Proflavine

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Proflavine
Acridine-3,6-diamine 200.svg
Names
Preferred IUPAC name
Acridine-3,6-diamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.976 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: WDVSHHCDHLJJJR-UHFFFAOYSA-N Yes check.svgY
  • 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
  • n1c3c(cc2c1cc(N)cc2)ccc(c3)N
Properties
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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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 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 proflavine. [3]

In astronomical spectroscopy proflavine present in interstellar clouds (derived from the modification in meteorites of polycyclic aromatic hydrocarbons by heteroatoms) strongly absorbs in the blue region at 445  nm. This makes difficult the recording of the spectra of stars that lie behind the clouds. [4]

References

  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. Bibcode:2017KIJMS...3..272G. doi: 10.1016/j.kijoms.2017.07.003 .
  3. ↑ 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.
  4. ↑ 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.
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