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C9705

Concanamycin A

≥70% (HPLC), crystals, vacuolar-type v-ATPase inhibitor

Synonym(s):

Folimycin

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About This Item

Empirical Formula (Hill Notation):
C46H75NO14
CAS Number:
80890-47-7
Molecular Weight:
866.09
NACRES:
NA.77
PubChem Substance ID:
24893186
UNSPSC Code:
12352200
MDL number:
MFCD00210037
Beilstein/REAXYS Number:
3560277
Assay:
≥70% (HPLC)
Form:
solid film
Quality level:
200
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Product Name

Concanamycin A, ≥70% (HPLC)

Quality Level

200

assay

≥70% (HPLC)

form

solid film

antibiotic activity spectrum

viruses

mode of action

enzyme | inhibits

storage temp.

−20°C

SMILES string

CCC1C(O)C(C)C\C(C)=C\C=C\C(OC)C(OC(=O)\C(OC)=C\C(C)=C\C(C)C1O)C(C)C(O)C(C)[C@]2(O)C[C@@H](O[C@H]3C[C@@H](O)[C@H](OC(N)=O)[C@@H](C)O3)[C@H](C)C(O2)\C=C\C

InChI

1S/C46H75NO14/c1-13-16-34-28(7)37(58-38-22-33(48)43(31(10)57-38)60-45(47)53)23-46(54,61-34)30(9)41(51)29(8)42-35(55-11)18-15-17-24(3)19-26(5)39(49)32(14-2)40(50)27(6)20-25(4)21-36(56-12)44(52)59-42/h13,15-18,20-21,26-35,37-43,48-51,54H,14,19,22-23H2,1-12H3,(H2,47,53)/b16-13+,18-15+,24-17+,25-20+,36-21-/t26?,27?,28-,29?,30?,31-,32?,33-,34?,35?,37-,38+,39?,40?,41?,42?,43-,46+/m1/s1

InChI key

DJZCTUVALDDONK-LWLXYWDNSA-N

General description

Chemical structure: macrolide
Concanamycin A belongs to the plecomacrolide family and comprises an 18-membered tetraenic macrolide ring.

Application

Concanamycin A has been used:
  • as a lysosomal inhibitor in young and old fibroblasts
  • as a vacuolar-type H+-ATPase inhibitor in presynaptic vesicles
  • as a lysosomal acidification blocker in HepG2 hepatocytes cells

Biochem/physiol Actions

Concanamycin A (ConA) inhibits acidification of organelles and perforin-mediated cytotoxicity. It is a vacuolar-type v-ATPase inhibitor. ConA possesses antiprotozoal and antineoplastic properties. It mediates inhibition of the negative factor (Nef) protein of the human immunodeficiency virus.

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pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Eye Irrit. 2

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
0000537336
0000533577
0000535953
0000534692
0000533577

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Mark M Painter et al.
Proceedings of the National Academy of Sciences of the United States of America, 117(38), 23835-23846 (2020-09-10)
Nef is an HIV-encoded accessory protein that enhances pathogenicity by down-regulating major histocompatibility class I (MHC-I) expression to evade killing by cytotoxic T lymphocytes (CTLs). A potent Nef inhibitor that restores MHC-I is needed to promote immune-mediated clearance of HIV-infected
Stephen F Haydock et al.
Microbiology (Reading, England), 151(Pt 10), 3161-3169 (2005-10-07)
The macrolide antibiotic concanamycin A has been identified as an exceptionally potent inhibitor of the vacuolar (V-type) ATPase. Such compounds have been mooted as the basis of a potential drug treatment for osteoporosis, since the V-ATPase is involved in the
Hideaki Toda et al.
Developmental and comparative immunology, 35(1), 88-93 (2010-09-04)
T cell-mediated cytotoxicity occurs via pathways based on perforin or Fas mechanisms. Perforin is a protein present in the cytoplasmic granules of CD8(+) cytotoxic T lymphocytes and is secreted to form pores on target cell membranes. In fish, although the
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