Monomers, Macromonomers [Biomaterials/Biocompatible Materials Research Reagents]

We present in this category the monomers used for biomaterials research classified according to their chemical structures such as acrylic monomers, lactone monomers, dithiol monomers, and diisocyanate monomers.

Among them acrylic monomers contain largest number of products and are often utilized for biomaterials or biocompatible materials research, using conventional radical polymerization or controlled radical polymerization. In addition to the common monomers for biomaterials research including 2-hydroxyethyl methacrylate (HEMA) [M0085]¹⁾ and N-isopropylacrylamide (NIPAAm) [I0401]²⁾, TCI has zwitterionic monomers or monomers with reactive functional groups useful for conjugation with proteins or peptides present in our catalog.

Zwitterionic monomers contain both cationic and anionic groups in the same molecule. Common zwitterionic monomer structures include phosphobetaines, sulfobetaines, and carboxybetaines.^3,4) One of the phosphobetaine zwitterionic monomers, 2-(methacryloyloxy)ethyl 2-(trimethylammonio)ethyl phosphate (MPC) [M2005]⁵⁾ is the most studied zwitterionic monomer and has been applied to toiletries or soft contact lenses.⁴⁾ TCI offers 3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propane-1-sulfonate (SPE) [M1971]⁶⁾ as a sulfobetaine monomer，3-[[2-(methacryloyloxy)ethyl]dimethylammonio]propionate [M2359]⁷⁾ and 3-[(3-acrylamidopropyl)dimethylammonio]propanoate [A3279]⁷⁾ as carboxybetaine monomers.

Zwitterionic polymers synthesized from its zwitterionic monomers are expected to be applied to surface coating materials in medical devices including stents, catheters, and membranes for dialysis.^4,8,9,10,11) Research towards drug delivery system (DDS) have been increasing lately; e.g. application as nanomicellar drug carriers,¹²⁾ as coating materials for nanoparticles with prolonged blood circulation,¹³⁾ and as hydrogels providing sustained release of the therapeutic materials.¹⁴⁾ Application for assays or diagnosis are also expected, and noise reduction of a glucose sensor by coating electrodes by zwitterionic polymers was also reported.¹⁵⁾ In addition, cell culture mediums are another promising application of zwitterionic monomers. For example, expansion of human hematopoietic stem cells with reduced differentiation on a zwitterionic hydrogel was reported.¹⁶⁾

As monomers are helpful for the conjugation of polymers with proteins or peptides, TCI provides N-succinimidyl acrylate [S0814] and N-succinimidyl methacrylate [S0812] having NHS ester moiety which react with primary amines, and pentafluorophenyl acrylate [P2179] and pentafluorophenyl methacrylate [P2289] having pentafluorophenyl ester group, etc.

References

• 1) Permeation of water through some hydrogels
• • F. Refojo, J. Appl. Polym. Sci. 1965, 9, 3417.
• 2) Cellular interactions with synthetic polymer surfaces in culture
• • J. Lydon, T. W Minett, B. J Tighe, Biomaterials 1985, 6, 396.
• 3) Molecular design of zwitterionic polymer interfaces: Searching for the difference
• • A. Laschewsky, A. Rosenhahn, Langmuir 2019, 35, 1056.
• 4) Zwitterionic polymers and hydrogels for antibiofouling applications in implantable devices
• • N. Erathodiyil, H. Chan, H. Wu, J. Y. Ying, Mater. Today 2020, 38, 84.
• 5) Preparation of Phospholipid Polymers and Their Properties as Polymer Hydrogel Membranes
• • K. Ishihara, T. Ueda, N. Nakabayashi, Polym. J. 1990, 22, 355.
• 6) Influence of Composition on Properties of Hydrogels of 2-Hydroxyethyl Methacrylate with a Sulphobetaine Comonomer
• • J. M Rego, M. B Huglin, Polym. J. 1991, 23, 1425.
• 7) Synthesis and characteristics of the poly(carboxybetaine)s and the corresponding cationic polymers
• • D.‐J. Liaw, C.‐C. Huang, W.‐F. Lee, J. Borbély, E.‐T. Kang, J. Polym. Sci. A: Polym. Chem. 1997, 35, 3527.
• 8) Cell membrane-inspired phospholipid polymers for developing medical devices with excellent biointerfaces
• • Y. Iwasaki, K. Ishihara, Sci. Technol. Adv. Mater. 2012, 13, 064101.
• 9) Latest advances in zwitterionic structures modified dialysis membranes
• • F. Refojo, J. Appl. Polym. Sci 1965, 9, 3417.
• 10) Vascular catheters with a nonleaching poly-sulfobetaine surface modification reduce thrombus formation and microbial attachment
• • S. Smith, Z. Zhang, M. Bouchard, J. Li, H. S. Lapp, G. R. Brotske, D. L. Lucchino, D. Weaver, L. A. Roth, A. Coury, J. Biggerstaff, S. Sukavaneshvar, R. Langer, C. Loose, Sci. Transl. Med. 2012, 4, 153ra132.
• 11) Zwitterionic poly-carboxybetaine coating reduces artificial lung thrombosis in sheep and rabbits
• • R. Ukita, K. Wu, X. Lin, N. M. Carleton, N. Naito, A. Lai, C. Do-Nguyen, C. T. Demarest, S. Jiang, K. E. Cook, Acta Biomaterialia 2019, 92, 71.
• 12) Micelles with ultralow critical micelle concentration as carriers for drug delivery
• • Y. Lu, Zhanguo Yue, J. Xie, W. Wang, H. Zhu, E. Zhang, Z. Cao, Nat. Biomed. Eng. 2018, 2, 318.
• 13) Biodegradable zwitterionic polymer membrane coating endowing nanoparticles with ultra-long circulation and enhanced tumor photothermal therapy
• • S. Peng, B. Ouyang, Y. Men, Y. Du, Y. Cao, R. Xie, Z. Pang, S. Shen, W. Yang, Biomaterials 2020, 231, 119680.
• 14) Injectable, self-healable zwitterionic cryogels with sustained microRNA - cerium oxide nanoparticle release promote accelerated wound healing
• • G. Sener, S. A. Hilton, M. J. Osmond, C. Zgheib, J. P. Newsom, L. Dewberry, S. Singh, T. S. Sakthivel, S. Seal, K. W. Liechty, M. D. Krebs, Acta Biomaterialia 2020, 101, 262.
• 15) Reduction of measurement noise in a continuous glucose monitor by coating the sensor with a zwitterionic polymer
• • X. Xie, J. C. Doloff, V. Yesilyurt, A. Sadraei, J. J. McGarrigle, M. Omami, O. Veiseh, S. Farah, D. Isa, S. Ghani, I. Joshi, A. Vegas, J. Li, W. Wang, A. Bader, H. H. Tam, J. Tao, H. Chen, B. Yang, K. A. Williamson, J. Oberholzer, R. Langer, D. G. Anderson, Nat. Biomed. Eng. 2018, 2, 894.
• 16) Expansion of primitive human hematopoietic stem cells by culture in a zwitterionic hydrogel
• • T. Bai, J. Li, A. Sinclair, S. Imren, F. Merriam, F. Sun, M. B. O’Kelly, C. Nourigat, P. Jain, J. J. Delrow, R. S. Basom, H.-C. Hung, P. Zhang, B. Li, S. Heimfeld, S. Jiang, C. Delaney, Nat. Med. 2019, 5, 1566.

Related Product Category Page

• Drug Delivery Systems (DDS)