MTDIA HCl
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MedKoo CAT#: 407244

CAS#: 1399840-35-7 (HCl)

Description: MTDIA, also known as MT-DADMe-ImmA, and Methylthio-DADMe-Immucillin A, is a MTAP inhibitor. Human 5'-methylthioadenosine phosphorylase (MTAP) is solely responsible for 5'-methylthioadenosine (MTA) metabolism to permit S-adenosylmethionine salvage. Transition-state (TS) analogues of MTAP are in development as anticancer candidates. TS analogues of MTAP incorporate a cationic nitrogen and a protonated 9-deazaadenine leaving group, which are mimics of the ribocation transition state. MT-ImmA and MT-DADMe-ImmA are two examples of these TS analogues.


Price and Availability

Size
Price

5mg
USD 150
50mg
USD 850
Size
Price

10mg
USD 250
100mg
USD 1450
Size
Price

25mg
USD 450
200mg
USD 2150

MTDIA HCl, purity > 98%, is in stock. The same day shipping out after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 407244
Name: MTDIA HCl
CAS#: 1399840-35-7 (HCl)
Chemical Formula: C13H20ClN5OS
Exact Mass: 293.131
Molecular Weight: 329.85
Elemental Analysis: C, 47.34; H, 6.11; Cl, 10.75; N, 21.23; O, 4.85; S, 9.72


Related CAS #: 1399840-35-7 (HCl)   653592-04-2 (free base)    

Synonym: MTDIA; MTDIA HCl; Methylthio-DADMe-Immucillin A; MT-DADMe-ImmA; MT-DADMe-ImmA HCl

IUPAC/Chemical Name: (3R,4S)-1-((4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl)-3-hydroxy-4-((methylthio)methyl)pyrrolidin-1-ium chloride

InChi Key: XQKMBJFGNRIATG-UXQCFNEQSA-N

InChi Code: InChI=1S/C13H19N5OS.ClH/c1-20-6-9-4-18(5-10(9)19)3-8-2-15-12-11(8)16-7-17-13(12)14;/h2,7,9-10,15,19H,3-6H2,1H3,(H2,14,16,17);1H/t9-,10+;/m1./s1

SMILES Code: NC(N=CN=C12)=C2NC=C1C[N+]3([H])C[C@@H]([C@H](C3)O)CSC.[Cl-]


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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, not in water

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).

Harmonized System Code:
293490


Additional Information


References

1: Evans GB, Furneaux RH, Lenz DH, Painter GF, Schramm VL, Singh V, Tyler PC. Second generation transition state analogue inhibitors of human 5'-methylthioadenosine phosphorylase. J Med Chem. 2005 Jul 14;48(14):4679-89. PubMed PMID: 16000004.

2: Tang B, Kadariya Y, Chen Y, Slifker M, Kruger WD. Expression of MTAP inhibits tumor-related phenotypes in HT1080 cells via a mechanism unrelated to its enzymatic function. G3 (Bethesda). 2014 Nov 11;5(1):35-44. doi: 10.1534/g3.114.014555. PubMed PMID: 25387827; PubMed Central PMCID: PMC4291467.

3: Wang S, Thomas K, Schramm VL. Catalytic site cooperativity in dimeric methylthioadenosine nucleosidase. Biochemistry. 2014 Mar 11;53(9):1527-35. doi: 10.1021/bi401589n. Epub 2014 Feb 21. PubMed PMID: 24502544; PubMed Central PMCID: PMC3977580.

4: Guan R, Tyler PC, Evans GB, Schramm VL. Thermodynamic analysis of transition-state features in picomolar inhibitors of human 5'-methylthioadenosine phosphorylase. Biochemistry. 2013 Nov 19;52(46):8313-22. doi: 10.1021/bi401188w. Epub 2013 Nov 8. PubMed PMID: 24148083; PubMed Central PMCID: PMC3870587.

5: Schramm VL, Gutierrez JA, Cordovano G, Basu I, Guha C, Belbin TJ, Evans GB, Tyler PC, Furneaux RH. Transition state analogues in quorum sensing and SAM recycling. Nucleic Acids Symp Ser (Oxf). 2008;(52):75-6. doi: 10.1093/nass/nrn038. PubMed PMID: 18776260; PubMed Central PMCID: PMC2725438.

6: Basu I, Cordovano G, Das I, Belbin TJ, Guha C, Schramm VL. A transition state analogue of 5'-methylthioadenosine phosphorylase induces apoptosis in head and neck cancers. J Biol Chem. 2007 Jul 20;282(29):21477-86. Epub 2007 Jun 4. PubMed PMID: 17548352.

7: Lee JE, Singh V, Evans GB, Tyler PC, Furneaux RH, Cornell KA, Riscoe MK, Schramm VL, Howell PL. Structural rationale for the affinity of pico- and femtomolar transition state analogues of Escherichia coli 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase. J Biol Chem. 2005 May 6;280(18):18274-82. Epub 2005 Mar 3. PubMed PMID: 15746096.