Proflavine

Proflavine
Names
	IUPAC name acridine-3,6-diamine
Identifiers
CAS Number	92-62-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8452 ;
ChEMBL	ChEMBL55400 ;
ChemSpider	6832 ;
DrugBank	DB01123 ;
ECHA InfoCard	100.001.976
KEGG	C11181 ;
PubChem CID	7099;
UNII	CY3RNB3K4T ;
CompTox Dashboard (EPA)	DTXSID9043776 ;
	InChI InChI=1S/C13H11N3/c14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10/h1-7H,14-15H2 Key: WDVSHHCDHLJJJR-UHFFFAOYSA-N ; InChI=1/C13H11N3/c14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10/h1-7H,14-15H2 Key: WDVSHHCDHLJJJR-UHFFFAOYAC;
	SMILES n1c3c(cc2c1cc(N)cc2)ccc(c3)N;
Properties
Chemical formula	C13H11N3
Molar mass	209.252 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Proflavine, also called proflavin and diaminoacridine, is an acriflavine derivative, a disinfectant bacteriostatic against many gram-positive bacteria.[1] It has been used in the form of the dihydrochloride and hemisulfate salts as a topical antiseptic, and was formerly used as a urinary antiseptic.

Proflavine is also known to have a mutagenic effect on DNA by intercalating between nucleic acid base pairs. It differs from most other mutagenic components by causing basepair-deletions or basepair-insertions and not substitutions. In the presence of light, proflavine can induce double-stranded breaks in DNA.[2]

Proflavine absorbs strongly in the blue region at 445 nm (in water at pH 7) with molar extinction coefficient of c. 40,000.[3]

References

Denny (2002). "Acridine Derivatives as Chemotherapeutic Agents". Current Medicinal Chemistry. 9 (18): 1655–65. doi:10.2174/0929867023369277. PMID 12171548.
Gatasheh, Mansour K; Kannan, S; Hemalatha, K; Imrana, N (2017). "Proflavine an acridine DNA intercalating agent and strong antimicrobial possessing potential properties of carcinogen". Karbala International Journal of Modern Science. 3 (4): 272–278. doi:10.1016/j.kijoms.2017.07.003.
Sarre, Peter J. (2006). "The Diffuse Interstellar Bands: A Major Problem in Astronomical Spectroscopy". Journal of Molecular Spectroscopy. 238 (1): 1–10. arXiv:astro-ph/0608113. Bibcode:2006JMoSp.238....1S. doi:10.1016/j.jms.2006.03.009. S2CID 16872032.

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[1] Denny (2002). "Acridine Derivatives as Chemotherapeutic Agents". Current Medicinal Chemistry. 9 (18): 1655–65. doi:10.2174/0929867023369277. PMID 12171548.

[2] Gatasheh, Mansour K; Kannan, S; Hemalatha, K; Imrana, N (2017). "Proflavine an acridine DNA intercalating agent and strong antimicrobial possessing potential properties of carcinogen". Karbala International Journal of Modern Science. 3 (4): 272–278. doi:10.1016/j.kijoms.2017.07.003.

[sarre-3] Sarre, Peter J. (2006). "The Diffuse Interstellar Bands: A Major Problem in Astronomical Spectroscopy". Journal of Molecular Spectroscopy. 238 (1): 1–10. arXiv:astro-ph/0608113. Bibcode:2006JMoSp.238....1S. doi:10.1016/j.jms.2006.03.009. S2CID 16872032.