phenylenediamines

Summary

Summary: Aniline compounds that contain two amino groups. They are used as a precursor in the synthesis of HETEROCYCLIC COMPOUNDS and POLYMERS. p-Phenylenediamine is used in the manufacture of HAIR DYES and is an ALLERGEN.

Top Publications

  1. Sosted H, Johansen J, Andersen K, Menne T. Severe allergic hair dye reactions in 8 children. Contact Dermatitis. 2006;54:87-91 pubmed
    ..The clinical consequences of these reactions are unknown. A re-evaluation of the risk assessment/risk management for hair dyes is required...
  2. Xu W, Wu Y, Bi Y, Tan L, Gan Y, Wang K. Activation of voltage-gated KCNQ/Kv7 channels by anticonvulsant retigabine attenuates mechanical allodynia of inflammatory temporomandibular joint in rats. Mol Pain. 2010;6:49 pubmed publisher
  3. Mani B, O Dowd J, Kumar L, Brueggemann L, Ross M, Byron K. Vascular KCNQ (Kv7) potassium channels as common signaling intermediates and therapeutic targets in cerebral vasospasm. J Cardiovasc Pharmacol. 2013;61:51-62 pubmed publisher
    ..In conclusion, we identify Kv7 channels as common targets of vasoconstrictor spasmogens and as candidates for therapeutic intervention for cerebral vasospasm...
  4. Maljevic S, Wuttke T, Seebohm G, Lerche H. KV7 channelopathies. Pflugers Arch. 2010;460:277-88 pubmed publisher
    ..We also assess the therapeutic potential of KV7 channels; in particular, how the activation of KV7 channels by the compounds retigabine and R-L3 may be useful for treatment of epilepsy or cardiac arrhythmia...
  5. Brueggemann L, Kakad P, Love R, Solway J, DOWELL M, Cribbs L, et al. Kv7 potassium channels in airway smooth muscle cells: signal transduction intermediates and pharmacological targets for bronchodilator therapy. Am J Physiol Lung Cell Mol Physiol. 2012;302:L120-32 pubmed publisher
  6. Goebel C, Coenraads P, Rothe H, Kunze G, Kock M, Schlatter H, et al. Elicitation of the immune response to p-phenylenediamine in allergic patients: the role of dose and exposure time. Br J Dermatol. 2010;163:1205-11 pubmed publisher
    ..Usage of hair dye products containing p-phenylenediamine (PPD) is a concern for PPD-allergic individuals...
  7. Tian J, Li H, Luo Y, Wang L, Zhang Y, Sun X. Poly(o-phenylenediamine) colloid-quenched fluorescent oligonucleotide as a probe for fluorescence-enhanced nucleic acid detection. Langmuir. 2011;27:874-7 pubmed publisher
  8. Wang L, Zhang Y, Tian J, Li H, Sun X. Conjugation polymer nanobelts: a novel fluorescent sensing platform for nucleic acid detection. Nucleic Acids Res. 2011;39:e37 pubmed publisher
    ..This results in desorption of the hybridized complex from PN surface and subsequent recovery of fluorescence. We also show that the sensing platform described herein can be used for multiplexing detection of nucleic acid sequences...
  9. Iannotti F, Panza E, Barrese V, Viggiano D, Soldovieri M, Taglialatela M. Expression, localization, and pharmacological role of Kv7 potassium channels in skeletal muscle proliferation, differentiation, and survival after myotoxic insults. J Pharmacol Exp Ther. 2010;332:811-20 pubmed publisher
    ..These data collectively highlight neural K(v)7 channels as significant pharmacological targets to regulate skeletal muscle proliferation, differentiation, and myotoxic effects of drugs...

More Information

Publications62

  1. Shalaby S, Elmasry M, Abd Elrahman A, Abd Elkarim M, Abd Elhaleem Z. Clinical profile of acute paraphenylenediamine intoxication in Egypt. Toxicol Ind Health. 2010;26:81-7 pubmed publisher
    ..In conclusion, PPD causes serious multisystem toxicity and its selling to the public should be officially restricted...
  2. McCallum L, Pierce S, England S, Greenwood I, Tribe R. The contribution of Kv7 channels to pregnant mouse and human myometrial contractility. J Cell Mol Med. 2011;15:577-86 pubmed publisher
    ..Consequently, activation of the encoded channels represents a novel mechanism for treatment of preterm labour...
  3. Rode F, Svalø J, Sheykhzade M, Rønn L. Functional effects of the KCNQ modulators retigabine and XE991 in the rat urinary bladder. Eur J Pharmacol. 2010;638:121-7 pubmed publisher
    ..In conclusion, this study demonstrates an efficacious KCNQ dependent effect of retigabine and XE991 on rat bladder contractility...
  4. Ipavec V, Martire M, Barrese V, Taglialatela M, Curro D. KV7 channels regulate muscle tone and nonadrenergic noncholinergic relaxation of the rat gastric fundus. Pharmacol Res. 2011;64:397-409 pubmed publisher
    ..KV7 channel activators could be useful relaxant agents of the gastric smooth muscle...
  5. Hooff G, van Huizen N, Meesters R, Zijlstra E, Abdelraheem M, Abdelraheem W, et al. Analytical investigations of toxic p-phenylenediamine (PPD) levels in clinical urine samples with special focus on MALDI-MS/MS. PLoS ONE. 2011;6:e22191 pubmed publisher
    ..Finally, PPD concentrations were determined in clinical urine samples of cases of acute intoxication and the applied technique was expanded to identify MAPPD and DAPPD in the identical samples...
  6. Brickel N, Gandhi P, VanLandingham K, Hammond J, Derossett S. The urinary safety profile and secondary renal effects of retigabine (ezogabine): a first-in-class antiepileptic drug that targets KCNQ (K(v)7) potassium channels. Epilepsia. 2012;53:606-12 pubmed publisher
    ..The reported clinical effects of RTG/EZG are consistent with its documented effects on bladder smooth muscle in preclinical studies. RTG/EZG should be used with caution in patients at risk of urinary retention...
  7. Qian J, Liu Y, Cui J, Xu Z. Gold(I)-catalyzed synthesis of 1,5-benzodiazepines directly from o-phenylenediamines and alkynes. J Org Chem. 2012;77:4484-90 pubmed publisher
    A unique gold(I)-catalyzed highly atom-economic synthesis of 1,5-benzodiazepines directly from o-phenylenediamines and alkynes has been achieved for the first time.
  8. Orhan G, Wuttke T, Nies A, Schwab M, Lerche H. Retigabine/Ezogabine, a KCNQ/K(V)7 channel opener: pharmacological and clinical data. Expert Opin Pharmacother. 2012;13:1807-16 pubmed publisher
    ..Retigabine/Ezogabine (RTG) is a third-generation antiepileptic drug (AED) with a novel mechanism of action. It enhances the activity of voltage-gated K(V)7 potassium channels...
  9. Chrispal A, Begum A, Ramya I, Zachariah A. Hair dye poisoning--an emerging problem in the tropics: an experience from a tertiary care hospital in South India. Trop Doct. 2010;40:100-3 pubmed publisher
    ..It is imperative to raise public awareness of the potential toxicity of the dye as well as to educate physicians about the need for aggressive and early treatment...
  10. Jepps T, Olesen S, Greenwood I. One man's side effect is another man's therapeutic opportunity: targeting Kv7 channels in smooth muscle disorders. Br J Pharmacol. 2013;168:19-27 pubmed publisher
    ..This review discusses the potential of targeting Kv7 channels in the smooth muscle to treat diseases such as hypertension, bladder instability, constipation and preterm labour...
  11. Dost R, Rostock A, Rundfeldt C. The anti-hyperalgesic activity of retigabine is mediated by KCNQ potassium channel activation. Naunyn Schmiedebergs Arch Pharmacol. 2004;369:382-90 pubmed
    ..Since the anti-allodynic effect can be inhibited by linopirdine we can conclude that the potassium channel opening properties of retigabine are critically involved in its ability to reduce neuropathic pain response...
  12. Martire M, D Amico M, Panza E, Miceli F, Viggiano D, Lavergata F, et al. Involvement of KCNQ2 subunits in [3H]dopamine release triggered by depolarization and pre-synaptic muscarinic receptor activation from rat striatal synaptosomes. J Neurochem. 2007;102:179-93 pubmed
  13. Murata M, Nishimura T, Chen F, Kawanishi S. Oxidative DNA damage induced by hair dye components ortho-phenylenediamines and the enhancement by superoxide dismutase. Mutat Res. 2006;607:184-91 pubmed
    ..Permanent oxidant hair dyes are consisted of many chemical components including ortho-phenylenediamines. To clarify the mechanism of carcinogenesis by hair dyes, we examined DNA damage induced by mutagenic ortho-..
  14. White J, Gilmour N, Jeffries D, Duangdeeden I, Kullavanijaya P, Basketter D, et al. A general population from Thailand: incidence of common allergens with emphasis on para-phenylenediamine. Clin Exp Allergy. 2007;37:1848-53 pubmed
    ..No data exist on incidence of senitization to PPD resulting from the use of commercial hair dye preparations over a defined time period...
  15. McCallum L, Greenwood I, Tribe R. Expression and function of K(v)7 channels in murine myometrium throughout oestrous cycle. Pflugers Arch. 2009;457:1111-20 pubmed publisher
    ..05), whereas retigabine (K(v)7 activator) significantly relaxed uterine tissues (p < 0.001). These data are the first to characterise KCNQ and KCNE gene expression in a cell type outside of neurons and the cardiovascular system...
  16. Lange W, Geissendörfer J, Schenzer A, Grötzinger J, Seebohm G, Friedrich T, et al. Refinement of the binding site and mode of action of the anticonvulsant Retigabine on KCNQ K+ channels. Mol Pharmacol. 2009;75:272-80 pubmed publisher
    ..This pocket, which is formed at the interface of two adjacent subunits, may be present only in the open state of the channel, consistent with the idea that retigabine stabilizes an open-channel conformation...
  17. Main M, Cryan J, Dupere J, Cox B, Clare J, Burbidge S. Modulation of KCNQ2/3 potassium channels by the novel anticonvulsant retigabine. Mol Pharmacol. 2000;58:253-62 pubmed
    ..Because the heteromeric KCNQ2/3 channel has recently been reported to underlie the M-current, it is likely that M-current modulation can explain the anticonvulsant actions of retigabine in animal models of epilepsy...
  18. Maljevic S, Wuttke T, Lerche H. Nervous system KV7 disorders: breakdown of a subthreshold brake. J Physiol. 2008;586:1791-801 pubmed publisher
  19. Warbrick E, Dearman R, Lea L, Basketter D, Kimber I. Local lymph node assay responses to paraphenylenediamine: intra- and inter-laboratory evaluations. J Appl Toxicol. 1999;19:255-60 pubmed
    ..Taken together, these data confirm the stability of LLNA responses both with time and between laboratories and provide additional support for the use of derived EC3 values in the assessment of relative skin sensitizing potency...
  20. Hirano K, Kuratani K, Fujiyoshi M, Tashiro N, Hayashi E, Kinoshita M. Kv7.2-7.5 voltage-gated potassium channel (KCNQ2-5) opener, retigabine, reduces capsaicin-induced visceral pain in mice. Neurosci Lett. 2007;413:159-62 pubmed
    ..e., the number of licking) induced by the capsaicin treatment and prolonged the latency to first licking. These data provide the first evidence that increased KCNQ channel conductance plays an inhibitory role in the visceral pain pathway...
  21. Neri I, Guareschi E, Savoia F, Patrizi A. Childhood allergic contact dermatitis from henna tattoo. Pediatr Dermatol. 2002;19:503-5 pubmed
    ..In one case a patch test was positive for PPD. We suggest that the fashion of temporary henna tattoos in children is to be discouraged due to the serious consequences that a sensitization to PPD could have in their future...
  22. Stanley L, Skare J, Doyle E, Powrie R, D Angelo D, Elcombe C. Lack of evidence for metabolism of p-phenylenediamine by human hepatic cytochrome P450 enzymes. Toxicology. 2005;210:147-57 pubmed
  23. Peretz A, Degani N, Nachman R, Uziyel Y, Gibor G, Shabat D, et al. Meclofenamic acid and diclofenac, novel templates of KCNQ2/Q3 potassium channel openers, depress cortical neuron activity and exhibit anticonvulsant properties. Mol Pharmacol. 2005;67:1053-66 pubmed
    ..These compounds potentially constitute novel drug templates for the treatment of neuronal hyperexcitability including epilepsy, migraine, or neuropathic pain...
  24. Streng T, Christoph T, Andersson K. Urodynamic effects of the K+ channel (KCNQ) opener retigabine in freely moving, conscious rats. J Urol. 2004;172:2054-8 pubmed
    ..Retigabine is a novel anticonvulsant drug that not only augments gamma-aminobutyric acid mechanisms, but also opens voltage gated K+ channels (KCNQ). In this study we investigated the effects of retigabine on detrusor activity in rats...
  25. Chan Y, Ng S, Goh C. Positive patch-test reactions to para-phenylenediamine, their clinical relevance and the concept of clinical tolerance. Contact Dermatitis. 2001;45:217-20 pubmed
    ..3 continued using PPD hair dyes: 2 had recurrent contact dermatitis and 1 avoided dermatitis with meticulous technique. The 2 patients with clinical tolerance continued using PPD hair dyes with no dermatitis...
  26. Schrøder R, Jespersen T, Christophersen P, Strøbaek D, Jensen B, Olesen S. KCNQ4 channel activation by BMS-204352 and retigabine. Neuropharmacology. 2001;40:888-98 pubmed
    ..KCNQ2, KCNQ2/Q3, and KCNQ3/Q4 channels were activated to a similar degree as KCNQ4 channels by 10 microM of BMS-204352 and retigabine, respectively. The compounds are, thus, likely to be general activators of M-like currents...
  27. Rundfeldt C, Netzer R. The novel anticonvulsant retigabine activates M-currents in Chinese hamster ovary-cells tranfected with human KCNQ2/3 subunits. Neurosci Lett. 2000;282:73-6 pubmed
    ..Since the function of this channel is reduced in a hereditary epilepsy syndrome, retigabine may be the first anticonvulsant to directly target the deficit observed in a channelopathy...
  28. Rundfeldt C, Netzer R. Investigations into the mechanism of action of the new anticonvulsant retigabine. Interaction with GABAergic and glutamatergic neurotransmission and with voltage gated ion channels. Arzneimittelforschung. 2000;50:1063-70 pubmed
    ..No significant interaction with NMDA induced currents was observed...
  29. Martire M, Castaldo P, D Amico M, Preziosi P, Annunziato L, Taglialatela M. M channels containing KCNQ2 subunits modulate norepinephrine, aspartate, and GABA release from hippocampal nerve terminals. J Neurosci. 2004;24:592-7 pubmed
    ..These findings provide novel evidence for a major regulatory role of KCNQ2 K+ channel subunits in neurotransmitter release from rat hippocampal nerve endings...
  30. Matulich J, Sullivan J. A temporary henna tattoo causing hair and clothing dye allergy. Contact Dermatitis. 2005;53:33-6 pubmed
  31. Li X, Ma X, Sun J, Huang M. Powerful reactive sorption of silver(I) and mercury(II) onto poly(o-phenylenediamine) microparticles. Langmuir. 2009;25:1675-84 pubmed publisher
    ..8 wt %, (2) small diameter of Ag nanoparticles of around 10-20 nm, (3) narrow size distribution, (4) intrinsic electrical conductivity that is much higher than that of original PoPD microparticles without Ag...
  32. Elmedyb P, Calloe K, Schmitt N, Hansen R, Grunnet M, Olesen S. Modulation of ERG channels by XE991. Basic Clin Pharmacol Toxicol. 2007;100:316-22 pubmed
    ..In conclusion, great care should be taken when choosing the concentration of XE991 to use for experiments on native potassium channels or animal studies in order to be able to conclude on selective KCNQ channel-mediated effects...
  33. Wuttke T, Seebohm G, Bail S, Maljevic S, Lerche H. The new anticonvulsant retigabine favors voltage-dependent opening of the Kv7.2 (KCNQ2) channel by binding to its activation gate. Mol Pharmacol. 2005;67:1009-17 pubmed
    ..We propose that RTG binds to a hydrophobic pocket formed upon channel opening between the cytoplasmic parts of S5 and S6 involving Trp236 and the channel's gate, which could well explain the strong shift in voltage-dependent activation...
  34. DeLeo V. p-Phenylenediamine. Dermatitis. 2006;17:53-5 pubmed
  35. Tatulian L, Delmas P, Abogadie F, Brown D. Activation of expressed KCNQ potassium currents and native neuronal M-type potassium currents by the anti-convulsant drug retigabine. J Neurosci. 2001;21:5535-45 pubmed
    ..In unclamped neurons, retigabine produced a hyperpolarization and reduced the number of action potentials produced by depolarizing current injections, without change in action potential configuration...
  36. Wickenden A, Yu W, Zou A, Jegla T, Wagoner P. Retigabine, a novel anti-convulsant, enhances activation of KCNQ2/Q3 potassium channels. Mol Pharmacol. 2000;58:591-600 pubmed
    ..Our findings identify KCNQ2/Q3 channels as a molecular target for retigabine and suggest that activation of KCNQ2/Q3 channels may be responsible for at least some of the anticonvulsant activity of this agent...
  37. Cunningham M, Hayward J, Shane B, Tindall K. Distinction of mutagenic carcinogens from a mutagenic noncarcinogen in the big blue transgenic mouse. Environ Health Perspect. 1996;104 Suppl 3:683-6 pubmed
  38. Tatulian L, Brown D. Effect of the KCNQ potassium channel opener retigabine on single KCNQ2/3 channels expressed in CHO cells. J Physiol. 2003;549:57-63 pubmed
    ..Thus, steady-state kinetics were modified to favour the open channel configuration...
  39. Schenzer A, Friedrich T, Pusch M, Saftig P, Jentsch T, Grötzinger J, et al. Molecular determinants of KCNQ (Kv7) K+ channel sensitivity to the anticonvulsant retigabine. J Neurosci. 2005;25:5051-60 pubmed
    ..Transfer of the tryptophan into the KCNQ1 scaffold resulted in retigabine-sensitive heteromers, suggesting that the tryptophan is necessary in all KCNQ subunits forming a functional tetramer to confer drug sensitivity...
  40. Hu T, Bailey R, Morrall S, Aardema M, Stanley L, Skare J. Dermal penetration and metabolism of p-aminophenol and p-phenylenediamine: application of the EpiDerm human reconstructed epidermis model. Toxicol Lett. 2009;188:119-29 pubmed publisher
    ..Characterising the metabolic capability of EpiDerm tissue is important for the evaluation of this model for use in genotoxicity testing...
  41. Roza C, Lopez Garcia J. Retigabine, the specific KCNQ channel opener, blocks ectopic discharges in axotomized sensory fibres. Pain. 2008;138:537-45 pubmed publisher
    ..Results indicate that KCNQ channel opening at axotomized endings may constitute a novel and selective mechanism for modulation of some neuropathic pain symptoms...
  42. Xu S, Ye M, Xu D, Li X, Pan C, Zou H. Matrix with high salt tolerance for the analysis of peptide and protein samples by desorption/ionization time-of-flight mass spectrometry. Anal Chem. 2006;78:2593-9 pubmed
    ..Furthermore, it has been found that this matrix can also effectively suppress the cation ion adduction of the peptides in the presence of high concentrations of metal ions in sample solution...
  43. Kirkland D, Beevers C. Induction of LacZ mutations in Muta Mouse can distinguish carcinogenic from non-carcinogenic analogues of diaminotoluenes and nitronaphthalenes. Mutat Res. 2006;608:88-96 pubmed
    ..Robust carcinogenicity data are needed to determine whether 2-NNT can induce tumours in the liver and bladder...
  44. Krasteva M, Bons B, Ryan C, Gerberick G. Consumer allergy to oxidative hair coloring products: epidemiologic data in the literature. Dermatitis. 2009;20:123-41 pubmed
    ..Data from studies in Asia are difficult to interpret. Pooled prevalence rates of positive patch-test reactions to PPD were calculated for the three continents...
  45. Søsted H, Rastogi S, Andersen K, Johansen J, Menne T. Hair dye contact allergy: quantitative exposure assessment of selected products and clinical cases. Contact Dermatitis. 2004;50:344-8 pubmed
    ..Hair dye allergy may cause severe clinical reactions, and the current regulation is insufficient in protection of the users. A preventive strategy is needed...
  46. Mosley Foreman C, Choi J, Wang S, Yu H. Phototoxicity of phenylenediamine hair dye chemicals in Salmonella typhimurium TA102 and human skin keratinocytes. Food Chem Toxicol. 2008;46:3780-4 pubmed publisher
    b>Phenylenediamines (PD) are dye precursors used to manufacture hair dyes...
  47. Passmore G, Selyanko A, Mistry M, Al Qatari M, Marsh S, Matthews E, et al. KCNQ/M currents in sensory neurons: significance for pain therapy. J Neurosci. 2003;23:7227-36 pubmed
    ..It is suggested that IK(M) plays a key role in controlling the excitability of nociceptors and may represent a novel analgesic target...
  48. White J, Basketter D, Pease C, Sanders D, McFadden J. Intermittent exposure to low-concentration paraphenylenediamine can be equivalent to single, higher-dose exposure. Contact Dermatitis. 2007;56:262-5 pubmed
    ..Hence, intermittent exposure to lower concentrations of PPD may be equivalent to higher concentration, one-off exposure...
  49. Dressler W, Appelqvist T. Plasma/blood pharmacokinetics and metabolism after dermal exposure to para-aminophenol or para-phenylenediamine. Food Chem Toxicol. 2006;44:371-9 pubmed
    ..Overall, the results suggest that topically applied PAP or PPD are metabolised in the skin, presumably by N-acetyltransferase-1 resulting in systemic exposure to acetylated metabolites, and not to their parent arylamines...
  50. Wang L, Tsai S. Simultaneous determination of oxidative hair dye p-phenylenediamine and its metabolites in human and rabbit biological fluids. Anal Biochem. 2003;312:201-7 pubmed
    ..30) as the mobile phase. A comparison of the results obtained from HPLC-UV shows agreement...
  51. Yeung S, Schwake M, Pucovsky V, Greenwood I. Bimodal effects of the Kv7 channel activator retigabine on vascular K+ currents. Br J Pharmacol. 2008;155:62-72 pubmed publisher
    ..This study investigated the functional and electrophysiological effects of the Kv7 channel activator, retigabine, on murine portal vein smooth muscle...
  52. Miceli F, Soldovieri M, Martire M, Taglialatela M. Molecular pharmacology and therapeutic potential of neuronal Kv7-modulating drugs. Curr Opin Pharmacol. 2008;8:65-74 pubmed
  53. Di Prisco M, Puig L, Alomar A. Contact dermatitis due to para-phenylenediamine (PPD) on a temporal tattoo with henna. Cross reaction to azoic dyes. Invest Clin. 2006;47:295-9 pubmed