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Merck

M0440

Mitomicina C from Streptomyces caespitosus

meets USP testing specifications

Sinónimos:

Mitomycin

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About This Item

Fórmula empírica (notación de Hill):
C15H18N4O5
Número CAS:
50-07-7
Peso molecular:
334.33
UNSPSC Code:
12352203
NACRES:
NA.76
PubChem Substance ID:
24896554
EC Number:
200-008-6
Beilstein/REAXYS Number:
7231816
MDL number:
MFCD00078109

Nombre del producto

Mitomicina C from Streptomyces caespitosus, meets USP testing specifications

InChI

1S/C15H18N4O5/c1-5-9(16)12(21)8-6(4-24-14(17)22)15(23-2)13-7(18-13)3-19(15)10(8)11(5)20/h6-7,13,18H,3-4,16H2,1-2H3,(H2,17,22)/t6-,7+,13+,15-/m1/s1

InChI key

NWIBSHFKIJFRCO-WUDYKRTCSA-N

SMILES string

[H][C@]12CN3C4=C([C@@H](COC(N)=O)[C@@]3(OC)[C@@]1([H])N2)C(=O)C(N)=C(C)C4=O

biological source

Streptomyces caespitosus

color

blue-violet

solubility

H2O: 40 mg/mL, clear to very slightly hazy, colorless
H2O: soluble

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

Quality Level

200

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Categorías relacionadas

Biochem/physiol Actions

Modo de acción: Este producto es un agente alquilante dirigido específicamente a la secuencia del nucleósido de guanina 5′-CpG-3′. Inhibe la síntesis de ADN mediante reacción covalente con el ADN al establecer enlaces transversales entre las cadenas complementarias del ADN. Esta interacción evita la separación de las cadenas de ADN complementarias, inhibiendo así la replicación del ADN.

Espectro antimicrobiano: La mitomicina C tiene una fuerte actividad antitumoral, en especial contra las células tumorales de la ascitis de Ehrlich, y una fuerte acción bactericida contra las bacterias grampositivas y gramnegativas.

Application

Mitomycin C is produced by a strain of actinomyces, Streptomyces caespitosus. It contains three anticancer moieties, quinine, urethane, and aziridine groups. It is used to generate mitotically inactive feeder cells in cell culture systems, such as the mitotically inactive fibroblasts used in embryonic stem cell systems.

Disclaimer

Stock solutions should be filter sterilized and stored at 2-8 °C in the dark. Solutions at pH 6-9 can be stored at 0-5 °C for up to a week, but if a precipitate forms, a fresh solution should be prepared - the precipitated solution has been proven toxic to cells.

General description

Chemical structure: aziridine

Preparation Note

Mitomycin C is soluble in water at .5 mg/mL, with a pH of 6.0-7.5. It undergoes rapid degradation in acidic solutions with pH<6, and is mostly likely to retain activity in solutions with a pH between 6-9.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

hcodes

H300,H351

Hazard Classifications

Acute Tox. 2 Oral - Carc. 2

Clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
MKCZ7342
MKCW2164
MKCW8454
MKCW8455
MKCR0172

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Visite la Librería de documentos

Scott C Jeffrey et al.
Journal of medicinal chemistry, 48(5), 1344-1358 (2005-03-04)
Antibody-drug conjugates (ADCs) were prepared consisting of DNA minor groove binder drugs (MGBs) attached to monoclonal antibodies (mAbs) through peptide linkers designed to release drugs inside the lysosomes of target cells. The site of linker attachment on the MGB was
Leonard L Gunderson et al.
International journal of radiation oncology, biology, physics, 87(4), 638-645 (2013-09-17)
The long-term update of US GI Intergroup RTOG 98-11 anal cancer trial found that concurrent chemoradiation (CCRT) with fluorouracil (5-FU) plus mitomycin had a significant impact on disease-free survival (DFS) and overall survival (OS) compared with induction plus concurrent 5-FU plus
Annika Gillis et al.
Applied and environmental microbiology, 80(14), 4138-4152 (2014-05-06)
GIL01, Bam35, GIL16, AP50, and Wip1 are tectiviruses preying on the Bacillus cereus group. Despite the significant contributions of phages in different biological processes, little is known about the dealings taking place between tectiviruses and their Gram-positive bacterial hosts. Therefore
Xin Wang et al.
Nature medicine, 19(4), 473-480 (2013-03-26)
Sorting nexin 27 (SNX27), a brain-enriched PDZ domain protein, regulates endocytic sorting and trafficking. Here we show that Snx27(-/-) mice have severe neuronal deficits in the hippocampus and cortex. Although Snx27(+/-) mice have grossly normal neuroanatomy, we found defects in
D Hompes et al.
Journal of surgical oncology, 109(6), 527-532 (2014-01-01)
Oxaliplatin and Mitomycin C (MMC) are both suitable as intraperitoneal chemotherapy agents in HIPEC for peritoneal carcinomatosis (PC) of colorectal cancer (CRC). Patient cohorts from two different HIPEC-centers underwent cytoreductive surgery and HIPEC with Oxaliplatin (39 patients) and MMC (56
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