10-Decarbamoylmitomycin C

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581995

CAS#: 26909-37-5

Description: 10-Decarbamoylmitomycin C, also known as decarbamoylmitomycin C, alkylates DNA and forms deoxyguanosine monoadducts and interstrand crosslinks; is used in cancer treatments.

Chemical Structure

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10-Decarbamoylmitomycin C
CAS# 26909-37-5
Instruction

Theoretical Analysis

MedKoo Cat#: 581995
Name: 10-Decarbamoylmitomycin C
CAS#: 26909-37-5
Chemical Formula: C14H17N3O4
Exact Mass: 291.12
Molecular Weight: 291.310
Elemental Analysis: C, 57.72; H, 5.88; N, 14.42; O, 21.97

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: 10-Decarbamoylmitomycin C; 10-Decarbamoyl mitomycin C; BRN 5608775; CCRIS 5160; DCMC; Decarbamoyl mitomycin C; Decarbamoylmitomycin C; Decarbamylmitomycin C

IUPAC/Chemical Name: (1aS,8S,8aR,8bS)-6-amino-8-(hydroxymethyl)-8a-methoxy-5-methyl-1,1a,2,8,8a,8b-hexahydroazirino[2',3':3,4]pyrrolo[1,2-a]indole-4,7-dione

InChi Key: OUADMZZEIRSDSG-NKFUZKMXSA-N

InChi Code: InChI=1S/C14H17N3O4/c1-5-9(15)12(20)8-6(4-18)14(21-2)13-7(16-13)3-17(14)10(8)11(5)19/h6-7,13,16,18H,3-4,15H2,1-2H3/t6-,7+,13+,14-/m1/s1

SMILES Code: CO[C@]12[C@H]3N[C@H]3CN1C4=C([C@H]2CO)C(=O)C(=C(C)C4=O)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 291.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Zacarias O, Aguilar W, Paz MM, Tsukanov S, Zheng M, Cheng SY, Pradhan P, Champeil E. Isolation and Rationale for the Formation of Isomeric Decarbamoylmitomycin C- N(6)-deoxyadenosine Adducts in DNA. Chem Res Toxicol. 2018 Aug 20;31(8):762-771. doi: 10.1021/acs.chemrestox.8b00102. Epub 2018 Aug 2. PubMed PMID: 30035537.

2: Ahn K, O YM, Ji YG, Cho HJ, Lee DH. Synergistic Anti-Cancer Effects of AKT and SRC Inhibition in Human Pancreatic Cancer Cells. Yonsei Med J. 2018 Aug;59(6):727-735. doi: 10.3349/ymj.2018.59.6.727. PubMed PMID: 29978609; PubMed Central PMCID: PMC6037593.

3: Aguilar W, Paz MM, Vargas A, Zheng M, Cheng SY, Champeil E. Interdependent Sequence Selectivity and Diastereoselectivity in the Alkylation of DNA by Decarbamoylmitomycin C. Chemistry. 2018 Sep 6;24(50):13278-13289. doi: 10.1002/chem.201802038. Epub 2018 Aug 10. PubMed PMID: 29958326.

4: Aguilar W, Paz MM, Vargas A, Clement CC, Cheng SY, Champeil E. Sequence-Dependent Diastereospecific and Diastereodivergent Crosslinking of DNA by Decarbamoylmitomycin C. Chemistry. 2018 Apr 20;24(23):6030-6035. doi: 10.1002/chem.201705771. Epub 2018 Mar 27. PubMed PMID: 29504661.

5: Champeil E, Cheng SY, Huang BT, Conchero-Guisan M, Martinez T, Paz MM, Sapse AM. Synthesis of Mitomycin C and Decarbamoylmitomycin C N(2) deoxyguanosine-adducts. Bioorg Chem. 2016 Apr;65:90-9. doi: 10.1016/j.bioorg.2016.02.003. Epub 2016 Feb 11. PubMed PMID: 26894558; PubMed Central PMCID: PMC4807628.

6: Xiao G, Kue P, Bhosle R, Bargonetti J. Decarbamoyl mitomycin C (DMC) activates p53-independent ataxia telangiectasia and rad3 related protein (ATR) chromatin eviction. Cell Cycle. 2015;14(5):744-54. doi: 10.1080/15384101.2014.997517. PubMed PMID: 25565400; PubMed Central PMCID: PMC4418290.

7: Hoffman S, Martin D, Meléndez A, Bargonetti J. C. elegans CEP-1/p53 and BEC-1 are involved in DNA repair. PLoS One. 2014 Feb 20;9(2):e88828. doi: 10.1371/journal.pone.0088828. eCollection 2014. PubMed PMID: 24586407; PubMed Central PMCID: PMC3930633.

8: Champeil E, Paz MM, Lukasiewicz E, Kong WS, Watson S, Sapse AM. Synthesis of a major mitomycin C DNA adduct via a triaminomitosene. Bioorg Med Chem Lett. 2012 Dec 1;22(23):7198-200. doi: 10.1016/j.bmcl.2012.09.052. Epub 2012 Sep 25. PubMed PMID: 23079525.

9: Boamah EK, Brekman A, Tomasz M, Myeku N, Figueiredo-Pereira M, Hunter S, Meyer J, Bhosle RC, Bargonetti J. DNA adducts of decarbamoyl mitomycin C efficiently kill cells without wild-type p53 resulting from proteasome-mediated degradation of checkpoint protein 1. Chem Res Toxicol. 2010 Jul 19;23(7):1151-62. doi: 10.1021/tx900420k. PubMed PMID: 20536192; PubMed Central PMCID: PMC2907727.

10: Paz MM, Ladwa S, Champeil E, Liu Y, Rockwell S, Boamah EK, Bargonetti J, Callahan J, Roach J, Tomasz M. Mapping DNA adducts of mitomycin C and decarbamoyl mitomycin C in cell lines using liquid chromatography/ electrospray tandem mass spectrometry. Chem Res Toxicol. 2008 Dec;21(12):2370-8. doi: 10.1021/tx8002615. PubMed PMID: 19053323; PubMed Central PMCID: PMC2630229.

11: Boamah EK, White DE, Talbott KE, Arva NC, Berman D, Tomasz M, Bargonetti J. Mitomycin-DNA adducts induce p53-dependent and p53-independent cell death pathways. ACS Chem Biol. 2007 Jun 15;2(6):399-407. Epub 2007 May 25. PubMed PMID: 17530733; PubMed Central PMCID: PMC2886584.

12: Palom Y, Suresh Kumar G, Tang LQ, Paz MM, Musser SM, Rockwell S, Tomasz M. Relative toxicities of DNA cross-links and monoadducts: new insights from studies of decarbamoyl mitomycin C and mitomycin C. Chem Res Toxicol. 2002 Nov;15(11):1398-406. PubMed PMID: 12437330.

13: Abbas T, Olivier M, Lopez J, Houser S, Xiao G, Kumar GS, Tomasz M, Bargonetti J. Differential activation of p53 by the various adducts of mitomycin C. J Biol Chem. 2002 Oct 25;277(43):40513-9. Epub 2002 Aug 14. PubMed PMID: 12183457.

14: Li VS, Tang MS, Kohn H. The effect of C(5) cytosine methylation at CpG sequences on mitomycin-DNA bonding profiles. Bioorg Med Chem. 2001 Apr;9(4):863-73. PubMed PMID: 11354669.

15: Li VS, Reed M, Zheng Y, Kohn H, Tang M. C5 cytosine methylation at CpG sites enhances sequence selectivity of mitomycin C-DNA bonding. Biochemistry. 2000 Mar 14;39(10):2612-8. PubMed PMID: 10704210.

16: Huh N, Rege AA, Yoo B, Kogan TP, Kohn H. Design, synthesis, and evaluation of mitomycin-tethered phosphorothioate oligodeoxynucleotides. Bioconjug Chem. 1996 Nov-Dec;7(6):659-69. PubMed PMID: 8950485.

17: Kim SY, Rockwell S. Cytotoxic potential of monoalkylation products between mitomycins and DNA: studies of decarbamoyl mitomycin C in wild-type and repair-deficient cell lines. Oncol Res. 1995;7(5):39-47. PubMed PMID: 8534933.

18: Rockwell S, Kim SY. Cytotoxic potential of monoalkylation products between mitomycins and DNA: studies of decarbamoyl mitomycin C in wild-type and repair-deficient cell lines. Oncol Res. 1995;7(1):39-47. Corrected and republished in: Oncol Res. 1995;7(5):39-47. PubMed PMID: 7549043.

19: Basu AK, Hanrahan CJ, Malia SA, Kumar S, Bizanek R, Tomasz M. Effect of site-specifically located mitomycin C-DNA monoadducts on in vitro DNA synthesis by DNA polymerases. Biochemistry. 1993 May 11;32(18):4708-18. PubMed PMID: 8490017.

20: Tucker JD, Jones NJ, Allen NA, Minkler JL, Thompson LH, Carrano AV. Cytogenetic characterization of the ionizing radiation-sensitive Chinese hamster mutant irs1. Mutat Res. 1991 Mar;254(2):143-52. PubMed PMID: 1900570.