CAS 108212-75-5

Caliquéamicine γ1I

Description :

Caliquéamicine γ1I est un antibiotique antitumoral puissant dérivé de la bactérie Micromonospora echinospora. Il appartient à la classe des composés enediyne, connus pour leur capacité à induire des ruptures de brins d'ADN, entraînant des effets cytotoxiques dans les cellules se divisant rapidement. Ce composé présente une structure complexe caractérisée par un noyau bicyclique unique contenant une partie enediyne hautement réactive, qui est cruciale pour son mécanisme d'action. Caliquéamicine γ1I est particulièrement remarquable pour sa sélectivité envers les cellules cancéreuses, ce qui en fait un sujet d'intérêt dans les thérapies ciblées contre le cancer. Sa haute puissance s'accompagne d'une toxicité significative, nécessitant une manipulation et une administration prudentes dans les milieux cliniques. Le composé a été étudié pour son utilisation potentielle dans des conjugués anticorps-médicament, où il peut être lié à des anticorps ciblant spécifiquement les cellules tumorales, améliorant ainsi l'efficacité thérapeutique tout en minimisant les dommages aux tissus normaux. Dans l'ensemble, Caliquéamicine γ1I représente une avancée significative dans le développement d'agents chimiothérapeutiques, en particulier dans le contexte des stratégies de traitement ciblées contre le cancer.

Formule : C₅₅H₇₄IN₃O₂₁S₄

InChI : InChI=1S/C55H74IN3O21S4/c1-12-57-30-24-73-35(22-34(30)68-6)78-48-43(63)40(26(3)75-53(48)77-33-17-15-13-14-16-19-55(67)23-32(61)41(58-54(66)72-10)38(33)29(55)18-20-82-84-81-11)59-80-36-21-31(60)50(28(5)74-36)83-51(65)37-25(2)39(56)46(49(71-9)45(37)69-7)79-52-44(64)47(70-8)42(62)27(4)76-52/h13-14,18,26-28,30-31,33-36,40,42-44,47-48,50,52-53,57,59-60,62-64,67H,12,20-24H2,1-11H3,(H,58,66)/b14-13-,29-18+/t26-,27+,28-,30+,31+,33+,34+,35+,36+,40-,42+,43+,44-,47-,48-,50-,52+,53+,55+/m1/s1

Code InChI : InChIKey=HXCHCVDVKSCDHU-PJKCJEBCSA-N

SMILES : C(\CSSSC)=C/1\C=2[C@@H](O[C@H]3[C@H](O[C@H]4C[C@H](OC)[C@@H](NCC)CO4)[C@@H](O)[C@H](NO[C@H]5C[C@H](O)[C@H](SC(=O)C6=C(OC)C(OC)=C(O[C@H]7[C@H](O)[C@H](OC)[C@@H](O)[C@H](C)O7)C(I)=C6C)[C@@H](C)O5)[C@@H](C)O3)C#C/C=C\C#C[C@]1(O)CC(=O)C2NC(OC)=O

Synonymes :

• Benzenecarbothioic acid, 4-((6-deoxy-3-O-methyl-alpha-L-mannopyranosyl)oxy)-3-iodo-5,6-dimethoxy-2-methyl-, 4''-ester with methyl (8-((4,6-dideoxy-2-O-(2,4-dideoxy-4-(ethylamino)-3-O-methyl-alpha-L-threo-pentapyranosyl)-4-(((2,6-dideoxy-4-thio-beta-D-ribo-hexopyranosyl)oxy)amino)-beta-D-glucopyranosyl)oxy)-1-hydroxy-13-(2-(methyltrithio)ethylidene)-11-oxobicyclo(7.3.1)trideca-4,9-diene-2,6-diyn-10-yl)carbamate, (1R-(1R*,4Z,8S*,13E))-
• Benzenecarbothioic acid, 4-[(6-deoxy-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methyl-, 4′′-ester with methyl [8-[[4,6-dideoxy-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-<smallcap>L</smallcap>-threo-pentopyranosyl]-4-[[(2,6-dideoxy-4-thio-β-<smallcap>D</smallcap>-ribo-hexopyranosyl)oxy]amino]-β-<smallcap>D</span>-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]carbamate, [1R-(1R*,4Z,8S*,13E)]-
• Calicheamicin
• Calicheamicin γ₁
• Calicheamicin γ₁^I
• Calicheamicin γ_1α^I
• Calichemicin gamma1
• Calichemicin γ₁
• Carbamic acid, ((1R,4Z,8S,13E)-8-((4,6-dideoxy-4-(((2,6-dideoxy-4-S-(4-((6-deoxy-3-O-methyl-alpha-L-mannopyranopyranosyl)oxy)-3-iodo-5,6-dimethoxy-2-methylbenzoyl)-4-thio-beta-D-ribo-hexopyranosyl)oxy)amino)-2-O-(2,4-dideoxy-4-(ethylamino)-3-O-methyl-alpha-L-threo-pentopyranosyl)-beta-D-glucopyranosyl)oxy)-1-hydroxy-13-(2-(methyltrithio)ethylidene)-11-oxobicyclo(7.3.1)trideca-4,9-diene-2,6-diyn-10-yl)-, methyl ester
• Carbamic acid, N-[(1R,4Z,8S,13E)-8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-<smallcap>D</smallcap>-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-<smallcap>L</smallcap>-threo-pentopyranosyl]-β-<smallcap>D</span>-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester
• Carbamic acid, [(1R,4Z,8S,13E)-8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-<smallcap>D</smallcap>-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-<smallcap>L</smallcap>-threo-pentopyranosyl]-β-<smallcap>D</span>-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester
• Carbamic acid, [8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-<span class="text-smallcaps">L</smallcap>-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-<smallcap>D</smallcap>-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-<smallcap>L</smallcap>-threo-pentopyranosyl]-β-<smallcap>D</span>-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester, [1R-(1R*,4Z,8S*,13E)]-
• LL-E 33288γ1-I
• S-(6-{[(5-{[5-(ethylamino)-4-methoxytetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-{[(2S,5Z,9R,13E)-9-hydroxy-12-[(methoxycarbonyl)amino]-13-[2-(methyltrisulfanyl)ethylidene]-11-oxobicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl]oxy}-2-methyltetrahydro-2H-pyran-3-yl)amino]oxy}-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl) 4-[(3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzenecarbothioate (non-preferred name)
• S-[(2R,3S,4S,6S)-6-({[(2R,3S,4S,5R)-5-{[(2S,4S,5S)-5-(ethylamino)-4-methoxytetrahydro-2H-pyran-2-yl]oxy}-4-hydroxy-6-{[(2S,5Z,9S,13E)-9-hydroxy-12-[(methoxycarbonyl)amino]-13-[2-(methyltrisulfanyl)ethylidene]-11-oxobicyclo[7.3.1]trideca-1(12),5-diene-3,7-diyn-2-yl]oxy}-2-methyltetrahydro-2H-pyran-3-yl]amino}oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl] 4-{[(2S,3R,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy}-3-iodo-5,6-dimethoxy-2-methylbenzenecarbothioate (non-preferred name)
• Benzenecarbothioic acid, 4-[(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methyl-, 4′′-ester with methyl [8-[[4,6-dideoxy-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-4-[[(2,6-dideoxy-4-thio-β-D-ribo-hexopyranosyl)oxy]amino]-β-D-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]carbamate, [1R-(1R*,4Z,8S*,13E)]-
• Calicheamicin γ1αI
• Carbamic acid, N-[(1R,4Z,8S,13E)-8-[[4,6-dideoxy-4-[[[2,6-dideoxy-4-S-[4-[(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy]-3-iodo-5,6-dimethoxy-2-methylbenzoyl]-4-thio-β-D-ribo-hexopyranosyl]oxy]amino]-2-O-[2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl]-β-D-glucopyranosyl]oxy]-1-hydroxy-13-[2-(methyltrithio)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl]-, methyl ester
• Calichemicin γ1

Calicheamicin

CAS : 108212-75-5

Calicheamicin

Degré de pureté : ≥98%

Masse moléculaire : 1368.35g/mol

Ref: 54-BUP01291

Calicheamicin γ1

CAS : 108212-75-5

Formule : C₅₅H₇₄IN₃O₂₁S₄

Masse moléculaire : 1368.37

Ref: 4Z-C-170001

Calicheamicin gamma1

CAS : 108212-75-5

Calicheamicin γ1 is a highly potent cytotoxic agent used as a payload in antibody–drug conjugates (ADCs). It binds to the minor groove of DNA and induces double-strand breaks through a radical-mediated mechanism, leading to cell death even at extremely low concentrations. Its remarkable potency makes it effective for targeted cancer therapies when precisely delivered to tumor cells via an antibody.

Formule : C₅₅H₇₄IN₃O₂₁S₄

Degré de pureté : Min. 98 Area-%

Couleur et forme : Powder

Masse moléculaire : 1,368.35 g/mol

Ref: 3D-FC165036

Calicheamicin

CAS : 108212-75-5

Calicheamicin (Calicheamicin γ1) is an antitumor antibiotic and is a DNA synthesis inhibitor. It also is a cytotoxic agent that causes double-strand DNA breaks.

Formule : C₅₅H₇₄IN₃O₂₁S₄

Degré de pureté : 98.22% - 98.78%

Couleur et forme : Solid

Masse moléculaire : 1368.35

Ref: TM-T14858