Synonym
Methotrexate-alpha-alanine; Mtx-ala;
IUPAC/Chemical Name
(S)-5-(((S)-1-carboxyethyl)amino)-4-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)-5-oxopentanoic acid
InChi Key
IYWOCQLKOJVCQN-NHYWBVRUSA-N
InChi Code
InChI=1S/C23H27N9O6/c1-11(22(37)38)27-21(36)15(7-8-16(33)34)29-20(35)12-3-5-14(6-4-12)32(2)10-13-9-26-19-17(28-13)18(24)30-23(25)31-19/h3-6,9,11,15H,7-8,10H2,1-2H3,(H,27,36)(H,29,35)(H,33,34)(H,37,38)(H4,24,25,26,30,31)/t11-,15-/m0/s1
SMILES Code
C[C@@H](C(O)=O)NC([C@H](CCC(O)=O)NC(C1=CC=C(N(CC2=NC3=C(N)N=C(N)N=C3N=C2)C)C=C1)=O)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
525.52
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 |
1: Huennekens FM. Development of methotrexate alpha-peptides as prodrugs for activation by enzyme-monoclonal antibody conjugates. Adv Enzyme Regul. 1997;37:77-92. PubMed PMID: 9381987.
2: Vitols KS, Haag-Zeino B, Baer T, Montejano YD, Huennekens FM. Methotrexate-alpha-phenylalanine: optimization of methotrexate prodrug for activation by carboxypeptidase A-monoclonal antibody conjugate. Cancer Res. 1995 Feb 1;55(3):478-81. PubMed PMID: 7834611.
3: Haenseler E, Esswein A, Vitols KS, Montejano Y, Mueller BM, Reisfeld RA, Huennekens FM. Activation of methotrexate-alpha-alanine by carboxypeptidase A-monoclonal antibody conjugate. Biochemistry. 1992 Jan 28;31(3):891-7. PubMed PMID: 1731945.
4: Esswein A, Hänseler E, Montejano Y, Vitols KS, Huennekens FM. Construction and chemotherapeutic potential of carboxypeptidase-A/monoclonal antibody conjugate. Adv Enzyme Regul. 1991;31:3-12. Review. PubMed PMID: 1877392.
5: Kuefner U, Esswein A, Lohrmann U, Montejano Y, Vitols KS, Huennekens FM. Occurrence and significance of diastereomers of methotrexate alpha-peptides. Biochemistry. 1990 Nov 20;29(46):10540-5. PubMed PMID: 2271663.
