Home Other Building Blocks (melle-4)cyclosporin

(melle-4)cyclosporin

CAS No.:
143205-42-9
Catalog Number:
AG00A9TL
Molecular Formula:
C62H111N11O12
Molecular Weight:
1202.6112
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
98%
1 week
United States
$523
- +
5mg
98%
1 week
United States
$1707
- +
Product Description
Catalog Number:
AG00A9TL
Chemical Name:
(melle-4)cyclosporin
CAS Number:
143205-42-9
Molecular Formula:
C62H111N11O12
Molecular Weight:
1202.6112
MDL Number:
MFCD00912625
IUPAC Name:
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-24-[(2S)-butan-2-yl]-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18-tris(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
InChI:
InChI=1S/C62H111N11O12/c1-25-28-29-40(15)52(75)51-56(79)65-43(27-3)58(81)67(18)33-47(74)71(22)50(39(14)26-2)55(78)66-48(37(10)11)61(84)68(19)44(30-34(4)5)54(77)63-41(16)53(76)64-42(17)57(80)69(20)45(31-35(6)7)59(82)70(21)46(32-36(8)9)60(83)72(23)49(38(12)13)62(85)73(51)24/h25,28,34-46,48-52,75H,26-27,29-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b28-25+/t39-,40+,41-,42+,43-,44-,45-,46-,48-,49-,50-,51-,52+/m0/s1
InChI Key:
RPJPZDVUUKWPGT-FOIHOXPVSA-N
SMILES:
C/C=C/C[C@H]([C@H]([C@H]1C(=O)N[C@@H](CC)C(=O)N(C)CC(=O)N(C)[C@@H]([C@H](CC)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)O)C
UNII:
96262S4I14
Properties
Complexity:
2330  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
13  
Defined Bond Stereocenter Count:
1  
Exact Mass:
1201.841g/mol
Formal Charge:
0
Heavy Atom Count:
85  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
1202.635g/mol
Monoisotopic Mass:
1201.841g/mol
Rotatable Bond Count:
15  
Topological Polar Surface Area:
279A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.5  
Literature
Title Journal
Potent nonimmunosuppressive cyclophilin inhibitors with improved pharmaceutical properties and decreased transporter inhibition. Journal of medicinal chemistry 20141023
In vitro effects of cyclosporine A and tacrolimus on regulatory T-cell proliferation and function. Transplantation 20120727
Efficacy and mechanism of hypoxic postconditioning in salvage of ex vivo human rectus abdominis muscle from hypoxia/reoxygenation injury. European journal of pharmacology 20120705
Mitochondrial permeability transition in the diabetic heart: contributions of thiol redox state and mitochondrial calcium to augmented reperfusion injury. Journal of molecular and cellular cardiology 20120501
Ischemic postconditioning protects liver from ischemia-reperfusion injury by modulating mitochondrial permeability transition. Transplantation 20120215
Administration of naked plasmid encoding hepatic stimulator substance by hydrodynamic tail vein injection protects mice from hepatic failure by suppressing the mitochondrial permeability transition. The Journal of pharmacology and experimental therapeutics 20110901
Cyclosporine A, FK506, and NIM811 ameliorate prolonged CBF reduction and impaired neurovascular coupling after cortical spreading depression. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20110701
Safety, pharmacokinetics, and antiviral activity of the cyclophilin inhibitor NIM811 alone or in combination with pegylated interferon in HCV-infected patients receiving 14 days of therapy. Antiviral research 20110301
N-methyl-4-isoleucine cyclosporine attenuates CCl -induced liver fibrosis in rats by interacting with cyclophilin B and D. Journal of gastroenterology and hepatology 20110301
NIM811 prevents mitochondrial dysfunction, attenuates liver injury, and stimulates liver regeneration after massive hepatectomy. Transplantation 20110227
Inhibition of mitochondrial permeability transition to prevent the post-cardiac arrest syndrome: a pre-clinical study. European heart journal 20110101
Inhibition of cyclophilins alters lipid trafficking and blocks hepatitis C virus secretion. Virology journal 20110101
Cyclosporine A inhibits in vitro replication of betaretrovirus associated with primary biliary cirrhosis. Liver international : official journal of the International Association for the Study of the Liver 20100701
Roles of mitophagy and the mitochondrial permeability transition in remodeling of cultured rat hepatocytes. Autophagy 20091101
NIM811 (N-methyl-4-isoleucine cyclosporine), a mitochondrial permeability transition inhibitor, attenuates cholestatic liver injury but not fibrosis in mice. The Journal of pharmacology and experimental therapeutics 20081201
Postconditioning for salvage of ischemic skeletal muscle from reperfusion injury: efficacy and mechanism. American journal of physiology. Regulatory, integrative and comparative physiology 20080801
Inhibition of human immunodeficiency virus type 1 replication in human cells by Debio-025, a novel cyclophilin binding agent. Antimicrobial agents and chemotherapy 20080401
Increased mitochondrial calcium coexists with decreased reperfusion injury in postconditioned (but not preconditioned) hearts. American journal of physiology. Heart and circulatory physiology 20080101
Attenuation of acute mitochondrial dysfunction after traumatic brain injury in mice by NIM811, a non-immunosuppressive cyclosporin A analog. Experimental neurology 20080101
Minocycline and N-methyl-4-isoleucine cyclosporin (NIM811) mitigate storage/reperfusion injury after rat liver transplantation through suppression of the mitochondrial permeability transition. Hepatology (Baltimore, Md.) 20080101
NIM811, a nonimmunosuppressive cyclosporine analogue, suppresses collagen production and enhances collagenase activity in hepatic stellate cells. Liver international : official journal of the International Association for the Study of the Liver 20071101
Post-treatment with the cyclosporin derivative, NIM811, reduced indices of cell death and increased the volume of spared tissue in the acute period following spinal cord contusion. Journal of neurotrauma 20071001
NIM811, a mitochondrial permeability transition inhibitor, prevents mitochondrial depolarization in small-for-size rat liver grafts. American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons 20070501
Protective effects of NIM811 in transient focal cerebral ischemia suggest involvement of the mitochondrial permeability transition. Journal of neurotrauma 20070501
Pretreatment with the cyclosporin derivative, NIM811, improves the function of synaptic mitochondria following spinal cord contusion in rats. Journal of neurotrauma 20070401
Determination of N-methyl-4-isoleucine-cyclosporin (NIM811) in human whole blood by high performance liquid chromatography-tandem mass spectrometry. Biomedical chromatography : BMC 20070301
In vitro infection of immortalized primary hepatocytes by HCV genotype 4a and inhibition of virus replication by cyclosporin. Microbiology and immunology 20070101
Chemical genetics approach to hepatitis C virus replication: cyclophilin as a target for anti-hepatitis C virus strategy. Reviews in medical virology 20070101
Evaluation of the anti-hepatitis C virus effects of cyclophilin inhibitors, cyclosporin A, and NIM811. Biochemical and biophysical research communications 20060512
Specific inhibition of the mitochondrial permeability transition prevents lethal reperfusion injury. Journal of molecular and cellular cardiology 20050201
Postconditioning inhibits mitochondrial permeability transition. Circulation 20050118
Mitochondrial permeability transition in acetaminophen-induced necrosis and apoptosis of cultured mouse hepatocytes. Hepatology (Baltimore, Md.) 20041101
Mitochondrial permeability transition in cardiomyocyte apoptosis during acute graft rejection. American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons 20040701
Synthesis of non-immunosuppressive cyclophilin-Binding cyclosporin A derivatives as potential anti-HIV-1 drugs. Bioorganic & medicinal chemistry letters 20031215
Cyclosporin A blocks muscle differentiation by inducing oxidative stress and inhibiting the peptidyl-prolyl-cis-trans isomerase activity of cyclophilin A: cyclophilin A protects myoblasts from cyclosporin A-induced cytotoxicity. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20021001
Inhibition of the mitochondrial permeability transition by the nonimmunosuppressive cyclosporin derivative NIM811. Molecular pharmacology 20020701
The non-immunosuppressive cyclosporin A analogue SDZ NIM 811 inhibits cyclophilin A incorporation into virions and virus replication in human immunodeficiency virus type 1-infected primary and growth-arrested T cells. The Journal of general virology 19970401
The human immunodeficiency virus type 1 capsid p2 domain confers sensitivity to the cyclophilin-binding drug SDZ NIM 811. Journal of virology 19960901
Inhibition of HIV-1 replication by cyclosporine A or related compounds correlates with the ability to disrupt the Gag-cyclophilin A interaction. Virology 19960801
Mode of action of SDZ NIM 811, a nonimmunosuppressive cyclosporin A analog with activity against human immunodeficiency virus (HIV) type 1: interference with HIV protein-cyclophilin A interactions. Journal of virology 19950401
Mode of action of SDZ NIM 811, a nonimmunosuppressive cyclosporin A analog with activity against human immunodeficiency virus type 1 (HIV-1): interference with early and late events in HIV-1 replication. Journal of virology 19950201
Inhibition of human immunodeficiency virus type 1 replication by SDZ NIM 811, a nonimmunosuppressive cyclosporine analog. Antimicrobial agents and chemotherapy 19940801
Properties