PMID- 12904083
OWN - NLM
STAT- MEDLINE
DCOM- 20030909
LR  - 20181221
IS  - 0022-2623 (Print)
IS  - 0022-2623 (Linking)
VI  - 46
IP  - 17
DP  - 2003 Aug 14
TI  - Conformationally defined retinoic acid analogues. 5. Large-scale synthesis and 
      mammary cancer chemopreventive activity for 
      (2E,4E,6Z,8E)-8-(3',4'-dihydro-1'(2'H)-naphthalen-1'-ylidene)-3,7-dimethyl-2,4,6-octatrienoic 
      acid (9cUAB30).
PG  - 3766-9
AB  - Retinoids that activate the nuclear retinoid X receptors (RXRs) display potential 
      for chemoprevention of breast cancer. We previously reported that 9cUAB30 (1) is 
      an RXR-selective retinoid. To explore its in vivo chemopreventive activity, 
      multigram quantities of 1 were needed. Here, we describe a modified synthesis 
      that yields up to 100 g of 1. We further demonstrate that 1 is very effective in 
      the prevention of N-methyl-N-nitrosourea induced mammary cancers in rats without 
      signs of toxicity.
FAU - Atigadda, Venkatram R
AU  - Atigadda VR
AD  - Department of Chemistry, University of Alabama at Birmingham, 901 South 14th 
      Street, Birmingham, AL 35294, USA.
FAU - Vines, Kimberly K
AU  - Vines KK
FAU - Grubbs, Clinton J
AU  - Grubbs CJ
FAU - Hill, Donald L
AU  - Hill DL
FAU - Beenken, Samuel L
AU  - Beenken SL
FAU - Bland, Kirby I
AU  - Bland KI
FAU - Brouillette, Wayne J
AU  - Brouillette WJ
FAU - Muccio, Donald D
AU  - Muccio DD
LA  - eng
GR  - 1P50 CA 89019/CA/NCI NIH HHS/United States
GR  - R01 CA 73844/CA/NCI NIH HHS/United States
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PT  - Research Support, U.S. Gov't, P.H.S.
PL  - United States
TA  - J Med Chem
JT  - Journal of medicinal chemistry
JID - 9716531
RN  - 0 (Anticarcinogenic Agents)
RN  - 0 (Fatty Acids, Unsaturated)
RN  - 0 (Naphthalenes)
RN  - 0 (Receptors, Retinoic Acid)
RN  - 0 (Retinoid X Receptors)
RN  - 0 (Transcription Factors)
RN  - 5688UTC01R (Tretinoin)
RN  - PFP09575EX (UAB 30)
SB  - IM
MH  - Animals
MH  - Anticarcinogenic Agents/*chemical synthesis/chemistry/pharmacology
MH  - Drug Screening Assays, Antitumor
MH  - Fatty Acids, Unsaturated/*chemical synthesis/chemistry/pharmacology
MH  - Female
MH  - Mammary Neoplasms, Experimental/*prevention & control
MH  - Naphthalenes/*chemical synthesis/chemistry/pharmacology
MH  - Rats
MH  - Rats, Sprague-Dawley
MH  - Receptors, Retinoic Acid/agonists
MH  - Retinoid X Receptors
MH  - Stereoisomerism
MH  - Transcription Factors/agonists
MH  - Tretinoin/*analogs & derivatives/*chemical synthesis/pharmacology
EDAT- 2003/08/09 05:00
MHDA- 2003/09/10 05:00
CRDT- 2003/08/09 05:00
PHST- 2003/08/09 05:00 [pubmed]
PHST- 2003/09/10 05:00 [medline]
PHST- 2003/08/09 05:00 [entrez]
AID - 10.1021/jm030095q [doi]
PST - ppublish
SO  - J Med Chem. 2003 Aug 14;46(17):3766-9. doi: 10.1021/jm030095q.