Phenylbiguanide

Names

[ CAS No. ]:
102-02-3

[ Name ]:
Phenylbiguanide

[Synonym ]:
N-Phenyliminodicarbonimidic Diamide
Phenylbiguanide
MFCD00179077
1-(diaminomethylidene)-2-phenylguanidine
EINECS 202-998-5

Biological Activity

[Description]:

Phenylbiguanide is a 5-HT3 receptor selective agonist with an EC50 of 3.0±0.1 μM.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Research Areas >> Neurological Disease

[Target]

5-HT3 Receptor:3 μM (EC50)

[In Vitro]

Phenylbiguanide (1-Phenylbiguanide) is a 5-HT3 receptor selective agonist with pEC50s of 5.57, 4.07, and 4.47 for r5-HT3A(b), h5-HT3A, m5-HT3A(b) , respectively[1]. The effect of Phenylbiguanide (1-Phenylbiguanide hydrochloride) in promoting the growth of the HT29 cell line is investigated. Phenylbiguanide causes a dose dependent proliferation of HT29 cells after 48 hours incubation. The maximum proliferation is at a 5HT concentration of 12.5 μM (P≤0.01). Phenylbiguanide significantly stimulates the growth of cells at concentrations of 3.125 μM (P≤0.05) and 6.25 μM (P≤0.01)[2].

[In Vivo]

In anaesthetised mice, Phenylbiguanide (PBG), a drug that is known to stimulate cardiopulmonary afferent C-fibres,is injected into the right atrium of the heart and mapped c-Fos expression within specific regions of the central nervous system. Intraatrial injection of PBG produces a reflex cardiorespiratory response including a pronounced bradycardia and a respiratory depression[3].

[Cell Assay]

HT29 cells are washed with Phosphate buffer saline (PBS) and harvested with a 0.5% trypsin solution at 50-60% confluency. Cells are then added to wells at a density of 104 cells/well in a 96-well plate to a final volume of 100 μL/well. After 24 hours of incubation at 37°C in a 5% CO2 atmosphere, the culture medium is replaced with 200 μL fresh culture medium containing 5HT hydrochloride, Phenylbiguanide hydrochloride at concentrations of: 3.125, 6.25, 12.5, 25, 50, and 100 µM . Cells cultured solely in media served as negative controls. After 48 hours of incubation at 37°C in a 5% CO2 atmosphere, the culture medium is removed and 8 µL MTT reagent (diluted in PBS at a concentration of 4 mg/mL) is added to 50 μL of fresh culture medium at a final concentration of 0.55 mg/mL. The optimum incubation period time is determined in a pilot study[2].

[Animal admin]

Mice[3] Adult male specified pathogen free (SPF) BALB/c mice (28-33 g; n=10) are used throughout this study. All mice have free access to water and food in a light (12: 12 h light/ dark cycle, lights on at 0700 h) and temperature-controlled (21-23°C) environment. Mice are randomly assigned to two treatment groups, 1) intra-atrial injection of 0.9% saline (controls, n=5) or 2) intra-atrial injection of vehicle containing Phenylbiguanide (n=5). For the PBGinjected group, mice are injected with an effective dose of Phenylbiguanide (1-1.5 μg in 10-15 μL saline) . This is repeated five times in total with each injection separated by 8-10 min. For control mice, each mouse receives five saline injections (10-15 μL each), also at 8-10 min intervals[3].

[References]

[1]. Mair ID, et al. Pharmacological characterization of a rat 5-hydroxytryptamine type3 receptor subunit (r5-HT_3A(b)) expressed in Xenopus laevis oocytes. Br J Pharmacol. 1998 Aug;124(8):1667-74.

[2]. Ataee R, et al. Study of 5HT3 and HT4 receptor expression in HT29 cell line and human colon adenocarcinoma tissues. Arch Iran Med. 2010 Mar;13(2):120-5.

[3]. de Vries A, et al. Characterisation of c-Fos expression in the central nervous system of mice following right atrialinjections of the 5-HT3 receptor agonist Phenylbiguanide. Auton Neurosci. 2005 Dec 30;123(1-2):62-75.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.33g/cm3

[ Boiling Point ]:
388.4ºC at 760mmHg

[ Melting Point ]:
135-142 °C(lit.)

[ Molecular Formula ]:
C₈H₁₁N₅

[ Molecular Weight ]:
177.20600

[ Flash Point ]:
188.7ºC

[ Exact Mass ]:
177.10100

[ PSA ]:
100.28000

[ LogP ]:
1.88000

[ Vapour Pressure ]:
3.08E-06mmHg at 25°C

[ Index of Refraction ]:
1.656

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DU2450000

CHEMICAL NAME :: Biguanide, 1-phenyl-

CAS REGISTRY NUMBER :: 102-02-3

LAST UPDATED :: 198505

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C8-H11-N5

MOLECULAR WEIGHT :: 177.24

WISWESSER LINE NOTATION :: MUYZMYUM&MR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MPHEAE Medicina et Pharmacologia Experimentalis. (Basel, Switzerland) V.12-17, 1965-67. For publisher information, see PHMGBN. Volume(issue)/page/year: 16,267,1967

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DU2450000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Cardiovascular afferents cause the release of 5-HT in the nucleus tractus solitarii; this release is regulated by the low- (PMAT) not the high-affinity transporter (SERT).

J. Physiol. 593(7) , 1715-29, (2015)

The nucleus tractus solitarii (NTS) integrates inputs from cardiovascular afferents and thus is crucial for cardiovascular homeostasis. These afferents primarily release glutamate, although 5-HT has a...

Microvascular dilation evoked by chemical stimulation of C-fibers in rats.

J. Appl. Physiol. 118(1) , 55-60, (2015)

Activation of pulmonary C-fibers can reflexively decrease heart rate, blood pressure, and peripheral vascular resistance. However, the effects of these afferents on microvascular tone remain incomplet...

5-HT1D receptor inhibits renal sympathetic neurotransmission by nitric oxide pathway in anesthetized rats.

Vascul. Pharmacol. 72 , 172-80, (2015)

Although serotonin has been shown to inhibit peripheral sympathetic outflow, serotonin regulation on renal sympathetic outflow has not yet been elucidated. This study investigated which 5-HT receptor ...

Related Compounds

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