Iodohexestrols. I. Synthesis and photoreactivity of iodinated hexestrol derivatives

Katzenellenbogen, John A.; Hsiung, Hansen M.

doi:10.1021/bi00679a028

Cited by 13 publications

(5 citation statements)

References 14 publications

(13 reference statements)

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“…[2,4,6,7-3H]Estradiol (92 Ci/mmol), [6,7-3H]estradiol (42 Ci/mmol), 5a-[1,2-3H]dihydrotestosterone (55 Ci/mmol), and Nal25I (in low-pH high-concentration solution) were obtained from New England Nuclear. Unlabeled steroids were purchased from Steraloids, (Wilton, NH).…”

Section: Methodsmentioning

confidence: 99%

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Interaction of 16 alpha-[125I]iodo-estradiol with estrogen receptor and other steroid-binding proteins.

Hochberg¹,

Rosner²

1980

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

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This communication describes the synthesis of 16a["25Iliodo-estradiol "125I-E2) with specific activities >1000Ci/mmol (1 Ci = 3.7 X 10 becquerels). We show that it binds to the same specific estrogen receptor sites as does [3Hjestradiol and that it does so with an affinity that is indistinguishable from that for the latter steroid. This is true for receptor obtained from calf uterus and from a pool of human mammary carcinomas.There is no significantbinding of 125I-E2 to the testosteroneestradiol-binding globulin of human plasma. 125I-E2 also binds tightly to anti-estradiol antibodies raised against estradiol derivatized at carbons 3,6, and 17. Finally, we show that unlabeled I-E2 is an active estrogen in vivo as demonstrated by its ability to increase uterine weight in ovariectomized rats.The demonstration of receptors for steroid hormones necessitated the synthesis of such hormones with high degrees of specific radioactivity. Jensen and Jacobson (1) accomplished this task by synthesizing 3H-labeled estradiol (E2) with a sufficiently high specific activity and then showing that estrogen target tissues retained the 3H-labeled hormone even when the hormone concentration in blood was lower. These observations, together with the subsequent elucidation of soluble estrogen receptors (2) in the cytoplasm of estrogen target tissues, formed the foundation for a new area of both basic and applied research in steroid hormone action.

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Section: Methodsmentioning

confidence: 99%

“…These advantages of y-emitting isotopes are well known and the search for an estrogen containing such an isotope (3), which could bind specifically to estrogen receptors, has not been neglected (4)(5)(6)(7)(8). Until recently, attempts to synthesize appropriate compounds were unsuccessful.…”

mentioning

confidence: 99%

Interaction of 16 alpha-[125I]iodo-estradiol with estrogen receptor and other steroid-binding proteins.

Hochberg¹,

Rosner²

1980

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

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“…[26][27][28][29][30][31][32][33][34][35][36]. Several authors have also indicated that photoaffinity labelling is not a stoichiometric reaction ( [13], and references therein), but this problem has been overcome by using larger amounts of protein to obtain information about the active site.…”

Section: Discussionmentioning

confidence: 99%

Study of the rat liver S-adenosylmethionine synthetase active site with 8-azido ATP

Deigner

Mato

Pajares

1995

Biochemical Journal

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The active site of rat liver S-adenosylmethionine synthetase was studied using 8-azido ATP, a photolabile analogue of ATP. Both forms of the enzyme, tetramer and dimer, could be labelled by using concentrations of the analogue similar to the KmATP values for each form, 350 microM and 1 mM respectively. Labelling of both S-adenosylmethionine synthetase forms with 8-azido [alpha-32P]ATP, followed by tryptic digestion and purification by HPLC, afforded one specifically labelled peptide in each case. Identification of the labelled peptide by amino acid analysis and peptide sequencing, and comparison with the enzyme sequence, indicated that the same peptide (267-286) was modified in both enzyme forms. The results are discussed on the basis of the high degree of similarity that this peptide shows in all the known S-adenosylmethionine synthetase sequences.

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“…[3H]Hexestrol (86 Ci/mmol) was prepared by the method of Williams and Ronzio (1950), as described previously (Katzenellenbogen and Hsiung, 1975).…”

Section: Methodsmentioning

confidence: 99%

Estrogen photoaffinity labels. 1. Chemical and radiochemical synthesis of hexestrol diazoketone and azide derivatives; photochemical studies in solution

Katzenellenbogen¹,

Myers²,

Johnson³

et al. 1977

Biochemistry

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Two photosensitive estrogen derivatives, hexestrol diazoketopropyl ether (5) and hexestrol azide (8a), have been synthesized in radiolabeled form, and their photochemical behavior in solution has been studied. The radiolabeled compounds were prepared in good yields according to improved synthetic procedures; they are stable and were obtained with specific activities in the range of 50-100 Ci per mmol and radiochemical purities in excess of 95%. A simpler model system, phenyl diazoketoprophyl ether, was used to study the photochemical behavior of the diazoketopropyl ether group. Direct irradiation of this compound at 254 nm in methanol led to 33% insertion product (methoxyketone) and 67% Wolff rearrangement product (ester). Irradiation of [3H]hexestrol diazoketopropyl ether (5) in methanol gives mainly nonpolar photoproducts (presumed to be the methoxy ketone and ester); however, irradiation in aqueous medium leads to large amounts of free hexestrol (52%). Photolysis of hexestrol azide (8a) in either methanol or water gives the corresponding amine in low yield as the only identifiable photoproduct.

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Iodohexestrols. I. Synthesis and photoreactivity of iodinated hexestrol derivatives

Cited by 13 publications

References 14 publications

Interaction of 16 alpha-[125I]iodo-estradiol with estrogen receptor and other steroid-binding proteins.

Interaction of 16 alpha-[125I]iodo-estradiol with estrogen receptor and other steroid-binding proteins.

Study of the rat liver S-adenosylmethionine synthetase active site with 8-azido ATP

Estrogen photoaffinity labels. 1. Chemical and radiochemical synthesis of hexestrol diazoketone and azide derivatives; photochemical studies in solution

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