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Methylthiazoletetrazolium

HCID 64966
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
13146-93-5
표준 SMILES
Cc1nc(-[n+]2nc(-c3ccccc3)nn2-c2ccccc2)sc1C
InChIKey
FTZIQBGFCYJWKA-UHFFFAOYSA-N
분자식
C18H16N5S+
평균 분자량
334.4 g/mol
단동위원소 질량
334.11264171

개요

3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium is an organic cation that is tetrazolium substituted with a dimethylthiazolyl group and two phenyl groups. The cation exists in two resonance forms. It is an organic cation and a member of tetrazoles.

이름 및 식별자

우선 이름
Methylthiazoletetrazolium
IUPAC
2-(3,5-diphenyltetrazol-2-ium-2-yl)-4,5-dimethyl-1,3-thiazole

이름 및 동의어

Thiazolyl Blue cation010O4LC9TS2H-Tetrazolium, 2-(4,5-dimethyl-2-thiazolyl)-3,5-diphenyl-2-(4,5-Dimethyl-2-thiazolyl)-3,5-diphenyl-2H-tetrazoliumRefChem:818709MTT (2H-TETRAZOLIUM,2-(4,5-DIMETHYL-2THIAZOLYL)-3,CMethylthiazoletetrazolium13146-93-5thiazolyl blue tetrazoliumUNII-010O4LC9TS3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium
이름 더 보기
2-(4,5-dimethyl-1,3-thiazol-2-yl)-3,5-diphenyl-2H-tetrazol-3-ium3-(4,5-dimethyl-1,3-thiazol-2-yl)-2,5-diphenyl-2H-tetrazol-3-ium2-(4,5-Dimethyl-1,3-thiazol-2-yl)-3,5-diphenyltetrazol-2-ium bromideMTT tetrazoliumNMeH3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium BromideMolMap_000036SCHEMBL52720

데이터베이스 식별자

CAS
13146-93-5、298-93-1
PubChem CID
64966
DTXSID
DTXSID701202933
ChEBI
CHEBI:53238
UNII
010O4LC9TS
Nikkaji
J231.977B、J361.778E

물성

구조 계산 물성

XLogP
6.5
극성 표면적
75.7 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
4
회전 가능 결합 수
3
무거운 원자 수
24
형식 전하
1
복잡도
410

실험 및 물리화학적 성질

LogPlog Kow = -2.32 /Estimated/
Color/FormYellow powder
Solubility · 2건

Solubility in 2-methoxyethanol, 20 mg/mL; ethanol, 20 mg/mL

Solubility in water, 10 mg/mL

Melting Point195 °C (decomposes)
Vapor Pressure5.11X10-11 mm Hg at 25 °C /Estimated/
Henry's Law ConstantHenry's Law constant= 5.4X10-22 atm-cu m/mole at 25 °C /Estimated/
Other Experimental PropertiesHydroxyl radical reaction rate constant= 1.7X10-11 cu cm/molecule-sec at 25 °C /Estimated/

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 및 보호

Disposal Methods · 1건

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

독성 정보

Interactions · 2건

KB cells were treated with MTT at final concentrations up to 0.2 mg/ml alone or in combination with methotrexate (10 and 32 uM). When used alone, as little as 0.025 mg/ml increased population doubling time from 26 hr (control) to 96 hr. At 0.2 mg/ml or higher, total cell number declined. MTT, 0.1 mg/ml, reduced the number of cells in S and G2/M phases after 8 hr treatment. However, no significant effect was seen at 2 and 4 hr. The effect of 0.2 mg/ml MTT was more immediate and more pronounced, resulting in accumulation of cells in G0/G1 and S phases. MTT in combination with methotrexate produced a more significant perturbation in the KB cell cycle.

...Phenazine methosulfate (PMS) and MTT are often used in combination: however, PMS did not potentiate the mutagenicity of MTT.

Non-Human Toxicity Excerpts · 3건

/GENOTOXICITY/ Tetrazolium salts, in combination with phenazine methosulfate (PMS) are widely used laboratory reagents. PMS, and 3 tetrazolium salts (MTT, [3-(4,5-dimethylthiazolyl-2)-2,5-diphenyl tetrazolium bromide]; TTC,[2,3,5-triphenyl tetrazolium chloride]; and NBT, [2,2'-di-p-nitrophenyl-5,5'-diphenyl-3,3'-(3,3'-dimethoxy-4,4' were tested for mutagenicity in a range of Escherichia coli WP2 (trp-) and Salmonella typhimurium ... . Without S-9, PMS was mutagenic to E. coli uvrApKM101 /and/ S. typhimurium TA 100 and TA 98 giving (in the dose range 0.5-10 ug/plate) linear dose response curves with slopes of 2.3, 1.3 and 0.5 revertants/nmol respectively. Addition of /rat liver/ S-9 drastically reduced the mutagenicity of PMS in these bacteria. MTT, in the absence of S-9, was mutagenic to E. coli uvrApKM101, S.typhimurium TA 100 and TA 98, giving linear dose-response curves with slopes of 3.8, 12.1 and 1.0 respectively, at doses ranging from 0.5 to 10 or 50 ug/plate. Addition of S-9 markedly reduced the mutagenicity of MTT. MTT was very weakly mutagenic in E. coli WP2 (0.22 revertants/nmol), significantly more mutagenic in WP2 uvrA (1.29 revertants/nmol), and non-mutagenic in WP2 lexA (negative slope due to toxicity), suggesting that MTT causes excisable misrepair DNA damage. PMS and MTT are often used in combination: however, PMS did not potentiate the mutagenicity of MTT.

화학 및 산업

용도 및 제조

Uses · 5건

Tetrazolium salts are used for the detection of dehydrogenase activity or any other enzyme systems where redox equivalents are generated. Due to this feature, they are an extremely useful tool in academic and clinical research as well as for many diagnostic applications, eg: (1) aids and cancer research, cell and molecular biology: for testing cell proliferation and cell viability and for cytotoxicity tests (2) Enzyme diagnostics and clinical chemistry: for the assay of dehydrogenase activity and other enzyme systems which form redox equivalents; for the determination of dehydrogenase substrate concentrations; for the detection of glucose, ethanol, glycerol and other substrates which develop redox equivalents in a coupled reaction (3) Immuno histochemistry: for the detection of alkaline phosphatase (4) Histology and pathology: for the histochemical detection of dehydrogenase (5) In seed nurseries: for testing seed viability.

Tetrazolium salts are widely used for detecting redox potential of cells for viability, cytotoxicity and proliferation assays. ... Reduction of MTT remains the most common assay for tetrazolium salt-based viability testing.

Tetrazolium salts for detecting redox potential in living cells and tissues: 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide. Applications: superoxide generation by fumarate reductase and nitric oxide synthase; mitochondrial dehydrogenase activity; cell viability and proliferation; neuronal cell death; platelet activation; tumor cell adhesion and invasion; multidrug resistance; in vitro toxicity testing /from table/

The MTT assay is frequently used in anti-HIV and antineoplastic drug screening for the evaluation of cell survival and proliferation.

For more Uses (Complete) data for METHYLTHIAZOLETETRAZOLIUM (6 total), please visit the HSDB record page.

General Manufacturing Information · 4건

The MTT assay is simple, accurate and yields reproducible results. This method has been developed originally by Mossman in 1983. The key component is (3-[4,5-dimethylthiazol-2-yl]- 2,5-diphenyl tetrazolium bromide) or MTT. Mitochondrial dehydrogenases of viable cells cleave the tetrazolium ring, leading to the formation of purple crystals which are insoluble in aqueous solutions. The crystals are re-dissolved in acidified isopropanol and the resulting purple solution is measured spectrophotometrically. An increase or decrease in cell number results in a concomitant change in the amount of formazan formed, indicating the degree of cytotoxicity caused by the test material (IC50).

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

/ALTERNATIVE IN VITRO TESTS/ ... /The authors/... investigated the effects of MTT on cell growth and cell cycle distribution using DNA flow cytometry. KB cells were treated with MTT at final concentrations up to 0.2 mg/ml alone or in combination with methotrexate (10 and 32 uM). When used alone, as little as 0.025 mg/ml increased population doubling time from 26 hr (control) to 96 hr. At 0.2 mg/ml or higher, total cell number declined. MTT, 0.1 mg/ml, reduced the number of cells in S and G2/M phases after 8 hr treatment. However, no significant effect was seen at 2 and 4 hr. The effect of 0.2 mg/ml MTT was more immediate and more pronounced, resulting in accumulation of cells in G0/G1 and S phases. MTT in combination with methotrexate produced a more significant perturbation in the KB cell cycle. Although the MTT assay measures cell viability and proliferation via mitochondrial dehydrogenases, it showed definite effects on cellular DNA content and cell proliferation. These observations question the credibility of such an assay, indicating it may be measuring combined effects of MTT and drug and not drug alone.

/OTHER TOXICITY INFORMATION/ Despite widespread use of various tetrazolium assays, the mechanisms of bioreduction of these compounds have not been fully elucidated. /The authors/ investigated the capacity of tetrazolium salts to penetrate through intact cell plasma membranes. 5-Cyano-2,3-ditolyl tetrazolium chloride (CTC) and 3-(4,5-dimethylthiazol-2-yl)-2,5 diphenyltetrazolium bromide (MTT) tetrazolium salts appear to represent examples of species that are reduced by different mechanisms. /The authors/ provide evidence suggesting that MTT readily crosses intact plasma membranes and is reduced intracellularly. MTT appears to be reduced by both plasma membrane and intracellular reductases; reducing cells are not damaged and remain metabolically active for at least 45 min. In contrast, CTC remains extracellular with respect to viable cells and thus requires plasma membrane permeable electron carrier to be reduced efficiently. However, reduction of CTC in the presence of an electron carrier inflicts damage on plasma membranes. The intracellular vs extracellular sites of reduction of tetrazolium salts were established on the basis of deposition of formazans. Crystals of formazan were detected using fluorescence or backscattered light confocal laser microscopy. /The authors/ postulate that the capacity of a tetrazolium salt to cross intact plasma membranes constitutes an important experimental variable which needs to be controlled in order to correctly interpret the outcome of tetrazolium assays designed to measure cellular production of oxygen radicals, activity of mitochondrial, cytosolic, or outer membrane reductases, etc.

Antidote and Emergency Treatment · 2건

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

A tetrazolium salt has been used to develop a quantitative colorimetric assay for mammalian cell survival and proliferation. The assay detects living, but not dead cells and the signal generated is dependent on the degree of activation of the cells. This method can therefore be used to measure cytotoxicity, proliferation or activation. The results can be read on a multiwell scanning spectrophotometer (ELISA reader) and show a high degree of precision.

/The authors/ compared the MTT assay to the standard clonogenic assay and had good agreement of surviving fraction /of murine solid tumor cells/ after radiation doses of 2 and 4 Gy. It is possible, therefore, to adapt the MTT assay for use with cell suspensions prepared directly from fresh murine tumors. This may provide a methodology for the determination of the clinical radiosensitivity of tumors including fresh clinical tumor specimens.

A microcytotoxicity assay employing a tetrazolium salt has been adapted for testing the response of human leukemic blast cells to a variety of chemotherapeutic agents. After exposure to various concentrations of drugs, the viability of fresh leukemic blast cells was measured using a tetrazolium salt, MTT, which is converted to blue formazan crystals by living cells. The amount of formazan produced was quantitated using a microtiter plate spectrophotometer.