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Constant variation in structure and function of geometrical isomers of acitretin under natural light

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Title Constant variation in structure and function of geometrical isomers of acitretin under natural light
 
Creator Murayama, Akira
Suzuki, Takakazu
Iwamoto, Minoru
Kunchala, Sridhar Rao
 
Description 22-27
Acitretin, a beneficial retinoid, was
shown to undergo constant structural interconversions among its geometrical
isomers (all-trans-acitretin, 9-cis-acitretin, 13-cis-acitretin,
9, 13-di-cis-acitretin, etc.) by photoisomerization under natural light.
The photoisomerization was zero order reaction with an apparent velocity of
4×10-7 M/min under illumination by

white fluorescent lamps (1, 200 1x). An equilibrium
mixture of the geometrical isomers (all-trans-acitretin 20%, 9-cis-acitretin
15%, 13-cis-acitretin 30%, 9, 13-di-cis-acitretin 15%, and unidentified
compounds 20%) was formed at around 30 min. Equilibrium mixtures with similar
composition were obtained by photoisomerization reactions starting from other

geometrical isomers. Geometrical isomers of
acitretin thus formed, showed different effects to induce differentiation of human
acute promyelocytic leukemia cells (HL-60 cells): activity of all-trans-acitretin
(ED50, 3.2×10-6M), 9-cis-acitretin (ED50,
2.3×10-5M), 13-cis-acitretin (ED50, 1.1×10-5M),
9, 13-di-cis-acitretin (ED50, 2.6×10-6M)
9-cis-Acitretin acted synergistically with all-trans-acitretin, 13-cis-acitretin
and 9, 13-di-cis-acitretin on HL-60 cells. On the other side, all-trans-acitretin,
13-cis-acitretin and 9, 13-di-cis-acitretin acted additively. Geometrical
isomers of acitretin showed different effects on differentiation of human epidermal
keratinocytes; expression of keratinocyte differentiation markers, keratin 1 and
kerati 10, were suppressed more strongly by 9-cis-acitretin and 13-cis-acitretin
as compared to all-trans-acitretin or 9, 13-di-cis-acitretin.
 
Date 2013-07-15T06:04:02Z
2013-07-15T06:04:02Z
2002-02
 
Type Article
 
Identifier 0975-0959 (Online); 0301-1208 (Print)
http://hdl.handle.net/123456789/19745
 
Language en_US
 
Rights CC Attribution-Noncommercial-No Derivative Works 2.5 India
 
Publisher NISCAIR-CSIR, India
 
Source IJBB Vol.39(1) [February 2002]