Napsamycin A
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| Category | Antibiotics |
| Catalog number | BBF-01996 |
| CAS | 126049-03-4 |
| Molecular Weight | 852.91 |
| Molecular Formula | C39H48N8O12S |
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Description
Napsamycin A is an antibiotic produced by Str.sp. HIL Y-82, 11372. It has antibacterial activity against Pseudomonas aeruginosa and other pseudomonas, but has weak antibacterial activity against other Gram-positive and negative bacteria.
Specification
| IUPAC Name | 2-[[1-[[1-[[(E)-[5-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-2-ylidene]methyl]amino]-3-[(6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-methylamino]-1-oxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-3-(3-hydroxyphenyl)propanoic acid |
| Canonical SMILES | CC(C(C(=O)NC=C1CC(C(O1)N2C=CC(=O)NC2=O)O)NC(=O)C(CCSC)NC(=O)NC(CC3=CC(=CC=C3)O)C(=O)O)N(C)C(=O)C4CC5=C(CN4)C=CC(=C5)O |
| InChI | InChI=1S/C39H48N8O12S/c1-20(46(2)35(54)28-16-23-15-25(49)8-7-22(23)18-40-28)32(34(53)41-19-26-17-30(50)36(59-26)47-11-9-31(51)44-39(47)58)45-33(52)27(10-12-60-3)42-38(57)43-29(37(55)56)14-21-5-4-6-24(48)13-21/h4-9,11,13,15,19-20,27-30,32,36,40,48-50H,10,12,14,16-18H2,1-3H3,(H,41,53)(H,45,52)(H,55,56)(H2,42,43,57)(H,44,51,58)/b26-19+ |
| InChI Key | XWORGFMCZJWEQG-LGUFXXKBSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 1131.0±75.0°C at 760 mmHg |
| Melting Point | >190°C (dec.) |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Peripheral tissular analysis of rapamycin's effect as a neuroprotective agent in vivo
Alfredo Gonzalez-Alcocer, Yareth Gopar-Cuevas, Adolfo Soto-Dominguez, Maria de Jesus Loera-Arias, Odila Saucedo-Cardenas, Roberto Montes de Oca-Luna, Humberto Rodriguez-Rocha, Aracely Garcia-Garcia Naunyn Schmiedebergs Arch Pharmacol. 2022 Oct;395(10):1239-1255. doi: 10.1007/s00210-022-02276-6. Epub 2022 Jul 27.
Rapamycin is the best-characterized autophagy inducer, which is related to its antiaging and neuroprotective effects. Although rapamycin is an FDA-approved drug for human use in organ transplantation and cancer therapy, its administration as an antiaging and neuroprotective agent is still controversial because of its immunosuppressive and reported side effects. Therefore, it is critical to determine whether the dose that exerts a neuroprotective effect, 35 times lower than that used as an immunosuppressant agent, harms peripheral organs. We validated the rapamycin neuroprotective dosage in a Parkinson's disease (PD) model induced with paraquat. C57BL/6 J mice were treated with intraperitoneal (IP) rapamycin (1 mg/kg) three times per week, followed by paraquat (10 mg/kg) twice per week for 6 weeks, along with rapamycin on alternate days. Rapamycin significantly decreased dopaminergic neuronal loss induced by paraquat. Since rapamycin's neuroprotective effect in a PD model was observed at 7 weeks of treatment; we evaluated its effect on the liver, kidney, pancreas, and spleen. In addition, we prolonged treatment with rapamycin for 14 weeks. Tissue sections were subjected to histochemical, immunodetection, and morphometric analysis. Chronic rapamycin administration does not affect bodyweight, survival, and liver or kidney morphology. Although the pancreas tissular architecture and cellular distribution in Langerhans islets are modified, they may be reversible. The spleen B lymphocyte and macrophage populations were decreased. Notably, the lymphocyte T population was not affected. Therefore, chronic administration of a rapamycin neuroprotective dose does not produce significant tissular alterations. Our findings support the therapeutic potential of rapamycin as a neuroprotective agent.
2. The effect of rapamycin and its analogues on age-related musculoskeletal diseases: a systematic review
Hong Lin, Felipe Salech, Anthony Lim, Sara Vogrin, Gustavo Duque Aging Clin Exp Res. 2022 Oct;34(10):2317-2333. doi: 10.1007/s40520-022-02190-0. Epub 2022 Jul 21.
Background: Preclinical studies have shown a therapeutic role of the mechanistic/mammalian target of rapamycin complex 1 (mTORC1) inhibition with rapamycin and its analogues (rapalogues) on several age-related musculoskeletal disorders (MSKD). However, the applicability to humans of these findings is unknown. Objective: To assess the efficacy of rapalogues on age-related MSKD in humans. Methods: We conducted a systematic review according to the PRISMA guidelines. MEDLINE, EMBase, EMCare, and Cochrane Central Registry of Controlled Trials were searched for original studies examining the effects of rapalogues on outcomes linked to the age-related MSKD in humans. This review is registered in the PROSPERO database (University of New York; registration number CRD42020208167). Results: Fourteen studies met the inclusion criteria and were analyzed. The effect of rapamycin and other rapalogues, including everolimus and temsirolimus, on bone, muscle and joints have been evaluated in humans; however, considerable variability concerning the subjects' age, inclusion criteria, and drug administration protocols was identified. In bone, the use of rapamycin is associated with a decrease in bone resorption markers dependent on osteoclastic activity. In muscle, rapamycin and rapalogues are associated with a reduction in muscle protein synthesis in response to exercise. In the context of rheumatoid arthritis, rapamycin and rapalogues have been associated with clinical improvement and a decrease in inflammatory activity. Conclusion: Although there are studies that have evaluated the effect of rapamycin and rapalogues on MSKD in humans, the evidence supporting its use is still incipient, and the clinical implication of these results on the development of osteoporosis, sarcopenia, or osteosarcopenia has not been studied, opening an interesting field for future research.
3. Bioproperties, Nanostructured System and Analytical and Bioanalytical Methods for Determination of Rapamycin: A Review
Karen Cristina Dos Santos, Leidiana Rocha Dos Reis, Camila Fernanda Rodero, Rafael Miguel Sábio, Alberto Gomes Tavares Junior, Maria Palmira Daflon Gremião, Marlus Chorilli Crit Rev Anal Chem. 2022;52(5):897-905. doi: 10.1080/10408347.2020.1839737. Epub 2020 Nov 2.
The drug rapamycin is a potent inhibitor of the mTOR complex, acting directly in the signaling cascade of this protein complex; interrupting cell proliferation, in addition to being an extremely efficient immunosuppressant. Currently this drug is being used in several types of cancer. Rapamycin has been a target of great interest within nanomedicine involving nanostructured systems for drug delivery aiming to increase the bioactivity and bioavailability of this drug. In addition, there is a constant search for analytical methods to identify and quantify this drug. Numerous high-performance liquid chromatography analytical techniques, mass spectrometry and immunoassay techniques have been employed efficiently in an attempt to develop increasingly sensitive analytical methods. Thus, this review sought to bring together current and relevant scientific works involving rapamycin and; besides analytical methods more used for quantification of this molecule.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
