Testosterone Receptor Binding Mimic Constructed Using Molecular Imprinting

Cheong, Soo-Hwan; McNiven, Scott; Rachkov, A. E.; Levi, Raphael; Yano, Kazuyoshi; Karube, Isao

doi:10.1021/ma961014l

Cited by 144 publications

(65 citation statements)

References 33 publications

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“…The capacity factor (k') was calculated as (t À t o ) / t o , where t is retention time of the solute and t o is the retention time of the void marker; the separation factor of a given nontemplate analyte was defined as a = k' t / k' x , where k' t and k' x is the capacity factors of the template and the other compound, respectively [10]. The imprinting factor (I) is defined as I = k' i / k' n where k' i and k n , refer to the imprinted and nonimprinted polymers [8].…”

Section: Chromatographic Evaluationmentioning

confidence: 99%

“…The amount of the bound template was determined as the difference between the amount in reference tubes (containing no polymer) and the amount of free Tst in the sample. The polymers imprinted against Tst, Aen and Adien as well as the nonimprinted one were synthesized under the conditions employed in our previous works [8,9]: template±monomer ratio 1 : 8, CHCl 3 as porogen. The structure of the templates used is very similar: Aen possesses a keto group at the C-17 position instead of the OH group in Tst, Adien contains an additional double bond between C-1 and C-2 compared with Aen (Fig.…”

Section: Batch Rebinding Experimentsmentioning

confidence: 99%

“…Moreover, the abundance of steroids, possessing the same core structure as well as variable arrangements of the substituted functional groups, allows the systematic investigation of the role of these functional groups and their combinations in the process of molecular recognition. Our previous studies of the polymers imprinted against testosterone [8,9] have enabled us to suggest so-called two-point binding of template inside recognition sites and the leading role of hydrogen bonds between the OH group at C-17 of testosterone and carboxyl group of methacrylic acid. To get additional evidence in favor of this assumption and to elucidate the role of steroids' C-3 keto group it seemed promising to use as template some steroids without an OH group.…”

mentioning

confidence: 99%

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Molecularly imprinted polymers as artificial steroid receptors

Rachkov

Cheong

El’skaya

et al. 1998

Polym. Adv. Technol.

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The polymers selective to six different steroids (testosterone, Δ4‐androstene‐3,17‐dione, 1,4‐androstadiene‐3,17‐dione, β‐estradiol, progesterone, testosterone propionate) have been synthesized using molecular imprinting based on noncovalent interactions. Analysis of the influence of structural features of the steroids under study has shown that molecules with a relatively rigid structure and the OH group at C‐17 position are the most efficient templates for methacrylic acid‐containing imprinted polymers. The chromatographic study of the polymers synthesized has demonstrated a strong dependence of the selectivity and intensity of interaction with analytes on the composition of solvents used both as porogen and chromatographic mobile phase. To obtain polymers with highly selective recognition sites and to create the optimal conditions for molecular recognition, all possible interactions (between template and functional monomer, template and solvent, solvent and functional monomer) should be taken into account. The batch rebinding study of testosterone by the imprinted polymer in acetonitrile has revealed some heterogeneity of recognition sites, and permitted determination of Kass = 1.05 × 104 M−1, ΔG° = −5.4 kcal/mol and N = 1.2 μmol/g for high‐affinity sites and Kass = 0.33 × 104 M−1, ΔG° = −4.8 kcal/mol and N = 2.2 μmol/g for low‐affinity sites. The results obtained show how it is possible to regulate in different modes the molecular recognition by imprinted polymers as well as to fabricate polymers possessing the necessary properties depending on their practical application.© 1998 John Wiley & Sons, Ltd.

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Section: Chromatographic Evaluationmentioning

confidence: 99%

Section: Batch Rebinding Experimentsmentioning

confidence: 99%

mentioning

confidence: 99%

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Molecularly imprinted polymers as artificial steroid receptors

Rachkov

Cheong

El’skaya

et al. 1998

Polym. Adv. Technol.

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“…In aprotic solvents such as acetonitrile and chloroform, ethyl adenine-9-acetate and N-Z-L-Glu MIPs were prepared successively with MAA as functional monomer [1,30]. Often, a large excess of MAA in the synthesis step is required for recognition to be observed and then only in solvents of low to medium polarity and hydrogen bond capacity [31]. The excess of functional monomer results in a portion not being associated with imprinted sites.…”

Section: Selection Of Functional Monomermentioning

confidence: 99%

Synthesis and binding site characteristics of 2,4,6-trichlorophenol-imprinted polymers

et al. 2008

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2,4,6-Trichlorophenol (2,4,6-TCP)-imprinted micro-and submicrospheres prepared by precipitation polymerization were compared with templated materials obtained by conventional bulk polymerization. The influence of the type and amount of functional monomer, the type and amount of cross-linker, polymerization temperature, porogen, and the ratio of template molecule and functional monomer to cross-linker on the size of the obtained particles were investigated. UV-Vis spectrophotometer experiments revealed that the microsphere polymers provided higher affinity to the template in contrast to imprinted polymers prepared by bulk polymerization. The binding properties of the microspheres, including binding isotherms and affinity distribution, were studied via Freundlich isotherm affinity distribution (FIAD) analysis. The obtained results indicated that microspheres prepared by precipitation polymerization provided superior rebinding properties during equilibrium binding in contrast to bulk polymers and submicrosphere polymers. Moreover, release experiments showed that 80% of rebound 2,4,6-TCP was released from the imprinted microspheres within the first 2 h, while more intimately bound 2,4,6-TCP molecules were released in the following 40 h. The morphologies and porosities of the resulting imprinted materials were characterized by scanning electron microscopy (SEM) and Brunauer-Emmett-Teller (BET) analysis, respectively. The microsphere polymers exhibited a regular spherical shape with a high degree of monodispersity to the corresponding bulk polymers. Furthermore, the micro-and submicrospheres were characterized by narrow distribution of pores in contrast to a heterogeneity index of m=0.6647 for the microsphere imprinted polymer.

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“…For instance, Cheong et al have shown a higher absorption of estradiol by MIP imprinted for testosterone. 12 The time-dependent release of T from the MIP to water in the absence of Hy is summarized in Table II. It is apparent that even after 24 h, nearly 55% of the compound is retained in the MIP.…”

Section: Release Of T To Water In the Presence Of Hymentioning

confidence: 99%

On the application of molecularly imprinted poly(HEMA) as a template responsive release system

Sreenivasan

1999

J. Appl. Polym. Sci.

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2-Hydroxy-ethyl-methacrylate-based molecularly imprinted polymer imprinted for hydrocortisone was found to absorb a considerable amount of testosterone. The release of testosterone to water was found to be very slow. Its release was, however, rapid in the presence of the print molecule (hydrocortisone). This opens up the possibility of developing drug release systems capable of modulating the release with respect to the presence of specific molecules. Such systems could be used in the release of steroids and peptides.

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Testosterone Receptor Binding Mimic Constructed Using Molecular Imprinting

Cited by 144 publications

References 33 publications

Molecularly imprinted polymers as artificial steroid receptors

Molecularly imprinted polymers as artificial steroid receptors

Synthesis and binding site characteristics of 2,4,6-trichlorophenol-imprinted polymers

On the application of molecularly imprinted poly(HEMA) as a template responsive release system

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