Synonym
Methopterin; 10-Methylfolic acid; NSC 107144; NSC107144; NSC-107144; alpha-Methopterin;
IUPAC/Chemical Name
(4-(((2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl)(methyl)amino)benzoyl)-L-glutamic acid
InChi Key
HLIXOCXUWGDBNP-ZDUSSCGKSA-N
InChi Code
InChI=1S/C20H21N7O6/c1-27(9-11-8-22-16-15(23-11)18(31)26-20(21)25-16)12-4-2-10(3-5-12)17(30)24-13(19(32)33)6-7-14(28)29/h2-5,8,13H,6-7,9H2,1H3,(H,24,30)(H,28,29)(H,32,33)(H3,21,22,25,26,31)/t13-/m0/s1
SMILES Code
O=C(O)CC[C@@H](C(O)=O)NC(C1=CC=C(N(CC2=CN=C3NC(N)=NC(C3=N2)=O)C)C=C1)=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
>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
Biological target:
Methopterin has the activation and bone resorption function of murine osteoclasts.
In vitro activity:
This study is to observe the effects of methopterin on the activation and bone resorption function of murine osteoclasts, which were obtained by induction from bone marrow cell and purified to the purity of 70%-80%. The results showed that methopterin (0.1-10 micromol x L(-1)) inhibited the proliferation of osteoclasts, methopterin (0.1-10 micromol x L(-1)) could inhibit the activation and bone resorption function of osteoclasts and induced the apoptosis of osteoclasts. Methopterin (0.01-10 micromol x L(-1)) also decreased the mRNA expression of RANK, but only at 1-10 micromol x L(-1) decreased the mRNA expression of MMP-9.
Reference: Yao Xue Xue Bao. 2008 Oct;43(10):1025-31. https://pubmed.ncbi.nlm.nih.gov/19127866/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
455.43
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. Li P, Wang L, Wang WJ. [Effects of methopterin on osteoclasts and study of its mechanism of action]. Yao Xue Xue Bao. 2008 Oct;43(10):1025-31. Chinese. PMID: 19127866.
2. Li HM, Lu SD, Xia X, Xu P, Wang F, Huang Q. [Protective effects of transplantation of hCNTF-transfected cell line on axotomy-induced degeneration of retinal ganglion cells]. Zhonghua Yan Ke Za Zhi. 2005 Feb;41(2):119-22. Chinese. PMID: 15840336.
In vitro protocol:
1. Li P, Wang L, Wang WJ. [Effects of methopterin on osteoclasts and study of its mechanism of action]. Yao Xue Xue Bao. 2008 Oct;43(10):1025-31. Chinese. PMID: 19127866.
2. Li HM, Lu SD, Xia X, Xu P, Wang F, Huang Q. [Protective effects of transplantation of hCNTF-transfected cell line on axotomy-induced degeneration of retinal ganglion cells]. Zhonghua Yan Ke Za Zhi. 2005 Feb;41(2):119-22. Chinese. PMID: 15840336.
1: Li L, Wang JJ, Cheng JM. [Laparoscopic salpingotomy for tubal pregnancy: comparison of linear salpingotomy with and without suturing]. Zhonghua Yi Xue Za Zhi. 2016 Aug 9;96(30):2424-6. doi: 10.3760/cma.j.issn.0376-2491.2016.30.012. Chinese. PubMed PMID: 27545036.
2: Zou B, Han Z, Wang Z, Bian J, Xu J, Wang H, Yang M, Pei F, Li S, Xu Z. Neoadjuvant therapy combined with a BMP regimen for treating penile cancer patients with lymph node metastasis: a retrospective study in China. J Cancer Res Clin Oncol. 2014 Oct;140(10):1733-8. doi: 10.1007/s00432-014-1720-5. Epub 2014 Jun 7. PubMed PMID: 24906876.
3: Li P, Wang L, Wang WJ. [Effects of methopterin on osteoclasts and study of its mechanism of action]. Yao Xue Xue Bao. 2008 Oct;43(10):1025-31. Chinese. PubMed PMID: 19127866.
4: Yu JP, Zhang YZ, Li XY. [Effect of strengthening Pi and activating blood circulation therapy on serum levels of adrenocorticotrophic hormone and vascular endothelial growth factor in rheumatoid arthritis patients]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2007 Jul;27(7):593-5. Chinese. PubMed PMID: 17717914.
5: Li HM, Lu SD, Xia X, Xu P, Wang F, Huang Q. [Protective effects of transplantation of hCNTF-transfected cell line on axotomy-induced degeneration of retinal ganglion cells]. Zhonghua Yan Ke Za Zhi. 2005 Feb;41(2):119-22. Chinese. PubMed PMID: 15840336.
6: Poe M, Hoogsteen K, Matthews DA. Proton magnetic resonance studies on Escherichia coli dihydrofolate reductase. Assignment of histidine C-2 protons in binary complexes with folates on the basis of the crystal structure with methotrexate and on chemical modifications. J Biol Chem. 1979 Sep 10;254(17):8143-52. PubMed PMID: 38247.
7: Poe M. Acidic dissociation constants of folic acid, dihydrofolic acid, and methotrexate. J Biol Chem. 1977 Jun 10;252(11):3724-8. PubMed PMID: 16913.
8: Martins JM, Pitombeira Mda S, Figueiredo DG. [Leukosarcomatous meningopathy successfully treated with intrathecal a-methopterin]. Rev Assoc Med Bras. 1966 Dec;12(12):502-4. Portuguese. PubMed PMID: 5241540.
9: KRISHNAMURTHY V, BRAGANCA BM. DETOXICATION OF A-METHOPTERIN AND AMINOPTERIN BY THE ACETYLATING ENZYME OF LIVER. Biochim Biophys Acta. 1963 Aug 13;74:456-66. PubMed PMID: 14071589.
10: WOODRUFF MF. Prolonged survival of skin homografts in adult mice following sub-lethal irradiation, injection of donor-strain spleen cells and administration of A-methopterin. Nature. 1962 Aug 18;195:727-8. PubMed PMID: 14008234.
11: KRISHNAMURTHY V, BRAGANCA BM. Inactivation of A-methopterin by the acetylating enzyme system from pigeon liver. Nature. 1961 Oct 7;192:68-9. PubMed PMID: 14459700.
12: CONDIT PT, ELIEL LP. Effects of large infrequent doses of a-methopterin on acute leukemia in children. J Am Med Assoc. 1960 Jan 30;172:451-3. PubMed PMID: 13811472.
13: LIPSETT MB, BERGENSTAL DM. Metabolic effects of A-methopterin in man. Cancer Res. 1959 Jan;19(1):89-92. PubMed PMID: 13618890.
14: UPHOFF DE. Alteration of homograft reaction by A-methopterin in lethally irradiated mice treated with homologous marrow. Proc Soc Exp Biol Med. 1958 Dec;99(3):651-3. PubMed PMID: 13614453.
15: SARTORELLI AC, LEPAGE GA. Effects of A-methopterin on the purine biosynthesis of susceptible and resistant TA3 ascites cells. Cancer Res. 1958 Dec;18(11):1336-9. PubMed PMID: 13608443.
16: TOMISEK AJ, KELLY HJ, REID MR, SKIPPER HE. Chromatographic studies of purine metabolism. III. Effects of A-methopterin on formate-C14 utilization in mice bearing susceptible and dependent L1210 leukemia. Arch Biochem Biophys. 1958 Nov;78(1):83-94. PubMed PMID: 13595905.
17: TOMISEK AJ, KELLY HJ, REID MR, SKIPPER HE. Chromatographic studies of purine metabolism. II. The mechanism of E. coli inhibition by A-methopterin. Arch Biochem Biophys. 1958 Jul;76(1):45-55. PubMed PMID: 13560011.
18: VENDITTI JM, HUMPHREYS SR, MANTEL N, GOLDIN A. Influence of the duration of treatment with A-methopterin on the survival time of mice with advanced leukemia (L1210). Cancer Res. 1957 Oct;17(9):917-22. PubMed PMID: 13472684.
19: DREW RM. Induction of resistance to A-methopterin in Diplococcus pneumoniae by Deoxyribonucleic acid. Nature. 1957 Jun 15;179(4572):1251-2. PubMed PMID: 13440953.
20: WINZLER RJ, WILLIAMS AD, BEST WR. Metabolism of human leukocytes in vitro. I. Effects of A-methopterin on formate-C14 incorporation. Cancer Res. 1957 Feb;17(2):108-16. PubMed PMID: 13413846.
