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Chemical Compound Review

D-DOC     4-amino-1-[(2R,4R)-2- (hydroxymethyl)-1,3...

Synonyms: CHEMBL300793, SureCN1844439, AC1L9RF9, (+/-)-DOC, cis-Dioxolane-C, ...
 
 
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Disease relevance of cis-Dioxolane-C

  • Thus, a significant number of patients with essential hypertension presumably have an alteration in 18-OH DOC secretion [1].
  • The marked hypokalemia in DOC-water and DOC-salt hypertension was associated with a slight loss of red cell K+ and an increase in mean cellular hemoglobin content (MCHC), indicative of cell shrinkage [2].
  • Na+-fed animals responded to DOC administration with a large increment in net acid excretion and complete correction of metabolic acidosis [3].
  • Monotherapy with ONO-4817 or DOC inhibited formation of lung metastasis by PC14PE6 and H226 cells [4].
  • It is believed that alterations in electrolyte balance induced by DOC or spironolactone caused changes in adrenocortical function which greatly modified the usual pathophysiological response to myocardial infarction [5].
 

Psychiatry related information on cis-Dioxolane-C

  • PRA was significantly increased by Adx, captopril treatment, and water deprivation, and was almost suppressed by Nx, DOC-salt, and DOC-salt plus captopril treatment.(ABSTRACT TRUNCATED AT 250 WORDS)[6]
  • Our purpose was to determine the therapeutic efficacy of a selective-spectrum MMPI, ONO-4817 (inhibits MMP-2 and MMP-9 but not MMP-1), against established lung micrometastasis in combination with a cytotoxic anticancer drug, DOC, in a nude mouse model [4].
  • However, the best Fe(2+)/H(2)O(2) dosage was 1200 mg/L Fe(2+)/800 mg/L H(2)O(2) at pH 4 and in reaction time of 20 min for mineralization of DOC and COD [7].
 

High impact information on cis-Dioxolane-C

  • Patients with normal and low renin hypertension had similar changes in plasma 18-OH DOC levels with sodium restriction [1].
  • At low methyl-4-mercaptobutyrimidate (MMB) concentrations (0.26 mg/ml) only 30% of the ribosomes were cross-linked to the microsomal membranes, as shown by the puromycin-KCl test, but membranes could still be solubilized with 1% DOC [8].
  • A sequential increase in liver RNA concentration, [14C]leucine incorporation into DOC-soluble proteins and into immunoprecipitable catalase, and an increase in liver size and peroxisomal volume per gram liver, characterize the trophic effect of the drug used [9].
  • CUL7: A DOC domain-containing cullin selectively binds Skp1.Fbx29 to form an SCF-like complex [10].
  • We studied the effects on blood pressure and heart rate of two different phenylethanolamine N-methyltransferase (PNMT) inhibitors in normotensive, in two-kidney renal hypertensive, and in deoxycorticosterone-salt (DOC-salt) hypertensive rats [11].
 

Chemical compound and disease context of cis-Dioxolane-C

 

Biological context of cis-Dioxolane-C

  • However, in DOC-salt hypertensive rats, it reduced arterial pressure to approximately normal levels and concomitantly slowed pulse rate [11].
  • A model is presented which accounts for the kinetics of exchange of (21R)- and (21S)-[21-3H]DOC with water, interconversion of DOC and isoDOC, and the epimerization of isoDOC at C-20 [15].
  • In conclusion, dietary calcium supplementation attenuates the rise in peripheral vascular resistance that accompanies DOC-salt hypertension [16].
  • Hypokalemia induced by dietary K+ deficiency caused alterations in red cell cation transport, content, and cell volume which were qualitatively similar but more pronounced than those seen in DOC-salt hypertension [2].
  • The effect of changes in dietary sodium intake and of DOC hypertension on plasma atrial natriuretic peptide (PANP), and affinity (Kd) and number (Bmax) of vascular atrial natriuretic peptide binding sites was studied in the rat [17].
 

Anatomical context of cis-Dioxolane-C

  • Four weeks after local DOC implantation, despite MHC class II expression, second-set allogeneic skin rejection showed similar survival to first-set allogeneic skin rejection and DOC appeared to function as osteoblasts [18].
  • Results showed that osteogenic cells differentiated from MSC (DOC) in vitro did not express the MHC class II molecule, were incapable of inducing allogeneic lymphocyte proliferation in mixed lymphocyte culture or generating CTL, were inhibitory in ongoing lymphocyte proliferation, and secreted anti-inflammatory cytokines (IL-10 and TGF-beta) [18].
  • Sodium and potassium ion transport accelerations in erythrocytes of DOC, DOC-salt, two-kidney, one clip, and spontaneously hypertensive rats. Role of hypokalemia and cell volume [2].
  • Since plasma DOC and DOC-SO4 are not interconverted, we conclude that both steroids are secretory products, presumably from the adrenal cortex [19].
  • Concomitant with matrix-stimulated proliferation, we observed a marked reduction in PC containing alpha vascular smooth muscle actin (alpha VSMA), as seen by immunofluorescence using affinity-purified antibodies (173/615 positive pericytes on DOC matrix (28%) vs. 221/285 (77%) positive on glass) [20].
 

Associations of cis-Dioxolane-C with other chemical compounds

  • A partial characterization of the substrata indicates that the substratum prepared by deoxycholic acid extraction (DOC-derived substratum) is enriched with fibronectin and type IV collagen [21].
  • In the rat urinary bioassay, 19-nor DOC shows no antagonist activity when injected with aldosterone; in the absence of aldosterone, 19-nor DOC acts as a mineralocorticoid agonist, with an apparent potency 10-30% that of aldosterone [22].
  • The percentage increases in the brain and plasma concentrations of pregnenolone, progesterone, 3alpha,5alpha-TH PROG, and 3alpha,5alpha-TH DOC, apparent 20 min after a single intraperitoneal injection of ethanol (1 g/kg), were thus markedly greater in isolated rats than in group-housed animals [23].
  • Provision of DOC as substrate for the endogenous aldosterone synthase and 11beta-hydroxylase did not significantly increase brain aldosterone or corticosterone content [24].
  • In a different group of rats ganglionic blockade with chlorisondamine also caused a greater decrease in blood pressure in DOC-salt rats compared to controls (99 +/- 6 vs 58 +/- 4 mm Hg, respectively) [25].
 

Gene context of cis-Dioxolane-C

 

Analytical, diagnostic and therapeutic context of cis-Dioxolane-C

  • In conclusion, DOC retained their immunoprivileged and immunomodulatory properties in vitro, but the latter was lost following transplantation [18].
  • Withdrawal of DOC-salt combined with low-salt diet for 11 weeks did not result in a discernible regression of these intimal changes despite normalization of blood pressure [30].
  • Systemic and regional hemodynamic measurements were determined by the radioactive microsphere technique in conscious and unrestrained rats (kidneys intact) with DOC-salt-induced hypertension that were pair-fed either a normal calcium (0.6% by weight, n = 12) or a calcium-supplemented (high-calcium) diet (2.5% by weight, n = 12) [16].
  • In addition, combined use of ONO-4817 with DOC significantly suppressed the tumor burden of H226 and PC14PE6 cells in the lung and prolonged the survival of PC14PE6-bearing mice compared to ONO-4817 or DOC alone [4].
  • Addition of Triton-X or DOC to 35,000g supernatants of hair bulb and melanoma homogenates followed by centrifugation at 100,000g results in a marked enhancement of T1 when the latter supernatants are treated with trypsin [31].

References

  1. The regulation of plasma 18-hydroxy 11-deoxycorticosterone in man. Williams, G.H., Braley, L.M., Underwood, R.H. J. Clin. Invest. (1976) [Pubmed]
  2. Sodium and potassium ion transport accelerations in erythrocytes of DOC, DOC-salt, two-kidney, one clip, and spontaneously hypertensive rats. Role of hypokalemia and cell volume. Duhm, J., Göbel, B.O., Beck, F.X. Hypertension (1983) [Pubmed]
  3. Mineralocorticoid-stimulated renal acidification: the critical role of dietary sodium. Harrington, J.T., Hulter, H.N., Cohen, J.J., Madias, N.E. Kidney Int. (1986) [Pubmed]
  4. A third-generation matrix metalloproteinase (MMP) inhibitor (ONO-4817) combined with docetaxel suppresses progression of lung micrometastasis of MMP-expressing tumor cells in nude mice. Yamamoto, A., Yano, S., Shiraga, M., Ogawa, H., Goto, H., Miki, T., Zhang, H., Sone, S. Int. J. Cancer (2003) [Pubmed]
  5. Opposing effects of deoxycorticosterone and spironolactone on isoprenaline-induced myocardial infarction. Wexler, B.C. Cardiovasc. Res. (1979) [Pubmed]
  6. Angiotensinogen concentration in the cerebrospinal fluid in different experimental conditions in the rat. Ruiz, P., Basso, N., Grinspon, D., Mangiarua, E., Cannata, M.A. Hypertension (1983) [Pubmed]
  7. Decolorization of a baker's yeast industry effluent by Fenton oxidation. Pala, A., Erden, G. Journal of hazardous materials. (2005) [Pubmed]
  8. Proteins of rough microsomal membranes related to ribosome binding. II. Cross-linking of bound ribosomes to specific membrane proteins exposed at the binding sites. Kreibich, G., Freienstein, C.M., Pereyra, B.N., Ulrich, B.L., Sabatini, D.D. J. Cell Biol. (1978) [Pubmed]
  9. Structure, composition, physical properties, and turnover of proliferated peroxisomes. A study of the trophic effects of Su-13437 on rat liver. Leighton, F., Coloma, L., Koenig, C. J. Cell Biol. (1975) [Pubmed]
  10. CUL7: A DOC domain-containing cullin selectively binds Skp1.Fbx29 to form an SCF-like complex. Dias, D.C., Dolios, G., Wang, R., Pan, Z.Q. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  11. Blood pressure response to central and/or peripheral inhibition of phenylethanolamine N-methyltransferase in normotensive and hypertensive rats. Black, J., Waeber, B., Bresnahan, M.R., Gavras, I., Gavras, H. Circ. Res. (1981) [Pubmed]
  12. Contribution of vasopressin to hypertension. Share, L., Crofton, J.T. Hypertension (1982) [Pubmed]
  13. Pressor responsiveness to vasopressin in the rat with DOC-salt hypertension. Crofton, J.T., Share, L., Wang, B.C., Shade, R.E. Hypertension (1980) [Pubmed]
  14. Metabolism of progesterone to DOC, corticosterone and 18OHDOC in cultured human melanoma cells. Slominski, A., Gomez-Sanchez, C.E., Foecking, M.F., Wortsman, J. FEBS Lett. (1999) [Pubmed]
  15. Presence of epimerase activity in hamster liver corticosteroid side chain isomerase. Monder, C., Martin, K.O., Bogumil, J. J. Biol. Chem. (1980) [Pubmed]
  16. Systemic and regional hemodynamic effects of dietary calcium supplementation in mineralocorticoid hypertension. DiPette, D.J., Greilich, P.E., Kerr, N.E., Graham, G.A., Holland, O.B. Hypertension (1989) [Pubmed]
  17. Rat atrial natriuretic peptide vascular receptor: effect of alterations in sodium balance and of DOC hypertension. Morton, J.J., Lyall, F., Wallace, E.C. J. Hypertens. (1987) [Pubmed]
  18. The immunogenicity and immunomodulatory function of osteogenic cells differentiated from mesenchymal stem cells. Liu, H., Kemeny, D.M., Heng, B.C., Ouyang, H.W., Melendez, A.J., Cao, T. J. Immunol. (2006) [Pubmed]
  19. Origin and production rates of deoxycorticosterone and deoxycorticosterone sulfate in men and nonpregnant women. Casey, M.L., MacDonald, P.C. J. Clin. Endocrinol. Metab. (1983) [Pubmed]
  20. Pericyte growth and contractile phenotype: modulation by endothelial-synthesized matrix and comparison with aortic smooth muscle. Newcomb, P.M., Herman, I.M. J. Cell. Physiol. (1993) [Pubmed]
  21. Substratum-induced stress fiber assembly in vascular endothelial cells during spreading in vitro. Yost, J.C., Herman, I.M. J. Cell. Sci. (1990) [Pubmed]
  22. 19-Nor deoxycorticosterone (19-nor DOC): mineralocorticoid receptor affinity higher than aldosterone, electrolyte activity lower. Funder, J.W., Mercer, J., Ingram, B., Feldman, D., Wynne, K., Adam, W.R. Endocrinology (1978) [Pubmed]
  23. Social isolation-induced increase in the sensitivity of rats to the steroidogenic effect of ethanol. Serra, M., Pisu, M.G., Floris, I., Cara, V., Purdy, R.H., Biggio, G. J. Neurochem. (2003) [Pubmed]
  24. Is aldosterone synthesized within the rat brain? Gomez-Sanchez, E.P., Ahmad, N., Romero, D.G., Gomez-Sanchez, C.E. Am. J. Physiol. Endocrinol. Metab. (2005) [Pubmed]
  25. Contributions of vasopressin and other pressor systems to DOC-salt hypertension in rats. Mento, P.F., Wang, H.H., Sawyer, W.H. Proc. Soc. Exp. Biol. Med. (1984) [Pubmed]
  26. Characterization of the DOC1/APC10 subunit of the yeast and the human anaphase-promoting complex. Grossberger, R., Gieffers, C., Zachariae, W., Podtelejnikov, A.V., Schleiffer, A., Nasmyth, K., Mann, M., Peters, J.M. J. Biol. Chem. (1999) [Pubmed]
  27. Effects of endothelin-1 and endothelin-3 on blood pressure in conscious hypertensive rats. Watanabe, T.X., Kumagaye, S., Nishio, H., Nakajima, K., Kimura, T., Sakakibara, S. J. Cardiovasc. Pharmacol. (1989) [Pubmed]
  28. Homology modelling of the ligand binding domain of mineralocorticoid receptor: close structural kinship with glucocorticoid receptor ligand binding domain and their similar binding mode with DOC (de-oxy corticosterone). Dey, R., Roychowdhury, P. J. Biomol. Struct. Dyn. (2002) [Pubmed]
  29. Interaction of Disabled-1 and the GTPase activating protein Dab2IP in mouse brain. Homayouni, R., Magdaleno, S., Keshvara, L., Rice, D.S., Curran, T. Brain Res. Mol. Brain Res. (2003) [Pubmed]
  30. Effects of hypertension and its reversal on aortic intima lesions of the rat. Haudenschild, C.C., Prescott, M.F., Chobanian, A.V. Hypertension (1980) [Pubmed]
  31. Action of trypsin and detergents on tyrosinase of normal and malignant melanocytes. Quevedo, W.C., Holstein, T.J., Bienieki, T.C. Proc. Soc. Exp. Biol. Med. (1975) [Pubmed]
 
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