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MedKoo Cat#: 571026 | Name: Aniline mustard

Description:

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

Aniline mustard is an alkylating mustard with anti-neoplastic activity. Aniline mustard forms covalent linkages with nucleophilic centers, resulting in depurination, base miscoding and strand scission, and crosslinking of DNA strands, all of which contribute to its cytotoxicity.

Chemical Structure

Aniline mustard
Aniline mustard
CAS#553-27-5

Theoretical Analysis

MedKoo Cat#: 571026

Name: Aniline mustard

CAS#: 553-27-5

Chemical Formula: C10H13Cl2N

Exact Mass: 217.0425

Molecular Weight: 218.12

Elemental Analysis: C, 55.07; H, 6.01; Cl, 32.50; N, 6.42

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Aniline mustard; Lymphocin; Mesylerythrol; NSC-18429
IUPAC/Chemical Name
Aniline, N,N-bis(2-chloroethyl)-
InChi Key
ROSJKFFLIXTTAW-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H13Cl2N/c11-6-8-13(9-7-12)10-4-2-1-3-5-10/h1-5H,6-9H2
SMILES Code
ClCCN(CCCl)C1=CC=CC=C1
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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 218.12 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
1: Chen CH, Hu TH, Huang TC, Chen YL, Chen YR, Cheng CC, Chen CT. Delineation of G-Quadruplex Alkylation Sites Mediated by 3,6-Bis(1-methyl-4-vinylpyridinium iodide)carbazole-Aniline Mustard Conjugates. Chemistry. 2015 Nov 23;21(48):17379-90. doi: 10.1002/chem.201502595. Epub 2015 Oct 13. PubMed PMID: 26769627. 2: Fedeles BI, Zhu AY, Young KS, Hillier SM, Proffitt KD, Essigmann JM, Croy RG. Chemical genetics analysis of an aniline mustard anticancer agent reveals complex I of the electron transport chain as a target. J Biol Chem. 2011 Sep 30;286(39):33910-20. doi: 10.1074/jbc.M111.278390. Epub 2011 Aug 10. PubMed PMID: 21832047; PubMed Central PMCID: PMC3190774. 3: Benckhuysen C, Ter Hart HG, Van Dijk PJ. Enhanced cytostatic effectiveness of aniline mustard against 7,12-dimethylbenz[a]anthracene-induced rat mammary tumors during regression in response to ovariectomy. Cancer Treat Rep. 1981 Jul-Aug;65(7-8):567-74. PubMed PMID: 6788369. 4: McClean S, Costelloe C, Denny WA, Searcey M, Wakelin LP. Sequence selectivity, cross-linking efficiency and cytotoxicity of DNA-targeted 4-anilinoquinoline aniline mustards. Anticancer Drug Des. 1999 Jun;14(3):187-204. PubMed PMID: 10500495. 5: Gourdie TA, Valu KK, Gravatt GL, Boritzki TJ, Baguley BC, Wakelin LP, Wilson WR, Woodgate PD, Denny WA. DNA-directed alkylating agents. 1. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the reactivity of the mustard. J Med Chem. 1990 Apr;33(4):1177-86. PubMed PMID: 2319563. 6: Panthananickal A, Hansch C, Leo A. Structure-activity relationship of aniline mustards acting against B-16 melanoma in mice. J Med Chem. 1979 Oct;22(10):1267-9. PubMed PMID: 513075. 7: Hansch C, Telzer BR, Zhang L. Comparative QSAR in toxicology: examples from teratology and cancer chemotherapy of aniline mustards. Crit Rev Toxicol. 1995;25(1):67-89. Review. PubMed PMID: 7734060. 8: Leo A, Panthananickal A, Hansch C, Theiss J, Shimkin M, Andrews AW. A comparison of mutagenic and carcinogenic activities of aniline mustards. J Med Chem. 1981 Jul;24(7):859-64. PubMed PMID: 7277394. 9: Trafalis D, Geromichalou E, Dalezis P, Nikoleousakos N, Sarli V. Synthesis and evaluation of new steroidal lactam conjugates with aniline mustards as potential antileukemic therapeutics. Steroids. 2016 Nov;115:1-8. doi: 10.1016/j.steroids.2016.07.009. Epub 2016 Jul 26. PubMed PMID: 27473822. 10: Gravatt GL, Baguley BC, Wilson WR, Denny WA. DNA-directed alkylating agents. 4. 4-anilinoquinoline-based minor groove directed aniline mustards. J Med Chem. 1991 May;34(5):1552-60. PubMed PMID: 2033580. 11: Fan JY, Valu KK, Woodgate PD, Baguley BC, Denny WA. Aniline mustard analogues of the DNA-intercalating agent amsacrine: DNA interaction and biological activity. Anticancer Drug Des. 1997 Apr;12(3):181-203. PubMed PMID: 9154110. 12: Gamcsik MP, Millis KK, Hamill TG. Kinetics of the conjugation of aniline mustards with glutathione and thiosulfate. Chem Biol Interact. 1997 Jun 6;105(1):35-52. PubMed PMID: 9233374. 13: Chipman JK, Hirom PC, Millburn P. Biliary excretion and enterohepatic circulation of aniline mustard metabolites in the rat and the rabbit. Biochem Pharmacol. 1980 May 1;29(9):1299-301. PubMed PMID: 7397013. 14: Kapuriya N, Kapuriya K, Zhang X, Chou TC, Kakadiya R, Wu YT, Tsai TH, Chen YT, Lee TC, Shah A, Naliapara Y, Su TL. Synthesis and biological activity of stable and potent antitumor agents, aniline nitrogen mustards linked to 9-anilinoacridines via a urea linkage. Bioorg Med Chem. 2008 May 15;16(10):5413-23. doi: 10.1016/j.bmc.2008.04.024. Epub 2008 Apr 15. PubMed PMID: 18450456. 15: Prakash AS, Denny WA, Wakelin LP. Differences in sequence selectivity of DNA alkylation by isomeric intercalating aniline mustards. Chem Biol Interact. 1990;76(2):241-8. PubMed PMID: 2225231. 16: Young CW, Yagoda A, Bittar ES, Smith SW, Grabstald H, Whitmore W. Therapeutic trial of aniline mustard in patients with advanced cancer. Comparison of therapeutic response with cytochemical assessment of tumor cell beta-glucuronidase activity. Cancer. 1976 Nov;38(5):1887-95. PubMed PMID: 991104. 17: Schneider MR, Schuderer ML. Cytotoxic estrogens: anilin mustard linked 1,1,2-triphenylbut-1-enes with mammary tumor inhibiting activity. Arch Pharm (Weinheim). 1989 Jan;322(1):59-62. PubMed PMID: 2730288. 18: Boritzki TJ, Palmer BD, Coddington JM, Denny WA. Identification of the major lesion from the reaction of an acridine-targeted aniline mustard with DNA as an adenine N1 adduct. Chem Res Toxicol. 1994 Jan-Feb;7(1):41-6. PubMed PMID: 8155823. 19: Gourdie TA, Prakash AS, Wakelin LP, Woodgate PD, Denny WA. Synthesis and evaluation of DNA-targeted spatially separated bis(aniline mustards) as potential alkylating agents with enhanced DNA cross-linking capability. J Med Chem. 1991 Jan;34(1):240-8. PubMed PMID: 1992124. 20: Palmer BD, Wilson WR, Cliffe S, Denny WA. Hypoxia-selective antitumor agents. 5. Synthesis of water-soluble nitroaniline mustards with selective cytotoxicity for hypoxic mammalian cells. J Med Chem. 1992 Aug 21;35(17):3214-22. PubMed PMID: 1507207.