ID: ALA2170855

Max Phase: Preclinical

Molecular Formula: C72H66N8O12S4

Molecular Weight: 678.84

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[n+]1ccc(-c2c3nc(c(-c4cc[n+](C)cc4)c4ccc([nH]4)c(-c4cc[n+](C)cc4)c4nc(c(-c5cc[n+](C)cc5)c5ccc2[nH]5)C=C4)C=C3)cc1.Cc1ccc(S(=O)(=O)[O-])cc1.Cc1ccc(S(=O)(=O)[O-])cc1.Cc1ccc(S(=O)(=O)[O-])cc1.Cc1ccc(S(=O)(=O)[O-])cc1

Standard InChI:  InChI=1S/C44H37N8.4C7H8O3S/c1-49-21-13-29(14-22-49)41-33-5-7-35(45-33)42(30-15-23-50(2)24-16-30)37-9-11-39(47-37)44(32-19-27-52(4)28-20-32)40-12-10-38(48-40)43(36-8-6-34(41)46-36)31-17-25-51(3)26-18-31;4*1-6-2-4-7(5-3-6)11(8,9)10/h5-28H,1-4H3,(H,45,46,47,48);4*2-5H,1H3,(H,8,9,10)/q+3;;;;/p-3/b41-33-,41-34-,42-35-,42-37-,43-36-,43-38-,44-39-,44-40-;;;;

Standard InChI Key:  AKZFRMNXBLFDNN-GVHKZQBISA-K

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 678.84

Molecular Weight (Monoisotopic): 678.3197

AlogP: 6.62

#Rotatable Bonds: 4

Polar Surface Area: 72.88

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa:

CX Basic pKa: 4.66

CX LogP: -9.42

CX LogD: -9.42

Aromatic Rings: 7

Heavy Atoms: 52

QED Weighted: 0.21

Np Likeness Score: 0.07

References

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2. Cohn EP, Wu KL, Pettus TR, Reich NO..  (2012)  A new strategy for detection and development of tractable telomerase inhibitors.,  55  (8): [PMID:22413845] [10.1021/jm201191d]

3. Perrone R, Nadai M, Frasson I, Poe JA, Butovskaya E, Smithgall TE, Palumbo M, Palù G, Richter SN..  (2013)  A dynamic G-quadruplex region regulates the HIV-1 long terminal repeat promoter.,  56  (16): [PMID:23865750] [10.1021/jm400914r]

4. González-Delgado JA, Kennedy PJ, Ferreira M, Tomé JP, Sarmento B..  (2016)  Use of Photosensitizers in Semisolid Formulations for Microbial Photodynamic Inactivation.,  59  (10): [PMID:26569024] [10.1021/acs.jmedchem.5b01129]

5. Wang C, Carter-Cooper B, Du Y, Zhou J, Saeed MA, Liu J, Guo M, Roembke B, Mikek C, Lewis EA, Lapidus RG, Sintim HO..  (2016)  Alkyne-substituted diminazene as G-quadruplex binders with anticancer activities.,  118  [PMID:27132164] [10.1016/j.ejmech.2016.04.030]

6. Kaulage M, Maji B, Bhat J, Iwasaki Y, Chatterjee S, Bhattacharya S, Muniyappa K..  (2016)  Discovery and Structural Characterization of G-quadruplex DNA in Human Acetyl-CoA Carboxylase Gene Promoters: Its Role in Transcriptional Regulation and as a Therapeutic Target for Human Disease.,  59  (10): [PMID:27058681] [10.1021/acs.jmedchem.6b00453]

7. Belmonte-Reche E, Martínez-García M, Guédin A, Zuffo M, Arévalo-Ruiz M, Doria F, Campos-Salinas J, Maynadier M, López-Rubio JJ, Freccero M, Mergny JL, Pérez-Victoria JM, Morales JC..  (2018)  G-Quadruplex Identification in the Genome of Protozoan Parasites Points to Naphthalene Diimide Ligands as New Antiparasitic Agents.,  61  (3): [PMID:29323491] [10.1021/acs.jmedchem.7b01672]

8. Kaulage MH, Maji B, Pasadi S, Ali A, Bhattacharya S, Muniyappa K..  (2018)  Targeting G-quadruplex DNA structures in the telomere and oncogene promoter regions by benzimidazole‒carbazole ligands.,  148  [PMID:29459277] [10.1016/j.ejmech.2018.01.091]

9. Sobotta L, Skupin-Mrugalska P, Piskorz J, Mielcarek J..  (2019)  Porphyrinoid photosensitizers mediated photodynamic inactivation against bacteria.,  175  [PMID:31096157] [10.1016/j.ejmech.2019.04.057]

10. Wang S, Yang D, Singh M, Joo H, Rangel VM, Tran A, Phan E, Xue L..  (2019)  Thiazole orange - Spermine conjugate: A potent human telomerase inhibitor comparable to BRACO-19.,  175  [PMID:31071547] [10.1016/j.ejmech.2019.04.041]

11. Otvagin VF, Kuzmina NS, Kudriashova ES, Nyuchev AV, Gavryushin AE, Fedorov AY..  (2022)  Conjugates of Porphyrinoid-Based Photosensitizers with Cytotoxic Drugs: Current Progress and Future Directions toward Selective Photodynamic Therapy.,  65  (3.0): [PMID:35050607] [10.1021/acs.jmedchem.1c01953]

Source

Source(1):

• Scientific Literature