Dequalinium chloride | CAS#522-51-0 | bacteriostat

MedKoo Cat#: 598172 | Name: Dequalinium chloride

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dequalinium chloride is a topical bacteriostat that is available as various salts. It is used in wound dressings and mouth infections and may also have antifungal action, but may cause skin ulceration.

Chemical Structure

Dequalinium chloride

CAS#522-51-0 (chloride)

Theoretical Analysis

MedKoo Cat#: 598172

Name: Dequalinium chloride

CAS#: 522-51-0 (chloride)

Chemical Formula: C30H40Cl2N4

Exact Mass: 526.2630

Molecular Weight: 527.57

Elemental Analysis: C, 68.30; H, 7.64; Cl, 13.44; N, 10.62

Price and Availability

Size	Price	Availability
250mg	USD 350.00	2 Weeks
500mg	USD 550.00	2 Weeks
1g	USD 850.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

4028-98-2 (acetate) 6707-58-0 (cation) 522-51-0 (chloride) Dequalinium Bromide

Synonym

Dequalinium chloride; Dequavagyn; Dequalinium Dichloride; Dekamin; Dequafungan; NSC 166454; NSC-166454; NSC166454;

IUPAC/Chemical Name

1,1'-(decane-1,10-diyl)bis(4-amino-2-methylquinolin-1-ium) chloride

InChi Key

LTNZEXKYNRNOGT-UHFFFAOYSA-N

InChi Code

InChI=1S/C30H38N4.2ClH/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34;;/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*1H

SMILES Code

CC1=CC(N)=C2C=CC=CC2=[N+]1CCCCCCCCCC[N+]3=C4C=CC=CC4=C(N)C=C3C.[Cl-].[Cl-]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dequalinium Chloride is a selective blocker of apamin-sensitive K+ channels.

In vitro activity:

Pretreatment of a monolayer of B16 F10 cells with 250 nM of a DECA analog in the presence of UV irradiation for 5 min resulted in complete inhibition of cell motility for up to 4 h in a time-lapse motility assay and 40 to 60% inhibition of cell migration in a Boyden chamber, and inhibition by 40 to 60% of intracellular phosphatidylserine/Ca(2+)-dependent PKC catalytic activity, signifying inactivation of a conventional PKC isoform. Because PKCalpha is the only conventional PKC isoform detected in B16 F10 cells, a stably transfected clone expressing a kinase-defective mutant of PKCalpha was developed that exhibited a substantial loss of adhesion and motility and was refractory to further inhibition by DECA. These findings identify PKCalpha catalytic activity both as a mechanistic component of cell motility and adhesion and as a critical intracellular target of DECA. These studies further suggest that the combined use of UV with nanomolar concentrations of DECA offers an effective chemotherapeutic approach to inhibit metastatic behavior of melanoma cells. Reference: Mol Pharmacol. 2000 Oct;58(4):729-37. https://pubmed.ncbi.nlm.nih.gov/10999942/

In vivo activity:

In the present study, the mechanisms of spontaneous CF discharge-evoked pauses and the output modulation of cerebellar PCs were investigated in urethane-anesthetized mice using in vivo whole-cell recording techniques and pharmacological methods. Similar to the perfusion of calcium-free solution, blocking SK channel activity with the selective antagonist dequalinium (10 μM; Dunn, 1994), induced an increase in SS firing rate (Figure7A) accompanied by a decreased AHP amplitude (Figure7B). In the presence of dequalinium, the SS frequency was 176.3 ± 8.5% of baseline (ACSF: 100.0 ± 6.7%; F = 28, P = 0.0008; ANOVA; n = 6 cells; Figures 7A,C), and the mean pause was 14.7 ± 6.2 ms, which was significantly shorter that control conditions (ACSF: 94.5 ± 10.6 ms; P < 0.001. Application of dequalinium decreased the AHP amplitude to 13.5 ± 6.9% of baseline (ACSF: 100.0 ± 7.7%; F = 217, P < 0.0001; ANOVA; n = 6 cells; Figures 7A,E). In addition, the effect of repeated CF stimulation at 1 Hz on SS activity was examined in the presence of dequalinium (10 μM). Application of dequalinium induced an increase in SS firing rate (Figure,8A), the mean frequency of SS firing was 146.3 ± 4.8% of baseline (ACSF: 99.9 ± 4.2%; F = 204, P < 0.001; ANOVA; n = 7 cells; Figures 8A,B), but without effect the mean value of CV (Figure 8C). Reference: Front Cell Neurosci. 2017 Aug 22;11:247. https://pubmed.ncbi.nlm.nih.gov/28878623/

	Solvent	mg/mL	mM
Solubility
	DMSO	3.0	5.69

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 527.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Rotenberg SA, Smiley S, Ueffing M, Krauss RS, Chen LB, Weinstein IB. Inhibition of rodent protein kinase C by the anticarcinoma agent dequalinium. Cancer Res. 1990 Feb 1;50(3):677-85. PMID: 2297708. 2. Sullivan RM, Stone M, Marshall JF, Uberall F, Rotenberg SA. Photo-induced inactivation of protein kinase calpha by dequalinium inhibits motility of murine melanoma cells. Mol Pharmacol. 2000 Oct;58(4):729-37. doi: 10.1124/mol.58.4.729. PMID: 10999942. 3. Weiss MJ, Wong JR, Ha CS, Bleday R, Salem RR, Steele GD Jr, Chen LB. Dequalinium, a topical antimicrobial agent, displays anticarcinoma activity based on selective mitochondrial accumulation. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5444-8. doi: 10.1073/pnas.84.15.5444. PMID: 3474661; PMCID: PMC298874 4. Jin XH, Wang HW, Zhang XY, Chu CP, Jin YZ, Cui SB, Qiu DL. Mechanisms of Spontaneous Climbing Fiber Discharge-Evoked Pauses and Output Modulation of Cerebellar Purkinje Cell in Mice. Front Cell Neurosci. 2017 Aug 22;11:247. doi: 10.3389/fncel.2017.00247. PMID: 28878623; PMCID: PMC5572406.

In vitro protocol:

In vivo protocol:

1. Weiss MJ, Wong JR, Ha CS, Bleday R, Salem RR, Steele GD Jr, Chen LB. Dequalinium, a topical antimicrobial agent, displays anticarcinoma activity based on selective mitochondrial accumulation. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5444-8. doi: 10.1073/pnas.84.15.5444. PMID: 3474661; PMCID: PMC298874. 2. Jin XH, Wang HW, Zhang XY, Chu CP, Jin YZ, Cui SB, Qiu DL. Mechanisms of Spontaneous Climbing Fiber Discharge-Evoked Pauses and Output Modulation of Cerebellar Purkinje Cell in Mice. Front Cell Neurosci. 2017 Aug 22;11:247. doi: 10.3389/fncel.2017.00247. PMID: 28878623; PMCID: PMC5572406.

1: Lopes dos Santos Santiago G, Grob P, Verstraelen H, Waser F, Vaneechoutte M. Susceptibility testing of Atopobium vaginae for dequalinium chloride. BMC Res Notes. 2012 Mar 19;5:151. doi: 10.1186/1756-0500-5-151. PubMed PMID: 22429611; PubMed Central PMCID: PMC3325845. 2: Weissenbacher ER, Donders G, Unzeitig V, Martinez de Tejada B, Gerber S, Halaška M, Špaček J; Fluomizin Study Group. A comparison of dequalinium chloride vaginal tablets (Fluomizin®) and clindamycin vaginal cream in the treatment of bacterial vaginosis: a single-blind, randomized clinical trial of efficacy and safety. Gynecol Obstet Invest. 2012;73(1):8-15. doi: 10.1159/000332398. Epub 2011 Dec 24. PubMed PMID: 22205034. 3: Mendling W, Weissenbacher ER, Gerber S, Prasauskas V, Grob P. Use of locally delivered dequalinium chloride in the treatment of vaginal infections: a review. Arch Gynecol Obstet. 2016 Mar;293(3):469-84. doi: 10.1007/s00404-015-3914-8. Epub 2015 Oct 27. Review. PubMed PMID: 26506926; PubMed Central PMCID: PMC4757629. 4: Timaner M, Bril R, Kaidar-Person O, Rachman-Tzemah C, Alishekevitz D, Kotsofruk R, Miller V, Nevelsky A, Daniel S, Raviv Z, Rotenberg SA, Shaked Y. Dequalinium blocks macrophage-induced metastasis following local radiation. Oncotarget. 2015 Sep 29;6(29):27537-54. doi: 10.18632/oncotarget.4826. PubMed PMID: 26348470; PubMed Central PMCID: PMC4695007. 5: Della Casa V, Noll H, Gonser S, Grob P, Graf F, Pohlig G. Antimicrobial activity of dequalinium chloride against leading germs of vaginal infections. Arzneimittelforschung. 2002;52(9):699-705. PubMed PMID: 12404886. 6: Theodoropoulos D, Rova A, Smith JR, Barbu E, Calabrese G, Vizirianakis IS, Tsibouklis J, Fatouros DG. Towards boron neutron capture therapy: the formulation and preliminary in vitro evaluation of liposomal vehicles for the therapeutic delivery of the dequalinium salt of bis-nido-carborane. Bioorg Med Chem Lett. 2013 Nov 15;23(22):6161-6. doi: 10.1016/j.bmcl.2013.09.003. Epub 2013 Sep 10. PubMed PMID: 24080462. 7: Rau I, Bössmann K. [Effects of dequalinium chloride and sanguinarine on the ultrastructure of early supragingival plaque]. Oralprophylaxe. 1991 Dec;13(4):133-41. German. PubMed PMID: 1818603. 8: Krämer W. [Doubleblind test of dequalinium chloride in 60 children with oral moniliasis]. Fortschr Med. 1977 May 12;95(18):1246. German. PubMed PMID: 324879. 9: Boschetti C, Fronza G, Fuganti C, Grasselli P, Magnone AG, Mele A, Pellegatta C. A nuclear magnetic resonance method for the determination of the purity of commercial dequalinium chloride. Arzneimittelforschung. 1995 Nov;45(11):1217-21. PubMed PMID: 8929243. 10: Hiegel K, Spangenberg B. New method for the quantification of dequalinium cations in pharmaceutical samples by absorption and fluorescence diode array thin-layer chromatography. J Chromatogr A. 2009 Jun 19;1216(25):5052-6. doi: 10.1016/j.chroma.2009.04.002. Epub 2009 Apr 9. PubMed PMID: 19446824. 11: Bleday R, Weiss MJ, Salem RR, Wilson RE, Chen LB, Steele G Jr. Inhibition of rat colon tumor isograft growth with dequalinium chloride. Arch Surg. 1986 Nov;121(11):1272-5. PubMed PMID: 3778199. 12: Gruber I, Bork T. [The efficacy of dequalinium chloride/benzalkonium chloride as well as medicinal plants on the gingiva]. Dtsch Zahn Mund Kieferheilkd Zentralbl. 1991;79(1):3-8. German. PubMed PMID: 9272987. 13: García-Pérez AI, Galeano E, Nieto E, Estañ MC, Sancho P. Dequalinium induces cytotoxicity in human leukemia NB4 cells by downregulation of Raf/MEK/ERK and PI3K/Akt signaling pathways and potentiation of specific inhibitors of these pathways. Leuk Res. 2014 Jul;38(7):795-803. doi: 10.1016/j.leukres.2014.01.009. Epub 2014 Jan 28. PubMed PMID: 24811390. 14: Krämer W. [Treatment of tonsillitis with dequalinium chloride]. Fortschr Med. 1977 Apr 28;95(16):1108-10. German. PubMed PMID: 856702. 15: Taylor RB, Toasaksiri S, Reid RG, Wood D. Determination of the quaternary ammonium compounds dequalinium and cetylpyridinium chlorides in candy-based lozenges by high-performance liquid chromatography. Analyst. 1997 Sep;122(9):973-6. PubMed PMID: 9374026. 16: Mobacken H, Romanus M. Microvascular response to local application of dequalinium chloride. A vital microscopical study of hamster's cheek pouch and a microangiographic study of rabbit's ear. Br J Dermatol. 1975 Jan;92(1):63-72. PubMed PMID: 1156545. 17: Orzáez M, Gortat A, Sancho M, Carbajo RJ, Pineda-Lucena A, Palacios-Rodríguez Y, Pérez-Payá E. Characterization of dequalinium as a XIAP antagonist that targets the BIR2 domain. Apoptosis. 2011 May;16(5):460-7. doi: 10.1007/s10495-011-0582-4. PubMed PMID: 21340509. 18: Gamboa-Vujicic G, Emma DA, Liao SY, Fuchtner C, Manetta A. Toxicity of the mitochondrial poison dequalinium chloride in a murine model system. J Pharm Sci. 1993 Mar;82(3):231-5. PubMed PMID: 8450414. 19: Petersen EE, Weissenbacher ER, Hengst P, Spitzbart H, Weise W, Wolff F, Dreher E, Ernst U, Della Casa V, Pohlig G, Graf F, Kaiser RR. Local treatment of vaginal infections of varying etiology with dequalinium chloride or povidone iodine. A randomised, double-blind, active-controlled, multicentric clinical study. Arzneimittelforschung. 2002;52(9):706-15. PubMed PMID: 12404887. 20: Hunold W. [Disorders of the nose, mouth and throat. Therapeutic experiences with a dequalinium chloride solution for gargling in a clinical comparative study]. ZFA (Stuttgart). 1978 Feb 28;54(6):354-6. German. PubMed PMID: 636530.