Retinoid


Retinoid

The retinoids are a class of chemical compounds that are related chemically to vitamin A. Retinoids are used in medicine, primarily due to the way they regulate epithelial cell growth.

Retinoids have many important and diverse functions throughout the body including roles in vision, regulation of cell proliferation and differentiation, growth of bone tissue, immune function, and activation of tumor suppressor genes.

Research is also being done into their ability to treat skin cancers. Currently 9-cis retinoic acid may be used topically to help treat skin lesions from Kaposi's sarcoma.

Types

There are three generations of Retinoids:

* First generation retinoids: which include retinol, retinal, tretinoin (retinoic acid, Retin-A), isotretinoin and alitretinoin.

* Second generation retinoids: which include etretinate and its metabolite acitretin.

* Third generation retinoids: which include tazarotene , bexarotene and Adapalene.

tructure

The basic structure of the retinoid molecule consist of a cyclic end group, a polyene side chain and a polar end group. The conjugated system formed by alternating C=C double bonds in the polyene side chain are responsible for the color of retinoids (typically yellow, orange, or red). Hence, many retinoids are chromophores. Alternation of side chains and end groups creates the various classes of retinoids.

First and Second generation retinoids are able to bind with several retinoid receptors due to the flexibility imparted by their alternating single and double bonds.

Third generation retinoids are less flexible than First and Second generation retinoids and therefore, interact with fewer retinoid receptors.

Absorption

The major source of retinoids from the diet are retinyl esters derived from animal sources. Retinyl esters are hydrolyzed in the intestinal lumen to yield free retinol and the corresponding fatty acid (i.e. palmitate or stearate). After hydrolysis, retinol is taken up by the enterocytes. Retinyl ester hydrolysis requires the presence of bile salts that serve to solubilize the retinyl esters in mixed micelles and to activate the hydrolyzing enzymes [Noy, N. (2006) "Vitamin A", "Biochemical, Physiological, & Molecular Aspects of Human Nutrition", M. H. Stipanuk 2nd Ed.]

Several enzymes that are present in the intestinal lumen may be involved in the hydrolysis of dietary retinyl esters. Cholesterol esterase is secreted into the intestinal lumen from the pancreas and has been shown in vitro to display retinyl ester hydrolase activity. In addition, a retinyl ester hydrolase that is intrinsic to the brush-border membrane of the small intestine has been characterized in the rat as well as in the human. The different hydrolyzing enzymes are activated by different types of bile salts and have distinct substrate specificites. For example, whereas the pancreatic estrase is selective for short-chain retinyl esters, the brush-border membrane enzyme preferentially hydrolyzes retinyl esters containing a long-chain fatty acid such as palmitate or stearate. Retinol enters the absorptive cells of the small intestine, preferentially in the all-trans-retinol form .

Uses

Retinoids are used in the treatment of many diverse diseases and are effective in the treatment of a number of dermatological conditions such as inflammatory skin disordersFact|date=February 2007, skin cancersFact|date=February 2007, disorders of increased cell turnover (e.g. psoriasis)Fact|date=February 2007, and photoagingFact|date=February 2007.

Common skin conditions treated by retinoids include acne and psoriasisFact|date=February 2007.

Toxicity

Toxic effects occur with prolonged high intake. The specific toxicity is related to exposure time and the exposure concentration. A medical sign of chronic poisoning is the presence of painful tender swellings on the long bones. Anorexia, skin lesions, hair loss, hepatosplenomegaly, papilloedema, bleeding, general malaise, pseudotumor cerebri, and death may also occur.

Chronic overdose also causes an increased liability of biological membranes and of the outer layer of the skin to peel. [citation needed]

Recent research [citation needed] has suggested a role for retinoids in cutaneous adverse effects for a variety of drugs including the Antimalarial drug proguanil. It is proposed that drugs such as proguanil act to disrupt retinoid homeostasis.

References

* The Pharmacological Basis of Therapeutics -Goodman & Gilman 10th EDT.

* Clinical Pharmacology -P.N. Bennett & M.J. Brown

ee also

*Adapalene
*Hypervitaminosis A syndrome
*Biotinylated retinoids

External links

*


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Synonyms:

Look at other dictionaries:

  • Retinoid — Ret i*noid, a. [Gr. ??? resin + oid.] Resinlike, or resinform; resembling a resin without being such. [1913 Webster] …   The Collaborative International Dictionary of English

  • retinoid — [ret′ n oid΄] n. any of a large class of natural or synthetic, photosensitive chemical compounds that are similar to vitamin A, including retinoic acid and retinal …   English World dictionary

  • Retinoid — Retinoide sind chemische Substanzen, die in ihrer chemischen Struktur oder in ihrer biologischen Aktivität verwandt mit dem Retinol (Vitamin A) sind. [1] Inhaltsverzeichnis 1 Definitionsgeschichte 2 Therapeutisch eingesetzte Retinoide 2.1 Nicht… …   Deutsch Wikipedia

  • retinoid — 1. Resembling a resin; resinous. [G. retine, resin, + eidos, resemblance] 2. Resembling the retina. [Mediev. L. retina] 3. In plural form, term used to describe the natural forms and synthetic analogs of retinol. * * * ret·i·noid ret ən .ȯid n …   Medical dictionary

  • retinoid — noun Date: 1976 any of various synthetic or naturally occurring analogs of vitamin A …   New Collegiate Dictionary

  • retinoid — /ret n oyd /, n. 1. Biochem. any of a group of substances related to vitamin A and functioning like vitamin A in the body. adj. 2. resembling the retina. [1975 80; RETIN(OL) + OID] * * * …   Universalium

  • retinoid — 1. adjective Of or pertaining to the retina 2. noun Any of a class of compounds related to vitamin A …   Wiktionary

  • Retinoid — Re|ti|no|id [↑ Retin u. ↑ oid], das; s, e: Sammelbez. für physiol. aktive Derivate des Retinols (Vitamin A1), z. B. Retinale, Retinylester u. Retinoesäuren sowie deren synthetische Analoga u. Stereoisomere. Manchmal werden die R. zu den… …   Universal-Lexikon

  • Retinoid — Retino|i̱d [Kurzbildung aus ↑Retinol u. ↑...id] s; [e]s, e (meist Mehrz.): Bez. für Derivate von Vitamin A …   Das Wörterbuch medizinischer Fachausdrücke

  • retinoid — [ rɛtɪnɔɪd] noun Biochemistry any of a group of compounds having effects like those of vitamin A …   English new terms dictionary