO-PEG-NHS). Crosslinking reagent, the activated form of HO-PEG-COOH [3, 4]
HO-PEG-PA ≥95% Hydroxyl PEG Propionic Acid (Hydroxyl PEG Propanoic Acid, HO-PEG-PA). COOH group is stable and can be activated
HO-PEG-SPA ≥95% Hydroxyl PEG Succinimidyl Propionate (Hydroxyl PEG Succinimidyl Propanoate, HO-PEG-SPA). Crosslinking reagent, the activated form of HO-PEG-PA
HO-PEG-NH2 ≥95% Hydroxyl PEG Amine (HO-PEG-NH2). NH2 group is stable and can be activated [8]
HS-PEG-CM ≥95% Thiol PEG Carboxyl (HS-PEG-COOH, Thiol PEG Acetic Acid, HS-PEG-CM). HS is thiol reactive, while COOH is stable and can be activated [5, 6]
HS-PEG-SPA ≥95% Thiol PEG Succinimidyl Propionate (HS-PEG-SPA). HS is thiol reactive while COOH is stable and can be activated
HS-PEG-SGA >90% Thiol PEG Succinimidyl Glutaramide (HS-PEG-SGA). Crosslinking PEG reagent. Longer hydrolysis half-life compared to the SCM NHS PEG ester. [7]
HS-PEG-NH2 ≥95% Thiol PEG Amine (HS-PEG-NH2). HS is thiol reactive and NH2 is stable and can be activated [9]
NH2-PEG-COOH ≥95% Amine PEG Carboxyl (NH2-PEG-COOH). Both COOH and NH2 groups are stable and can be activated [10, 11, 40, 41]
TBOC-PEG-OH ≥95% TBOC Amine PEG Hydroxyl (TBOC-PEG-OH). Crosslinking PEG reagent. Tert-butyloxycarbonyl (Boc) protection group can be removed by treatment with trifluoroacetic acid (TFA) or other common acids to provide a free amine [12]
TBOC-PEG-NH2 ≥95% TBOC Amine PEG Amine (TBOC-PEG-NH2). Crosslinking PEG reagent. Tert-butyloxycarbonyl (Boc) protection group can be removed by treatment with trifluoroacetic acid (TFA) or other common acids to provide a free amine [13]
TBOC-PEG-CM ≥95% TBOC Amine PEG Carboxyl (TBOC-PEG-COOH, TBOC-PEG-CM, TBOC PEG Acetic Acid). Tert-butyloxycarbonyl (Boc) protection group can be removed by treatment with trifluoroacetic acid (TFA) or other common acids to provide a free amine [15]
TBOC-PEG-SCM >90% TBOC Amine PEG SCM Ester (TBOC-PEG-SCM, TBOC-PEG-NHS, ). Crosslinking PEG for ADC development. Tert-butyloxycarbonyl (Boc) protection group can be removed by treatment with trifluoroacetic acid (TFA) or other common acids to provide a free amine [18]
TBOC-PEG-SPA >90% TBOC Amine PEG Succinimidyl Propionate (TBOC-PEG-SPA). Crosslinking PEG for ADC development. Tert-butyloxycarbonyl (Boc) protection group can be removed by treatment with trifluoroacetic acid (TFA) or other common acids to provide a free amine
FMOC-PEG-OH ≥95% FMOC Amine PEG Hydroxyl (FMOC-PEG-OH) Crosslinking PEG reagent. The 9-fluorenylmethoxycarbonyl (Fmoc) group can be removed by treatment with piperidine to release a free amine
FMOC-PEG-NH2 ≥95% FMOC Amine PEG Amine (FMOC-PEG-NH2). Crosslinking PEG reagent. 9-fluorenylmethoxycarbonyl (Fmoc) group can be removed by treatment with piperidine to release a free amine [14]
FMOC-PEG-CM ≥95% FMOC Amine PEG Carboxyl (FMOC-PEG-COOH, FMOC-PEG-CM, FMOC-PEG-Acetic Acid). The 9-fluorenylmethoxycarbonyl (Fmoc) group can be removed by treatment with piperidine to release a free amine [16, 17]
FMOC-PEG-SCM >90% FMOC Amine PEG NHS Ester (FMOC-PEG-SCM, FMOC-PEG-NHS). The 9-fluorenylmethoxycarbonyl (Fmoc) group can be removed by treatment with piperidine to release a free amine [19]
FMOC-PEG-SPA >90% FMOC Amine PEG Succinimidyl Propionate (FMOC PEG SPA). The 9-fluorenylmethoxycarbonyl (Fmoc) group can be removed by treatment with piperidine to release a free amine [19]
ACLT-PEG-SCM >90% Acrylate PEG NHS Ester (ACLT-PEG-NHS, ACLT-PEG-SCM). Light sensitive PEG, will crosslink with exposure to ultraviolet light [20-22]
ACLT-PEG-SPA >90% Acrylate PEG Succinimidyl Propionate (ACLT-PEG-SPA). Light sensitive PEG, will crosslink with exposure to ultraviolet light
MAL-PEG-OH ≥95% Maleimide PEG Hydroxyl (MAL-PEG-OH). Maleimide is thiol reactive and Hydroxyl is stable [23]
MAL-PEG-NH2 ≥95% Maleimide PEG Amine (MAL-PEG-NH2). Maleimide is thiol reactive and Amine is stable and can be activated [24]
MAL-PEG-CM ≥95% Maleimide PEG Carboxyl (MAL-PEG-CM, MAL-PEG-COOH). Maleimide is thiol reactive and Carboxyl is stable and can be activated [25]
MAL-PEG-NHS (SCM) >90% Maleimide PEG NHS Ester, the activated form of MAL-PEG-COOH [26-31]
BIOTIN-PEG-NHS >90% Biotin PEG SCM Ester. Biotin can be attached to avidin-containing surfaces or molecules; NHS ester reacts with amine groups [32]
BIOTIN-PEG-MAL ≥95% Biotin PEG Maleimide. Crosslinking reagent for ADC development. Biotin can be attached to avidin-containing surfaces or molecules; Maleimide group is thiol reactive [33]
BIOTIN-PEG-SGA ≥95% Biotin PEG Succinimidyl Glutaramide. Biotin can be attached to avidin-containing surfaces or molecules; SGA has a longer hydrolysis half-life compared with SCM NHS Ester [38]
OPSS-PEG-NHS (SCM) >90% OPSS PEG NHS Ester. Ortho-pyridyl disulfide (OPSS) is thiol reactive; NHS ester can be reacted with Amine groups [34]
AZIDE-PEG-NHS (SCM) >90% Azide PEG NHS Ester. The Azide group may be reduced to amine by hydrogenolysis; Click chemistry PEG reagent for reaction with alkynes [35]
AZIDE-PEG-NH2 ≥95% Azide PEG Amine. The Azide group may be reduced to amine by hydrogenolysis; Click PEG reagent for reaction with alkynes [36]
ALKYNE-PEG-MAL ≥95% Alkyne PEG Maleimide. Click PEG reagent for reaction with azides [37]
Other Heterobifunctional PEGs:
Monodisperse (Discrete) Heterobifunctional PEGs
Monodisperse Heterobifunctional PEGs 
Multiarm Heterobifunctional (3ARM, 4ARM, 6ARM and 8ARM PEGs) 
Multiarm Heterobifunctional PEGs 
Linear PEG Raw Materials (Methoxy PEG Hydroxyl and Benzyl PEG Hydroxyl)
PEG RAW MATERIAL MAIN PEAK FRACTION BY GPC  POLYDISPERSITY BY GPC
Methoxy PEG Hydroxyl ≥95% ≤ 1.05-1.10
BENZYL PEG Hydroxyl ≥95% ≤ 1.05
References:
    1. Xiao-Ding Xu, X.-D., et al., Smart and hyper-fast responsive polyprodrug nanoplatform for targeted cancer therapy, Biomaterials, 2016, Volume 76, Pages 238-249.
    2. Jones, S.K, et al., Folate Receptor Targeted Delivery of siRNA and Paclitaxel to Ovarian Cancer Cells via Folate Conjugated Triblock Copolymer to Overcome TLR4 Driven Chemotherapy Resistance, Biomacromolecules, 2016, 17 (1), 76-87.
    3. Jaskula-Sztul, R., et al., Thailandepsin A-loaded and octreotide-functionalized unimolecular micelles for targeted neuroendocrine cancer therapy, Biomaterials, 2016, 91:1-0.
    4. Chen, G., et al., KE108-conjugated unimolecular micelles loaded with a novel HDAC inhibitor thailandepsin-A for targeted neuroendocrine cancer therapy, Biomaterials, 2016, 97, p. 22-33.
    5. Koshkina, O., et al., Tuning the Surface of Nanoparticles: Impact of Poly (2‐ethyl‐2‐oxazoline) on Protein Adsorption in Serum and Cellular Uptake. Macromolecular Bioscience. 2016.
    6. Wang, L., et al., Sea-Urchin-Like Au Nanocluster with Surface-Enhanced Raman Scattering in Detecting Epidermal Growth Factor Receptor (EGFR) Mutation Status of Malignant Pleural Effusion, ACS Applied Materials & Interfaces, 2015, 7 (1), 359-369.
    7. Harrison, E., et al., A Comparison of Gold Nanoparticle Surface Co-functionalization and the Effect on Stability, Non-specific Protein Adsorption and Internalization. Materials Science and Engineering: C. 2016.
    8. Xu, Y., et al., Triphenylphosphonium-modified poly (ethylene glycol)-poly (ε-caprolactone) micelles for mitochondria-targeted gambogic acid delivery, International Journal of Pharmaceutics, 2017, 522(1):21-33.
    9. Politi, J., et al., Reversible sensing of heavy metal ions using lysine modified oligopeptides on porous silicon and gold, Sensors and Actuators B: Chemical, 2017, V. 244, P. 142-150.
    10. Zhao, L., et al., An intraocular drug delivery system using targeted nanocarriers attenuates retinal ganglion cell degeneration. Journal of Controlled Release. 2017.
    11. Sanna, V., et al., Targeted nanoparticles encapsulating (−)-epigallocatechin-3-gallate for prostate cancer prevention and therapy, Scientific Reports, 2017, 7:41573.
    12. Yu, H., et al., Enzyme sensitive, surface engineered nanoparticles for enhanced delivery of camptothecin, Journal of Controlled Release, 2015, Volume 216, Pages 111-120.
    13. Huo, M., et al., Tumor-targeted delivery of sunitinib base enhances vaccine therapy for advanced melanoma by remodeling the tumor microenvironment, Journal of Controlled Release, 2017, V. 245, P. 81-94.
    14. Kim, H.C., et al., Folic Acid-Functionalized Polythiophene for Targeted Cellular Imaging, Journal of Nanoscience and Nanotechnology, 2016, Volume 16, Number 1, pp. 189-195(7).
    15. Chen, F., et al., Glycyrrhetinic acid-decorated and reduction-sensitive micelles to enhance the bioavailability and anti-hepatocellular carcinoma efficacy of tanshinone IIA, Biomater. Sci., 2016,4, 167-182.
    16. Veiman, K.-L., et al., PEG shielded MMP sensitive CPPs for efficient and tumor specific gene delivery in vivo, Journal of Controlled Release 2015, 209: 238-247.
    17. Guarnieri, D., et al., Tumor‐activated prodrug (TAP)‐conjugated nanoparticles with cleavable domains for safe doxorubicin delivery, Biotechnology and Bioengineering 2015, 112(3): 601-611.
    18. Balasso, A., et al., Re-programming pullulan for targeting and controlled release of doxorubicin to the hepatocellular carcinoma cells, European Journal of Pharmaceutical Sciences, 2017.
    19. Zhang, J., et al., Liver-targeted antiviral peptide nanocomplexes as potential anti-HCV therapeutics, Biomaterials, Volume 70, November 2015, Pages 37-47.
    20. Slaughter, G., et al., Fabrication of palladium nanowire array electrode for biofuel cell application, Microelectronic Engineering, 2016, Volume 149, Pages 92-96.
    21. Wang, Y., et al., Electroresponsive Nanoparticles Improve Antiseizure Effect of Phenytoin in Generalized Tonic-Clonic Seizures. Neurotherapeutics. 2016:1-1.
    22. Lauridsen, H.M., et al., Ultrathin and elastic hydrogels regulate human neutrophil extravasation across endothelial-pericyte bilayers, PloS one, 2017, 12(2).
    23. Fang, Z., et al., Targeted osteosarcoma chemotherapy using RGD peptide-installed doxorubicin-loaded biodegradable polymeric micelle, Biomedicine & Pharmacotherapy, 2017, V. 85, P. 160-168.
    24. Verbeke, C. S., et al., Multicomponent Injectable Hydrogels for Antigen-Specific Tolerogenic Immune Modulation, Adv. Healthcare Mater. 2017, 6.
    25. Zhao, L., et al., An intraocular drug delivery system using targeted nanocarriers attenuates retinal ganglion cell degeneration. Journal of Controlled Release. 2017.
    26. Lopes, C.D.F., et al., BDNF gene delivery mediated by neuron-targeted nanoparticles is neuroprotective in peripheral nerve injury, Biomaterials, 2017, V. 121, P. 83-9627.
    27. Nascimento, A.V., et al., Overcoming cisplatin resistance in non-small cell lung cancer with Mad2 silencing siRNA delivered systemically using EGFR-targeted chitosan nanoparticles, Acta Biomaterialia, 2017, V. 47, P. 71-80
    28. Mesken, J., et al., Modifying plasmid-loaded HSA-nanoparticles with cell penetrating peptides–Cellular uptake and enhanced gene delivery, International journal of pharmaceutics, 2017, 522(1):198-209.
    29. Chen, H., et al., Dual aptamer modified dendrigraft poly-L-lysine nanoparticles for overcoming multi-drug resistance through mitochondrial targeting. Journal of Materials Chemistry B. 2017.
    30. Ji, Y., et al., A Novel Pseudo-Protein-Based Biodegradable Nanomicellar Platform for the Delivery of Anticancer Drugs, Small 2017, 13, 1601491.
    31. Dadras, P., et al., Formulation and evaluation of targeted nanoparticles for breast cancer theranostic system. European Journal of Pharmaceutical Sciences, 2017, 97:47-54.
    32. Son, Y.J., et al., Electrospun Nanofibrous Sheets for Selective Cell Capturing in Continuous Flow in Microchannels, Biomacromolecules, 2016.
    33. Khare, R., et al., Identification of Adenovirus Serotype 5 Hexon Regions That Interact with Scavenger Receptors, J. Virology, 2012, 86(4) p: 2293-2301.
    34. Feng, Y., et al., Evaluation of Electrospun PCL-PIBMD Meshes Modified with Plasmid Complexes in Vitro and in Vivo. Polymers, 2016, 8(3), p.58.
    35. Dai, Q., et al., Monoclonal Antibody-Functionalized Multilayered Particles: Targeting Cancer Cells in the Presence of Protein Coronas, ACS Nano 2015 9 (3), 2876-2885.
    36. . Guo, Y., et al., Cell Microenvironment-Controlled Antitumor Drug Releasing-Nanomicelles for GLUT1-Targeting Hepatocellular Carcinoma Therapy, ACS Applied Materials and Interfaces 2015.
    37. Zhou, Z., et al., Herceptin conjugated PLGA-PHis-PEG pH sensitive nanoparticles for targeted and controlled drug delivery, International Journal of Pharmaceutics, 2015, Volume 487, Issues 1–2, Pages 81-90.
    38. Ju, L., et al., Von Willebrand factor-A1 domain binds platelet glycoprotein Ibα in multiple states with distinctive force-dependent dissociation kinetics, Thrombosis Research, 2015, Volume 136, Issue 3, Pages 606-612.
    39. Alpsoy, L., et al., Synthesis and Characterization of Carboxylated Luteolin (CL)-Functionalized SPION, Journal of Superconductivity and Novel Magnetism, 2017.
    40. Clawson, G.A., et al., A Cholecystokinin B Receptor-Specific DNA Aptamer for Targeting Pancreatic Ductal Adenocarcinoma, Nucleic acid therapeutics, 2017, 27(1):23-35.
    41. Clawson, G.A., et al., A Cholecystokinin B Receptor-Specific DNA Aptamer for Targeting Pancreatic Ductal Adenocarcinoma, Nucleic acid therapeutics, 2017, 27(1):23-35.Founded in 2001 by recognized experts in PEG synthesis and PEGylation, JenKem Technology specializes exclusively in the development and manufacturing of high quality polyethylene glycol (PEG) products and derivatives, and related custom synthesis and PEGylation services. JenKem Technology is ISO 9001 and ISO 13485 certified, and adheres to ICH Q7A guidelines for GMP manufacture. The production of JenKem® PEGs is back-integrated to on-site manufacturing from ethylene oxide, enabling facile traceability for GMP regulated customers. JenKem Technology caters to the PEGylation needs of the pharmaceutical, biotechnology, medical device and diagnostics, and emerging chemical specialty markets, from laboratory scale through large commercial scale.