Synonym
Salicyl-AMS; Salicyl AMS; SalicylAMS; MMV-687700; MMV 687700; MMV687700; Salicyl-Adenosine Monosulfamate
IUPAC/Chemical Name
[(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-(2-hydroxybenzoyl)sulfamate
InChi Key
SABYITLYKSVAAD-CNEMSGBDSA-N
InChi Code
InChI=1S/C17H18N6O8S/c18-14-11-15(20-6-19-14)23(7-21-11)17-13(26)12(25)10(31-17)5-30-32(28,29)22-16(27)8-3-1-2-4-9(8)24/h1-4,6-7,10,12-13,17,24-26H,5H2,(H,22,27)(H2,18,19,20)/t10-,12-,13-,17-/m1/s1
SMILES Code
O=S(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O)(NC(C4=CC=CC=C4O)=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
>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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
466.43
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 |
1: Bythrow GV, Mohandas P, Guney T, Standke LC, Germain GA, Lu X, Ji C, Levendosky K, Chavadi SS, Tan DS, Quadri LEN. Kinetic Analyses of the Siderophore Biosynthesis Inhibitor Salicyl-AMS and Analogues as MbtA Inhibitors and Antimycobacterial Agents. Biochemistry. 2019 Feb 12;58(6):833-847. doi: 10.1021/acs.biochem.8b01153. Epub 2019 Jan 10. PubMed PMID: 30582694.
2: Lun S, Guo H, Adamson J, Cisar JS, Davis TD, Chavadi SS, Warren JD, Quadri LE, Tan DS, Bishai WR. Pharmacokinetic and in vivo efficacy studies of the mycobactin biosynthesis inhibitor salicyl-AMS in mice. Antimicrob Agents Chemother. 2013 Oct;57(10):5138-40. doi: 10.1128/AAC.00918-13. Epub 2013 Jul 15. PubMed PMID: 23856770; PubMed Central PMCID: PMC3811451.
