Tiron

Names

[ CAS No. ]:
149-45-1

[ Name ]:
Tiron

[Synonym ]:
MFCD00149531
Pyrocatechol-3,5-disulfonic Acid Disodium Salt Monohydrate
4,5-dihydroxybenzene-1,3-disulfonic acid disodium salt
tlron
disodium 1,2-dihydroxybenzene-3,5-disulfonate
1,3-Benzenedisulfonic acid, 4,5-dihydroxy-, disodium salt
Tiron
4,5-Dihydroxy-1,3-benzenedisulfonic acid disodium salt
TIRON(TM)
Disodium 4,5-dihydroxy-1,3-benzenedisulfonate
Disodium-1,2-dihydroxybenzene-3,5-disulfonate
YOE'S REAGENT
Sodium 4,5-dihydroxybenzene-1,3-disulfonate hydrate
tiferron
Tiferron Monohydrate
Disodium 4,5-Dihydroxybenzene-1,3-disulfonate Monohydrate
1,3-Benzenedisulfonic acid, 4,5-dihydroxy-, sodium salt (1:2)
Disodium 4,5-dihydroxybenzene-1,3-disulfonate
Sodium Pyrocatechol-2,4-disulfonate
sdd
EINECS 205-741-5
sodium catechol disulfonate
Pyrocatechol-3,5-disulfonic acid disodium salt
1,2-dihydroxybenzene-3,5-disulfonic acid disodium salt
Tiron TIRON(R)
Catechol-3,5-disulfonic Acid Disodium Salt Monohydrate

Biological Activity

[Description]:

Tiron is a non-toxic chelator of a variety of metals. Tiron is cell permeable analog of vitamin E and function as hydroxyl radical and superoxide scavenger. Tiron is an orally active antioxidant. Tiron can be used to alleviate acute metal overload in animals[1][2][3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

[In Vitro]

Tiron (10 mM) 保护中国仓鼠 V79 细胞免受 H2O2 诱导的细胞毒性[1]。 Tiron (0-20 mM) 保护超螺旋 DNA 免受金属介导的超氧化物依赖性链断裂[1]。 Tiron (50 nM-200 nM, 48 h) 抑制 HG 诱导的新生大鼠心肌细胞凋亡[3]。 Tiron (50 nM-200 nM, 48 h) 降低新生大鼠心肌细胞内的骨桥蛋白[3]。 Tiron (0.2 mM，2 小时) 抑制 UVB 诱导的 HDF 中 MMP-1 和 MMP-3 的上调[4]。 Tiron (0.7 mM，48 小时) 增加 S 期和 G2/M 期 PT4 细胞的百分比[5]。 Cell Cycle Analysis[5] Cell Line: PT4 cells Concentration: 0.7 mM Incubation Time: 48 h Result: Increased the percentage of PT4 cells in S and G2/M phases, along with a reduction of cells in the G0/G1 phase.

[In Vivo]

Tiron (200 mg/kg，灌胃) 改善小鼠气道重塑模型中的氧化应激和炎症[2]。 Tiron (300 mg/kg，i.p.，每日一次，持续两周) 减轻了 STZ 诱导的糖尿病小鼠左心室心肌细胞的凋亡[3]。 Animal Model: BALB/c mice challenged with Ovalbumin (OVA) aerosol for 8 weeks[2] Dosage: 200 mg/kg Administration: Oral gavage. Result: Inhibited levels of NOx, IL-13 and TGF-β1, and immunoreactivity of NF-κB. Animal Model: STZ-induced diabetic mice[3] Dosage: 300 mg/kg Administration: i.p., daily for two weeks. Result: Reduced the levels of total oxidized proteins and advanced glycation end products (AGEs)-related proteins. Inhibited cardiac myocyte apoptosis. Decreased PKCδ localization on plasma membrane.

[References]

[1]. Krishna CM, et al. The catecholic metal sequestering agent 1,2-dihydroxybenzene-3,5-disulfonate confers protection against oxidative cell damage. Arch Biochem Biophys. 1992 Apr;294(1):98-106. 2.

[2]. El-Sherbeeny NA, et al. Tiron ameliorates oxidative stress and inflammation in a murine model of airway remodeling. Int Immunopharmacol. 2016 Oct;39:172-180.

[3]. Jiang P, et al. Tiron ameliorates high glucose-induced cardiac myocyte apoptosis by PKCδ-dependent inhibition of osteopontin. Clin Exp Pharmacol Physiol. 2017 Jul;44(7):760-770.

[4]. Lu J, et al. Tiron Inhibits UVB-Induced AP-1 Binding Sites Transcriptional Activation on MMP-1 and MMP-3 Promoters by MAPK Signaling Pathway in Human Dermal Fibroblasts. PLoS One. 2016 Aug 3;11(8):e0159998.

[5]. Monticone M, et al. NAC, tiron and trolox impair survival of cell cultures containing glioblastoma tumorigenic initiating cells by inhibition of cell cycle progression. PLoS One. 2014 Feb 28;9(2):e90085.

Chemical & Physical Properties

[ Melting Point ]:
300 °C

[ Molecular Formula ]:
C₆H₆Na₂O₉S₂

[ Molecular Weight ]:
314.201

[ Exact Mass ]:
313.914307

[ PSA ]:
180.85000

[ LogP ]:
1.00330

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
soluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CZ9263000

CHEMICAL NAME :: m-Benzenedisulfonic acid, 4,5-dihydroxy-, disodium salt

CAS REGISTRY NUMBER :: 149-45-1

LAST UPDATED :: 199701

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C6-H4-O8-S2.2Na

MOLECULAR WEIGHT :: 314.20

WISWESSER LINE NOTATION :: WSO&R BQ CQ ESWO &-NA- 2

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 :: 6060 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 30 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 30 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Embryo or Fetus - fetal death

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 100 ug/plate

REFERENCE :: ABCHA6 Agricultural and Biological Chemistry. (Maruzen Co. Ltd., POB 5050, Tokyo International, Tokyo 100-31, Japan) V.25- 1961- Volume(issue)/page/year: 45,327,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X7554 No. of Facilities: 78 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 388 (estimated) No. of Female Employees: 155 (estimated)

Safety Information

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ WGK Germany ]:
3

[ RTECS ]:
CZ9263000

[ HS Code ]:
29082000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2908999090

[ Summary ]:
2908999090 halogenated, sulphonated, nitrated or nitrosated derivatives of phenols or phenol-alcohols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%