3-Iodobenzyl-guanidine hemisulfate

Product Name3-Iodobenzyl-guanidine hemisulfate
CAS87862-25-7
MFC16H22I2N6O4S
MW648.26
EINECS
MOL File87862-25-7.mol

Chemical Properties

storage temp.	2-8°C
solubility	DMSO: 2 mg/ml; DMSO:PBS (pH 7.2) (1:4): 0.2 mg/ml
form	A crystalline solid
color	White to off-white
InChI	1S/2C8H10IN3.H2O4S/c29-7-3-1-2-6(4-7)5-12-8(10)11;1-5(2,3)4/h21-4H,5H2,(H4,10,11,12);(H2,1,2,3,4)
InChIKey	XNACDNPGABUBFR-UHFFFAOYSA-N
SMILES	OS(O)(=O)=O.NC(=N)NCc1cccc(I)c1.NC(=N)NCc2cccc(I)c2

Safety Information

WGK Germany	3
HS Code	2909309090
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

m-Iodobenzylguanidine (MIBG) is an analogue of norepinephrine with anticancer activity. It inhibits cell growth in a panel of human and mouse leukemia, fibrosarcoma, melanoma, and neuroblastoma cell lines when used at a concentration of 20 μg/ml and reduces clonogenic survival of L1210 leukemia cells in a concentration-dependent manner. MIBG increases survival in N₁E155 and L1210 mouse xenograft models when administered at doses of 40 and 20 mg/kg, respectively. It selectively accumulates in chromaffin tissues and tumors and formulations containing radiolabeled forms of MIBG have been used as imaging agents in the diagnosis and treatment of neuroendocrine tumors. MIBG also inhibits ADP-ribose linkage to membrane proteins in turkey erythrocyte membranes.

Chemical Properties

Colourless to off-white solid

Uses

m-Iodobenzylguanidine Hemisulfatecan be used to demethylate and oxidize membrane-associated DNA. It has also been employed to develop a cell-based high-throughput screening assay to identify anti-hepatitis C virus compounds.

Biochem/physiol Actions

Antitumor agent which inhibits ADP ribosylation.

in vivo

Iobenguane sulfate (MIBG hemisulfate) (20 mg/kg; i.p.; daily on days 3-6) shows antitumor activity^[1].
The survival of male strain AF mice inoculates with N1E115 neuroblastoma and treats according to NIH protocols for new drug testing with 9 daily injections of Iobenguane sulfate (40 mg/kg), Marking prolongation of sugvival but no cures were observed^[1].
Iobenguane sulfate testes for its toxicity on male strain AF (N1Ell5) mice with 5 daily injections. At 50 mg/kg body weight, all animals died after 1-4 doses and 4/16 animals died on a schedule of 44 mg/kg^[1].

Animal Model:	DBA/2 (L1210)) mice^[1]
Dosage:	i.p.; daily on days 3-6
Administration:	20 mg/kg
Result:	Considerable prolongation of survival and some cures were obtained.

References

[1] L A SMETS J W B Bout. Cytotoxic and antitumor effects of the norepinephrine analogue meta-iodo-benzylguanidine (MIBG).[J]. Cancer Chemotherapy and Pharmacology, 1988, 21 1: 9-13. DOI: 10.1007/bf00262730
[2] CORNELIA LOESBERG Lou A S Henny van Rooij. Meta-iodobenzylguanidine (MIBG), a novel high-affinity substrate for cholera toxin that interferes with cellular mono(ADP-ribosylation)[J]. Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 1990, 1037 1: Pages 92-99. DOI: 10.1016/0167-4838(90)90106-p

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