Structural requirements for the action of steroids as quenchers of albumin fluorescence

Romeu, A; Martino, Elba E.; Stoppani, A. O. M.

doi:10.1016/0005-2760(75)90033-8

Cited by 14 publications

(9 citation statements)

References 22 publications

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“…4). For 5␣-androstane-3,17-dione, results were similar to the reduction of 4-androstene-3,17-dione, i.e., with the guidance of BSA, it yielded C-17 reduced product, again proving the binding of steroids to BSA chiefly involves the A, B, and C rings instead of the B, C, and D rings proposed by Romeu et al (1975Romeu et al ( , 1976. For 4-cholestene-3-one, there is only one C-3 keto group.…”

Section: Resultssupporting

confidence: 81%

“…Selective reduction of one of the two has been attempted using molecularly imprinted polymers as a regio auxiliary (Bystrom et al, 1993) and with various reducing agents (D'Incan et al, 1982;Paradisi and Zecchini, 1982;Robinson and Henderson, 1972). Romeu et al investigated binding between steroids and albumins using a fluorescence technique, and concluded that binding to albumin chiefly involved the B, C, and D rings of steroids and the C-17 side chains; while the C-3 end lies at the extremity of the binding site (Romeu et al, 1975(Romeu et al, , 1976. Therefore, if we use BSA as a regio auxiliary and use a nonselective reducing agent (e.g., NaBH 4 , NaCNBH 3 , etc.)…”

Section: Introductionmentioning

confidence: 99%

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New approach to regioselective synthesis: Using proteins in vitro as guidance—regioselective reduction of steroids with guidance from bovine serum albumin

Liu

Kayser²

2003

Biotech & Bioengineering

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A novel approach for regioselective synthesis is described. The approach uses the unique binding properties of protein as a guide to achieve regioselectivity. Specifically, steroids, e.g., 4-androstene-3,17-dione, were reduced selectively at carbon 17 using bovine serum albumin (BSA) as a regio auxiliary. The approach has resulted in a high yield (ca. 91%) in an environmental friendly aqueous medium. Both (1)H NMR and (13)C NMR data show that the BSA-assisted reduction of the steroid render the reaction regioselective compared to the control reaction. Various control reactions were performed to verify that the unique binding of BSA to steroids was the origin of regioselectivity. After one cycle of the reduction reaction, BSA was reconditioned such that it could be reused five or more times. This novel approach could be used to develop practical and "green" methods for regioselective synthesis.

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Section: Resultssupporting

confidence: 81%

Section: Introductionmentioning

confidence: 99%

New approach to regioselective synthesis: Using proteins in vitro as guidance—regioselective reduction of steroids with guidance from bovine serum albumin

Liu

Kayser²

2003

Biotech & Bioengineering

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“…DHEAS can form a mass-action driven complex with albumin, the quantity of complex decreasing with decreasing DHEAS content. The albumin molecule has great flexibility and exists in different configurations when bound to various ligands, there being a mutuality of interaction so that the configurations of both albumin and ligands in the complexes may be different from those in the unbound states (30)(31)(32)(33)(34)(35). We posit that DHEAS at 10 Ϫ5 M concentration or less forms a 1:1 complex with albumin (32) that has a greater affinity for T than unbound albumin has for FIG.…”

Section: Discussionmentioning

confidence: 97%

Potentially predictive and manipulable blood serum correlates of aging in the healthy human male: Progressive decreases in bioavailable testosterone, dehydroepiandrosterone sulfate, and the ratio of insulin-like growth factor 1 to growth hormone

Morley

Kaiser

Raum

et al. 1997

Proc. Natl. Acad. Sci. U.S.A.

266

119

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A cross-sectional survey was made in 56 exceptionally healthy males, ranging in age from 20 to 84 years. Measurements were made of selected steroidal components and peptidic hormones in blood serum, and cognitive and physical tests were performed. Of those blood serum variables that gave highly significant negative correlations with age (r > ؊0.6), bioavailable testosterone (BT), dehydroepiandrosterone sulfate (DHEAS), and the ratio of insulinlike growth factor 1 (IGF-1) to growth hormone (GH) showed a stepwise pattern of age-related changes most closely resembling those of the age steps themselves. Of these, BT correlated best with significantly age-correlated cognitive and physical measures. Because DHEAS correlated well with BT and considerably less well than BT with the cognitive and physical measures, it seems likely that BT and͞or substances to which BT gives rise in tissues play a more direct role in whatever processes are rate-limiting in the functions measured and that DHEAS relates more indirectly to these functions. The high correlation of IGF-1͞GH with age, its relatively low correlation with BT, and the patterns of correlations of IGF-1͞GH and BT with significantly age-correlated cognitive and physical measures suggest that the GH-IGF-1 axis and BT play independent roles in affecting these functions. Serial determinations made after oral ingestion of pregnenolone and data from the literature suggest there is interdependence of steroid metabolic systems with those operational in control of interrelations in the GH-IGF-1 axis. Longitudinal concurrent measurements of serum levels of BT, DHEAS, and IGF-1͞GH together with detailed studies of their correlations with agecorrelated functional measures may be useful in detecting early age-related dysregulations and may be helpful in devising ameliorative approaches.

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“…These results suggest that the bias of E 1 -S in unstripped serum could be caused by binding to proteins, a phenomenon which was reported and studied previously [16][17][18][19][20]. Steroids interact with bovine plasma albumin at a binding region that involves tryptophanyl, tyrosyl, arginyl and lysyl residues [20].…”

Section: Accuracy Of Quality Controls Of E 1 -S and Protein Binding Imentioning

confidence: 64%

“…E 1 -S was found to strongly bind to albumin at two sites [16,18]. It has also been shown that the benzenoid A-ring and sulfate group in the vicinity of C-3 increase the interaction between the steroid and albumin [19]. Since only E 1 -S but none of the other four sulfates apparently binds to proteins, it is reasonable to attribute E 1 -S protein binding to the specific benzenoid structure of the steroid.…”

Section: Accuracy Of Quality Controls Of E 1 -S and Protein Binding Imentioning

confidence: 98%

Validated LC–MS/MS simultaneous assay of five sex steroid/neurosteroid-related sulfates in human serum

Dury¹,

Ke²,

Gonthier³

et al. 2015

The Journal of Steroid Biochemistry and Molecular Biology

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Structural requirements for the action of steroids as quenchers of albumin fluorescence

Cited by 14 publications

References 22 publications

New approach to regioselective synthesis: Using proteins in vitro as guidance—regioselective reduction of steroids with guidance from bovine serum albumin

New approach to regioselective synthesis: Using proteins in vitro as guidance—regioselective reduction of steroids with guidance from bovine serum albumin

Potentially predictive and manipulable blood serum correlates of aging in the healthy human male: Progressive decreases in bioavailable testosterone, dehydroepiandrosterone sulfate, and the ratio of insulin-like growth factor 1 to growth hormone

Validated LC–MS/MS simultaneous assay of five sex steroid/neurosteroid-related sulfates in human serum

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