Nogalamycin

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Nogalamycin is a anthracycline antibiotic that is produced by the bacteria Streptomyces nogalater. It is known for its unique structure and its ability to intercalate DNA, which makes it a potent inhibitor of DNA replication and RNA synthesis.

Structure

Nogalamycin has a complex structure that consists of an aglycone (nogalamycinone) and three sugar residues. The aglycone is a tetracyclic aromatic system with a quinone moiety, which is responsible for its ability to intercalate DNA. The sugar residues are rhodosamine, nogalamine, and nogalose, which are attached to the aglycone via glycosidic bonds.

Mechanism of action

Nogalamycin intercalates between the base pairs of DNA, disrupting the double helix structure and inhibiting the function of DNA polymerase, an enzyme that is essential for DNA replication. It also inhibits RNA synthesis by binding to RNA polymerase, preventing it from transcribing DNA into RNA. This dual action makes nogalamycin a potent inhibitor of cell division and protein synthesis, which are essential processes for the survival and proliferation of cells.

Uses

Due to its ability to inhibit DNA replication and RNA synthesis, nogalamycin has been studied for its potential use as an anticancer drug. However, its clinical use has been limited due to its high toxicity and the development of resistance by cancer cells. Research is ongoing to develop derivatives of nogalamycin that have improved efficacy and reduced toxicity.

See also

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Types of antibacterials
Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)
30S
50S
Oxazolidinone (initiation inhibitors)
Peptidyl transferase
MLS (transpeptidation/translocation)
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
Extended
spectrum
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Monobactams
β-lactamase inhibitors
Polypeptides
Lipopeptides
- Insert into bacterial cell wall causing perforation and depolarization: Daptomycin - Surfactin
Other
- Inhibits PG elongation and crosslinking: Ramoplanin§
Intracellular
- Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)

- DADAL/AR inhibitors (Cycloserine)

- bactoprenol inhibitors (Bacitracin)
Other
- Hydrolyze NAM-NAG

- - lysozyme - Tyrothricin - - Gramicidin - - Tyrocidine - Isoniazid#

- Teixobactin


Antibacterials that inhibit nucleic acid (J01E, J01M)
Antifolates
(inhibit bacterial
purine metabolism,
inhibiting DNA/RNA synthesis)

DHFR inhibitors - 2,4-Diaminopyrimidine (Brodimoprim - Iclaprim - Ormetoprim - Pyrimethamine - Tetroxoprim - Trimethoprim)
Sulfonamides (DHPS inhibitors)
Short-acting - Sulfisomidine - Sulfamethizole - Sulfadimidine (Sulfamethazine - Sulfadimerazine - Sulfadimezine) - Sulfapyridine (Sulfasalazine) - Sulfafurazole (Acetyl sulfisoxazole) - Sulfanilamide (Prontosil) - Sulfathiazole (Phthalylsulfathiazole - Succinylsulfathiazole) - Sulfathiourea

Intermediate-acting - Sulfamethoxazole - Sulfadiazine - Sulfamoxole

Long-acting - Sulfadimethoxine - Sulfadoxine - Sulfalene - Sulfametomidine - Sulfametoxydiazine - Sulfamethoxypyridazine - Sulfaperin - Sulfamerazine - Sulfaphenazole - Sulfamazone

Other/ungrouped - Mafenide - Sulfacetamide - Sulfaclozine - Sulfadicramide - Sulfaguanidine - Sulfametrole - Sulfanitran

Combinations - Trimethoprim/sulfamethoxazole - Ormetoprim/sulfadimethoxine - Pyrimethamine/dapsone - Pyrimethamine/sulfadoxine

Other DHPS inhibitors - Acediasulfone - Dapsone - Solasulfone - Sulfoxone

Quinolones
(inhibit topoisomerase/DNA gyrase)

1st Generation - Cinoxacin - Flumequine - Nalidixic acid - Oxolinic acid - Pipemidic acid - Piromidic acid - Rosoxacin

Fluoroquinolones
2nd Gen - Ciprofloxacin - Ofloxacin - Enoxacin - Fleroxacin - Lomefloxacin - Nadifloxacin - Levonadifloxacin - Alalevonadifloxacin - Norfloxacin - Pefloxacin - Rufloxacin

3rd Gen - Levofloxacin - Balofloxacin - Grepafloxacin - Pazufloxacin - Sparfloxacin - Temafloxacin - Tosufloxacin

4th Gen - Besifloxacin - Delafloxacin - Gatifloxacin - Finafloxacin - Gemifloxacin - Moxifloxacin - Clinafloxacin - Garenoxacin - Prulifloxacin - Sitafloxacin - Trovafloxacin - Alatrofloxacin

Veterinary use - Danofloxacin - Difloxacin - Enrofloxacin - Ibafloxacin - Marbofloxacin - Orbifloxacin - Pradofloxacin - Sarafloxacin

Newer non-fluorinated - Nemonoxacin - Ozenoxacin Related (DNA gyrase) - Aminocoumarins (Novobiocin)

Anaerobic DNA inhibitors

Nitroimidazole derivatives - Secnidazole

RNA synthesis inhibitors

Rifamycins - Rifampicin - Rifabutin - Rifapentine - Rifaximin - Rifalazil
Lipiarmycins - Fidaxomicin


Antibacterials: others (J01X, D06AX)
Other/ungrouped


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  • Nogalamycin colored structure

  • Nogalamycinone structure

  • Nogalose and Nogalamine structures

  • Tailoring enzymes in nogalamycin biosynthesis

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Contributors: Prab R. Tumpati, MD