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Chemical Compound Review

Allylene     prop-1-yne

Synonyms: Propyne, Propynylidyne, TETRAPROPYLENE, methylvinylene, CHEMBL116902, ...
 
 
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Disease relevance of Allylene

  • We evaluate C-5 propyne pyrimidine modified phosphorothioate antisense oligonucleotides (ONs) targeted against two human cell cycle proteins that are aberrantly expressed in breast cancer: p34cdc2 kinase and cyclin B1 [1].
  • Inhibition of human immunodeficiency virus type-1 env expression by C-5 propyne oligonucleotides specific for Rev-response element stem-loop V [2].
  • We conclude that C-5 propyne oligodeoxynucleotides in accordance with previous findings by others are superior to unmodified phosphorothioates in providing inhibition of HIV-1 in a sequence-dependent manner and that this inhibition can be conferred by oligodeoxynucleotides in free solution [3].
 

High impact information on Allylene

  • For some niche applications, like the production of MMA from propyne, hydroesterification seems to have an advantage as compared to hydroformylation due to the high activity and selectivity of the Pd(OAc)2/(2-pyridyl)diphenylphosphine catalyst [4].
  • These data demonstrate the potency, specificity, and utility of C-5 propyne modified antisense ONs as biological tools and illustrate the redundancy of cell cycle protein function that can occur in cancer cells [1].
  • In summary, we found that C-5 propyne modified antisense oligonucleotides could reach the target cells (in this case basal keratinocytes) after topical administration to psoriatic but not normal skin [5].
  • Removing a single propyne two base pairs away from a mismatch in a PrODN:RNA duplex eliminates the enhancement in specificity [6].
  • Inhibition of gene expression by anti-sense C-5 propyne oligonucleotides detected by a reporter enzyme [7].
 

Chemical compound and disease context of Allylene

  • A 15-mer C-5 propyne modified phosphorothioate oligodeoxynucleotide antisense to rev was approximately 5-fold more effective in providing viral inhibition compared to a 28-mer unmodified phosphorothioate oligodeoxynucleotide targeted to the same sequence and previously shown to inhibit HIV-1 in a sequence-dependent manner [3].
 

Biological context of Allylene

  • Thus, a dramatic finding is that C-5 propyne 2'-deoxy phosphorothioate ONs, once hybridized to RNA, are completely effective at preventing mRNA translation [8].
  • Kinetics studies of the OH-initiated oxidation of 2-butyne, propyne, and acetylene were conducted at 100 Torr and 298 K using turbulent flow chemical ionization mass spectrometry [9].
 

Associations of Allylene with other chemical compounds

  • Intermediates formed in halogen addition (X = Br, Cl, F) to alkynes (ethyne, propyne, 2-butyne, trifluoromethylethyne, trimethylsilylethyne, and 1-trimethylsilylpropyne) were studied computationally by MP2 at the MP2/6-311++G(3df,3pd) level and/or by DFT at the B3LYP/6-31+G(d) level [10].
  • The distinct differences between the results of allene with those of propyne and 2-butyne suggest the observed absorption features following 193-nm photolysis of these molecules are likely to be composite with contributions from a number of transient species other than propargyl radicals [11].
  • The C 1s excitation spectra of propyne (HC2CH3), 3,3,3-trifluoropropyne (HC2CF3), and propargyl alcohol (HC3CH3OH) have been studied using synchrotron radiation and ion time-of-flight mass spectrometry [12].
  • Combustion of P2 RFG produced higher amounts of isobutene, propene, propyne, propadiene and methanol compared to combustion of EUCG [13].
 

Gene context of Allylene

  • Injection of C-5 propyne 2'-O-allyl phosphodiester ON/RNA hybrids resulted in expression of T antigen, implying that the ONs dissociated from the RNA in cells which likely accounted for their low potency [8].
  • RNase H-independent inhibition of protein synthesis could be achieved by targeting either the 5'-untranslated region or the 5'-splice junction of SV40 large T antigen using 2'-O-allyl phosphodiester ONs which contained C-5 propynylpyrimidines (C-5 propyne) [8].
  • The results of our analysis point to the unique ability of C-5 propyne dU ODNs to selectively bind to RNA within cells and activate cleavage of RNA by RNase H leading to potent inhibition of gene expression [14].
  • Inhibition of HIV-1 in vitro by C-5 propyne phosphorothioate antisense to rev [3].
 

Analytical, diagnostic and therapeutic context of Allylene

References

  1. Elucidation of gene function using C-5 propyne antisense oligonucleotides. Flanagan, W.M., Su, L.L., Wagner, R.W. Nat. Biotechnol. (1996) [Pubmed]
  2. Inhibition of human immunodeficiency virus type-1 env expression by C-5 propyne oligonucleotides specific for Rev-response element stem-loop V. Fenster, S.D., Wagner, R.W., Froehler, B.C., Chin, D.J. Biochemistry (1994) [Pubmed]
  3. Inhibition of HIV-1 in vitro by C-5 propyne phosphorothioate antisense to rev. Lund, O.S., Nielsen, J.O., Hansen, J.E. Antiviral Res. (1995) [Pubmed]
  4. Palladium-catalyzed Reppe carbonylation. Kiss, G. Chem. Rev. (2001) [Pubmed]
  5. C-5 propyne-modified oligonucleotides penetrate the epidermis in psoriatic and not normal human skin after topical application. White, P.J., Gray, A.C., Fogarty, R.D., Sinclair, R.D., Thumiger, S.P., Werther, G.A., Wraight, C.J. J. Invest. Dermatol. (2002) [Pubmed]
  6. C5-(1-propynyl)-2'-deoxy-pyrimidines enhance mismatch penalties of DNA:RNA duplex formation. Barnes, T.W., Turner, D.H. Biochemistry (2001) [Pubmed]
  7. Inhibition of gene expression by anti-sense C-5 propyne oligonucleotides detected by a reporter enzyme. Hamel, Y., Lacoste, J., Frayssinet, C., Sarasin, A., Garestier, T., François, J.C., Hélène, C. Biochem. J. (1999) [Pubmed]
  8. Site and mechanism of antisense inhibition by C-5 propyne oligonucleotides. Moulds, C., Lewis, J.G., Froehler, B.C., Grant, D., Huang, T., Milligan, J.F., Matteucci, M.D., Wagner, R.W. Biochemistry (1995) [Pubmed]
  9. Kinetics and mechanistic studies of the atmospheric oxidation of alkynes. Yeung, L.Y., Pennino, M.J., Miller, A.M., Elrod, M.J. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  10. Probing the intermediates of halogen addition to alkynes: bridged halonium versus open halovinyl cation; a theoretical study. Okazaki, T., Laali, K.K. J. Org. Chem. (2005) [Pubmed]
  11. UV-absorption spectra of the radical transients generated from the 193-nm photolysis of allene, propyne, and 2-butyne. Fahr, A., Laufer, A.H. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  12. Carbon 1s excitation spectroscopy of propyne, trifluoropropyne, and propargyl alcohol. Yang, L., Neville, J.J. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2005) [Pubmed]
  13. Combustion of gasolines in premixed laminar flames European certified and California phase 2 reformulated gasoline. Håkansson, A., Strömberg, K., Pedersen, J., Olsson, J.O. Chemosphere (2001) [Pubmed]
  14. Antisense gene inhibition by C-5-substituted deoxyuridine-containing oligodeoxynucleotides. Gutierrez, A.J., Matteucci, M.D., Grant, D., Matsumura, S., Wagner, R.W., Froehler, B.C. Biochemistry (1997) [Pubmed]
  15. Structure-activity relationships in cell culture. Wagner, R.W. Ciba Found. Symp. (1997) [Pubmed]
 
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