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69824

Sigma-Aldrich

Mitomycin C from Streptomyces caespitosus

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About This Item

Empirical Formula (Hill Notation):
C15H18N4O5
CAS Number:
Molecular Weight:
334.33
Beilstein/REAXYS Number:
7231816
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

mode of action

DNA synthesis | interferes

storage temp.

2-8°C

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

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

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General description

Chemical structure: aziridine

Biochem/physiol Actions

Mode of Action: This product is an alkylating agent that specifically targets the guanine nucleoside sequence 5′-CpG-3′. It inhibits DNA synthesis by covalently reacting with DNA, forming crosslinks between complementary strands of DNA. This interaction prevents separation of complementary DNA strands, inhibiting DNA replication.

Antimicrobial Spectrum: Mitomycin C has strong antitumor activity, especially against Ehrlich ascites tumor cells, and strong bactericidal action against gram-positive and gram-negative bacteria.

Other Notes

Vial contains 2 mg mitomycin C and 48 mg NaCl (increases solubility).

pictograms

Health hazardExclamation mark

signalword

Warning

hcodes

pcodes

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
Roger D James et al.
The Lancet. Oncology, 14(6), 516-524 (2013-04-13)
Chemoradiation became the standard of care for anal cancer after the ACT I trial. However, only two-thirds of patients achieved local control, with 5-year survival of 50%; therefore, better treatments are needed. We investigated whether replacing mitomycin with cisplatin in
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
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
Lars Petter Jordheim et al.
Molecular pharmacology, 84(1), 12-24 (2013-04-13)
The benefit of cancer chemotherapy based on alkylating agents is limited because of the action of DNA repair enzymes, which mitigate the damage induced by these agents. The interaction between the proteins ERCC1 and XPF involves two major components of

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