US 11,905,236 B2
Dynamic combinatorial library based on pseudopeptides and its use for the detection of cysteine and other biothiols
Igancio Alfonso Rodriguez, Barcelona (ES); Jordi Sola Oller, Barcelona (ES); and Maria Lafuente Fabra, Barcelona (ES)
Assigned to CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC), Madrid (ES)
Appl. No. 17/042,667
Filed by CONSEJO SUPERIOR DE INVESTIGACIONES CIENTIFICAS (CSIC), Madrid (ES)
PCT Filed Apr. 4, 2019, PCT No. PCT/ES2019/070226
§ 371(c)(1), (2) Date Sep. 28, 2020,
PCT Pub. No. WO2019/193231, PCT Pub. Date Oct. 10, 2019.
Claims priority of application No. ES201830330 (ES), filed on Apr. 4, 2018.
Prior Publication US 2021/0139419 A1, May 13, 2021
Int. Cl. G01N 33/58 (2006.01); G01N 33/68 (2006.01); C07C 321/06 (2006.01)
CPC C07C 321/06 (2013.01) [G01N 33/582 (2013.01); G01N 33/6815 (2013.01)] 16 Claims
OG exemplary drawing
 
1. A mixture of molecules comprising at least a compound as defined by formula (I):

OG Complex Work Unit Chemistry
or an isomer or a salt thereof, wherein:
Ra and Rb are independently selected from H, —CONRR′, —COOR, —NRR′, —OH, —C(NH)NH2, —CH(OH)CH3, aryl-(C6-C10) or heteroaryl-(C6-C10);
R and R′ are independently selected from H or alkyl-(C1-C5);
m is an integer selected from 0, 1, 2, 3 or 4;
n is an integer selected from 1 or 2;
at least a compound of formula (II):

OG Complex Work Unit Chemistry
or an isomer or a salt thereof, wherein:
n′ is an integer selected from 1 or 2;
and at least a compound of formula (III):

OG Complex Work Unit Chemistry
or an isomer or a salt thereof, wherein:
Rc represents an aromatic chromophore;
Y is selected from NHCO or CONH;
Z is selected from H, —NH2, —OH or —COOH;
p is an integer selected from 0, 1, 2 or 3.
 
14. An in vitro method for the detection of a compound of formula (IV):

OG Complex Work Unit Chemistry
or an isomer or a salt thereof, wherein:
Rd is selected from H or S(CH2)qCH(NH2)COOH;
q is an integer selected from 1, 2 or 3
in a sample comprising the following steps:
a) mixing at least a compound of formula (I) with at least a compound of formula (II) and at least a compound of formula (III) according to claim 1;
b) contacting the sample comprising the compound of formula (IV) with the mixture of step (a);
c) measuring the fluorescence emission of the mixture obtained in step (b);
d) detecting a significant deviation from a standard; and
e) assigning the sample to the group of samples comprising a compound of formula (IV) when a significant difference has been detected in stage (d).