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Chemical Compound Review

Propan-1,2-Diol     propane-1,2-diol

Synonyms: Dowfrost, Prolugen, Sirlene, Sirlenl, propylenglycol, ...
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Disease relevance of propylene glycol

  • Salmonella spp., but not E. coli, have acquired by horizontal transfer the ability to synthesize B12 and degrade propanediol [1].
  • A new isolation procedure for propanediol dehydratase increases by a factor of about 16 the yield of enzyme obtainable from Klebsiella pneumoniae; the enzyme thus isolated has a specific activity of 95 +/- 4 units/mg [2].
  • Analyses showed that the S. typhimurium propanediol dehydratase was related to coenzyme B12-dependent glycerol dehydratases from Citrobacter freundii and Klebsiella pneumoniae [3].
  • MATERIAL AND METHODS: A total of 1408 human 2PN embryos were cryopreserved using a Planer Kryo 10 Series III freezing unit (TS Scientific, Perkasie, Pa) after dehydration/equilibration through Propanediol (Sigma Chemical, St. Louis, Mo) and sucrose [4].
  • Human ovarian tissue was cryopreserved using propanediol and sucrose and grafted under the renal capsule of bilaterally oophorectomized severe combined immunodeficient (SCID) mice [5].

High impact information on propylene glycol

  • The branch of enteric taxa from which Salmonella spp. and E. coli evolved appears to have lost the ability to synthesize B12 and the ability to use it in propanediol and glycerol degradation [1].
  • The cyclization/cleavage of 3',5'-uridyluridine to form 2',3'-cyclic uridylic acid is very effectively catalyzed by Eu3+, and the cyclization/cleavage of the 1-p-nitrophenyl phosphate ester of propane-1,2-diol also shows strong metal ion catalysis by Eu3+, Tb3+, and Yb3+ [6].
  • In this study we show that continued selection for aerobic growth on propanediol resulted in mutations in the oxidoreductase conferring increased resistance to MCO [7].
  • Here we address the determinants of Ape AP endonuclease activity using duplex DNA substrates that contain synthetic analogs of AP sites: tetrahydrofuranyl (F), propanediol (P), ethanediol (E), or 2-(aminobutyl)-1,3-propanediol (Q) [8].
  • In contrast, the specificity constant (kcat/Km) for E or P of Ape purified from HeLa cells was only 5-8-fold lower than for F [8].

Chemical compound and disease context of propylene glycol


Biological context of propylene glycol


Anatomical context of propylene glycol


Associations of propylene glycol with other chemical compounds

  • Plasma concentrations of ornidazole and its two major hydroxylated metabolites, M1 (alpha-(chloromethyl)-2-hydroxymethyl-5-nitroimidazole-1-ethanol) and M4 (3-(2-methyl-5-nitroimidazole 1-yl) 1,2 propane diol), were measured by HPLC [21].
  • The pdu operon encodes proteins for the catabolism of 1,2-propanediol; the nearby cob operon encodes enzymes for the biosynthesis of adenosyl-cobalamin (vitamin B12), a cofactor required for the use of propanediol [22].
  • The enzyme has a pH optimum of 6.5 for the reduction of L-lactaldehyde and of 9.5 for the dehydrogenation of L-1,2-propanediol [23].
  • Mutants that grow on L-1,2-propanediol as a carbon and energy source also depend on the ald gene product for the conversion of L-lactaldehyde to L-lactate [24].
  • Selection for increased aerobic growth rate on propanediol results in the escalation of basal synthesis of the NAD+-linked oxidoreductase encoded by fucO, a member of the fuc regulon for the utilization of L-fucose [25].
  • The amino acid prodrugs containing methoxy linker were the least stable while prodrugs containing propylene glycol linker were most stable [26].

Gene context of propylene glycol


Analytical, diagnostic and therapeutic context of propylene glycol

  • Complementation and expression studies with subclones constructed via PCR showed that three genes (pduCDE) are necessary and sufficient for propanediol dehydratase activity [3].
  • Cryopreservation of 2-cell mouse embryos using propanediol did not cause zona hardening but induced a small and significant softening, as gauged by the time taken for zona dissolution (2181 +/- 167 versus 1864 +/- 82 s) [30].
  • FTM (25 mg/kg) or vehicle (propanediol) was injected subcutaneously 30 minutes before the end of resuscitation [31].
  • After cryoprotective treatment in the presence of propanediol, cortical polymerized actin was no longer visible within the egg and along junctional feet but filamentous actin was still present after treatment with dimethylsulphoxide [32].
  • A total of 220 oocytes, obtained from volunteers who had undergone ovarian stimulation, were cryopreserved using a slow freeze-rapid thaw protocol with 1.5 M propanediol as the cryoprotectant [33].


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  2. Purification and subunit characterization of propanediol dehydratase, a membrane-associated enzyme. McGee, D.E., Richards, J.H. Biochemistry (1981) [Pubmed]
  3. Propanediol utilization genes (pdu) of Salmonella typhimurium: three genes for the propanediol dehydratase. Bobik, T.A., Xu, Y., Jeter, R.M., Otto, K.E., Roth, J.R. J. Bacteriol. (1997) [Pubmed]
  4. Potential factors affecting embryo survival and clinical outcome with cryopreserved pronuclear human embryos. Marrs, R.P., Greene, J., Stone, B.A. Am. J. Obstet. Gynecol. (2004) [Pubmed]
  5. Development of antral follicles in human cryopreserved ovarian tissue following xenografting. Gook, D.A., McCully, B.A., Edgar, D.H., McBain, J.C. Hum. Reprod. (2001) [Pubmed]
  6. Effects of metal ions, including Mg2+ and lanthanides, on the cleavage of ribonucleotides and RNA model compounds. Breslow, R., Huang, D.L. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  7. Evolution of an Escherichia coli protein with increased resistance to oxidative stress. Lu, Z., Cabiscol, E., Obradors, N., Tamarit, J., Ros, J., Aguilar, J., Lin, E.C. J. Biol. Chem. (1998) [Pubmed]
  8. Incision activity of human apurinic endonuclease (Ape) at abasic site analogs in DNA. Wilson, D.M., Takeshita, M., Grollman, A.P., Demple, B. J. Biol. Chem. (1995) [Pubmed]
  9. Propanediol oxidoreductases of Escherichia coli, Klebsiella pneumoniae and Salmonella typhimurium. Aspects of interspecies structural and regulatory differentiation. Ros, J., Aguilar, J. Biochem. J. (1985) [Pubmed]
  10. The propanediol utilization (pdu) operon of Salmonella enterica serovar Typhimurium LT2 includes genes necessary for formation of polyhedral organelles involved in coenzyme B(12)-dependent 1, 2-propanediol degradation. Bobik, T.A., Havemann, G.D., Busch, R.J., Williams, D.S., Aldrich, H.C. J. Bacteriol. (1999) [Pubmed]
  11. Crystal structure of an iron-dependent group III dehydrogenase that interconverts L-lactaldehyde and L-1,2-propanediol in Escherichia coli. Montella, C., Bellsolell, L., Pérez-Luque, R., Badía, J., Baldoma, L., Coll, M., Aguilar, J. J. Bacteriol. (2005) [Pubmed]
  12. Disruption of the fucose pathway as a consequence of genetic adaptation to propanediol as a carbon source in Escherichia coli. Hacking, A.J., Lin, E.C. J. Bacteriol. (1976) [Pubmed]
  13. Glycerol, ethylene glycol and propanediol elicit pimaricin biosynthesis in the PI-factor-defective strain Streptomyces natalensis npi287 and increase polyene production in several wild-type actinomycetes. Recio, E., Aparicio, J.F., Rumbero, A., Mart??n, J.F. Microbiology (Reading, Engl.) (2006) [Pubmed]
  14. Five promoters integrate control of the cob/pdu regulon in Salmonella typhimurium. Chen, P., Ailion, M., Bobik, T., Stormo, G., Roth, J. J. Bacteriol. (1995) [Pubmed]
  15. A single regulatory gene integrates control of vitamin B12 synthesis and propanediol degradation. Bobik, T.A., Ailion, M., Roth, J.R. J. Bacteriol. (1992) [Pubmed]
  16. Dual control of a common L-1,2-propanediol oxidoreductase by L-fucose and L-rhamnose in Escherichia coli. Chen, Y.M., Lin, E.C. J. Bacteriol. (1984) [Pubmed]
  17. Glycerol transport and phosphorylation by rat hepatocytes. Li, C.C., Lin, E.C. J. Cell. Physiol. (1983) [Pubmed]
  18. Estrogen decreases the responsiveness of subfornical organ neurons to angiotensinergic neural inputs from the lateral hypothalamic area in the female rat. Tanaka, J., Miyakubo, H., Nomura, M. Exp. Neurol. (2001) [Pubmed]
  19. Effects of supplementation with free radical scavengers on the survival and fertilization rates of mouse cryopreserved oocytes. Dinara, S., Sengoku, K., Tamate, K., Horikawa, M., Ishikawa, M. Hum. Reprod. (2001) [Pubmed]
  20. Observations on the morphology of pronuclei and nucleoli in human zygotes and implications for cryopreservation. Wright, G., Wiker, S., Elsner, C., Kort, H., Massey, J., Mitchell, D., Toledo, A., Cohen, J. Hum. Reprod. (1990) [Pubmed]
  21. Pharmacokinetics of ornidazole in patients with severe liver cirrhosis. Taburet, A.M., Delion, F., Attali, P., Thebault, J.J., Singlas, E. Clin. Pharmacol. Ther. (1986) [Pubmed]
  22. The control region of the pdu/cob regulon in Salmonella typhimurium. Chen, P., Andersson, D.I., Roth, J.R. J. Bacteriol. (1994) [Pubmed]
  23. Rhamnose-induced propanediol oxidoreductase in Escherichia coli: purification, properties, and comparison with the fucose-induced enzyme. Boronat, A., Aguilar, J. J. Bacteriol. (1979) [Pubmed]
  24. NAD-linked aldehyde dehydrogenase for aerobic utilization of L-fucose and L-rhamnose by Escherichia coli. Chen, Y.M., Zhu, Y., Lin, E.C. J. Bacteriol. (1987) [Pubmed]
  25. Constitutive activation of the fucAO operon and silencing of the divergently transcribed fucPIK operon by an IS5 element in Escherichia coli mutants selected for growth on L-1,2-propanediol. Chen, Y.M., Lu, Z., Lin, E.C. J. Bacteriol. (1989) [Pubmed]
  26. Chemical and enzymatic stability of amino acid prodrugs containing methoxy, ethoxy and propylene glycol linkers. Gupta, D., Gupta, S.V., Lee, K.D., Amidon, G.L. Mol. Pharm. (2009) [Pubmed]
  27. A mutant crp allele that differentially activates the operons of the fuc regulon in Escherichia coli. Zhu, Y., Lin, E.C. J. Bacteriol. (1988) [Pubmed]
  28. Genetic characterization of the pdu operon: use of 1,2-propanediol in Salmonella typhimurium. Walter, D., Ailion, M., Roth, J. J. Bacteriol. (1997) [Pubmed]
  29. Regulation of carbon and electron flow in Clostridium butyricum VPI 3266 grown on glucose-glycerol mixtures. Saint-Amans, S., Girbal, L., Andrade, J., Ahrens, K., Soucaille, P. J. Bacteriol. (2001) [Pubmed]
  30. Cryopreservation of oocytes and embryos: use of a mouse model to investigate effects upon zona hardness and formulate treatment strategies in an in-vitro fertilization programme. Matson, P.L., Graefling, J., Junk, S.M., Yovich, J.L., Edirisinghe, W.R. Hum. Reprod. (1997) [Pubmed]
  31. Mechanism responsible for the salutary effects of flutamide on cardiac performance after trauma-hemorrhagic shock: Upregulation of cardiomyocyte estrogen receptors. Yu, H.P., Yang, S., Choudhry, M.A., Hsieh, Y.C., Bland, K.I., Chaudry, I.H. Surgery (2005) [Pubmed]
  32. Solvent effects on cytoskeletal organization and in-vivo survival after freezing of rabbit oocytes. Vincent, C., Garnier, V., Heyman, Y., Renard, J.P. J. Reprod. Fertil. (1989) [Pubmed]
  33. Cryopreservation of human oocytes and fertilization by two techniques: in-vitro fertilization and intracytoplasmic sperm injection. Kazem, R., Thompson, L.A., Srikantharajah, A., Laing, M.A., Hamilton, M.P., Templeton, A. Hum. Reprod. (1995) [Pubmed]
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