Lysine-methotrexate | CAS# 80407-56-3 | anticancer

MedKoo Cat#: 591191 | Name: Lysine-methotrexate

Description:

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

Lysine-methotrexate is an anticancer drug. It is the lysine analog of methotrexate; inhibitor of dihydrofolate reductase.

Chemical Structure

Lysine-methotrexate

CAS#80407-56-3

Theoretical Analysis

MedKoo Cat#: 591191

Name: Lysine-methotrexate

CAS#: 80407-56-3

Chemical Formula: C21H27N9O3

Exact Mass: 453.2237

Molecular Weight: 453.51

Elemental Analysis: C, 55.62; H, 6.00; N, 27.80; O, 10.58

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Synonym

Lysine-methotrexate; ADMPL;

IUPAC/Chemical Name

L-Lysine, N2-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-

InChi Key

XERJQLWAFDLUGV-HNNXBMFYSA-N

InChi Code

InChI=1S/C21H27N9O3/c1-30(11-13-10-25-18-16(26-13)17(23)28-21(24)29-18)14-7-5-12(6-8-14)19(31)27-15(20(32)33)4-2-3-9-22/h5-8,10,15H,2-4,9,11,22H2,1H3,(H,27,31)(H,32,33)(H4,23,24,25,28,29)/t15-/m0/s1

SMILES Code

NCCCC[C@@H](C(O)=O)NC(C1=CC=C(N(CC2=NC3=C(N)N=C(N)N=C3N=C2)C)C=C1)=O

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lysine-methotrexate is an anticancer drug.

In vitro activity:

The ornithine (6a) and lysine (6b) analogues of methotrexate (1) have been synthesized via condensation of 4-amino-4-deoxy-N10-methylpteroic acid (2) with N gamma-carbobenzoxy-L-ornithine tert-butyl ester (3a) and N epsilon-carbobenzoxy-L-lysine tert-butyl ester (3b), respectively. Compounds 6a and 6b and their precursor Cbz acids (5a and 5b) show significant inhibition of dihydrofolate reductase. Reference: J Med Chem. 1982 Apr;25(4):475-7. https://pubmed.ncbi.nlm.nih.gov/7069726/

In vivo activity:

Furthermore, the use of different attachment sites in the methotrexate conjugates (α- or γ-carboxylic groups) affect their chemotactic activity. Specific cytotoxic activities and cytostatic effects of the conjugates on parasites and on murine and human cells of the macrophage/monocyte system respectively, suggest that these ligands may be used as a group of anti-Leishmania substances acting selectively on Leishmania and different hosts. Reference: Drug Deliv. 2016 Sep;23(7):2327-2337. https://pubmed.ncbi.nlm.nih.gov/23816643/

Preparing Stock Solutions

The following data is based on the product molecular weight 453.51 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.

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:

1. Singh VK, Subudhi BB. Development and characterization of lysine-methotrexate conjugate for enhanced brain delivery. Drug Deliv. 2016 Sep;23(7):2327-2337. doi: 10.3109/10717544.2014.984369. Epub 2014 Dec 5. PMID: 25475953. 2. Kempton RJ, Black AM, Anstead GM, Kumar AA, Blankenship DT, Freisheim JH. Lysine and ornithine analogues of methotrexate as inhibitors of dihydrofolate reductase. J Med Chem. 1982 Apr;25(4):475-7. doi: 10.1021/jm00346a026. PMID: 7069726. 3. Singh VK, Subudhi BB. Development and characterization of lysine-methotrexate conjugate for enhanced brain delivery. Drug Deliv. 2016 Sep;23(7):2327-2337. doi: 10.3109/10717544.2014.984369. Epub 2014 Dec 5. PMID: 25475953. 4. Díaz E, Köhidai L, Ríos A, Vanegas O, Silva A, Szabó R, Mező G, Hudecz F, Ponte-Sucre A. Leishmania braziliensis: cytotoxic, cytostatic and chemotactic effects of poly-lysine-methotrexate-conjugates. Exp Parasitol. 2013 Sep;135(1):134-41. doi: 10.1016/j.exppara.2013.06.007. Epub 2013 Jun 28. PMID: 23816643.

In vitro protocol:

In vivo protocol:

1. Singh VK, Subudhi BB. Development and characterization of lysine-methotrexate conjugate for enhanced brain delivery. Drug Deliv. 2016 Sep;23(7):2327-2337. doi: 10.3109/10717544.2014.984369. Epub 2014 Dec 5. PMID: 25475953. 2. Díaz E, Köhidai L, Ríos A, Vanegas O, Silva A, Szabó R, Mező G, Hudecz F, Ponte-Sucre A. Leishmania braziliensis: cytotoxic, cytostatic and chemotactic effects of poly-lysine-methotrexate-conjugates. Exp Parasitol. 2013 Sep;135(1):134-41. doi: 10.1016/j.exppara.2013.06.007. Epub 2013 Jun 28. PMID: 23816643.

1: Singh VK, Subudhi BB. Development and characterization of lysine-methotrexate conjugate for enhanced brain delivery. Drug Deliv. 2016 Sep;23(7):2327-2337. Epub 2014 Dec 5. PubMed PMID: 25475953. 2: Díaz E, Köhidai L, Ríos A, Vanegas O, Silva A, Szabó R, Mező G, Hudecz F, Ponte-Sucre A. Leishmania braziliensis: cytotoxic, cytostatic and chemotactic effects of poly-lysine-methotrexate-conjugates. Exp Parasitol. 2013 Sep;135(1):134-41. doi: 10.1016/j.exppara.2013.06.007. Epub 2013 Jun 28. PubMed PMID: 23816643. 3: Kempton RJ, Black AM, Anstead GM, Kumar AA, Blankenship DT, Freisheim JH. Lysine and ornithine analogues of methotrexate as inhibitors of dihydrofolate reductase. J Med Chem. 1982 Apr;25(4):475-7. PubMed PMID: 7069726.