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MedKoo Cat#: 598755 | Name: Lexitropsin

Description:

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

Lexitropsin is a novel anticancer agent.

Chemical Structure

Lexitropsin
CAS#110124-49-7

Theoretical Analysis

MedKoo Cat#: 598755

Name: Lexitropsin

CAS#: 110124-49-7

Chemical Formula: C20H29N5O4

Exact Mass: 403.2220

Molecular Weight: 403.48

Elemental Analysis: C, 59.54; H, 7.24; N, 17.36; O, 15.86

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
Lexitropsin;
IUPAC/Chemical Name
4-(5-acetamidofuran-2-carboxamido)-N-(3-(dimethylamino)propyl)-1-propyl-1H-pyrrole-2-carboxamide
InChi Key
QUHGSDZVAPFNLV-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H29N5O4/c1-5-10-25-13-15(12-16(25)19(27)21-9-6-11-24(3)4)23-20(28)17-7-8-18(29-17)22-14(2)26/h7-8,12-13H,5-6,9-11H2,1-4H3,(H,21,27)(H,22,26)(H,23,28)
SMILES Code
O=C(C1=CC(NC(C2=CC=C(NC(C)=O)O2)=O)=CN1CCC)NCCCN(C)C
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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lexitropsin is a novel anticancer agent.
In vitro activity:
TBD
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 403.48 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:
TBD
In vitro protocol:
TBD
In vivo protocol:
TBD
1: Anthony NG, Johnston BF, Khalaf AI, MacKay SP, Parkinson JA, Suckling CJ, Waigh RD. Short lexitropsin that recognizes the DNA minor groove at 5'-ACTAGT-3': understanding the role of isopropyl-thiazole. J Am Chem Soc. 2004 Sep 15;126(36):11338-49. PubMed PMID: 15355117. 2: Han X, Li C, Mosher MD, Rider KC, Zhou P, Crawford RL, Fusco W, Paszczynski A, Natale NR. Design, synthesis and biological evaluation of a novel class of anticancer agents: anthracenylisoxazole lexitropsin conjugates. Bioorg Med Chem. 2009 Feb 15;17(4):1671-80. doi: 10.1016/j.bmc.2008.12.056. Epub 2008 Dec 31. PubMed PMID: 19167892; PubMed Central PMCID: PMC2978248. 3: Gupta R, al-Said NH, Oreski B, Lown JW. Design, synthesis and topoisomerase II inhibition activity of 4'-demethylepipodophyllotoxin-lexitropsin conjugates. Anticancer Drug Des. 1996 Jun;11(4):325-38. PubMed PMID: 8679055. 4: Goodsell DS, Ng HL, Kopka ML, Lown JW, Dickerson RE. Structure of a dicationic monoimidazole lexitropsin bound to DNA. Biochemistry. 1995 Dec 26;34(51):16654-61. PubMed PMID: 8527438. 5: Inga A, Chen FX, Monti P, Aprile A, Campomenosi P, Menichini P, Ottaggio L, Viaggi S, Abbondandolo A, Gold B, Fronza G. N-(2-chloroethyl)-N-nitrosourea tethered to lexitropsin induces minor groove lesions at the p53 cDNA that are more cytotoxic than mutagenic. Cancer Res. 1999 Feb 1;59(3):689-95. PubMed PMID: 9973219. 6: Reinert KE, Stutter E, Zimmer C, Lown JW. DNA interaction of the imidazole-containing lexitropsin ImPy: titration viscometric study in comparison to netropsin. J Biomol Struct Dyn. 1995 Feb;12(4):847-55. PubMed PMID: 7779304. 7: Borer PN, LaPlante SR, Wang S, Levy GC. Analysis of DNA and DNA-lexitropsin interaction using multinuclear NMR and molecular dynamics. Biochem Pharmacol. 1988 May 1;37(9):1821-2. PubMed PMID: 2837242. 8: Randrianarivelo M, Zakrzewska K, Pullman B. Theoretical modeling of DNA-monocationic lexitropsin complexation: influence of ligand binding on DNA curvature. J Biomol Struct Dyn. 1989 Feb;6(4):769-79. PubMed PMID: 2559747. 9: Rao KE, Gosselin G, Mrani D, Périgaud C, Imbach JL, Bailly C, Hénichart JP, Colson P, Houssier C, Lown JW. Psoralen--lexitropsin hybrids: DNA sequence selectivity of photoinduced cross-linking from MPE footprinting and exonuclease III stop assay, and mode of binding from electric linear dichroism. Anticancer Drug Des. 1994 Jun;9(3):221-37. PubMed PMID: 8031454. 10: Anthony NG, Fox KR, Johnston BF, Khalaf AI, Mackay SP, McGroarty IS, Parkinson JA, Skellern GG, Suckling CJ, Waigh RD. DNA binding of a short lexitropsin. Bioorg Med Chem Lett. 2004 Mar 8;14(5):1353-6. PubMed PMID: 14980697. 11: Xie Y, Miller GG, Cubitt SA, Soderlind KJ, Allalunis-Turner MJ, Lown JW. Enediyne-lexitropsin DNA-targeted anticancer agents. Physicochemical and cytotoxic properties in human neoplastic cells in vitro, and intracellular distribution. Anticancer Drug Des. 1997 Apr;12(3):169-79. PubMed PMID: 9154109. 12: Kumar S, Jaseja M, Zimmermann J, Yadagiri B, Pon RT, Sapse AM, Lown JW. Molecular recognition and binding of a GC site-avoiding thiazole-lexitropsin to the decadeoxyribonucleotide d-[CGCAATTGCG]2: 1H-NMR evidence for thiazole intercalation. J Biomol Struct Dyn. 1990 Aug;8(1):99-121. PubMed PMID: 2177339. 13: Pućkowska A, Bartulewicz D, Markowska A, Zwierz K, Rózański A. Synthetic analogues of netropsin and distamycin. V. Synthesis of a carbocyclic bis-lexitropsin as potential DNA cleaving agent. Rocz Akad Med Bialymst. 1999;44:200-15. PubMed PMID: 10697435. 14: Plouvier B, Houssin R, Helbecque N, Colson P, Houssier C, Hénichart JP, Bailly C. Influence of the methyl substituents of a thiazole-containing lexitropsin on the mode of binding to DNA. Anticancer Drug Des. 1995 Mar;10(2):155-66. PubMed PMID: 7710636. 15: Pućkowska A, Drozdowska D, Midura-Nowaczek K. Carbocyclic analogues of lexitropsin--DNA affinity and endonuclease inhibition. Acta Pol Pharm. 2007 Mar-Apr;64(2):115-9. PubMed PMID: 17665860. 16: Borodulin VB, Zasedatelev AS, Gurskiĭ GV. [Interaction of lexitropsin with DNA: negative result of the attempt to detect complex AT/GC-specific binding]. Dokl Akad Nauk SSSR. 1987;294(5):1243-7. Russian. PubMed PMID: 3040363. 17: Romagnoli R, Baraldi PG, Iaconinoto MA, Carrion MD, Tabrizi MA, Gambari R, Borgatti M, Heilmann J. Synthesis and biological activity of alpha-bromoacryloyl lexitropsin conjugates. Eur J Med Chem. 2005 Nov;40(11):1123-8. Epub 2005 Jul 11. PubMed PMID: 16006014. 18: Singh MP, Kumar S, Joseph T, Pon RT, Lown JW. A 1H-NMR study of the DNA binding characteristics of thioformyldistamycin, an amide isosteric lexitropsin. Biochemistry. 1992 Jul 21;31(28):6453-61. PubMed PMID: 1321661. 19: Lee M, Hartley JA, Pon RT, Krowicki K, Lown JW. Sequence specific molecular recognition by a monocationic lexitropsin of the decadeoxyribonucleotide d-[CATGGCCATG]2: structural and dynamic aspects deduced from high field 1H-NMR studies. Nucleic Acids Res. 1988 Jan 25;16(2):665-84. PubMed PMID: 2829134; PubMed Central PMCID: PMC334684. 20: Gupta R, Liu J, Xie G, Lown JW. Novel DNA-directed alkylating agents consisting of naphthalimide, nitrogen mustard and lexitropsin moieties: synthesis, DNA sequence specificity and biological evaluation. Anticancer Drug Des. 1996 Dec;11(8):581-96. PubMed PMID: 9022747.

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