PMID- 16938270
OWN - NLM
STAT- MEDLINE
DCOM- 20061114
LR  - 20151119
IS  - 0006-291X (Print)
IS  - 0006-291X (Linking)
VI  - 349
IP  - 1
DP  - 2006 Oct 13
TI  - Synthesis, discovery and mechanism of 2,6-dimethoxy-N-(4-methoxyphenyl)benzamide 
      as potent depigmenting agent in the skin.
PG  - 39-49
AB  - In this study, a new skin-depigmenting agent, 
      2,6-dimethoxy-N-(4-methoxyphenyl)benzamide (DMPB), was synthesized using a 
      combination of benzoic acid and aniline. DMPB exhibited significant 
      depigmentation ability on the UV B-induced hyperpigmentation of the brown guinea 
      pig skin. In addition, the 100ppm treatment with this compound had a 30% 
      inhibitory effect on melanin pigment generation in the melan-a cell line without 
      significant cell toxicity. To search for relationship with the depigmentation, 
      the effects of DMPB on the tyrosinase and dopachrome tautomerase were evaluated. 
      DMPB had no effect on tyrosinase. However, it accelerated dopachrome 
      transformation into 5,6-dihydroxyindole-2-carboxylic acid (DHICA) in the presence 
      of dopachrome tautormerase. In addition, intracellular level of dopachrome 
      tautomerase in melan-a cells was increased by treatment of DMPB. These results 
      suggest that the pigment-lightening effects of DMPB might be due to biased 
      production of DHICA-eumelanin induced by dopachrome tautormerase activation.
FAU - Choi, Sang Yoon
AU  - Choi SY
AD  - Korea Food Research Institute, Songnam, Republic of Korea.
FAU - Hwang, Jae Sung
AU  - Hwang JS
FAU - Kim, Sanghee
AU  - Kim S
FAU - Kim, Sun Yeou
AU  - Kim SY
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20060810
PL  - United States
TA  - Biochem Biophys Res Commun
JT  - Biochemical and biophysical research communications
JID - 0372516
RN  - 0 (2,6-dimethoxy-N-(4-methoxyphenyl)benzamide)
RN  - 0 (Aniline Compounds)
RN  - 0 (Anisoles)
RN  - 0 (Benzamides)
RN  - 0 (Indoles)
RN  - 4790-08-3 (5,6-dihydroxy-2-indolylcarboxylic acid)
RN  - 8SKN0B0MIM (Benzoic Acid)
RN  - EC 1.14.18.1 (Monophenol Monooxygenase)
RN  - EC 5.3.- (Intramolecular Oxidoreductases)
RN  - EC 5.3.3.12 (dopachrome isomerase)
RN  - SIR7XX2F1K (aniline)
SB  - IM
MH  - Aniline Compounds/chemistry
MH  - Animals
MH  - Anisoles/*chemical synthesis/*chemistry
MH  - Benzamides/*chemical synthesis/chemistry
MH  - Benzoic Acid/chemistry
MH  - Cell Line, Tumor
MH  - Enzyme Activation
MH  - Guinea Pigs
MH  - Humans
MH  - Indoles/chemistry
MH  - Intramolecular Oxidoreductases/chemistry
MH  - Models, Chemical
MH  - Monophenol Monooxygenase/chemistry
MH  - Skin/*drug effects
EDAT- 2006/08/30 09:00
MHDA- 2006/11/15 09:00
CRDT- 2006/08/30 09:00
PHST- 2006/07/13 00:00 [received]
PHST- 2006/07/21 00:00 [accepted]
PHST- 2006/08/30 09:00 [pubmed]
PHST- 2006/11/15 09:00 [medline]
PHST- 2006/08/30 09:00 [entrez]
AID - S0006-291X(06)01689-5 [pii]
AID - 10.1016/j.bbrc.2006.07.206 [doi]
PST - ppublish
SO  - Biochem Biophys Res Commun. 2006 Oct 13;349(1):39-49. doi: 
      10.1016/j.bbrc.2006.07.206. Epub 2006 Aug 10.