M0440

Mitomycine C from Streptomyces caespitosus

Name: Mitomycine C from <I>Streptomyces caespitosus</I>
Brand: SIGMA

meets USP testing specifications

Synonyme(s) :

Mitomycin

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About This Item

Formule empirique (notation de Hill) :

C₁₅H₁₈N₄O₅

Numéro CAS:

50-07-7

Poids moléculaire :

334.33

UNSPSC Code:

12352203

NACRES:

NA.76

PubChem Substance ID:

24896554

EC Number:

200-008-6

Beilstein/REAXYS Number:

7231816

MDL number:

MFCD00078109

Nom du produit

Mitomycine 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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Catégories apparentées

Antibiotiques

Chimie et produits biochimiques

Produits biochimiques

Suppléments et réactifs pour la culture cellulaire

Biochem/physiol Actions

Mode d′action : Ce produit est un agent alkylant qui cible spécifiquement la guanine dans la séquence nucléosidique 5′-CpG-3′. Il inhibe la synthèse de l′ADN en réagissant de façon covalente et en formant des liaisons croisées entre les brins complémentaires d′ADN. Ceci empêche la séparation des brins complémentaires d′ADN, ce qui inhibe la réplication de l′ADN.

Spectre antimicrobien : La mitomycine C présente une activité antitumorale puissante, particulièrement envers les cellules du carcinome ascitique d′Ehrlich, et une forte activité bactéricide envers les bactéries à Gram négatif et à Gram positif.

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

GHS06,GHS08

signalword

Danger

hcodes

H300,H351

pcodes

P201 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 2 Oral - Carc. 2

Classe de stockage

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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Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Design, synthesis, and in vitro evaluation of dipeptide-based antibody minor groove binder conjugates.

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

Anal carcinoma: impact of TN category of disease on survival, disease relapse, and colostomy failure in US Gastrointestinal Intergroup RTOG 98-11 phase 3 trial.

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

Loss of sorting nexin 27 contributes to excitatory synaptic dysfunction by modulating glutamate receptor recycling in Down's syndrome.

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

The use of Oxaliplatin or Mitomycin C in HIPEC treatment for peritoneal carcinomatosis from colorectal cancer: a comparative study.

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

Homeostasis of thymus-derived Foxp3+ regulatory T cells is controlled by ultraviolet B exposure in the skin.

Sayuri Yamazaki et al.

Journal of immunology (Baltimore, Md. : 1950), 193(11), 5488-5497 (2014-10-29)

Accumulating evidence shows that immunological tolerance induced by Ag administration together with UVB irradiation is dependent on Foxp3(+) CD4(+) regulatory T (Treg) cells. However, the mechanisms by which UVB controls Treg cells in the skin are currently unclear. In this

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