PMID- 23685180
OWN - NLM
STAT- MEDLINE
DCOM- 20140121
LR  - 20130614
IS  - 1464-3391 (Electronic)
IS  - 0968-0896 (Linking)
VI  - 21
IP  - 14
DP  - 2013 Jul 15
TI  - Design, synthesis and evaluation of retinoids with novel bulky hydrophobic 
      partial structures.
PG  - 4342-50
LID - S0968-0896(13)00379-9 [pii]
LID - 10.1016/j.bmc.2013.04.053 [doi]
AB  - Many synthetic retinoids contain an aromatic structure with a bulky hydrophobic 
      fragment. In order to obtain retinoids with therapeutic potential that do not 
      bind to or activate retinoic acid X receptors (RXRs), we focused on the 
      introduction of novel hydrophobic moieties, that is, metacyclophane, phenalene 
      and benzoheptalene derivatives. The designed compounds were synthesized and their 
      agonistic activities towards RARs and RXRs were evaluated. Most of the active 
      compounds showed selectivity for RARalpha and RARbeta over RARgamma, and higher RARbeta 
      transactivating activity seemed to correlate with higher cell 
      differentiation-inducing activity towards promyelocytic leukemia cell line HL-60. 
      These compounds showed no agonistic activity towards RXRs.
CI  - Copyright (c) 2013 Elsevier Ltd. All rights reserved.
FAU - Amano, Yohei
AU  - Amano Y
AD  - Research Foundation Itsuu Laboratory, 2-28-10 Tamagawa, Setagaya-ku, Tokyo 
      158-0094, Japan. yamano@itsuu.or.jp
FAU - Noguchi, Masayuki
AU  - Noguchi M
FAU - Nakagomi, Madoka
AU  - Nakagomi M
FAU - Muratake, Hideaki
AU  - Muratake H
FAU - Fukasawa, Hiroshi
AU  - Fukasawa H
FAU - Shudo, Koichi
AU  - Shudo K
LA  - eng
PT  - Journal Article
DEP - 20130429
PL  - England
TA  - Bioorg Med Chem
JT  - Bioorganic & medicinal chemistry
JID - 9413298
RN  - 0 (Receptors, Retinoic Acid)
RN  - 0 (Retinoid X Receptors)
RN  - 0 (Retinoids)
SB  - IM
MH  - Cell Differentiation/drug effects
MH  - *Drug Design
MH  - HL-60 Cells
MH  - Humans
MH  - Hydrophobic and Hydrophilic Interactions
MH  - Molecular Structure
MH  - Protein Binding/drug effects
MH  - Receptors, Retinoic Acid/*agonists
MH  - Retinoid X Receptors/*agonists
MH  - Retinoids/chemical synthesis/*chemistry/*pharmacology
EDAT- 2013/05/21 06:00
MHDA- 2014/01/22 06:00
CRDT- 2013/05/21 06:00
PHST- 2013/03/30 00:00 [received]
PHST- 2013/04/20 00:00 [revised]
PHST- 2013/04/22 00:00 [accepted]
PHST- 2013/05/21 06:00 [entrez]
PHST- 2013/05/21 06:00 [pubmed]
PHST- 2014/01/22 06:00 [medline]
AID - S0968-0896(13)00379-9 [pii]
AID - 10.1016/j.bmc.2013.04.053 [doi]
PST - ppublish
SO  - Bioorg Med Chem. 2013 Jul 15;21(14):4342-50. doi: 10.1016/j.bmc.2013.04.053. Epub 
      2013 Apr 29.