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Titolo:
CONFORMATION-FUNCTION RELATIONSHIP OF VITAMIN-D - CONFORMATIONAL-ANALYSIS PREDICTS POTENTIAL SIDE-CHAIN STRUCTURE
Autore:
YAMADA S; YAMAMOTO K; MASUNO H; OHTA M;
Indirizzi:
TOKYO MED & DENT UNIV,INST MED & DENT ENGN,CHIYODA KU,2-3-10 SURUGADAI KANDA TOKYO 101 JAPAN
Titolo Testata:
Journal of medicinal chemistry
fascicolo: 9, volume: 41, anno: 1998,
pagine: 1467 - 1475
SICI:
0022-2623(1998)41:9<1467:CROV-C>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Soggetto:
D ENDOCRINE SYSTEM; DIFFERENTIATION-INDUCING ACTIVITY; LEUKEMIA CELLS HL-60; BIOLOGICAL-ACTIVITY; 1-ALPHA,25-DIHYDROXYVITAMIN D-3; D ANALOGS; GENE-REGULATION; D CALCIFEROL; CALCIUM; METABOLISM;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
63
Recensione:
Indirizzi per estratti:
Citazione:
S. Yamada et al., "CONFORMATION-FUNCTION RELATIONSHIP OF VITAMIN-D - CONFORMATIONAL-ANALYSIS PREDICTS POTENTIAL SIDE-CHAIN STRUCTURE", Journal of medicinal chemistry, 41(9), 1998, pp. 1467-1475

Abstract

In previous studies, we have grouped regions in space occupied by thevitamin D side chain into four: A, G, EA, and EG. We showed that the receptor (VDR) affinity of 1 alpha,25-dihydroxyvitamin D-3 derivativesincreases, in terms of side-chain region, in the order EG, G, A, and EA. We called this the active space group concept. In the present study, we used this active space group concept to analyze the conformation-activity relationship of about 40 representative potent 1 alpha,25-dihydroxyvitamin D-3 analogues. We initially listed structural modifications in the side chain of potent vitamin D analogues and estimated their potency factor. Possible side-chain conformations of representativeanalogues were calculated by the molecular mechanics method and plotted on a dot map compared with the regions A, G, EA, and EG. The cell-differentiating potency of the analogues was correlated with our activespace group concept with few exceptions. Among potent analogues with a natural configuration at C(20), the side chains of those with a 22-oxa, 22-ene, 16-ene, or a 18-nor modification were located in front of region EA (termed F). The side chains of the most potent 20-epi-22-oxa-24-homovitamin D analogues were concentrated at the left side of the EA region(L-EA). Thus, the side chains of almost all potent analogues were distributed around the EA region, and potency increased in the order A, F, EA, and L-EA.

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Documento generato il 21/09/20 alle ore 01:30:18