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C9705

Sigma-Aldrich

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
Beilstein:
3560277
MDL number:
MFCD00210037
UNSPSC Code:
12352200
PubChem Substance ID:
24893186
NACRES:
NA.77

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

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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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H319

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Christiane Ott et al.
Redox biology, 10, 266-273 (2016-11-09)
The overall decrease in proteolytic activity in aging can promote and accelerate protein accumulation and metabolic disturbances. To specifically analyze changes in macroautophagy (MA) we quantified different autophagy-related proteins (ATGs) in young, adult and old murine tissue as well as
Markus Huss et al.
The Journal of biological chemistry, 277(43), 40544-40548 (2002-08-21)
Vacuolar-type ATPase (V-ATPase) purified from the midgut of the tobacco hornworm Manduca sexta is inhibited 50% by 10 nm of the plecomacrolide concanamycin A, the specific inhibitor of V-ATPases. To determine the binding site(s) of that antibiotic in the enzyme
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