6-Methylisoxanthopterin

6-Methylisoxanthopterin
Names
	IUPAC name 2-Amino-6-methyl-1,8-dihydropteridine-4,7-dione
	Other names 6-MI; 6MI
Identifiers
CAS Number	712-38-9;
3D model (JSmol)	Interactive image;
ChemSpider	306197;
ECHA InfoCard	100.149.651
PubChem CID	345267;
UNII	ZFA4TQK4XW ;
CompTox Dashboard (EPA)	DTXSID00323009 ;
	InChI InChI=1S/C7H7N5O2/c1-2-5(13)10-4-3(9-2)6(14)12-7(8)11-4/h1H3,(H4,8,10,11,12,13,14) Key: DYXQYFTUVSIKIG-UHFFFAOYSA-N;
	SMILES CC1=NC2=C(NC1=O)NC(=NC2=O)N;
Properties
Chemical formula	C7H7N5O2
Molar mass	193.166 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

6-Methylisoxanthopterin (6MI) is a base analog for the nucleotide guanine. It is useful as a fluorescent indicator because unlike most other base analogs, quenching does not occur when it is incorporated into a double helix. In fact, it exhibits a 3 to 4-fold increase in quantum yield when it is incorporated into a duplex formation.^[1] This allows 6MI to be used to probe the dynamics of DNA or RNA helices using a technique such as fluorescence polarization anisotropy. ^[2]

References

^ Moreno, Andrew (2016). "Photophysical Characterization of Enhanced 6-Methylisoxanthopterin Fluorescence in Duplex DNA". The Journal of Physical Chemistry B. 120 (48): 12232–12248. doi:10.1021/acs.jpcb.6b07369. PMID 27934220.
^ Shi, Xuesong (2009). "Probing the Dynamics of the P1 Helix within the Tetrahymena Group I Intron". Journal of the American Chemical Society. 131 (27): 9571–9578. doi:10.1021/ja902797j. PMC 2758093. PMID 19537712.

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[1] Moreno, Andrew (2016). "Photophysical Characterization of Enhanced 6-Methylisoxanthopterin Fluorescence in Duplex DNA". The Journal of Physical Chemistry B. 120 (48): 12232–12248. doi:10.1021/acs.jpcb.6b07369. PMID 27934220.

[2] Shi, Xuesong (2009). "Probing the Dynamics of the P1 Helix within the Tetrahymena Group I Intron". Journal of the American Chemical Society. 131 (27): 9571–9578. doi:10.1021/ja902797j. PMC 2758093. PMID 19537712.

[1]

[2]

See also

References