Galactoflavin

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Galactoflavin
Galactoflavin.svg
Names
IUPAC name
7,8-Dimethyl-10-[(2S,3R,4S,5R)-2,3,4,5,6-pentahydroxyhexyl]benzo[g]pteridine-2,4-dione
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H22N4O7/c1-7-3-9-10(4-8(7)2)22(5-11(24)14(26)15(27)12(25)6-23)16-13(19-9)17(28)21-18(29)20-16/h3-4,11-12,14-15,23-27H,5-6H2,1-2H3,(H,21,28,29)/t11-,12+,14+,15-/m0/s1
    Key: RPADDAUXKBBASM-MXYBEHONSA-N
  • CC1=CC2=C(C=C1C)N(C3=NC(=O)NC(=O)C3=N2)C[C@@H]([C@H]([C@H]([C@@H](CO)O)O)O)O
Properties
C18H22N4O7
Molar mass 406.395 g·mol−1
AppearanceYellow solid
Melting point 260 °C (500 °F; 533 K) (dec)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Galactoflavin is a synthetic compound and riboflavin (vitamin B2) antagonist and antimetabolite. It is a biochemical tool used primarily in research to induce riboflavin deficiency in animal models and humans. It is structurally similar to riboflavin, where the ribose-derived side chain is replaced by a galactose-derived group.

Contents

Chemical properties

Galactoflavin's chemical formula is C18H22N4O7 and has a molecular weight of 406.40 g/mol. Galactoflavin appears as yellow crystals that decompose at 260 °C and exhibit absorption maxima at 223, 267, 370, and 445 nm. [1] It displays yellow-green fluorescence in water. [1]

Biological activity

As a riboflavin analog, galactoflavin competes with riboflavin in metabolic pathways, leading to depletion of riboflavin-containing coenzymes such as flavin mononucleotide (FMN) and flavin adenine dinucleotide (FAD) in tissues such as liver and kidney. [2] This antagonism results in riboflavin deficiency symptoms that are reversible with excess riboflavin supplementation. In rats, galactoflavin feeding reduces flavin content in mitochondria and affects oxidative phosphorylation. [3]

The antiriboflavin effect of galactoflavin was first demonstrated in 1945 and was found to produce riboflavin deficiency in rats reversible by excess riboflavin. [4]

In humans, galactoflavin rapidly induces riboflavin deficiency, with clinical signs including anemia, glossitis, angular stomatitis, and dermatitis appearing within weeks. [5]

Research uses

Galactoflavin has been employed to study the effects of riboflavin deficiency on growth, enzyme activity, and congenital malformations. [6] [7] [8] In pregnant rats, it induces multiple congenital abnormalities in embryos, including cardiovascular defects and hydrocephalus, by disrupting terminal electron transport systems. It has also been investigated for potential antitumor effects due to its ability to cause regression of tumors in rodents through riboflavin deficiency.

In mice, dietary galactoflavin affects hepatocyte ultrastructure. [9] It impairs adrenal ascorbic acid response to stress in rats. [10]

References

  1. 1 2 Merck Index (11th ed.), p. 678, 4239. Galactoflavin
  2. ↑ PROSKY L; BURCH HB; BEJRABLAYA D; LOWRY OH; COMBS AM (1964). "The Effects of Galactoflavin on Riboflavin Enzymes and Coenzymes". The Journal of Biological Chemistry. 239 (8): 2691–2695. doi: 10.1016/S0021-9258(18)93906-2 . PMID   14235554.
  3. ↑ Beyer, Robert E.; Lamberg, Stanley L.; Neyman, M. Arthur (1961). "The Effect of Riboflavin Deficiency and Galactoflavin Feeding on Oxidative Phosphorylation and Related Reactions in Rat Liver Mitochondria". Canadian Journal of Biochemistry and Physiology. 39: 73–88. doi:10.1139/o61-009.
  4. ↑ Gladys A. Emerson, Elizabeth Wurtz, and Oscar H. Johnson (1945). "The Antiriboflavin Effect of Galactoflavin". Journal of Biological Chemistry. 160 (1): 165–167. doi: 10.1016/S0021-9258(18)43108-0 .{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ↑ Lane, Montague; Alfrey, Clarence P.; Mengel, Charles E.; Doherty, Maureen A.; Doherty, Jean (1964). "The Rapid Induction of Human Riboflavin Deficiency with Galactoflavin". Journal of Clinical Investigation. 43 (3): 357–373. doi:10.1172/JCI104921. PMC   441929 . PMID   14135487.
  6. ↑ Nelson, Marjorie M.; Baird, Catherine D.C.; Wright, Howard V.; Evans, Herbert M. (1956). "Multiple Congenital Abnormalities in the Rat Resulting from Riboflavin Deficiency Induced by the Antimetabolite Galactoflavin". The Journal of Nutrition. 58: 125–134. doi:10.1093/jn/58.1.125. PMID   13286747.
  7. ↑ Aksu, Oguz; MacKler, Bruce; Shepard, Thomas H.; Lemire, Ronald J. (1968). "Studies of the development of congenital anomalies in embryos of riboflavin-deficient, galactoflavin fed rats. II. Role of the terminal electron transport systems". Teratology. 1 (1): 93–102. doi:10.1002/tera.1420010110. PMID   4302703.
  8. ↑ Lane, M.; Brindley, C. O. (1964). "Laboratory and Clinical Studies with the Riboflavin Antagonist, Galactoflavin". Experimental Biology and Medicine. 116: 57–61. doi:10.3181/00379727-116-29158. PMID   14200132.
  9. ↑ Tandler, Bernard; Hoppel, Charles L. (1974). "Ultrastructural effects of dietary galactoflavin on mouse hepatocytes". Experimental and Molecular Pathology. 21 (1): 88–101. doi:10.1016/0014-4800(74)90081-1. PMID   4370691.
  10. ↑ Slater, Grant G. (1959). "INFLUENCE OF GALACTOFLAVIN AND INANITION ON THE ADRENAL ASCORBIC ACID RESPONSE TO STRESS IN RATS1". Endocrinology. 65 (5): 731–738. doi:10.1210/endo-65-5-731. PMID   13831613.
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