Synthesis of molecularly imprinted polymers using an amidine-functionalized initiator for carboxylic acid recognition
Viltres-Portales, Marcia ; Alberto, Markel Denet Luaces and Ye, Lei LU
(2021)
In Reactive and Functional Polymers
165.
- Abstract
In traditional molecular imprinting reactions, the initial radicals generated by thermo- or photo-decomposition are randomly distributed in the reaction mixture. Because a noticeable portion of the initial radicals is able to cause self-polymerization of the crosslinking monomer, a significant part of the polymer product does not contain successfully imprinted molecular recognition sites. To solve this problem, we designed a molecular imprinting method using functionalized radical initiator to replace the conventional combination of initiator and functional monomer. Since the active radicals in the reaction mixture carry a template-binding moiety, the actual radical polymerization becomes more likely to take place nearby the molecular... (More)
In traditional molecular imprinting reactions, the initial radicals generated by thermo- or photo-decomposition are randomly distributed in the reaction mixture. Because a noticeable portion of the initial radicals is able to cause self-polymerization of the crosslinking monomer, a significant part of the polymer product does not contain successfully imprinted molecular recognition sites. To solve this problem, we designed a molecular imprinting method using functionalized radical initiator to replace the conventional combination of initiator and functional monomer. Since the active radicals in the reaction mixture carry a template-binding moiety, the actual radical polymerization becomes more likely to take place nearby the molecular template. As a result, the efficiency of molecular imprinting can be improved. In this work, we report the use of amidine-functionalized initiator to synthesize molecularly imprinted polymers (MIPs) for selective recognition of methotrexate, a cytostatic drug used for cancer therapy. As glutamic acid represents a substructure of methotrexate, we select to use N-terminal protected glutamic acid as template to synthesize the MIPs. An initiator, 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH) is used to provide strong interaction with the molecular template. Two MIPs synthesized using glutamic acid derivatives as templates display specific binding to the fluorescent amino acid derivative Fmoc-Glu. When the molecular binding is tested against methotrexate, the MIP particles also exhibit specific binding for the cytostatic drug. Using cationic functional initiator to target carboxyl epitope of molecular target, this work provides an additional example of molecular imprinting based on functionalized radical initiators.
(Less)
- author
- Viltres-Portales, Marcia
; Alberto, Markel Denet Luaces
and Ye, Lei
LU
- organization
- publishing date
- 2021-08-01
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Amidine, Cytostatic drug, Functional initiator, Glutamic acid, Methotrexate, Molecularly imprinted polymer
- in
- Reactive and Functional Polymers
- volume
- 165
- article number
- 104969
- publisher
- Elsevier
- external identifiers
-
- scopus:85109159760
- ISSN
- 1381-5148
- DOI
- 10.1016/j.reactfunctpolym.2021.104969
- language
- English
- LU publication?
- yes
- additional info
- Funding Information: The authors thank the European Commission for financial support to the project RECOPHARMA (grant number 778266 ) in Horizon 2020.
- id
- c1a20af7-a5b8-4503-abef-7488534c03d8
- date added to LUP
- 2021-08-18 13:56:51
- date last changed
- 2022-04-27 03:15:01
@article{c1a20af7-a5b8-4503-abef-7488534c03d8,
abstract = {{<p>In traditional molecular imprinting reactions, the initial radicals generated by thermo- or photo-decomposition are randomly distributed in the reaction mixture. Because a noticeable portion of the initial radicals is able to cause self-polymerization of the crosslinking monomer, a significant part of the polymer product does not contain successfully imprinted molecular recognition sites. To solve this problem, we designed a molecular imprinting method using functionalized radical initiator to replace the conventional combination of initiator and functional monomer. Since the active radicals in the reaction mixture carry a template-binding moiety, the actual radical polymerization becomes more likely to take place nearby the molecular template. As a result, the efficiency of molecular imprinting can be improved. In this work, we report the use of amidine-functionalized initiator to synthesize molecularly imprinted polymers (MIPs) for selective recognition of methotrexate, a cytostatic drug used for cancer therapy. As glutamic acid represents a substructure of methotrexate, we select to use N-terminal protected glutamic acid as template to synthesize the MIPs. An initiator, 2,2′-azobis(2-amidinopropane) dihydrochloride (AAPH) is used to provide strong interaction with the molecular template. Two MIPs synthesized using glutamic acid derivatives as templates display specific binding to the fluorescent amino acid derivative Fmoc-Glu. When the molecular binding is tested against methotrexate, the MIP particles also exhibit specific binding for the cytostatic drug. Using cationic functional initiator to target carboxyl epitope of molecular target, this work provides an additional example of molecular imprinting based on functionalized radical initiators.</p>}},
author = {{Viltres-Portales, Marcia and Alberto, Markel Denet Luaces and Ye, Lei}},
issn = {{1381-5148}},
keywords = {{Amidine; Cytostatic drug; Functional initiator; Glutamic acid; Methotrexate; Molecularly imprinted polymer}},
language = {{eng}},
month = {{08}},
publisher = {{Elsevier}},
series = {{Reactive and Functional Polymers}},
title = {{Synthesis of molecularly imprinted polymers using an amidine-functionalized initiator for carboxylic acid recognition}},
url = {{http://dx.doi.org/10.1016/j.reactfunctpolym.2021.104969}},
doi = {{10.1016/j.reactfunctpolym.2021.104969}},
volume = {{165}},
year = {{2021}},
}