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Chemical Compound Review

isoleucinate     2-amino-3-methyl-pentanoate

Synonyms: AC1NUTVY, ile(-), CHEBI:32612, isoleucine anion, 2-amino-3-methylpentanoate, ...
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Disease relevance of Isoleucine

  • In contrast, frequencies of ile/ile genotype at codon 105 and variant val-ala haplotype of GSTP1 was significantly higher (OR = 1.5; 95% CI = 1.0-2.0) and lower (OR = 1.4; 95% CI = 1.0-1.9) in oral cancer patients compare to controls, respectively [1].
  • Bacillus subtilis strains 168 met ile leu and 23 thy contain folates which differ from one another in the number of glutamyl residues [2].
  • Healthy older men, aged 64-72 years, with either a lower birth weight (LBW, <or=25th %ile; n = 16) or higher birth weight (HBW, >or=75th %ile; n = 13) had measurements of 1) net oxidative metabolism using indirect calorimetry before and for 6 h after a mixed meal (3,720 kJ) and 2) postprandial oxidation of exogenous [13C]palmitic acid [3].
  • RESULTS: The proportion of GSTP1 ile/ile tended to be higher in patients with endometriosis than control group, although the difference was not significant [odds ratio (OR)=1.53; 95% confidence interval (CI)=0.95-2.46] [4].
  • The study of mutants of Erwinia specifically unable to ferment cellobiose indicates that the mutations are clustered between arg and ile on the chromosome of this organism [5].

High impact information on Isoleucine

  • The plasma pharmacokinetics of vinblastine and N-(deacetyl-O-4-vinblastoyl-23)-L-ethyl isoleucinate (VileE) in mice have been studied as part of the preclinical investigations of VileE, a new investigational semisynthetic Vinca alkaloid [6].
  • Hereditary pancreatitis-associated mutation asn(21) --> ile stabilizes rat trypsinogen in vitro [7].
  • DNA sequence analysis has identified the 16S, 23S, and 5S rRNAs, two tRNAs (ile and ala) in the spacer region between the 16S and 23S rRNAs, and an f-met tRNA immediately following the 5S rRNA gene of all three operons [8].
  • This conclusion was confirmed by the finding that biotinylation of VT2c (which contains lys 53) prevented glycolipid receptor binding, whereas biotinylation of VT2e (in which lys 53 is substituted by ile) had no effect [9].
  • Functionally relevant polymorphisms, i.e., premature stop codons in the IFNA10 [Cys20Stop] and IFNA17 [58Stop] genes and an aminoacid (aa) substitution [ile 184Arg] in the IFNA17 gene were analyzed [10].

Chemical compound and disease context of Isoleucine


Biological context of Isoleucine

  • STUDY DESIGN: Fetal growth was measured at 28 weeks' gestation on 218 twins, including head circumference, abdominal circumference, and femur length, and characterized as > or < or =10th %ile; children were followed up until the age of three years [12].
  • Trichorionic vs monochorionic or dichorionic placentation resulted in 27% higher growth at the 10th %ile, 5% higher growth at the 50th %ile, and 4% higher growth at the 90th %ile by 34 weeks [13].
  • Amino acid analysis of the hydrolysis mixture yielded phosphoserine (Pser), asp, thr, ser, glu, gly, ala, val, ile, leu, and arg [14].
  • Thus, inflation of the PASG maintained carotid artery blood pressure wh ile decreasing splenic, abdominal and aortic flow as well as splenic hemorrhage, with a decrease in the death rate, over a 2-hour period [15].

Anatomical context of Isoleucine


Associations of Isoleucine with other chemical compounds

  • To test this hypothesis, the initial targets were the residues corresponding to these specific amino acids, a lys to glu change and an ile to val change at amino acid positions 307 and 482, respectively, of the TVMV polyprotein, as well as the combination of the two [18].
  • By following the time shift of the replication moment of the genes bac and met in the control culture and in the culture with the initial inhibition of DNA synthesis by nalidixic acid the start of replication of the chromosome was determined at 15 min before replication of the gene ile [19].

Gene context of Isoleucine

  • To study gene-gene interactions, a combined risk of gallbladder cancer due to ile/val or val/val were calculated in combination with null alleles of GSTM1 and GSTT1 or the *B allele of GSTM3, but there was no enhancement of risk [17].
  • The prevalence of the CYP1A1 (ile:val) polymorphism [including both the (ile/val) and (val/val) genotypes] was significantly higher in cases as compared to controls (17.6% versus 7.6%, respectively; crude odds ratio, 2.6; confidence interval, 1.2-5.7) [20].
  • Two additional mutations within the HC-Pro representing dipeptide changes thr-ser to ile-asp and thr-ala to leu-glu at amino acid positions (283/284) and (368/369), respectively, were also tested to further define the effects of mutations in this region on helper component activity [18].
  • Adduct levels tended to be higher in individuals with GSTM1 null, GSTT1 null or GSTP1 ile/ile genotypes [21].
  • Two site-specific mutations at the N-terminal end of hlyA (one at amino acid position 2 leading to a thr----pro exchange and another deleting ile and thr at positions 4 and 5) also do not affect the transport of the altered haemolysins [22].

Analytical, diagnostic and therapeutic context of Isoleucine


  1. Glutathione S-transferase M3 (A/A) genotype as a risk factor for oral cancer and leukoplakia among Indian tobacco smokers. Sikdar, N., Paul, R.R., Roy, B. Int. J. Cancer (2004) [Pubmed]
  2. Identification of poly-gamma-glutamyl chain lengths in folates of Bacillus subtilis. Hintze, D.N., Farmer, J.L. J. Bacteriol. (1975) [Pubmed]
  3. Substrate-energy metabolism and metabolic risk factors for cardiovascular disease in relation to fetal growth and adult body composition. Kensara, O.A., Wooton, S.A., Phillips, D.I., Patel, M., Hoffman, D.J., Jackson, A.A., Elia, M. Am. J. Physiol. Endocrinol. Metab. (2006) [Pubmed]
  4. Glutathione-S-transferase P1 gene polymorphism and susceptibility to endometriosis. Ertunc, D., Aban, M., Tok, E.C., Tamer, L., Arslan, M., Dilek, S. Hum. Reprod. (2005) [Pubmed]
  5. Cellobiose metabolism in Erwinia: genetic study. Barras, F., Chambost, J.P., Chippaux, M. Mol. Gen. Genet. (1984) [Pubmed]
  6. Plasma pharmacokinetics of vinblastine and the investigational Vinca alkaloid N-(deacetyl-O-4-vinblastoyl-23)-L-ethyl isoleucinate in mice as determined by high-performance liquid chromatography. van Tellingen, O., Beijnen, J.H., Nooijen, W.J., Bult, A. Cancer Res. (1993) [Pubmed]
  7. Hereditary pancreatitis-associated mutation asn(21) --> ile stabilizes rat trypsinogen in vitro. Sahin-Tóth, M. J. Biol. Chem. (1999) [Pubmed]
  8. Localization and structural analysis of the ribosomal RNA operons of Rhodobacter sphaeroides. Dryden, S.C., Kaplan, S. Nucleic Acids Res. (1990) [Pubmed]
  9. Capping and receptor-mediated endocytosis of cell-bound verotoxin (Shiga-like toxin). 1: Chemical identification of an amino acid in the B subunit necessary for efficient receptor glycolipid binding and cellular internalization. Khine, A.A., Lingwood, C.A. J. Cell. Physiol. (1994) [Pubmed]
  10. The interferon gene cluster: a candidate region for MS predisposition? Multiple Sclerosis Study Group. Miterski, B., Jaeckel, S., Epplen, J.T., Pöhlau, D., Hardt, C. Genes Immun. (1999) [Pubmed]
  11. Glutathione S-transferase polymorphisms and ovarian cancer treatment and survival. Beeghly, A., Katsaros, D., Chen, H., Fracchioli, S., Zhang, Y., Massobrio, M., Risch, H., Jones, B., Yu, H. Gynecol. Oncol. (2006) [Pubmed]
  12. Fetal phenotypes and neonatal and early childhood outcomes in twins. Luke, B., Brown, M.B., Hediger, M.L., Nugent, C., Misiunas, R.B., Anderson, E. Am. J. Obstet. Gynecol. (2004) [Pubmed]
  13. Birth weight references for triplets. Min, S.J., Luke, B., Min, L., Misiunas, R., Nugent, C., Van de Ven, C., Martin, D., Gonzalez-Quintero, V.H., Eardley, S., Witter, F.R., Mauldin, J.G., Newman, R.B. Am. J. Obstet. Gynecol. (2004) [Pubmed]
  14. Evidence for covalent binding between phosphopeptides and terminal deoxynucleotides in highly purified calf thymus DNA. Welsh, R.S. Radiation and environmental biophysics. (1987) [Pubmed]
  15. Pneumatic antishock garment decreases hemorrhage and mortality from splenic injury. Ali, J., Duke, K. Canadian journal of surgery. Journal canadien de chirurgie. (1991) [Pubmed]
  16. B- and T-lymphocyte micronuclei in chimney sweeps with respect to genetic polymorphism for CYP1A1 and GST1 (class Mu). Carstensen, U., Alexandrie, A.K., Högstedt, B., Rannug, A., Bratt, I., Hagmar, L. Mutat. Res. (1993) [Pubmed]
  17. Genetic polymorphisms in GSTM1, GSTT1, GSTP1, GSTM3 and the susceptibility to gallbladder cancer in North India. Pandey, S.N., Jain, M., Nigam, P., Choudhuri, G., Mittal, B. Biomarkers (2006) [Pubmed]
  18. Site-directed mutations in the potyvirus HC-Pro gene affect helper component activity, virus accumulation, and symptom expression in infected tobacco plants. Atreya, C.D., Atreya, P.L., Thornbury, D.W., Pirone, T.P. Virology (1992) [Pubmed]
  19. Cell cycle in Mycobacterium phlei. Konícek, J., Konícková-Radochová, M. Folia Microbiol. (Praha) (1984) [Pubmed]
  20. CYP1A1 and GSTM1 polymorphisms and oral cancer risk. Park, J.Y., Muscat, J.E., Ren, Q., Schantz, S.P., Harwick, R.D., Stern, J.C., Pike, V., Richie, J.P., Lazarus, P. Cancer Epidemiol. Biomarkers Prev. (1997) [Pubmed]
  21. Associations between smoking, GST genotypes and N7-methylguanine levels in DNA extracted from bronchial lavage cells. Lewis, S.J., Cherry, N.M., Niven, R.M., Barber, P.V., Povey, A.C. Mutat. Res. (2004) [Pubmed]
  22. Mutations affecting activity and transport of haemolysin in Escherichia coli. Ludwig, A., Vogel, M., Goebel, W. Mol. Gen. Genet. (1987) [Pubmed]
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