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Chemical Compound Review

CYCLOBUTANE     cyclobutane

Synonyms: Tetramethylene, HSDB 58, AGN-PC-0CPXHC, AG-E-92589, CHEBI:30377, ...
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Disease relevance of cyclobutane


High impact information on cyclobutane

  • In mutant Arabidopsis plants that are deficient in photoreactivating ultraviolet-induced cyclobutane pyrimidine dimers, recombination under elevated UV-B regimes greatly exceeds wild-type levels [6].
  • Here, RAD30 is shown to encode a DNA polymerase that can replicate efficiently past a thymine-thymine cis-syn cyclobutane dimer, a lesion that normally blocks DNA polymerases [7].
  • M13 ss DNA molecules containing cyclobutane pyrimidine dimers were maintained but not replicated in Xenopus oocytes yet were replicated in progesterone-matured oocytes [8].
  • Ligation-mediated polymerase chain reaction was used to analyze at nucleotide resolution the repair of cyclobutane pyrimidine dimers along the p53 gene in ultraviolet-irradiated human fibroblasts [9].
  • Because studies of others have shown that photoreactivation repair monomerizes the ultraviolet-induced cyclobutane dimers in DNA, but does not affect the other photoproducts, these results indicate that DNA damage can influence the duration of clonal life-span unless that damage is repaired [10].

Chemical compound and disease context of cyclobutane


Biological context of cyclobutane

  • UV-induced photoproducts (cyclobutane pyrimidine dimers, CPDs) in DNA are removed by nucleotide excision repair (NER), and the presence of transcription factors on DNA can restrict the accessibility of NER enzymes [16].
  • These data indicate that with both CS and XP cyclobutane dimers are major photoproducts generating reduced plasmid survival and increased mutation frequency [17].
  • Cyclobutane dimers were selectively removed before transfection by photoreactivation (PR), leaving nondimer photoproducts intact [17].
  • Methylation of the 3'-cytosine in the sequence 5' CCAGG 3' reduces the yield of (6-4) lesions, but not of cyclobutane dimers, at these sites [18].
  • The results show that the distribution of UV light-induced cyclobutane dimers within a defined sequence is similar whether the DNA is exposed to UV light as part of the chromosome of intact cells or as naked DNA [19].

Anatomical context of cyclobutane

  • To address this, we established mammalian cell lines expressing Neurospora crassa UV damage endonuclease (UVDE), which introduces a SSB with a 3'-OH immediately 5' to UV-induced cyclobutane pyrimidine dimers or 6-4 photoproducts and initiates an alternative excision repair process [20].
  • Insulin-like growth factor-1-mediated AKT activation postpones the onset of ultraviolet B-induced apoptosis, providing more time for cyclobutane thymine dimer removal in primary human keratinocytes [21].
  • Our results suggest that in CHO cells the repair pathway for aminofluorene DNA adducts is not the same as that for cyclobutane dipyrimidines [22].
  • Calf thymus proliferating cell nuclear antigen (PCNA) promoted DNA synthesis past cis-syn and trans-syn-I cyclobutane thymine dimers by calf thymus DNA polymerase delta (Pol delta) in vitro [23].
  • Two major ultraviolet-induced photolesions of TpT, a (6-4) photoproduct [T(6-4)T] and a cis-syn cyclobutane TT dimer (T=T), were incorporated into a predetermined site of one of the leading and lagging template strands of a double-stranded vector, and the modified DNAs were transfected into simian COS-7 cells [24].

Associations of cyclobutane with other chemical compounds


Gene context of cyclobutane


Analytical, diagnostic and therapeutic context of cyclobutane

  • This was confirmed by gel analysis, a T4 UV endonuclease nicking assay specific for cyclobutane-type dimers, and HPLC analysis of the photoproducts [34].
  • Sequence analysis of > 200 mutant plasmids showed that with CS cells a major mutational hot spot was caused by unrepaired cyclobutane dimers [17].
  • This protein was identified using electrophoretic mobility shift assays of immunopurified UV-irradiated oligonucleotide substrates containing a single, site-specific cyclobutane pyrimidine dimer or a pyrimidine (6-4) pyrimidinone photoproduct [35].
  • We studied the repair of UV-induced cyclobutane pyrimidine dimers at nucleotide resolution by ligation-mediated PCR [36].
  • Radioimmunoassays that detect pyrimidine-pyrimidone (6-4) photoproducts and cyclobutane dimers were used to determine the relative induction of these photoproducts in nucleosomal (core) and internucleosomal (linker) DNA in human cell chromatin irradiated with UV light [37].


  1. Recognition and repair of the cyclobutane thymine dimer, a major cause of skin cancers, by the human excision nuclease. Reardon, J.T., Sancar, A. Genes Dev. (2003) [Pubmed]
  2. Transcription-coupled repair removes both cyclobutane pyrimidine dimers and 6-4 photoproducts with equal efficiency and in a sequential way from transcribed DNA in xeroderma pigmentosum group C fibroblasts. van Hoffen, A., Venema, J., Meschini, R., van Zeeland, A.A., Mullenders, L.H. EMBO J. (1995) [Pubmed]
  3. Functional conservation near the 3' end of eukaryotic small subunit RNA: photochemical crosslinking of P site-bound acetylvalyl-tRNA to 18S RNA of yeast ribosomes. Ofengand, J., Gornicki, P., Chakraburtty, K., Nurse, K. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  4. Mechanism of SOS mutagenesis of UV-irradiated DNA: mostly error-free processing of deaminated cytosine. Tessman, I., Liu, S.K., Kennedy, M.A. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  5. UV endonuclease of Micrococcus luteus, a cyclobutane pyrimidine dimer-DNA glycosylase/abasic lyase: cloning and characterization of the gene. Shiota, S., Nakayama, H. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  6. Elevated UV-B radiation reduces genome stability in plants. Ries, G., Heller, W., Puchta, H., Sandermann, H., Seidlitz, H.K., Hohn, B. Nature (2000) [Pubmed]
  7. Efficient bypass of a thymine-thymine dimer by yeast DNA polymerase, Poleta. Johnson, R.E., Prakash, S., Prakash, L. Science (1999) [Pubmed]
  8. Arrested DNA replication in Xenopus and release by Escherichia coli mutagenesis proteins. Oda, N., Levin, J.D., Spoonde, A.Y., Frank, E.G., Levine, A.S., Woodgate, R., Ackerman, E.J. Science (1996) [Pubmed]
  9. Slow repair of pyrimidine dimers at p53 mutation hotspots in skin cancer. Tornaletti, S., Pfeifer, G.P. Science (1994) [Pubmed]
  10. DNA repair and longevity assurance in Paramecium tetraurelia. Smith-Sonneborn, J. Science (1979) [Pubmed]
  11. Kinetic analysis of the deamination reactions of cyclobutane dimers of thymidylyl-3',5'-2'-deoxycytidine and 2'-deoxycytidylyl-3',5'-thymidine. Lemaire, D.G., Ruzsicska, B.P. Biochemistry (1993) [Pubmed]
  12. Spore photoproduct (SP) lyase from Bacillus subtilis specifically binds to and cleaves SP (5-thyminyl-5,6-dihydrothymine) but not cyclobutane pyrimidine dimers in UV-irradiated DNA. Slieman, T.A., Rebeil, R., Nicholson, W.L. J. Bacteriol. (2000) [Pubmed]
  13. Synthesis of trans-1,2-cyclohexyldinitrilo tetramethylene phosphonic acid and its radiolabelling with 99mTc for the detection of skeletal metastases. Panwar, P., Chuttani, K., Mishra, P., Sharma, R., Mondal, A., Kumar Mishra, A. Nuclear medicine communications. (2006) [Pubmed]
  14. Measurement of cyclobutane thymidine dimers in melanocytic nevi and surrounding epidermis in human skin in situ. Wilms, L.C., Zhao, C., Snellman, E., Segerbäck, D., Hemminki, K. Mutagenesis (2002) [Pubmed]
  15. No adaptation to UV-induced immunosuppression and DNA damage following exposure of mice to chronic UV-exposure. Steerenberg, P.A., Daamen, F., Weesendorp, E., Van Loveren, H. J. Photochem. Photobiol. B, Biol. (2006) [Pubmed]
  16. Tight correlation between inhibition of DNA repair in vitro and transcription factor IIIA binding in a 5S ribosomal RNA gene. Conconi, A., Liu, X., Koriazova, L., Ackerman, E.J., Smerdon, M.J. EMBO J. (1999) [Pubmed]
  17. Ultraviolet-induced mutations in Cockayne syndrome cells are primarily caused by cyclobutane dimer photoproducts while repair of other photoproducts is normal. Parris, C.N., Kraemer, K.H. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  18. The C-C (6-4) UV photoproduct is mutagenic in Escherichia coli. Glickman, B.W., Schaaper, R.M., Haseltine, W.A., Dunn, R.L., Brash, D.E. Proc. Natl. Acad. Sci. U.S.A. (1986) [Pubmed]
  19. Distribution of UV light-induced damage in a defined sequence of human DNA: detection of alkaline-sensitive lesions at pyrimidine nucleoside-cytidine sequences. Lippke, J.A., Gordon, L.K., Brash, D.E., Haseltine, W.A. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  20. Cellular responses and repair of single-strand breaks introduced by UV damage endonuclease in mammalian cells. Okano, S., Kanno, S., Nakajima, S., Yasui, A. J. Biol. Chem. (2000) [Pubmed]
  21. Insulin-like growth factor-1-mediated AKT activation postpones the onset of ultraviolet B-induced apoptosis, providing more time for cyclobutane thymine dimer removal in primary human keratinocytes. Decraene, D., Agostinis, P., Bouillon, R., Degreef, H., Garmyn, M. J. Biol. Chem. (2002) [Pubmed]
  22. Quantification of aminofluorene adduct formation and repair in defined DNA sequences in mammalian cells using the UVRABC nuclease. Tang, M.S., Bohr, V.A., Zhang, X.S., Pierce, J., Hanawalt, P.C. J. Biol. Chem. (1989) [Pubmed]
  23. PCNA-induced DNA synthesis past cis-syn and trans-syn-I thymine dimers by calf thymus DNA polymerase delta in vitro. O'Day, C.L., Burgers, P.M., Taylor, J.S. Nucleic Acids Res. (1992) [Pubmed]
  24. The (6-4) photoproduct of thymine-thymine induces targeted substitution mutations in mammalian cells. Kamiya, H., Iwai, S., Kasai, H. Nucleic Acids Res. (1998) [Pubmed]
  25. Red cell sorbitol: an indicator of diabetic control. Malone, J.I., Knox, G., Benford, S., Tedesco, T.A. Diabetes (1980) [Pubmed]
  26. Similarities and differences between cyclobutane pyrimidine dimer photolyase and (6-4) photolyase as revealed by resonance Raman spectroscopy: Electron transfer from the FAD cofactor to ultraviolet-damaged DNA. Li, J., Uchida, T., Todo, T., Kitagawa, T. J. Biol. Chem. (2006) [Pubmed]
  27. T4 endonuclease V protects the DNA strand opposite a thymine dimer from cleavage by the footprinting reagents DNase I and 1,10-phenanthroline-copper. Latham, K.A., Taylor, J.S., Lloyd, R.S. J. Biol. Chem. (1995) [Pubmed]
  28. Structural chemistry of cyclic nucleotides. IV. Crystal and molecular structure of tetramethylene phosphoric acid. Coulter, C.L. J. Am. Chem. Soc. (1975) [Pubmed]
  29. p53 Binds and activates the xeroderma pigmentosum DDB2 gene in humans but not mice. Tan, T., Chu, G. Mol. Cell. Biol. (2002) [Pubmed]
  30. Rad23 is required for transcription-coupled repair and efficient overrall repair in Saccharomyces cerevisiae. Mueller, J.P., Smerdon, M.J. Mol. Cell. Biol. (1996) [Pubmed]
  31. In vivo recruitment of XPC to UV-induced cyclobutane pyrimidine dimers by the DDB2 gene product. Fitch, M.E., Nakajima, S., Yasui, A., Ford, J.M. J. Biol. Chem. (2003) [Pubmed]
  32. Rad26, the yeast homolog of the cockayne syndrome B gene product, counteracts inhibition of DNA repair due to RNA polymerase II transcription. Tijsterman, M., Brouwer, J. J. Biol. Chem. (1999) [Pubmed]
  33. Binding of the glucose-dependent Mig1p repressor to the GAL1 and GAL4 promoters in vivo: regulationby glucose and chromatin structure. Frolova, E., Johnston, M., Majors, J. Nucleic Acids Res. (1999) [Pubmed]
  34. Perturbation of maintenance and de novo DNA methylation in vitro by UVB (280-340 nm)-induced pyrimidine photodimers. Becker, F.F., Holton, P., Ruchirawat, M., Lapeyre, J.N. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  35. Evidence for a novel DNA damage binding protein in human cells. Ghosh, R., Peng, C.H., Mitchell, D.L. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  36. Lack of gene- and strand-specific DNA repair in RNA polymerase III-transcribed human tRNA genes. Dammann, R., Pfeifer, G.P. Mol. Cell. Biol. (1997) [Pubmed]
  37. Nonrandom induction of pyrimidine-pyrimidone (6-4) photoproducts in ultraviolet-irradiated human chromatin. Mitchell, D.L., Nguyen, T.D., Cleaver, J.E. J. Biol. Chem. (1990) [Pubmed]
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