Proflavine

Proflavine
Names
	Preferred 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). verify (what is ?) 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]^{[needs context]}

Proflavin is a fluorescent dye that is sometimes used in microscopic in-vivo imaging due to its intercalation properties. However, there was concern that women exposed to proflavin could develop cervical cancer since they have mutagenesis potential. However, the retrospective analysis performed by Pantano et. al. demonstrated that there is no increased cervical cancer risk after exposure to proflavin.^[4]

References

^ Denny WA (September 2002). "Acridine derivatives as chemotherapeutic agents". Current Medicinal Chemistry. 9 (18): 1655–1665. doi:10.2174/0929867023369277. PMID 12171548.
^ Gatasheh MK, Kannan S, Hemalatha K, Imrana N (December 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 PJ (July 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.
^ Pantano N, Hunt B, Schwarz RA, Parra S, Cherry K, Possati-Resende JC, et al. (November 2018). "Is Proflavine Exposure Associated with Disease Progression in Women with Cervical Dysplasia? A Brief Report". Photochemistry and Photobiology. 94 (6): 1308–1313. doi:10.1111/php.12976. PMC 6282608. PMID 29981148.

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[1] Denny WA (September 2002). "Acridine derivatives as chemotherapeutic agents". Current Medicinal Chemistry. 9 (18): 1655–1665. doi:10.2174/0929867023369277. PMID 12171548.

[2] Gatasheh MK, Kannan S, Hemalatha K, Imrana N (December 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 PJ (July 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.

[:1-4] Pantano N, Hunt B, Schwarz RA, Parra S, Cherry K, Possati-Resende JC, et al. (November 2018). "Is Proflavine Exposure Associated with Disease Progression in Women with Cervical Dysplasia? A Brief Report". Photochemistry and Photobiology. 94 (6): 1308–1313. doi:10.1111/php.12976. PMC 6282608. PMID 29981148.

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